Robby Allen - Former Head of Sales @Mixmax (Formerly @Flexport, @Zenefits) - Scaling SaaS Sales Functions Across Multiple Growth Phases, Hiring & Onboarding Sales Teams at Massive Scale, Building Sales Development Engines, Sales Compensation Plans

Guest:

Robby Allen - Former Head of Sales @Mixmax

(Founder @Buena Vista Ventures; Formerly @Flexport, @Zenefits)

Guest Background:

Robby was born and raised in San Francisco and knew from a young age that he wanted to build and scale companies. At Zenefits he took the outbound SDR team from 0-250+ reps. At Flexport he built a global outbound team across 3 continents. After that Robby was the head of sales at Mixmax, taking the team from a self-serve business to a B2B sales model.

Currently, Robby runs his own consulting practice: Buena Vista Ventures. Buena Vista focuses on emerging technology companies, mainly SaaS businesses, looking to build and scale high performing and efficient sales organizations.

Outside of the office, you can find Robby playing basketball or hiking to the top of a peak.

Guest Links:

LinkedIn

Episode Summary:

In this episode, we cover:

- Scaling SaaS Sales Functions Across Multiple Growth Phases

- Hiring & Onboarding Sales Teams at Massive Scale

- Building Sales Development Engines

- Sales Compensation Plans

Full Interview Transcript:

Naber:  Hello friends around the world. My name is Brandon Naber. Welcome to the Naberhood, where we have switched on, fun discussions with some of the most brilliant, successful, experienced, talented and highly skilled Sales and Marketing minds on the planet, from the world's fastest-growing companies. Enjoy!

Naber:  Hey everybody. We have Robby Allen on the show today. Robby was born and raised in San Francisco and knew from a young age that he wanted to build and scale companies. At Zenefits, which had a $4.5 billion evaluation on $584 million capital raised, Robby took the outbound SDR team from 0 to 250+ reps. Then at Flexport, which had a $3.2 billion valuation on $1.3 billion raised, Robby built a global outbound team across three continents. After that, Robby was the Head of Sales at Mixmax. Mixmax has raised $13 million, and he took that team from a self serve business to a B2B sales model. Currently, Robby runs his own consulting practice, Buena Vista Ventures, Buena Vista focuses on emerging technology companies, mainly SaaS businesses looking to build and scale high performing and efficient sales organizations. Outside the office you can find Robby playing basketball or hiking to the top of a peak. Here we go.

Naber:  Robby! Awesome to have you on the show today. How are you my man?

Robby Allen:     I'm good. I'm good, Thanks for having me, Brandon. It's good to be here.

Naber:  Good. Fresh off your recent trip to Europe. You're in a feel good mood. You've got good energy. I'm loving it. You and I have known each other for awhile, and I'm really happy and proud to be chatting with you today. I think there's a lot that the audience can learn from you. What I think we'll do, if it's okay with you, is we'll go into some personal stuff first - let the audience get to know you a little bit better. We'll go into a few different things around your basketball career. I want to talk about some of the things that you did growing up, get an idea for some of your interests, all the way from Robby as a kid and what you were interested in and what you were like, all the way through to the end of the end of school in Eugene. So, if you're okay with it, could you give us maybe five, seven minutes, and it will probably last a little bit longer than that because I'll ask questions, hopefully not too rudely, to explain a few things. But could you give us a few minutes on what Robby was like as a kid and what it was like being Robby Allen as a child growing up?

Robby Allen:     Yeah, sure. And to start, I'm super excited to be here. Super excited you're doing this. and can't wait to see the first handful of these episodes released into the wild. I think, given your network and the people you know it's going to be fun. But yeah, a little on me. So I was born and raised in San Francisco. People tell me that's something unique that live here, because so many people scratch, and claw, and work hard to move to San Francisco because, in the world of tech, it's considered to be the land of opportunity. I was fortunate in some ways to grow up right in the middle of it. And I knew at a really young age that I wanted to build and scale companies. It was just something where when I was five years old, I used to tell my mom that I wanted to put a suit on and can go downtown to work. Obviously the suit thing has changed, people don't wear suits anymore in San Francisco, unless you're in finance or something like that. But from a young age, I've been very interested in this notion of building things from scratch, building wealth, building value for markets and that sort of thing...

Naber:  Hey, can we pause on that just for a minute. Did you ever, did you have any businesses or ways of making money growing up? Well, actually there's a really good question that someone asked me the other day, and I want to pay it forward to the audience, and get your thoughts. What was your first way of making money?

Robby Allen:     Yeah, that's a good question. So I used to hustle Pokemon cards, if you remember what those are. I had a little business that in elementary school - and for folks that don't know, Pokemon was a Japanese trading card game that got really popular in Japan, and then overtook my generation, I guess - and I went to a Japanese bilingual school in San Francisco called Clarendon. So everybody there was first generation Japanese where their parents immigrated from Japan, and I happened to grow up right around the corner from there. So I went to school there. And so there was a lot of popularity around that and I saw an opportunity, I think, that was one example. I got into sneakers, when I started to really get into basketball. And so I started to buy and trade sneakers that were,popular. I would buy them when they were released for a cheaper price and sell them for a little bit more. It didn't make a lot of money, but it was something where I was able to get good at it, so to speak. Those were, I guess those were a couple things. I think that eventually scaled up until I landed in the world of sales where I think I really enjoyed that because it was something where I could control my own destiny, so to speak.

Naber:  Nice. Those are good examples. Wow. I mean...the purpose of the question, that comes from an executive that a at a company that I used to work at, but his take is that he believes that work ethic starts at a very young age and entrepreneurial spirit starts at a very young age. And that that is one of the hardest to teach in your twenties and thirties. And he feels that people don't necessarily develop that in their twenties and thirties. They actually develop it as at a really young age. So that was that's he purpose of asking that question. But you have some pretty kick ass examples. That's great. Quick insert here, what is your favorite sneaker you've ever traded for?

Robby Allen:     Oh, man. Yeah, so I think it's kind of a random one that most people won't know, but it's the story here, it's a pair of Air Flight 89's and my younger brother and our mutual best friend, who grew up around the corner from us in the Haight-Ashbury in San Francisco. When I was really young, we'd sell lemonade on the corner on hot days in San Francisco, and we would play up the fact that my mom grew lemons in the backyard, but mostly it was just the concentrated lemonade that you'd get from Safeway. And so we'd sell this. And then I remember I'm, the listeners won't know this, but I'm very tall. And so at a young age I became really big, and the whole cute factor of selling lemonade certainly drifted away from me, and I was no longer necessarily somebody who was an obvious candidate to sell lemonade. So I, naturally the opportunity still being there, I recruited my younger brother and our buddy Ian. A I sort of operated in the background, refilling and getting them out there. And we made enough money one Saturday afternoon, a sunny afternoon in the fall in San Francisco, where we could all go to a sneaker store on Haight Street and buy a pair of Air Flight 89's. And so I guess you could say that was a trade of labor and lemonade for sneakers. But, I'll never forget that pair because all three of us walked out of the store with the same shoes.

Naber:  That's a great story. Two things. One, what did you say something and lemonade? You said something and lemonade.

Naber:  Labor and lemonade.

Naber:  Labor and lemonade would be the title of your first book. Second of all, everyone of us mere mortals at six foot and under always wonders what it's to be tall. And, people always think of the upside, pun intended. But some of the downside could be you could retire from lemonade sales very early in your career. Which is, that could be a sad story. But it's a good story for you.

Naber:  I had to let that drift away, yeah.

Naber:  That's right, you're good. So let's talk about high school for a second. So you went to St I's College Prep in San Francisco, is that right? And played basketball?

Robby Allen:     Yep. Saint Ignatius, that's where I really got into sports. And yeah, I played basketball and did high jump at SI.

Naber:  Cool. What position do you play in Basketball?

Robby Allen:     I was I played power forward. I was pretty new to it...I started playing basketball really in high school. I was a baseball player before that, but an injury prevented me from continuing that path. So, I was tall and I could jump and I was pretty quick. So I started to pick up basketball, and they stuck me in at power forward, and I didn't really have a ton of skill per se. I was just springy and my batteries we're always charged. So I did that for four years, and then I went to college up at Oregon, at University of Oregon. And I decided not to follow the basketball path, but after about a year, sort of missed it. Missed the organized sports, missed the competition, and was one of those guys in college who you could basically see me at the rec center seven days a week playing pickup basketball. So I actually ended up finding a local junior college called Lane Community College. I met the coach and I got to know him, and he gave me a full scholarship, and I ended up going and playing two years of basketball at a little junior college in town. I was still going to University of Oregon, and I went to the business school and took a full load of credits there. And then unbeknownst to most people I knew, I was also taking the bus on the other side of town and taking a full load of credits at Community College just to play basketball. And it ended up being this really fun thing because community college, most people, you and I work with and know didn't spend any time in community college, and this is a little secret I have. And it ended up being amazing thing for me. You get to meet, you meet a lot of people that are decades older than you, and they're just now getting to getting around to going to school to maybe get an associate's degree or something that, to up level a little bit. And so it was humbling in the sense that I, I really grew to appreciate what I had, at the University that I was going to across town, and I got to get my two years of basketball in at that level, and that was all I needed, and went back to U of O and finished up my degree.

Naber:  Awesome man. Wow. Very cool. I love that you went after your passion, with a credits at this school, basketball at the school vengeance - missing your craft. One more thing, I think you've done some coaching in your, day as well while we're on the basketball. And when I say the basketball, I mean while you're on your basketball career? I got used to saying the basketball, or the football, or the baseball when I was in Australia. So sometimes I put the in front of a sport arbitrarily. Anyways, while we're on your basketball career. So let's talk about some of the coaching you did as well. What does your coaching career consist of?

Robby Allen:     Yeah, so, after hanging it up so to speak, from a couple of years playing in college, I...one of my assistant coaches from my college team, actually took an off season job as the head coach of a local high school team for Mohawk High. It's about 45 minutes outside of Eugene, Oregon. And, to give you an idea, I mean this is high school, probably had 200 students and at the...and I come from a school where there were probably 65 kids who tried out for the varsity basketball team every year, and only about 10 or so made it, it was a big thing...Seven kids showed up to the tryouts, so all seven kids made it. And this is ranging ranging from kids who had played basketball to had never played in their life. So this is a very different challenge. I think the team had finished in last place out of 10 people for the last 10 or so years. And so myself, and I recruited another buddy who played on the team with me to come be an assistant coach for the team, and it was more than a challenge. Because you know, we did not have any real semblance of talent on this team. But you got to know this group of kids, and we would take a yellow school bus two hours north and south of Eugene twice a week to go play games. And in some of these towns that I probably never would have otherwise set foot in my life. And I actually remember, at halftime, there was a game in, I can't even remember the name of the city, it was a western Oregon town. There was a hoedown at halftime, where about 30 people came out in cowboy boots and did a cowboy hoedown. And they had a live auction, or so they had a live raffle. And so they drew a raffle prize. There's dust and hay now all over the court, these kids have to come out and play the second half still. And they draw a number and someone in the crowd wins, and they're going crazy, and we don't know what the prize is. And they walk like 1500 pound pig basically, from the locker room. And they auctioned off a full grown male pig and somebody took home the pig...just to give you an idea of the spirit of some of these games. But that was was a learning experience for sure. But, the end of the story is we ended up finishing in second place in the league, which was the best they'd ever done. And, while it wasn't necessarily the team I would have picked or recruited myself because, frankly, we had we had to take a...there wasn't enough interest in the school. I started to really figure out that coaching was something I was passionate about, and that was a takeaway I brought with me. And still to this day, it's a guiding thing for me in terms of looking for opportunities to coach. Because even when you're making a small difference in a group of kids that are never going to play basketball at a high level, you can still have an impact on their life in a positive way. So that was a fun experience.

Naber:  Cool man. We're going to cover that in a little bit, a little bit more on coaching from a professional context. That's a great story. So that, that brings us to post-Eugene. You get out of sphere-O'Ducks in Eugene, and your first role after school is what?

Robby Allen:     Yeah, so I'm actually at the time working for a craft beer company that was based in Eugene - a company called Ninkasi Brewing Company. Their CEO was a former Wall Street guy who came back to Eugene and built this really, really successful fast-growing craft beer company. And I was able to finagle a job at that company, which as you can imagine, was a really fun job to have in college, and it made me very popular, especially during the summertime. And part of me thought I wanted to pursue that post college, but the more I dug into it, it just wasn't, it was more of something that...I like the idea of building this business, but it wasn't necessarily the industry I wanted to work in. So I had some people that I was close with giving me the advice that, starting a career in sales would be a good place to start. And I ended up taking a job at this company called People Matter, which was an HR technology company. And frankly didn't really know a lot about the business, didn't really have a great why for why I picked it other than it was the first door when it was an opportunity that opened up to me. The role was just a straight up outbound SDR role., the first outbound SDR the company had ever hired, reporting directly to the VP of sales. Little to no training, threw you out into the wild. And I flailed a little bit for, for probably about a month until really starting to get the hang of it. And I think the thing that I liked about it was the challenge of being able to basically directly challenge and try to add value to people that were often 20 years my senior, and help book meetings and that sort of thing. And I did really well at it against all odds. It wasn't something where I was necessarily set up for a ton of success, and that was something that I remembered and brought with me in future roles where I was the one responsible for hiring and training folks in that role...and that office was a satellite office for a company based in South Carolina, and I'm remember I was on a camping trip with my wife, girlfriend at the time, and I came back and I turned my phone on and somebody, I had 15 will voice messages and all my colleagues told me, hey, they shut the office down. I was as Oh my God. So, they closed the office down. It was something that I think I just didn't have enough business aptitude or savvy to see something that coming, per se. I was just focused on my own success, but it ended up being a blessing in disguise. I got introduced to a company called Zenefits, where a friend of mine worked. I had been a successful AE for nine months and like any successfully AE of nine months was convinced I should be an AE, but decided to take a step back to take a step forward. So I actually came in as an SDR at Zenefits. And I was an early employee there, and it was an amazing atmosphere. I mean, it was the kind of place where the phones were ringing all day, and there weren't enough sales people to take the number of demos that we were setting and the deals we were closing. And, so I came in there and it was the start of a really, really interesting journey. And I, I went from the top performing rep to becoming a manager, and building out this outbound team. They were sort of an all inbound shop before that. I built out a team of about 20 SDRs in San Francisco, hired a manager and placed them there. And the CEO, Parker, approached me and asked me, "hey, do you want to move out to Arizona and build this at 10x the scale." And I remember telling him no at first. I was like I'm a San Francisco kid, my girlfriend's here, all my friends and family are here. And I remember he told me this thing that always stuck with me. He said, "Robby, once or twice in your career, if you're lucky, a big, maverick tidal wave will come up behind you. And it's your decision if you want to grab a surfboard and jump in and try to ride it or not. And when a CEO tells you something that, it's kind of hard not to get fired up...So about two weeks later I was on a flight to Phoenix, and was moving out there. And over the course of the next two and a half years I built, and this is always kind of wild to say out loud, I'd built and scaled out at an SDR team of about 250. So we were hiring 30 SDRs every month, and really going from product market fit to repeatability to full-on hypergrowth, in this really condensed time period. And there are a ton of learnings and I'm sure some things that we'll be able to unpack along that journey. And it was a big growth experience for me. I was 25 years old, in a room full of 200 people that I'd hired in this whole organization we'd built out. And so learning just how to grow, with this growing business, personally. And how to uplevel my skills, and understand what the things were that I could do to add value at the certain different stages we went through. I was an amazing experience. So we went on a journey from a zero to $70 million in ARR over those three years. Which was a lot, and an amazing journey. And when that journey concluded, I had done everything I've set out to do at Zenefits and wanted to move back to the Bay Area. And so I came back to SF and actually got introduced to a company called Flexport. My old, my former former boss...

Naber:  Let's pause for a second because I want to keep your head space in the Zenefits zone for a minute because we'll hop into Flexport and a little bit. But there's just so much to unpack with Zenefits that while your head's on the space, I'd to keep it there for a few minutes. For those that are listening, you heard the amount of scale both from a hiring, bookings, and revenue perspective, and just an operational scale - just unbelievable. Somewhat unheard of hypergrowth scale you guys are operating at, and you being the spearhead of a lot of that operational execution for hiring to make sure that you're building pipeline and building the pipe for the sales team at scale. All the way through to making sure you have a pool of talent and a bench of talent to mobilize within the organization. All of that is obviously vitally important to the massive scale and results that you guys had. So let's pause on that for a minute. So first of all, let's talk about hiring teams. There's a lot of people that are going through either their version of hyper growth, or what would fit everyone's definition of hyper growth. Whether they're hiring a significant number of people in their head, or in reality they're hiring a lot of humans to do a various number of roles. So let's talk about that. So when you think about recruiting at massive scale, what are a couple of the fundamentals that people need to keep in mind and remember, or get right, that you think about as a framework for how you scaled that much growth for hiring?

Robby Allen:     Yeah, a great question. And I think, with the benefit of hindsight, I can probably speak a little bit more intelligently to it, then I could at the time.

Naber:  To all of our benefit actually, to all of our benefit.

Robby Allen:     Yeah. So I think the first thing that's just so important that you hear time and time again, but I think that there is no amount of time that you can spend that is too much, is getting your foundational team - your founding team, you're first team - right. And in in my case, I had the benefit of building out a team in San Francisco, and was able to sort of, get a couple - two of the top reps, my friends Alex Snatch and Andrew Case, both of whom became very close friends, and were at my wedding. and to this day are still very close friends - top reps in San Francisco and were able to get them to move about the Arizona with me. And so having that institutional knowledge there on the ground made such a big difference because there's already this dynamic of what excellence looks for every new hire that comes in. And I think that that's really important, And I think that for folks that are, that are starting a new role or coming into a new environment, if you're in a sales leadership position, whether you're an SDR manager, or VP of sales, or a VP of marketing, or whatever the case may be, you should probably already know who the first two or three people that you're going to recruit and hire into the organization are going to be. And the reason for that is because you can create an environment that you've got a little bit more control over, and create a culture that you're comfortable with and familiar with and that you can help integrate your new people into. Because once you start to add new folk onto the team, if you don't already have that foundational culture in place, you can't go back in time and rebuild it. And that can be a recipe for disaster. And so I was very fortunate to have benefited from that without necessarily prioritizing it. But it's something that I've learned now over the years that you, you can't really spend enough enough time in the beginning recruiting and focusing on who is going to be my founding go to market team.

Naber:  Yup. Yup. That makes sense. And then, let's talk about operationalization of that hiring as well. So your founding team, you need to get both the culture as well as that group right - the first few people on your team. Then we need to get into the actual operations of hiring that many people. Can you give us an understanding of...if you think about it this way - from the top of the funnel to the bottom of the funnel, or from one part of the operational execution to the other - what are some of the best practices from a recruitment perspective that you need to nail when you're hiring at scale?

Robby Allen:     Yeah, so I think it's a great question. And we went through many iterations of this. We went through me being the sole owner of top to bottom recruiting for this organization to having an internal recruiting team of 15 recruiters that were sort of running an engine. And so I saw every evolution along the way. And I think there were a couple of takeaways that I recommend to folks when I talked to them. And the first one is, when you think about your role as a leader, at the end of the day, it's your call. And the success or failure of the sort of decisions that you make when you're hiring people rest on your shoulders. And so when you think about what is the highest point of leverage that you have throughout the entire recruiting process? In my opinion, it's two things. One, it's setting the tone in terms of what to look for, and what our criteria are, and making that very evident so that everybody who's involved with the recruiting process is aligned on the same page, right? So defining the role but also making sure that you walk the walk in terms of the team that you're building along the way. So it's self represented. And the second thing is when you think about the leverage that you have as a leader or a hiring manager, it's actually this final stage interviews and the decision of go/no-go, and the ability to close candidates and then everything that happens after that in terms of the successful ramp and management of the team. And so the thing that I suggest to most folks, is please negotiate with your CEO, or the leader, or the person who you're recruiting to, whether you've got internal recruiting resources or outsourced external resources. you need the support in terms of I prospecting and management. We've proven in so many different aspects of the business, and we can take sales as an example that specializing the sales process in terms of appointment setters, and deal closers, is just more effective. And from a recruiting standpoint, you should think about it in a similar way. And so there's just going to be...it's nice for all of us to think that we can take a sniper approach to recruiting and just pick the four people we want to hire, hyperfocus on them, and close three out of four of them. But the reality of situation is that it's never been more competitive to recruit, really in any market. And that it's a candidates market so to speak. And so you want to get recruiters working for you. And it is worth the cost of admission. And it's just something to think about when you're either taking a new role or managing up, that you really want to help define the amount of work that, that recruiter's going to do for you. And so in the beginning at Zenefits, we had a couple of SF based recruiting firms doing a lot of this recruiting for us in Arizona. And I would take flights out there twice a week and hold full on interview days where we would do upwards of 10-15 interviews, and do batch hiring. But it allowed me to really isolate and focus on being super present in the interview, and making conscious decisions to place the right bets on these people that we were hiring. And that combined with the support of the folks that I mentioned earlier who were already high performers being involved with the process, allowed us to get a lot of those early hires right, and that helped us along the journey.

Naber:  Awesome, man. That's great. It's gold. One of the things that I always touch on with either my clients, or folks in groups, or keynotes, or whatever, is specialization. Once you get to specialization within the process of bringing great talent onboard and the operationalization of it - so bringing in sourcers, bringing in recruiters, and making sure you don't have generalists working on it, but specific people working on specific pieces of the process - it's a great analogy to sales that we've proven it out for SDR, for sales, for account management, customer success, the specialization across the entire spectrum. I mean it's just gold what just came out of your mouth. So I hope that people take that onboard. Two more things I want to talk about within Zenefits, and then we'll move on. So you're bringing in a shed load of those people all the time. And you're keeping your culture and your values in mind the whole time, while at the same time running at breakneck speed for bringing those people in. Two questions. One is, as you're evaluating talent at that scale - so some people that are listening are going to need to hire five people in a year, some people that are listening are gonna need to hire 500 people in a year, or maybe even 5,000 people in a year depending on,the level of responsibility that they have, listening on this conversation - So when you're thinking about bringing those people on board, interviewing all of them, sourcing all of them, what is the calibration method that you guys have used that has been most successful to make sure that you have multiple people inside the organization giving input on this person being the the right person to hire? So the right candidate, what's the calibration method that you found, that is most useful or valuable as you're going through that level of hiring at scale?

Robby Allen:     Yeah, it's a good question because I think the thing that worked well for us in the beginning was not necessarily the thing that worked well for us on the pathway along the journey. And that transition wasn't super smooth. And so I was the single point of accountability, or single point of failure success, however you want to state that. And that I made the hiring decision for the first hundred or so sales reps that we hired, where I was in every single interview. And so, as you can imagine, this absorbed a ton of my bandwidth, but we were fortunate to have a lot of support in terms of ramping and making reps successful and then hitting their numbers, and we were able to stay ahead of that. So I was able to do that. Handing off that decision responsibility took quite a bit of calibration. And I think that at the end of the day with recruiting, it's nice for organizations to have a fully calibrated, well-oiled recruiting machine where you can predictably make the same decisions about hires based on an agreed upon set of criteria and principles. And I think that there's companies out there that do this really well. It's really hard to do during a hyper growth phase. And I actually recommend, to most folks, that you hold onto a single point of accountability or a single decision in terms of this hiring, as long as you can. And then as you get folks up to speed and you're able to delegate out some of some of the hiring responsibilities, do that. But I think it is really the single most important thing that you can do, when you're at a hyper growth stage. And narrowing that level of responsibility for decision down to the smallest group of stakeholders possible, it may sound counterintuitive because a lot of bigger companies do as well where it's delegated across many people. But in my opinion, I think it's better to hold on to it. And when you get to a point where you've got folks that are...Because when you keep in mind we're hiring 30 new people to start on the first Monday of every month, that by the time we've got a hundred people on board, the most ramped folks that we have on the team had been there for four months. Now this is an experience in scale that most businesses what won't necessarily have to deal with. But I think to some degree, many hiring managers have been in a position where next most tenured individual just doesn't have a ton of tenure. So you have to work with those folks, and help them become owners, and help them really understand that as an owner of the business these are the specific things that we look for, and here's how you embody those certain principles, and those are things you need to work on. But for me it would actually was holding on to that as one of the singular most important points in my job, as long as I could.

Naber:  Yup. Solid. I like it. I lied, I actually have two more questions in addition to that other one. The next one in on onboarding. So, this is something that most people overlook and turn it into a checkbox exercise. What was it that you guys did to make sure that everyone - you mentioned this twice around setting them up for success - what did you do to make sure they were set up for success in the onboarding phase and anything after that? Anything you would include in that phase to make sure they're set up for success at massive scale, as you were bringing a lot of people on board in the sales function.

Robby Allen:     Yeah, that's a good question. So a couple things. We, had an owner of the onboarding program from day one. So one of the things that we did was we hired somebody into a sales enablement capacity as one of the very first hires that we made. And they ran a two week bootcamp, where we put folks through everything from systems training, to market training, to competitor intel, to pitching, to live role play, and we actually would have folks get certificates. And this was something that we took really seriously because, two reasons...One, it allowed us to create a system of measurement where we can say, okay, if we are able to deliver x amount of training, what output can we measure with...months down the line, weeks down the line. And that gave us actually a feedback loop that tied back into our recruiting conversations were actually talking about ramp success of people that we had recruited three months prior, in recruiting meetings. And I think it's important that you've got that feedback loop of success on hires all the way back to recruiters that isn't just anecdotal, but it's actually looking at the data performance based on, based on how these folks got ramped. So one thing was just creating an owner early on with sales enablement was critical. Systematizing it and having a way to measure rep performance week over week and having benchmarks and then really sticking to those. Making it clear that if new hires didn't hit certain criteria along this journey in their first three months, there wasn't going to be a grace period. I mean, it really was you needed to perform at a certain level, even in the early days. And so that wasn't so much putting numbers on the board in the first month as it was showing competence, and learning, and demonstration of ability to be coached, and some of the things that we looked for. And so those were a couple of things. And to be frank, that onboarding program, we needed to tear it down and rebuild it every 90 days because what we were measuring and what we were coaching on needed to be updated based on how the business had evolved, because it was such a dense time period during hypergrowth. Then you really have to constantly be looking at it through the lens of, is the foundation correct, and do we need to rebuild it? And it turned out we needed to rebuild it every 90 days. And so it was a lot of work. But, it created a lot more relief for the managers of those people and for the people themselves once they were able to pick up their bag, so to speak, and know that they have the skills to succeed.

Naber:  Cool. One more side question on that. Is there three things that you can say every person that is onboarding new sales development, sales talent, people within the sales and marketing org, or just generally onboarding...Are there a few things, maybe three things, that you have to put into or get right within your onboarding program or project?

Robby Allen:     Yeah, that's a good question. So I think the first thing is it everybody needs a crystal clear understanding of what their role is, and what what the value is that they're adding to the business. And hopefully this is something you did in the recruiting process, and it sounds obvious, but helping people understand why, what it is that they're doing is so critical to the overall success of the company and the vision of the company, creates a lot of buy in early on. And for a lot of people it's one of the reasons why they consider and decide to take a job in the first place, is what's the impact that I can have? How is this going to help me grow personally, but also this business grow? And helping create that reminder is, I think, really important. And then helping people feel, helping people understand how they can fail and that failure is appropriate, I think is really important too. And I think you have to define what that failure means, but people need to feel safe, safe to fail. And by fail, I don't necessarily mean fail to show up to work,. What I mean is fail, fail in an effort to do the right thing, right? So maybe you decided to call the CEO of a company that you're prospecting into, and you get a connect, and maybe your pitch wasn't quite as sharp as you wanted it to be. But at the end of the day, you were doing the right thing, you were calling up in the organization. That's something that you want to celebrate and help people understand that that's actually something where you're doing the right thing here. Now let's talk about how we can perform better, in that specific scenario. And so creating that environment, I think is really important too. And I think the third thing is you have to create a rigorous system of measurement. So what a lot of sales leaders do is they'll pair up a new hire with the top rep on the team, tell him to sit in on demos and take notes, for as long as they need. And then after about four weeks, let's start funneling demos so that new AE, or if it's an SDR let's start or funneling leads to that SDR. And then it just becomes this sink or swim type of an environment. And you see this perpetuated I think get a lot of sales orgs, and it's understandable. I think that most of most sales leaders are great at what they do because they're looking at the bottom line results, not necessarily the top line inputs of pipeline or new talent. But if you're not really rigorous about these are the specific things that you need to do to be successful, you institute this feeling in a rep that there isn't necessarily a repeatable playbook for success, and it's actually their responsibility to create a path to success. And so what ends up happening is every rep does something different. And when every reps doing something different, you can't scale. And so you never cross that chasm, from product market fit, to repeatability, to hypergrowth. And so once you've actually got folks doing things repeatably, now you can really press the gas, and make things happen a lot faster because you've at least got the knowledge that everybody is executing and selling in a similar fashion. But you can't do that unless that folks are getting ramped up the same way.

Naber:  Nice. Awesome. Man, great advice, Robby. Thanks. That's great. And then last question on Zenefits, and we'll move on after that. The machine that you put together, from a sales development perspective, from the outside looking in, just unbelievable - for all the different moving parts you had to piece together, and the best practices that you guys deployed while you were doing that. So someone that's building a sales development function, as you know, and as many people listening are going to have to do - either one, they're a sales leader and they're building sales development function. And a lot of people think that translates well, but oftentimes it doesn't. And number two, a founder, or someone that's never done this, or never been in sales before, or someone's the head of marketing, oftentimes they'll have to build sales development engine to try kick off and catalyze their first phases of growth, and then high growth, and then hyper growth. So when you're talking to people that are building sales development engines, like you did at Zenefits, and then ultimately you did at Flexport as well, which we'll get into in a second - what are the fundamentals, actually let's pull it back, not the fundamentals; What is your mindset when you're building a sales development engine, Robby? Let's start there.

Robby Allen:     Yeah. Well I think, when we think about a sales development engine, your typically building this because you don't have a marketing engine pumping out leads, right? You aren't necessarily really building this engine as a first investment in the business, in a lot of cases. Typically you've already got some salespeople in the org, and closing some deals, and you want to scale that function up. But when you look at some of the other inputs into where the demand is being created, you don't necessarily have the level of confidence in what those inputs are to scale that. So you think about, okay, let's take this matter into around hands. And so I think you have to have a hypothesis about, okay, if we're going to make this investment, there's two things that we need to get right. And the first thing is the economics need to make sense, meaning we're going to need to know pretty specifically what kinds of deals and customers we're going after here, what what the win rates and conversion rates are going to be, so that we can understand if we hire one SDR how many AEs this is going to support, and ultimately how we can make the economics of the model work. So the first thing is just having a hypothesis about...and often for companies, if you're going outbound, that's going to be a slightly more upmarket targeted customer, a named account that you understand to be in your demographic of product market fit. That's pretty typical, but it can depend. And then I think the second thing is we're investing in building a talent funnel for for the business. And, this looks different at every company. If you're at a very technical enterprise sale, it can be really challenging to have a 20 year veteran AE and a one year out of college SDR, and how are you going to bridge that gap and promote that person. And in some cases you can't. So I think for the folks that are thinking about their own career paths, definitely look for the type of company where you can get promoted and elevate into full cycle roles and see growth there as well, where it's not such a big bridge to jump. But in any case, the business needs to think about what are we going to do from a talent perspective. And the best companies develop this talent pool, and and ended up recruiting directly out of their SDR organization. And, so for a much lower cost, and much faster ramp time,and typically much more successful rep, they're able to scale up the AE part of the business too. So I think about the economics of the role itself, and then the payoff being not just the output of the role, but the multi year promotion path that you're seeing for folks that you're hiring into that role.

Naber:  Awesome. Awesome. Awesome. I mean, that's again, gold. Okay, cool. So let's walk Flexport now. So you get to a place where, you're ready to make a move. Why Flexport and tell us about that jump in a minute or so, and then we can talk about your experience there, and let us know what you did.

Robby Allen:     Yeah. So my former boss and VP of sales at Zenefits, Sam Blond, who's now the Chief Sales Officer over at Brex, he was consulting at the time for Flexport, and was helping out specifically with their SDR team. And so he introduced me to Ryan, who's the CEO of Flexport, and I had the chance to meet Ryan and some of the other folks on the team. And, basically, Flexport is this interesting business where it's a SaaS business in a sense that they are building a software as a service product, but really it's a freight forwarding business. And I personally had not spent any time in the logistics or freight forwarding industry. So it was a new dynamic. I mean, I remember taking some supply chain classes that were required in college, and I was practically asleep the whole time. I didn't really understand contextually why it mattered, but Flexport really helped bring out that perspective, and maybe we can talk about that later. But, they basically, the business itself...Freight forwarding and logistics is an interesting supply demand business. where there isn't necessarily a lot of inbound demand regardless of where you are in the market. Essentially importers, people who make physical products overseas need to basically employ third party freight forwarders like Flexport to help them move those goods wherever they need to go in the supply chain. But they're not necessarily signing up for demos on websites the way that you would with Marketo, or Salesforce, or something like that. So they needed to have an outbound strategy for new logos. And at the time it was a little bit Willy Nilly. There were a handful of Sdrs in San Francisco. They were doing a good job, but it wasn't really set up to scale. And so I got introduced and it was a cool opportunity to be for me, one because it was a completely different industry and a new mental challenge that I was just interested in. But when I looked at the business, I saw a couple of things. One, it was growing really quickly, in spite of having basically no predictable demand generation model. So that told me that despite the fact that there's a gap here, the business is growing exponentially. And that was really exciting to me. And two, there was a unique opportunity, for me to learn, where I was going to get a chance to scale out a global team. So we needed to hire SDRs in New York City, and LA, and Amsterdam, and Hong Kong, and San Francisco, and a few other markets. And so that was, that was a unique opportunity where I had only really operated in the US before. So I came on board, shortly after leaving Arizona and coming back to SF and took a role there as the Head of Global SDR.

Naber:  Very cool. So I have three things I want to talk about within your Flexport experience. Firstly, everyone has this moment, if they're going to look after global teams and businesses that have either global scale, global ambition, everyone has this moment where they move to a geographical diversification of focus and resources, away from just a single market or a single region within a market.This Is the first time, at least at scale, that you had had to do that, across different countries where you're diversifying both talent focus, resources that you're spending as well as using, and just your time management and decision making focus across multiple markets. What are some of the things that you learned, that someone needs to think about as they're diversifying across multiple markets, when you were doing this at Flexport?

Robby Allen:     Yeah. So it's a great question, and there's a couple things that I learned, kind of after the fact, that I think I almost wished I'd known at the time. But the big question, and that we wrestled with Zenefits, or sorry, at Flexport, in regards to building this SDR team, was to centralize it or to decentralize it. And so at the time when I joined, we were centralized, meaning we were booking and setting demos where all of our global offices in one office in San Francisco. So we were calling out into all these different geos. And the thinking was that because it was centralized, we would be...there was a central knowledge hub. We could help ramp reps faster. We could institute best practices. We could roll out change faster. We can just generally move faster. And to remind, at Zenefits, we were a centralized model, right where we had this giant office in Scottsdale, AZ. But what we figured out was that these global markets were really different. Outbound in Amsterdam will look very, very little like does in San Francisco, or New York City. It's just, it's a completely different game. And, similar to Hong Kong, which is worlds away, in terms of being able to prospect into accounts. And so we ended up deciding to decentralize it, which was the right decision because most of the subject matter expertise for that local market lived in that local market. And so you had a GM and you had some senior salespeople in that local market who could partner up with an SDR to help target the right types of accounts. And so I think for me that was actually a big exercise and just letting go. And not being the one to control all the campaigns that we were running and all of the different messaging we were using. And the advice that I got from a senior executive at Flexport at the time was encouraging me to think about the function as a service to the global GM's that we were working with, as a service provider. And it a sales person, you're not, you don't typically think of yourself as a service provider. But basically what they were telling me was that to really focus on listening to what the unique problems where in each of these markets and provide expertise and consultation on how to solve them, but ultimately give that local GM the credence and responsibility to make that decision. And honestly, it was hard for me. I came from a place where I was successful because I was the one who is controlling and making decisions for this big organization at Zenefits. And so Flexport was a challenge for me just in the sense that, success meant letting go and I'm bringing subject matter expertise to the table and making recommendations and offering it more as a consultant, but ultimately leaving those decisions to the local GM's. And so, to come back to your question about how I'd recommend folks who have global geos that they're selling into. I think you have to treat each one its own unique problem set and hopefully get an expert in there to be the owner of that problem set sooner rather than later, and then just provide support.

Naber:  Yeah, I see that a lot right now. Whether it is hyper growth businesses trying to scale from afar. So using SF or, or wherever their headquarters is, as a hub, and hiring a couple of people in a new office. Or whether they have a bunch of people in that new office or that new market and they're now moving to this model of having a GM where you have a local owner so that all of those issues, problems, and solutions can roll up through one person that understands the market versus multiple points of contact that need to then have multiple points of contact back at the hub where you've got different stakeholders that may or may not play ball, as well as others. And understanding that markets are different or situations are different. So I hear a lot of people talking about moving to that GM model as they, one, open up an office or, two, they move to it after they feel they've made enough mistakes with a non-GM model. I've heard a lot of tech businesses talk about that lately. How can you burn a lot of cash and a lot of resources as quickly as you make mistakes when you're in high growth or hypergrowth. So, I've heard a lot of people try to move away from that. The second thing I want to talk about with Flexport is Compensation Plans. So one of the things that - you and I have talked about this in the past a little bit - but one of the things that you did at Zenefits was you had to think about the construction, from a micro and mid macro perspective of putting together how people got paid, what the measurement was, and you guys have iterations and iterations of that over time. Especially as you scale, and as you either make mistakes or some things go well, and you doubled down, etc. So when you were at Flexport as well as at Zenefits - and you can talk about Mixmax too if you want, but don't move on to that too quickly - but from a comp plans perspective, what did you learn about putting together comp plans, and what are the landmines that people should try to avoid as they're putting together comp plans for sales and sales development reps?

Robby Allen:     Hmm. Yeah. so the first thing I did at Flexport was I moved it from a quarterly payout to a monthly payout. And the reason that I lobbied for this, and frankly spent a little bit of personal capital on it, was that inside sales rep need quick feedback loops. And the quickest feedback loop is the direct deposit into your bank account based on the prior month performance. And because it was taking 120 days to get that feedback loop, reps weren't necessarily feeling the way that they were performing in the way that you really want folks to feel, based on these incentives. And so we moved it to a monthly program and overnight, you would see, the folks that were performing the highest behaving a certain way, and folks that weren't behaving a different way. And that's not to say that folks were coming in and being gaudy about whatever their OTE's were. But it's more just to say that you noticed a difference in terms of what the first of the month and the last day of the month, and everything in between, looked when there are monthly feedback loops. So I'm a big fan of feedback loops early and often. And when you can program one of the most important feedback loops in sales, which is incentives and cash comp plans, you want to have that happen pretty frequently. and I think especially for SDR roles, if anybody listening to this is doing a quarterly payout, or in hopefully not anything longer than that, I would consider what the operational burden would be to maybe move that to a monthly payout. And if it's not too high, I would do it. And the reason why, just because reps benefit from that feedback, especially in a hyper growth environment. So that's the first thing that we did. And the next thing that we did was we move the goals up. And that's always a hard thing to do, but the team was performing well and so we moved the goals up, and the OTE stays the same. And I think that that's always a challenging thing for a young manager to do in their career, is help people get onboard doing more work for the same pay, so to speak. But we are fortunate to have some really talented people on the team that just owned it, and went out and crushed their numbers and set the bar really high. So yeah, I mean there's a lot of specific things that I can talk about with regards to comp plans, but I'm always the belief of system of rapid feedback loops, uncapped upside, as long as it's not going to put the business at risk in any way. Those are the two things that I always try to make sure are built into comp plans.

Naber:  Awesome, man. That's great. Great answer. And then, last thing, and this is more general because I know that you and I've had enough conversations where I believe that one of your superpowers is your, strategisation - that's a word... - for how you navigate your career and subsequent accurate execution...What I've always been impressed by is your ability to identify and understand very, very quickly - digest, ingest, and execute based on what you've learned, from a career development and a career navigation perspective - it's, it's fascinating to have conversations with you, especially over time. So when you're thinking about career development, career navigation, n your mind, tell us about your mindset for how people should be thinking about the next opportunities that they take - because you've had hundreds and hundreds of these types of discussions - and what actually matters.

Robby Allen:     Yeah, that's a good question. So the framework that I've used that has worked well for me, is I think there's really two things that actually matter when you think about and you evaluate an opportunity in your career. And this is what I tell people who are interviewing, or how I use this framework myself. And I think the first thing is the name on the front of the Jersey. And so at the end of the day, in the beginning of your career, it's easy to get caught up in minute details about specific roles that you're in, titles, and small variances in compensation and things that at the time feel really important. And certainly to some degree are important - titles matter, comp matters. But five to 10 years after you move on from that role and you're doing something different in your career, what people are going to look back on is what was the story of that company at what part of that journey did you participate in, and what was your role in the journey? And so I think when you think about the opportunities that you're evaluating, the name on the front of the jersey is going to matter a lot more, when it's all said and done. And people associating your name with the type of companies that really matter and that are lasting go through journeys, are the ones that are going to grow your career actually quite a bit more than titles and compensation, early on. And the next thing is the people you work with. And this is a tough thing to evaluate, but when you're going through the interview process, it's really important to do a thorough evaluation of the folks that you're going to work with. Your boss, your boss's boss, your peers. If you're coming into a leadership role, the folks that are going to be reporting directly to you, and anybody around your peripheral. And the reason being is you're going to spend more time with these people than you are your family. You're going to be in there grinding it out, working with these folks hip to hip, going on a journey. And what you figure out after you go on a journey, and then start a new journey, and look back is that all of these people that you work with go on to do more journeys. And the network that you build internally, the people that you work with, can create so many opportunities for you in the future, or not depending on the quality of talent of people you work with. So I just recommend that people are thoughtful about choosing the type of people they want to sign up to work with. and it can be hard in an interview process to really get a thorough understanding, but you've got internet resources at your disposal - use linkedin. Understand are the people that you're working with active online and the type of people that are investing in their own careers, because that's gonna pay off later. And I can't tell you how many deals in my career that have gone a lot smoother because I have an internal contact with somebody that I used to work with at Zenefits or at Flexport, when we're able to open the door and get directly to the decision maker and get to a decision a lot quicker. And that's one example of hundreds. But, the people that you work with and the name on the front of the Jersey are, are really the two things I think at the end of the day that actually matter.

Naber:  I love it. I love it. And, you mentioning that your network is your net worth is something that I think people remember and take away. That's awesome. So, let's hop into Mixmax. So you're at Flexport, you're making the move to Mixmax. Let's talk about that for a minute.

Robby Allen:     Yeah, sure. So, my journey at Flexport was going really well, and I ended up actually getting an introduction to an early stage founder, at Mixmax. And Mixmax is actually a tool that we were using at the time, and something I was really passionate about because it was a sales productivity tool that some of the teams were using internally at Flexport, that I thought showed a lot of promise and it's really interesting. And they were looking for a Head of Sales. And so we had a dialogue going, and the opportunity presented itself for me to jump in and own the full sales process end to end, and get to build a team out from scratch. And this was a business that had gone from about zero to 5 million in revenue, all on self serve. And so they're looking to take this jump into more of a B2B sales type of a model. And I jumped at the opportunity. It was the right timing and the right place for me to go earlier than I'd ever been before, and wrap my hands around the full share of the B2B sales model at the business. And so I came on board and recruited out a team of 10 reps, so five SDRs and five AE's. And we built out an SMB, and Mid-market, Enterprise Sales team, and went to market with it. And it was an amazing journey. And we went from about zero to a million in revenue on the B2B side in about six, seven months. And it's, it's funny because I looked at the time at Zenefits, and we did,six times that or something that, in that same time period. But this was harder, and almost meant more. Just because the market that we were competing in was very competitive and going from a self serve model to a B2B model was more challenging than I could have imagined.

Naber:  Okay. So, I wanna I wanna I wanna stay here for two specific topics. One of them is exactly what you just said. Going from a self serve business to a B2B or more towards an enterprise sales business - choosing enterprise loosely for the way that I say that, for defining it. But let's talk about that. Talk about the learnings you had going from that self serve business to a non self serve business as you were building at Mixmax. The learnings as in, what did you guys do well, and combining that with what do you wish you would have known at the time that you could have done differently. You don't need to define them in those terms, but comprehensively, what did you learn or what are your learnings from it?

Robby Allen:     Yeah, so I think the first thing is that when you have to understand that, despite the fact that we were pretty well established, early stage SaaS business, humming it away at about 5 million in revenue, you have to look at this switch to a B2B notion as a completely new exercise in product marketing fit. And the reason being is that the notion of convincing an entire org, or at least an entire team, to buy an an annual license of your product versus signing up for a much lower risk, per se, at a slightly higher cost and doing a monthly, it's just a completely different notion. And so I think one of the things that we didn't do well early on was that we tried a bunch of different plays. And what I mean by that is that we, the product had brought applicability from recruiting, to account management, to customer success, and sales, and SDR, and we didn't necessarily nail our niche until about a couple months in, when we started to figure out that AE teams were the right team. Oftentimes they were using products that were more designed for SDR's, just by nature of inheritance and not having other options, and that these were the folks that were typically signing up on their own, and these are the ones we want to go after. And so I use this analogy sometimes when I think about scaling playbooks across different phases of growth. But, if you look at it basketball, and I use a lot of basketball analogies, so you have to bear with me. But in the product market fit phase, all you're really looking for is a mismatch that you can exploit. And so if you've got one, let's say, player on the court that's taller, faster, stronger, can jump higher or has one move that you can repeatedly go to to get a bucket when you need it, that's where product market fit is. It's not a whole range of plays. It's one play. And so we figured out what that one play is, and we went there, and we started to scale it. And, in the back of your mind, you're telling yourself, okay, I know that we're gonna have to broaden this playbook a bit more, but part of this product market fit is repeatedly running that same play again, and again, and again.

Naber:  Hey, Robby - can you give an example from a sales perspective?

Robby Allen:     Yeah, sure. So, I think in the context of Mixmax, the way that our business works was we would land in accounts through self serve model, we would identify the ones where we had traction, we would go outbound, so to speak, where we would reach out to the folks using the product and convert those into larger paying accounts. Very similar, I'm sure, to what you guys did with Sales Navigator at Linkedin, right? And, and so basically what we look for there is okay, we're running a range of different plays. We're running plays against recruiting teams where we're seeing similar things, account management teams we're seeing similar things, we're seeing the win rates with a AE teams just a little bit higher. And we started to figure out why and it's because of a couple things. One, the buyer who in this case is the VP of Sales, or the leader of the Sales org, typically has a budget and decision making power, and there isn't necessarily any approval process beyond them. ,And so if we can make a business case and the AE's can go to their boss and say, we need this tool to be successful, it's typically a fast sales cycle and the win rates are better. And so we just looked at the data there and we understood, okay, this is a play that we can consistently run. And so we made a conscious effort to focus our efforts on that play. And we dug through our leads, and we focused on that play. And we honed our account lists, and we focused on our play, and we win with that play. And, you comb the lowest hanging fruit, and you have to go a level up. And once you've done that a few times, it's time to start thinking about, okay, how can we make this repeatable, where you can run an actual play, that can give you a predictable win percentage. And that's when you start to go to scale and repeatability.

Naber:  Yup. Cool. Walk us through, while we're on it, walk us through scale and repeatability. What are a few of the things that you're doing as a sales leader, or a sales and marketing leader, when you're trying to execute on and build scale and repeatability?

Robby Allen:     Yeah, and I think this is, this is a part of the business, just candidly that I think, Mixmax and a lot of other companies, they're making that transition right now, to scale and repeatability. It's a different, it's a different timeline for every business. At Zenefits, it was a short six month window, with Flexport it was longer, with Mixmax is something in the middle. But basically scale and repeatability is about running an actual play. So rather than you're thinking about the mismatch where we just throw the ball to the tallest guy, he just turns around and dunks it in for two points. You're actually running a play where you're involving multiple different people with the play. And so what you can do here is you can control the outcomes a little bit better. So let's say we want to run a pin down for a shooter to come out and shoot a three pointer and now we're looking at three points instead of two. Similarly, with scale and repeatability, now what we can do is actually involve, multiple people within an organization, sell across multiple departments, and create bigger deal sizes, and in some cases, faster sales cycles. So whatever it is that you're specifically after, if you're a more transactional business, that might be just reducing friction and creating faster sales cycles.-For more of a mid market or enterprise sale that might be about creating bigger deal values. But, with scale and repeatability you're at a place now where your sales cycle looks a lot more a full blown play that you can run with it predictable win percentage. So you know that if you run this play with the right type of account, 20, 25, 30% of the time you're going to win. And what that percentage looks like, is going to be a certain deal value. And what that allows you to do is build a business model around that and scale it. And there's a lot of work that goes into that, but arriving from just exploiting a mismatch, actually running a play with a predictable win percentage, that's a big jump. And there's a lot of steps it takes to get there. But really the biggest difference is that predictability in what that win percentage is going to be when you run that play.

Naber:  Yep. Nice. Awesome. And then hypergrowth, let's walk through that. Product market fit, scale and repeatability, you're moving onto hypergrowth. What am I focused on there?

Robby Allen:     Yeah. Yeah. and so the third phase in the journey, is if you come back to this basketball analogy, now we've actually got a play that we could run with a predictable win percentage, right? This pin down screen for a three point shot. In a hyper growth environment, typically now we are selling into multiple different market segments, and maybe it's mid-market, and enterprise, and SMB or maybe two of those. And typically we're selling across multiple verticals and multiple geos, right? So we're scaling this outfit. We've probably opened up offices outside of, if we're based in the Bay Area, outside of the Bay Area, or in maybe a slightly lower cost market. And now we actually have a playbook, and it's a range of situational plays that we can deploy with a predictable win percentage, depending on what that situation entails. And so to make this jump from running this pin down three point screen, which is our scale and repeatability play, we have to hire other highly competent sales leaders to help deploy this playbook, both from experience they have in the past, but also what we're seeing in the market. So by the time you get to hypergrowth, you need a team of people that can actually draw up these repeatable plays, and coach and train your organization to run these plays. It can't all come from one person, it just can't. One person can draw this play that can get you a predictable win percentage, and scale and repeatability, but the best leaders are going to deploy a team of lieutenants that are going to help them build out a full blown playbook, and train their org out. And so when you're at hyper growth, now you've got a range of plays that you can deploy based on the situation that are still going to give you that predictable win percentage. And it's basically just another stage of growth and scale that allows you to nail whatever the inputs are and have a reasonably predictable outcome.

Naber:  Cool. Excellent. Excellent. awesome. So then we move on, I've got a couple more questions, just probably two more, then we can round this out. Then you're moving on from Mixmax. Tell us, tell us after that both, what you've been doing, what you're up to now. Then, maybe I'll ask a couple questions to round it out.

Robby Allen:     Yeah, for sure. So, after leaving...I ended up deciding to leave Mixmax having gone through the journey and done what needed to be done there, in terms of this initial product market fit phase. I handed the reigns off to another sales leader who's now doing a really good job helping them bridge that gap to repeatability journey, and they're doing a really good job at that and I'm super excited to see where it shakes out. And actually since then, I've built my own consulting practice. Not necessarily because I intended, but because I've had enough people that I know, and respect, and I've worked with that have asked me for support and help, where I'm actually now basically consulting on a fulltime basis. And so I have a couple different clients that I work with, and basically what I do is I help folks skip a lot of the potholes that you can step in in the early days and get to scale, and repeatability, and set yourself up for hyper growth faster. And that ranges from a recruiting and building out sales and SDR teams, to strategy, to just improving operations, to sales ops and enablement, and the whole spectrum of whatever business needs because I've been fortunate to have experience in a lot of those things. And I typically just work with clients where I'm super interested in their business, and it's just a really good fit. I've been fortunate to be able to work that way, and that's what I'm doing today.

Naber:  Awesome man. That's great, and you're excellent at it. I've had enough conversations to know that it is, one of the things you were born to do. So, that's a good pause point. I have one more question and then we'll hop into some rapid fire. Actually, probably two more. When you're thinking about coaching teams, both coaching large teams as well as coaching individuals, are there any fundamental, or very simple frameworks that you can offer, where you think, this is my coaching framework or this is how I think about coaching? And some of the steps that I go through to execute that?

Robby Allen:     Yeah. Well I think fundamentally you need to look at coaching as different than management. Management is a little bit more of an operational exercise, where coaching is a lot more about empathy, and it's a lot more about - I use this word lightly, and I'm reading a book right now, so I have to give credit where credit's due, called Trillion Dollar Coach. It's a book by Eric Schmidt and some of the other Google executives, about Bill Campbell as a former college coach, it's a great book. And it talks a lot about creating an environment where people feel love, and feel they're loved, and feel they're in a safe place to perform and to fail. But also feel challenged in a way that they've never been challenged before. And so I think that when it comes to coaching, you're tapping a little bit more into empathy and people's will, more than you are necessarily in the x's and o's and the numbers side. It's a little bit more about what I like to call it, the why. What's your why, right? And that's something that I always tried to recruit for, and coach people on. And if you can tap into what that one thing is, that is a well of energy and power that can get people to perform at a level they never have before. And so when I think about coaching, I think about it as almost the opposite of management, in a way. and I think that the best leaders balance those two things, and it's hard to do.

Naber:  Yeah, absolutely. Absolutely. My last question, is around, a lot of different experiences - for folks that don't know in this audience, and they'll be able to see what your background is, on your profile, and I'll have gone through it already in the intro as well, but between Zenefits - $4.5 billion valuation, $584 million raised; Flexport $3.2 billion valuation, $1.3 billion raised; Mixmax $13d million raised. And now you're working with your clients, and the businesses that you work with, as well as individuals out of the companies that you're coaching, have just a massive range of different growth and hyper growth situations. You've just been at all the different spectrums on that hyper growth and growth spectrum of what can happen at a business at this phase, this phase, this phase, this phase. And you've got so much experience. So as you're thinking about the types of businesses, that you in particular, at early to mid-size businesses you're working with, what's the sweet spot of businesses that you like to work with? Or maybe even what are some of the attributes of the founders or the types of people you're working with at these businesses that you enjoy working with the most? So the reason I ask this question is two things. One, if someone's going to hire a full time person to do what you do, or if someone's going to try to hire a consultant to do what you're doing, they're going to need to know how to be operating in order to be the most attractive. So what is most attractive to you as you're going into a client, both from a business perspective as well as the people within those businesses that, in the types of companies you like to work for?

Robby Allen:     Yeah, it's a good question. What makes the sexiest client or the sexiest career opportunity? Yeah, I mean for me personally, I think that the most exciting part of the journey - and I've been, like you said, really fortunate to work for a range of different stages of the journey and get to play a role in shaping the growth of those different stages. so I feel I have at least enough context answer the question in earnest. And for me, it's sort of that moment right after product market fit, where, what ends up happening typically right after product market fit is you nail it, you start to understand, okay, this is the this is the packaging, the pricing, the overall presentation of the product, and the specific type of customer that we want to deploy it to. You start to get that out to the market and then all of a sudden you've got more demand than you know what to do with, right? A salesperson's dream, all the inbounds that you can drown in. And I think, folks will listen to this call, and probably roll their eyes and they go, "that's a brief moment of time.' But, really after you've started to get feedback from the market that you're really solving an important need for the customer. And the challenge then becomes, how do we actually scale a business around how we can support the broader market and go out and capture that demand. That's the part that I find most exciting. Because typically those businesses really don't understand how to do the messaging or pitch. Don't understand how to measure, and perform against KPIs, and understand - are we actually doing a good job at this? And I've had to build and rebuild that now for a range of different businesses that have grown very, very quickly. And I think that's the part of the journey that I enjoy most because so much can go wrong. So many businesses die during that stage. Many businesses don't reach product market fit, but even after they do, many still die. And I think that's the area where I personally love to work on. And when you think about highly effective startup salespeople, this type of person is a little bit different, a little bit crazy, a little bit very tolerant of risk. And there aren't a lot of really great startup sales people out there, just because I think a lot of people graduate from the amount of risk that you end up taking on as an early stage startup sales person. But those people who do love it, and I consider myself one of them, look for that moment where product market fit starts to click. And I think that, for businesses out there that are looking to bring in leaders, and are looking to bring in whether it's in a full time or part time capacity, I think, one way to package that is really by talking about in a very open and transparent way, what demand looks like, what customers are saying about your product, and what you think the business should look in two to three years. And then just being very transparent about what you know, and what you don't know, and where you need help. And I think that just going to be a really easy way for people to tell you, okay, here's specifically what I can help you with when you think about what that challenge is. So I don't know if that answers question, but that's how I think about it.

Robby Allen:     It does. It's great. It's great. And tons of valuable thought process in there as well. All right. Let's round it out with two rapid fire questions. You've been really generous your time, thanks so much. I really appreciate it man. First one, is a personal and professional question. I ask this to people on their birthdays every single year, but I'm going to ask you, even though it's not your birthday. What is the most valuable lesson you've learned professionally in the last 12 months?

Robby Allen:     Ooh, the most valuable lesson that I've learned professionally in the last 12 months on? I don't, I don't know that I have a great answer, but I can think of a couple of things that I have learned. I think that at the end of the day, working in consulting has been an interesting practice for me just because you're hired as a subject matter expert and expected to know the answers to things pretty quickly. But I think that something that you can get caught up in, whether it's in a full-time role or in a consulting role, is answering questions to look what you're talking about versus just admitting when you don't know. And I think, I've been saying, I don't know more than I ever have in my entire life. And I think one of the things that you start to learn as you get older, and learn, is that the more you learn, the less you know in a way, or the more you start to understand how little you know. So I think for me, in a professional context, I think it's helping be really honest about what the knowns and unknowns are for any specific situation. And then just operating based on as much logic as you can from that point. Versus coming in with assumptions or try trying to signal that you know more than you do. Just getting to a point where you're confident in yourself and you understand the things that you know and don't know, and own it. And then work on, in the background, learning things and shoring up your knowledge set. So I know that that's not super specific, but I think most people can probably really relate that there's a moment where you feel scared to admit that you don't know something, you end up admitting it, and then everything is better as a result of it. I think in general, it's better to operate, which is the full transparency of what you know and don't know.

Naber:  Yup, absolutely. Good one. Part B of that question, what's the most valuable lesson you've learned in the last 12 months, personally?

Robby Allen:     The most valuable lesson that I've, man, these are good questions. I wish you'd told me ahead of time time, so I could have prepared a sharp answer.

Naber:  Well, you're welcome. I can send Nicole a quick email, and she could send me an answer back for you if you want to.

Robby Allen:     Haha, okay. Interesting, yeah, I think that the most of the valuable lesson that I, and honestly this comes back to me personally for what I talked about earlier about your network being your net worth. I've been fortunate enough to work for a lot of really, really great people and who have hired great people, and put me in a position to then go hire great people. And I'm just getting to an age now where I'm seeing the benefit of that, where when I start to think about taking on a new client or looking at a new opportunity, I almost always start with my own network versus going exploring the market more broadly. And I think that that's just one of these compounding effects of work that I've put in earlier and getting the chance to work with really amazing people at a number of different companies, that we've talked about in depth. And I think that, just to reiterate a point I made earlier, you can't really invest enough in picking the people that you work with, in a smart way. And that's not necessarily just the people that you spend time in the office with. Those are also the people that you spend time with out of the office. I mean, for you and I, Brandon, we've been doing Skype calls and having conversations, and just getting to know each other over the last three, four years. And I consider you a very close friend as a result of that. But I've learned so much, and you haven't worked for any of the companies that I've worked for. And so you can go out and you can find, you can find these people outside of there too. So I just encourage people to throw yourself out there, and be vulnerable. But really, the compounding effect of the network you build happens later in life. And I'm like, just starting to see it right now. And it's, it's amazing.

Naber:  The fruits of the labor feel good. One quick plug on that, that I would add is, keeping the discipline both from a frequency and an accountability to actually make it happen, with those people that you've networked with, to make sure you catch up with frequently enough. And make sure that your mind yourself of why you loved talking in the first place, why you loved working together in the first place, why you love learning from each other. So the frequency, sorry the discipline of frequency and accountability of making it happen, are really important to have pull through in that set of advice. Good one, Robby. And then, the last question is a fun one. What can we learn from the NBA playoff results this year - the outcome, Kawhi Leonard, KD & Clay injuries. What can we learn from the playoff results that translates to finding and retaining great talent?

Robby Allen:     Whoo. Yeah, so I/we could do a whole separate podcast about this because this is one of my favourite topics...

Naber:  We should. This is my pitch to you. I just asked you one question, and not we just started a new podcast, this is amazing.

Robby Allen:     The Naberhood has got a lot of range, for sure. So my takeaway from the playoffs is that the role of the general manager in the NBA is quickly becoming one of the most important roles in the entire organization up there with who are the one or two best players you have on your team. And I think that that was demonstrated by Masai Ujiri, who's the GM and President of Basketball Ops in Toronto. During the mid-season he coordinated a trade, for Kawhi Leonard and Danny Green, for DeMar DeRozan who was a longtime favorite of that team. Over the last five years, he's drafted a whole host of really good players late in the rounds, because they're a good team, and they're not in the lottery. So in the late twenties, they're picking guys like Pascal Siakam and a bunch of guys that were big, big contributors in the playoffs. And just this last off season after they won the championship, The Washington Wizards offered him some insane contract, I think, something 10 million a year for a GM position.

Naber:  Plus equity, plus a ton of equity.

Robby Allen:     Yeah, plus equity. And I think what we're starting to figure out is that, the NBA is becoming more transactional, in terms of the life cycle of player's time on teams. Players are taking more control over their own careers. And the GM's that are thinking about this from like a Moneyball perspective, but also able to build relationship with guys, and guys want to play for them and with them because they have their best interests at hearts, are they guys that are winning. And so Bob Myers, of the Warriors, has been that guy for the last five years. But we're starting to see a whole new generation of these GM's coming into the fold. And so I think we're going to start to see is that this GM position in the NBA, is one of the most sought after and highly recruited roles, maybe even more than a head coach. And I think Masai is a perfect example of that.

Naber:  Hey everybody, thanks so much for listening. If you appreciate it and enjoyed the episode, go ahead and make a comment on the post for the episode on LinkedIn. If you love the Naberhood Podcast, would love for you to subscribe, rate, and give us a five star review on iTunes. Until next time, go get it.