Jenn Knight - Co-Founder & CTO @AgentSync (Formerly @Dropbox, @LinkedIn) - The Playbook for Building Business Systems, Tools, and Technology Teams, The Business Technology Team Superpowers @Stripe, @Dropbox, and @LinkedIn, End-to-End Process Thin

Guest:

Jenn Knight - Co-Founder & CTO @AgentSync

(Formerly @Stripe, @Dropbox, @LinkedIn, @Bluewolf)

Guest Background:

Jenn has worked with hypergrowth businesses like LinkedIn, Dropbox, and Stripe. At LinkedIn (IPO 2011, Acquired by Microsoft for $27B in  2016) Jenn was the Manager of Solutions Architecture. After 3 years at LinkedIn, Jenn joined Dropbox (IPO in March 2018, $10.5B Valuation). She was there for 3.5 years where she was the Head of Business Technology, managing technical teams spanning financial systems, sales systems, web services (CMS), integrations, and business intelligence infrastructure. Over an 18 month period, she scaled her teams from 15 to 35 people. Jenn has since joined Stripe ($20 Valuation, $785M Raised) for the last 2 years as the Head of Internal Systems.

Guest Links:

LinkedIn

Episode Summary:

In this episode, we cover:

- The Playbook for Building Business Systems, Tools, and Technology Teams - Mindset, Structure, Chronology, Methods, and Best Practices

- The Internal Business Technology Team Superpowers @Stripe, @Dropbox, and @LinkedIn

- How to be an End-to-End Process Thinker

- Stakeholder Management Tips & Advice

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 Jenn Knight on the show today. Jenn has worked hypergrowth businesses like LinkedIn, Dropbox, and Stripe. At LinkedIn (who IPO'd in 2011 and was acquired by Microsoft in 2016), Jenn was the Manager of Solutions Architecture. After three years at LinkedIn, Jenn joined Dropbox (who IPO'd in March, 2018 and they have a valuation of $10.5 billion). She was there for three and a half years where she was the Head of Business Technology managing Technical Teams spanning Financial Systems, Sales Systems, Web Services, Integrations and Business Intelligent Infrastructure. Over an 18 month period, she scaled her teams from 15 to 35 people. Since Jenn has joined Stripe (who has a $20 billion valuation on $785 million capital raised). For the last two and a half years, Jenn's been at Stripe as the Head of Internal Systems. Here we go.

Naber:  Jenn Knight. Awesome to have you on the show. How are you?

Jennifer Knight: I'm doing well. Thank you for having me.

Naber:  Awesome. Thank you for coming. It's amazing to have you. I'm excited for so many reasons. we know each other well and we've worked together in the past. But your brain, and getting to share that with people in the audience is really exciting for me. it's hard for me to contain some of the excitement with my emotions. But, I'm excited to go through some personal stuff today. So go through and dive into who Jenn is as a person. Start from where you grew up, and some stuff from your childhood. So people can get to know you a little better, like I do. And then, we'll hop into some professional stuff. Why don't we just get started. So, you grew up in San Francisco, you're smarty pants. Anyone that has met you for more than a minute knows that, but it's written in you DNA as well as your GPA, as well as your accolades. Walk us through, a few different things about what Jenn was like as a kiddo, and what it was like growing up with as Jenn Knight.

Jennifer Knight: Well, I grew up north of San Francisco, in Sonoma County, in Petaluma, which was a ton of fun. It has changed a lot now, but in the early nineties, it was very rural still. Get on your bike, ride into a field, find some mice, hang out. I was a pretty nerdy little kid. I grew up in a house that didn't have a TV. My Dad is an engineer, so we were always puttering on things. He had a garage full of tools, and we're always being taught new things. I was always encouraged to be outside or around. Got a computer pretty early, which was neat. My brother and I, very nerdy, would love to do things like see how many files we could delete to destroy the operating system, and then rebuild the thing. Built a few computers growing up, but really enjoyed that part of life. Yeah, I was a kid who had a little bit of a different experience growing up just because of the nature of my house. And spent lot of time outside, and a lot of time building and poking on computers, and just hanging out.

Naber:  Cool. Were you a particularly social kid?

Jennifer Knight: That's a funny question. I always had good friends, a few good friends. I think I'm still that way. I'm someone who finds people that resonate with me and I keep a few close. I really enjoy the company of others, but I've always been someone who has had two or three really close friends, than whole big group. And growing up I had to change schools in middle school. And so at 12 years old I had to move across to a school across town. And that taught me one that you can make new friends but was pretty scary I think at the time. So you get close to people in elementary school and then didn't get a chance to stay friends with those people. I had to make new friends at 12, which was great in the sense of it taught me that you can, and you can survive. But it definitely meant that I had a few folks that I kept close.

Naber:  Cool. I like it. A small, very close circle. And you said you were always building things, or tinkering, and having some nerdy fun. Tell us about a little bit of the nerdy, fun hobbies that had.

Jennifer Knight: I think, I actually laugh when I look back on this...A very good example of this is my fourth grade science project was about different forms of energy, and it was about potential versus kinetic energy and the conversion. So my Dad had me worked with me to solder a little, wind mill thing that was powered by candles. That might give you a good picture of what my house is like. And then we did things like gardening. That was always fun in the summer. Petaluma was a great place to grow a garden in the backyard, so my parents did that. Just those kinds of projects. Those are the ones I remember the most, I think partially because you get pictures of them, and they're the stories that get told. But there were always a million little things we were playing around with.

Naber:  Yeah. Cool. Love it. That's great. And let's see, quick stop on high school. What was high school like for you?

Jennifer Knight: High School was a lot of fun. I wanted to get out of Petaluma. I knew that that wasn't where I wanted to be, and I knew I wanted to go somewhere for college. In my family education was really important. So, all growing up it was, you're going to go to school, you're going to do well. You're gonna learn a lot. You're capable of learning a lot. You're very smart. Put your head down and learn. Go get opportunity. So that was just the ethos of my growing up. One thing I will say is my parents were not obsessed with grades, they didn't push me to be perfect. I weirdly pushed myself, and at some point they were like, you need to calm down a bit. But high school was a lot of fun. I had a really close, like once again, handful of very close friends. We all encouraged each other to go after where we wanted to go next. Really great study groups. It was also for me a hard time. My Mom was sick when I was growing up, and she got really sick again when I was about 16. So that was hard at home. My parents dealt with it really well, but I had the mix of trying to be the kid who was studying and then dealing with some things at home. So I think once again, close knit group of friends is really important for me because they were people that I could lean on and really knew what was happening in my life at. And the rest of it, was just getting through it.

Naber:  Interesting. Some things a lot of kids that age don't necessarily have to deal with obviously. So you wanted to get out of Petaluma, but you were trying to be perfect so you could have all the opportunities in the world to do that and chase your dreams. Your dreams brought you to Beantown Boston. So tell us about going to BU. Tell us about why, and what were like at BU.

Jennifer Knight: Yeah, so, my parents had saved a bit for us to go to school, but couldn't go anywhere. So one of the reasons that studying was really important for me, was ultimately getting scholarships, and getting the opportunity to go to school. And I actually went to Boston site unseen. I'd never been there. I didn't know anything about the school. Yeah, it was funny. So they reached out to me, and they offered me a really amazing scholarship, and it actually brought the price of the college down to closer to what a UC would be for me. And so I was making a decision whether to stay in California, or go somewhere else, and my parents were very open to encouraging me to try something new. My Dad said...he always jokes that I was running away from them. He said to me, "Leave California now. If you don't like it, wherever you go, you can always come back. But if you don't leave now, you may never actually leave the state, and and you may not see what the rest of the world's like." So, I accepted to BU, and I had a choice for my parents to come with me for orientation or to help me move in. So my Dad came with me for orientation, and that was the first time I saw saw the school and saw Boston.

Naber:  That's a very Jenn Knight thing to do. You're so adventurous and fearless. I love the courage and the fearlessness. It's cool. It's a good example.

Jennifer Knight: Looking back on it, it's funny, I think I was mildly terrified. But I really wanted to study international relations, and or something along that, and the UC schools that I was looking at only had international economics, and I'm more interested in people problems than technical problems actually. So BU had an amazing international relations school, and that was ultimately what encouraged me to go.

Naber:  Awesome. And international relations. And you also studied French in for a year in France, correct?

Jennifer Knight: I did, yeah. So I was a international relations major. Foreign Policy and Security in the Middle East was the focus of my studies, but I also did a minor in French.

Naber:  What was your experience like in France?

Jennifer Knight: It was an amazing experience. Once again, it's a different time now. At that time there were cell phones, but not really. There was internet, but not really. I didn't have a laptop with me that could connect to the internet very often. So it was an interesting experience at 19 to get on a plane and fly all the way across the world, and then get a calling card and get on a pay phone at seven o'clock at night to call your family, to handle the time zone difference. I was ready in that I had studied French in high school. I was also not ready in that I had not studied it for a semester before I went. But I had an a pretty incredible experience on my way over there. Being from the West Coast, the program that my school ran didn't actually coordinate my flights because they coordinated everything for kids on the east coast. So once again, I was put on a plane, and my parents said good luck. And when I landed in Paris, I had no idea that Charles de Gaulle was kind of a mess. I was running through the airport. and I saw the group that I was eventually gonna study with being guided through the airport by an adult. And I was running for a gate, to miss my flight. But I got to the gate, and right behind me showed up a woman who's about my age, and she had actually been studying English and in the US during the summer. And I had no idea what to do. And she just grabbed ahold of me, and she took me to the ticket table, and she handled everything. And we went to a different airport, got on a flight together to Leon. And then her parents drove me to Grenoble with her because they were going home. And it was totally surreal experience, but also one that I think back on a lot that the world is actually a very generous place, and it's a very kind place often, if you're open to it. And I know it has its rough edges, but at a young age being able to travel over there and see that people are people across the world, and people are willing to help, was really incredible start to the journey. And that things don't always go perfectly, but they will end well, was something that was fun. And then it was a crash course in trying to navigate another culture, which I've always looked back on and really appreciated what the program gave me. So it was a fun year.

Naber:  Very cool. Good story too. Good story. I always feel better when I talk to you, Jenn. You keep such an optimistic, positive light. So you studied at BU. Walk us through your first couple of gigs, up until before LinkedIn, so up through Bluewolf, and let's do some hops. Explain it. Typically we go through a few different things within those gigs. What I want to do is get to LinkedIn, Dropbox, and Stripe and talk through a couple of examples, and some of your superpowers, and we'll get there. But anyways, why don't you hop us through just so we have a good understanding of where you came from professionally. Hop us through some of those gigs and what you're up to. Maybe in like maybe like five, seven minutes.

Jennifer Knight: Yeah. Seeing as I studied a bunch in high school, I actually entered college as a sophomore, finishing in three and a half years because I took a bit of extra time to go to France. So I graduated actually December 2006. For family reasons with my Mom being sick, and not being very clear how long she was going to be doing well, I decided I wanted to come back to the west coast. I had the most useless degree on earth to come back to the west coast. There, there is very little to do with international relations with a focus on the Middle East in San Francisco Bay Area. So I came back had to figure out what I was going to do. And I ended up just on craigslist looking at jobs. That was the way back then, that and the newspaper. Which was 2007, and it sounds crazy, but that's the truth. LinkedIn was, I suppose, kind of a thing, but it was very, very small, not really a thing. It's just starting out. Right.

Naber:  It had volume of users, but not a lot of density and a lot of engagement. So it's just less useful at that point.

Jennifer Knight: Yeah. So I just applied, I mean, toeverything I could. And then I ended up getting a job as an Office Manager at a solar company in Berkeley. And I, with my college degree, went and answered the phones and opened to the mail. But it was the thing that afforded to me to get my first apartment, and my first foray out into the world. It was a great community of people. It was an opportunity for me to be in an environment where I could just see how I could help. And so I learned as much as I possibly could. I had a lot of fun working with the outsourced IT guys who would come in and help with the servers. And then, we hired a Director of IT, and he was a bit overwhelmed and he asked me if I wanted to help him Administer Salesforce, and so I started doing that. I was there for two and a half years. The company's split, part of it was sold off - the residential was sold off, stayed with industrial side, learned Salesforce development. I was quite lucky in that I became a Salesforce Administrator right before Salesforce opened up as a platform. And then my boss at the time taught me how to program on the platform. It's very similar to Java. Apex is Salesforce is language. So I got to iteratively roll into this platform as it was growing. And I was one of the first 500 administrators certified, which is very...I look back on it, and it's a nerdy moment in that...but just a good timing moment. So I was doing that, but I was pretty stuck. And after two and a half years, I was pretty burned out actually. When the company split, I was the only person doing my role. And I enjoyed a lot of my coworkers. I have, actually, one of my best friends from that job. But I just wasn't loving it anymore, and I was too tired actually to really look for what was next and know what I wanted to do next. So I decided to take six months off, and this was in 2008-2009. So everyone thought I was out of my mind. But I did, and it was really fun. I moved to San Francisco. I worked in nonprofit, so I actually did nonprofit work at, Salesforce nonprofit, at a women's community clinic and at an urban garden. So the women's community clinic in San Francisco and at the place that does urban gardening in Oakland. Helped them set up their Salesforce instances. The urban garden one was amazing. We use Salesforce to track plants, and pests, and tools, and acreage, and all sorts of crazy stuff that you wouldn't imagine. Yeah. So I did that, and when I moved to San Francisco, Craigslist again, my craigslist roommates - one worked at Salesforce as a Sales rep and one worked at Bluewolf as a Sales rep. And my roommate Chris, who worked at Bluewolf said, hey, we're looking for developers. I don't think you want a full time job right now, but do you want to come contract with us, and check it out? ...did some contract work, and then after probably four months I decided to join full time. And that was the first time...and one of the reasons I did it, that was the first time I got to figure out if I was any good. And when you do something alone, you have a sense like I knew I could make things work, I knew I could solve the problem, but I had never been around other Salesforce developers where people with technical backgrounds, to find out if I was actually good at it or not. And I had an amazing group of people and an amazing support system at Bluewolf to help me grow and some great mentors there. So I couldn't be more thankful for them. They were extremely patient as I was plotting through things, and then also threw me at some really, really tough challenges. So I was doing a lot of the development for west coast projects, by the time I left. Did that for about a year and a half...um, I am not a consultant. I love the design. I didn't love flying in, building something, and then leaving it. I also didn't love being on a plane all the time. So I hadn't really known that I was going to do with myself, but I put my profile up on LinkedIn, and then LinkedIn found me on LinkedIn. And that's how I ended up at LinkedIn.

Naber:  Nice. Awesome. Okay. We've got to LinkedIn. That's a really good story. You got to work on some, excellent cool projects, while you were trying to figure out your actual depth of your prowess around this new set of skills you were learning. But it's probably also really stimulating for you because you're such a smart person. You're also trying new things all the time, and wanting to build. So I'm going to guess that was really stimulating to learn this whole new world of technical bricks that you could build with.

Jennifer Knight: It was, it was a lot of fun. It also taught me that that skill set around Salesforce is something it can be really can be used anywhere. And it's something I talk about with my teams now. It's quite fun, and I think a lot of skills in a lot of different areas of the business are transferable, but if you want if you want to work at a small company, if you want to work at a big company, if you want to work in nonprofit, if you want to consult, there's kind of a home anywhere. And that is pretty liberating because you get to go pick your family, and pick where you want to be.

Naber:  Cool. Love it. All right. So, give us a quick chronology of what your responsibilities were, and what you're up to at LinkedIn. And then I have a couple of questions for you to follow-up and dig into your brilliant mind a little bit.

Jennifer Knight: So I joined LinkedIn as the first Salesforce developer, joined the team that was in existence. There were five at the time, and the were two of us who joined, myself and a woman who was also doing Salesforce administration at the same time. So we grew to a team of seven. I still work with today, one woman from that team. I could not be more thankful once again for what they taught me in terms of how to approach an environment and how to approach work, just work. I was the youngest by far, and I was coming down from San Francisco, and I'd come from...Bluewolf was a really young environment as well. So that ethos of chaos, and running around, and experimenting, and trying new things, and to go from that to a place where people were far more measured, I hadn't seen that before. It was, yeah, we can do this. Like we're gonna think about it, we're gonna make a plan, and we're gonna go after it. It was really intense. We were building a ton, but it was very focused and measured. and it wasn't all over the map, and that was both due to the team that I had around me, and also a lot of the partners that we had at LinkedIn. So I joined as a developer, and then I helped grow out the Salesforce Technical Architecture and Development team over the course of my three years there. And so I was responsible at the end for our project work. We restructured the team, our lead structure the team as a Plan, Build, Run. So PMO, a business analyst doing the business requirements gathering, build was my responsibility - so those were the big project work, and then run was kind of the day to day administration, and keeping the lights on, minor enhancements, things like that. My team would do both technical development, but also if there was a administrative component of configuration, we might partner with an Admin to do that.

Naber:  Nice. Very cool. One of the questions I have for you, and this is actually a good segue into that...you had a lot of experiences, at a lot of different teams, also built a lot of differe teams with LinkedIn, Dropbox, Stripe. You can go across those if you need to to pull experiences. But, is that the typical anatomy of a Internal Business Systems and Tools team? Or, if it's not, what is the typical anatomy, and can you give us a little bit of a breakdown?

Jennifer Knight: Yeah. So those functions are the three behaviors that you see across the board. Alex, who's my Manager at Dropbox, said way back in the day...it's people, process, technology. And that is true always. So do you have the partner, does the partner know how their processes articulated? Do you understand how to reinforce, and support, or automate, or speed up, or whatever you're trying to achieve, that process with technology? And then there's the iterative, like, continuing to keep that alive and continuing to improve it. I think about the world in that framing all of the time now, that's how we approach it. And so our team is staffed for each of those areas. The plan side is always about, let's sit down with the people we're partnering with, and let's understand their process. Now that team on my team is responsible for really understanding the business partners' process, and then starting to think about who do we need to engage with from the technology side to support that process? Then the build side is the actual team that's saying, okay, now I've got the process. How do we empower this with the tools we have? Or what tools do we need to go buy? And run, of course, being the day to day maintenance. Those functions always exist. They are not always carved out as specific teams because depending on size, you just don't have the resources. When I joined LinkedIn, each one of us was a little mini plan, build, run. There were only seven of us, and we were supporting a lot. And so we would go sit down, and get the requirements, and then we would go off, and going to build something, and then you're the one who kept it alive. And and then eventually when you got a little bit burned out on that area, you'd switch it to one of your other team members. So I ended up with Sales Development work because April was done thinking about that problem...and then we've cycled through. But those, those pillars exist. They just evolve. And how you structure the team varies quite a bit. There is not a perfect way to do that. I think it depends a lot about where the organization is, what they're valuing at the time, and then who do you have on staff. But the core behaviors that remain the same across LinkedIn, Dropbox and Stripe.

Naber:  Okay. That's awesome. That's a really good answer. Thank you so much. And while we're on LinkedIn, can you explain,what LinkedIn does extremely well from a Systems, Tools, Building leverage resources? And when you do that, could you lean into some of the things you do really well within the respect of Sales and Marketing? Because I think the audience is going to want to want to understand each one of these businesses, both what they were good at, why that's important, and how do they do it?

Jennifer Knight: Yeah. So it's been a few years since I was there, so I'm sure it's evolved. But one of one of the overarching things that I remember from that time is actually just Focus. I think LinkedIn did very well...and as a partner to it, I appreciated it a lot after I left. There's always thrash. Nothing's perfect, the business evolves. Part of my responsibility is to be flexible enough to accommodate the fact that business has changed. They chart a course, but it's not like...Product Development is exactly the same way. Factors change and they can change fairly rapidly. And so the needs of the business can change fairly rapidly. That said, knowing more now and seeing, having seen different environments, in the face of that, I'd say LinkedIn did very well on remaining focused and what the core objectives that they were trying to enforce were. And then systematizing those. And maybe doing some experiments on the edges of other like creative things that we could potentially do to drive the business, but making sure that we were focused on being excellent at a few things, doing those very well, and those being backbone things for the business. So it was the first time that I had to work on some of the end to end workflows around Demand Gen. And how do you think about that, and how are you optimizing that? And not about a lot of bells and whistles and not always about crazy experimentation. It was first let's get it right. We have a core business objective, and the objective is not changing. It's reduce the time to touch. Okay, let's go like nail that one to the wall. And then once we get that one done, we'll be find the next one, and we'll like nail that one down. And those are the focus areas that don't change, right? Even if your approach changes, or your markets change, they're just really core parts of how you want to operate a business. So that was something LinkedIn did very well. One of the reasons that I left LinkedIn though, on the system side, is that at the time that I was there we were very silo'd. So we had a lot of autonomy in the space that we operated in, in partnership with our Sales ops partners. But some processes are actually cross business units. And some Systems work best when they're integrated across. A good example of this is a CRM to Oracle. A CRM to an ERP. So Salesforce to Oracle, or Salesforce to Netsuite, or I mean, no one uses anything besides Salesforce. That's not entirely true, but, Dynamics to SAP, any of those. Those flows were something that were interesting to me, and I didn't have the opportunity to work on as much. We could influence it. We could encourage. We couldn't work on it as much. When I got to Dropbox, that was the first place that I was able to think about end-to-end flows. And that was an area...because I had the autonomy to go own those. So that was an area...I think LinkedIn did very well on the focus, focus in depth in a particular system space. But we struggled a bit on the cross Systems, from where I was sitting. This is not a universal picture, but but from where I was sitting. So when I moved to Dropbox, I got the opportunity to think more cross platform, and that helped smooth some of the edges across teams, which was a lot of fun. At Dropbox we were in a bit of a different mode, so we were doing a lot of crazy growth.

Naber:  Awesome. This is good. This is a good transition. So ell us what you're doing with Dropbox.

Jennifer Knight: So I joined there to do Sales Systems. It was still really early days. We were still hiring out our Sales operations team. And so, I at that point, learned the importance of the people process part. When you put technology first, it it proves to be a bit of a challenge. That one was...I learned a lot more about meeting my business partners where they were. I actually leaned more into some of the operations and business analyst part of my role. That was not what I was doing at LinkedIn, but at Dropbox by necessity, you're saying there's these three functions, I was doing plan and build and run. And as I hired my team out, I hired them to do run first, and then started building from there, so that I could figure out what the needs of the business were, and then try to make some educated decisions around what we were going to invest in on the technology side. We had a ton of fun and we were building from scratch. There are things at LinkedIn, even by the time I was there, that had become so complicated that you kinda didn't want to touch them. When I got to Dropbox, it was the first time I got to build an order to cash process. And had amazing partner, who was also new. He had never built it before, and he was coming from the finance side. And he was really passionate about making this a really amazing experience for people. And so we just partnered really closely together to make that happen and thought about how we did it end to end. We ended up over the course of probably two years, building a flow that I'm still very proud of, but it was very focused on these business objectives again. We wanted the experience of someone who was buying Dropbox through a contract, from a provisioning perspective, to mirror the experience of someone who was buying with a credit card. And that was our goal. So we set that as our goal, and then we also set a goal that along the way that we had as smooth as possible process with the Sales team, so that there was a lot of transparency about what was happening. Contracting, as some of you know, can be very complicated from the Sales side because there are legal people coming in, there's financial approvals, there is these multistep processes, and it can feel like it's taking forever and you have no idea what's going on. And then maybe the thing is signed, and now you don't know why your customer hasn't been given the Product because it's fallen into another manual process where someone has to go into some backend system. Or in the case of, and this was happening when I got there, you as a Sales rep now have to go into some backend system that you maybe don't fully understand and punch a bunch of buttons, and then hope that everything works out, and that your customer gets the Product they want. So we started once again with that focus, and we were really successful there. And those kinds of activities were the things that made my team successful. When we could find those focus areas, through our rapid growth, those are long pull items. They take a long time to get right, and if we kept focused on it, we were able to drive impact. So we were really...I brought that from LinkedIn, that focus in our space.

Naber:  Hey Jenn, can we pause there for a minute?0 So let's use the order to cash process that you built. Can you walk us through the phases you go through to build the case for it, plan out the project, resource and manage the project, you've got to have Internal buy-in, then you've got to have pull through for people, actually making sure that they do what they need to do in the field and the business? Can you walk us through using that as an example for number one, what the steps are? And number two, from a Sales and Marketing or just really from a stakeholder perspective, what are some of the best practices in working with your team so that we can be better at doing that? As you go through it.

Jennifer Knight: Yeah, so, let's break it down. How do we approach it? So now, one of the things that I think a lot about when I'm approaching these types of projects is how do we think about, an ask, and it's end to end? So one of the things about working with a Systems team is that we're ultimately accountable for the overall health of the Systems. And it's an interesting process for us to understand what a business is asking for. And then trying to put that in the context of either another set of business asks or the platform on the whole. And we also have situations where, there are multiple stakeholders. And order to cash is a good example of one. Demand Gen flows is another good example of that. Where as a business owner, or as maybe a Sales Manager, you're saying, in your inner mind thinking, it's taking too long for my teams to get contracts out the door. And then on the other side, the finance Systems team is thinking, like, I need to be able to ensure that this contract has the correct margins, or is feeling good about that. And the legal team is sitting there thinking like, what are these contracts terms? Let's make sure that those make sense for the business. So when we get these asks, part of what we think about on the more complicated asks, but even on the smaller ones, is who are all the players in this ask? What is it in the context of the larger process flow? And what is it in the context of the larger Systems? And that's something that I've had the opportunity to do a lot, and something I quite enjoy is how do we put this in, frame it out, and where it wants to be. The other thing that we need to do on our side, is thinking about how we get from point A to point B? And can we do it in one shot, or to your point, does it have to be a multistep process? And some of these things are quite complex, and so we're not going to win it all at once. So for us, starting with that problem statement and then working through with our business partners to get an alignment on the overall problem statement, what we ultimately want to achieve, and then agreeing on how do we iteratively get there. So what are interim wins along the way, or something that we benefit from, and we benefit from that partnership. In terms of resourcing and implementing a thread...I'd say it varies wildly depending on your circumstances. And Systems tends to be lagging behind the business. I have yet to be an environment where we weren't coming in two, or three, or four, six years late. It's just the nature of it. I think SaaS has this sheen on top of it, where you're just oh, I can just get a Salesforce account and probably have one person manage it, and it's going to be okay. Like it's easy, right? And actually, that's not wrong for a period of growth. But then when you start to get into these more complicated asks , or you start to get into Architecture questions, or you start to need to do development, then that tool becomes something quite serious to take charge of, and you need a team that is dedicated to it and experienced. I talked to folks about this a lot, where there's a whole period of time where you really just go experiment, like try to find your way. You don't need to hire a technical architect, and a full team, and everything right out the gate. But as your business starts to take off, and you start to have those needs, having an experienced person, who's seen it before, come in can really help you figure out what you want to navigate over the course of the next two years. So I think the resourcing thing, it's very varied. But if you want to tackle a more complex workflow, or you want to really empower a part of your business, that's the point where you start to think about these dedicated resources. And that's when I'm looking at it...for my team, when I come in, I look...survey the landscape. What are our biggest challenges? What do we want to think about? And what are our business partners talking about? What aren't they talking about that is probably going to doom us anyway. And then how do we line those up, and what kinds of resources do I need? Do I need a lot of business analysts? I might need a lot of business analysts right out the gate because I may need to spend time helping the business articulate their ask. That actually is a weird one. Often I work with business partners, and they're like, where's where's the admin? And where's the developer? And I'm saying, well those are execution folks and you want a partner right now is going to help you think through your process, and then make sure that we're reinforcing the right behaviors. So I'm going to actually get business analysts to define that. And then once we have those definitions, we have a bunch of different levers we can pull in terms of execution. I personally enjoy building teams that are really dedicated to the business. So we always have a mix of technical and BA full time on the team. Most of our projects, the big ones take 12, 18, 24 months. So you really want someone who is excited about the end to end and will build the continuity. But there are amazing, I worked for one, they're amazing partners who will come in and help you with resourcing. And we also pull that lever a lot on our team. But we do it in the context of making sure that we have the business requirements anchored, and we know what we're going after. S to kind of rewind back to your question to how we approach these things. What's important for us is understanding what we're solving, and being able to really work with the business to understand what their objective is. And if it's a project where we know it's going to take more than a quarter of more than a month to go after, making sure that that objective is something that is very solid. And that's what I was talking about earlier. Your objective being speed to lead, your objective being speed to contract...there's those kinds of objectives where even as time passes, we're going to keep after that. So we feel successful together over the course of the year or two it takes, and that we can measure our progress against it. The failure modes that I've seen is when we don't know what we're solving for and instead we get the kind of partnership where it's, I need this field, I need this thing. I've already solved it for you, justt go build it. We can do that. The probability that it will ultimately build into the kind of system or process that we both want together, is not super high end. On the margin, it's okay. We'll put in a field, we''ll kind of get going. We are here to empower and enable the business. And that's something that I talk about with my teams quite a bit. Like, our responsibility is to empower the business, and so we should understand where they're coming from and then try to get them there. Ideally we do it in partnership, and process, and Solution design. Sometimes we just have to crank.

Naber:  Cool. So that was awesome. That was an awesome answer. I love it. It's almost like you read it out of a book, so, and maybe you wrote the book. So, one more question, and then we'll move on to Stripe because you already gave an example with the order to cash and that was great. Actually, two more questions. You mentioned a couple things that Dropbox was doing well, but what's the one thing you think they do extremely well from a Business Systems, Internal Business Systems, Business Systems and tools, leverage resources that they're building, etc. What's one thing they do world-class? Why is it important? And how did they do it?

Jennifer Knight: An interesting question.

Naber:  I mean, LinkedIn was focus, if you had to say it in a few words, Dropbox is obviously world-class at a few things.

Jennifer Knight: So what I would say, and it was very different in its approach. When I got there, like I said, I started to do Sales Systems, and I got to grow in my role and pick up other teams. And so that's where I learned about Finance Systems, and ended up taking that over and building that. I'd say, maybe the flip side of what I was experiencing in terms of rigidity at LinkedIn, Dropbox had an environment where if you wanted to go tackle a problem ,and you could rally your resources around it, and you could get get the team together, we can go tackle the problem. And that was super, super fun. Obviously from a system side, I think that was a strength there, where we had once again the autonomy to go try to solve these problems and could get sponsorship to go solve these problems. If you could find your partner on the other side, and shake hands, and go after it we could move ourselves forward. And there wasn't resistance to that. There is a push to, however we get to a better place, let's get to that better place. Not about who you are, or what team you're sitting in, or my priorities versus your priorities, and how our roadmaps, and all that fun stuff. It was hey, we have this problem, and yeah, it's going to involve like three or four teams. Let's go figure out how to do that, and we'll get together, and we'll go agree on the problem, and we'll go solve the problem. And so we got that was one of the things that helped us build some of this really cool stuff and these experiences. And I'm really proud of the teams that did that because we thought about not ourselves. We thought about what we wanted to achieve both for our customers, but also our external customer experience, and we were able to drive to that. Even when it wasn't easy, even when we weren't aligned on exactly how we planned, that was something that we did really well there. And I think the culture of the company of empowering people within the company to go tackle those kinds of problems made that successful.

Naber:  Do you have any idea how they did that within the culture? Maybe it was like one or two things that empowered people to be able to go solve those problems, and have that autonomy?

Jennifer Knight: Yeah. And it was that way pretty much from day one. I mean, so there's flip side. Anyone can buy anything, right? Which, on on the system side, is its own like special crazy. But there wasn't like a specific tenant that we followed. There wasn't anything like that. The one thing that, Dropbox also did well, and LinkedIn had this, but they stressed it in a different way, was this concept that we called cupcake there, which is let's have fun together in this. And so I think that that empowering you to go out and like build community, build team, and have fun with it, was something that Drew and Arash really instilled. But there's not a like phrase or a specific behavior other than encouraging an environment of community, and communication, and through that you could go find your people, and find your path.

Naber:  Yeah. Yeah. It makes a lot of sense, and it's extremely empowering. I felt that when I was at Dropbox as well. But cupcake, it's a really good thing to add. Like having fun while we're doing it, and working on cool shit together That's pretty cool. And that's a good place to start for all the stuff you want to work on versus just what's necessary or having a less creative mindset around it or vantage point? Awesome. All right, let's move on to Stripe. So yyou're leaving Dropbox, you're heading to Stripe. Why do you make the jump to Stripe, and what are you up to there right now?

Jennifer Knight: So, it's been a progression of scope actually. Something that I laugh...I love my job because I get to be incredibly nosy and learn everything about the back end operating of a world. So at LinkedIn I got to learn so much about how Sales and Marketing think, what they prioritize, personalities, what's top of mind, what are the pressures, what are the challenges? I mean I knew it because I actually interviewed for some Sales jobs. I will never be a Salesperson. That is a such a hard job. And being on the technical side, I also appreciate the challenges of a technical world. But having the opportunity to be in with Sales teams and Marketing teams, and see how they think was something that I got to do at LinkedIn. I got to Dropbox, it was doing that and then I got the opportunity to learn how accountants think because I took over finance Systems. But it dropped off, and it's totally different world. I took an introduction to financial accounting after sitting in our first CFO's staff meeting because, I was like, I literally understand none of the terms. And I had an amazing partner in our revenue accountant. She was Sarah, she was patient person. I took over the finance Systems team, and we were working on a project. And she was describing debits and credits, and she's walking everything through with me, and she's willing to repeat herself as I'm stumbling through it. And I got to really understand that the pressures in their world are really fundamentally different than the pressures in Sales and Marketing. And they have external pressures with GAAP, and all of these other requirements that they're marching to. And so it got to learn about that. At Dropbox though, there was no mandate when I was there for the Business Technology team, we were slowly picking up pieces. And that was a fun way, but it was also hard. Sometimes, I was picking them up and they were healthy, and sometimes I was picking them up, and they were in an interesting place. So I'm going through that, and we were getting pretty big, pretty stable as a team. And then through a friend, ended up chatting with the CFO at Stripe, and they were looking for someone to lead Internal Systems. And that would be Finance, Sales, Marketing Support, People, the whole set. And that's what ultimately pulled me there. Also the fact Stripe earlier reminded me, in tone and approach, to LinkedIn in the early days. There was just something about it that, frankly, just felt familiar. And so that was why I decided to take that opportunity.

Naber:  It's amazing how often someone's tone and what they say...when you've been at a few different tech businesses, you understand what good culture looks like. And you walk into a place, and you're having all these conversations when you're going through the recruitment process. It's amazing how often it comes up where, some version of, it felt like I was coming home, or it felt like I was going to something that I already knew, and I could see like where the movie was going. I've seen this movie before. I've directed it. I like the culture because it feels like coming home. A few of those different things happen a lot when you're making your third, fourth, fifth jump into a lot of these businesses, you start to get a really good sense of the bullseye for what you want as well. Maybe I'm just ahead of my skis on that, but it sounds like that's you felt as well.

Jennifer Knight: Yeah, I think it's very true. At some point...So, I think everywhere you go, you learn, right? Every situation you're in, you learn. And you learn what works for you, and what doesn't work for you. And it's not even a judgment call. It's just part of who we all are, and what makes us happy. We find our people, and we're successful with our people, and hopefully we get an opportunity to meet many, many people of many different approaches. But I think at the point that you're talking about, for me, I think about the fact that...Of all the three places that I've been, that are roughly similar shape, they all have the same problems. So you're actually solving the same base problems very frequently.

Naber:  Can you run through some of these as you're thinking about them?

Jennifer Knight: Yeah, so, actually the reason I talk about order to cash is that's a problem for everyone, everywhere. It's a really complicated, really tough flow. It's hard to get right. It's really frustrating when it's not supported. And that's one that I've seen everywhere as a challenge. Data models, everyone gets their Salesforce data model wrong, everyone - like, it just, it happens. One of my first projects at LinkedIn was fixing the data model. One of my first projects at Dropbox was fixing data model. That can be really hard to fix. You can be like, oh, like that sounds simple. But you put the wrong data model in place, and then you lock it in place with a bunch of integration, and a bunch of automation, and a bunch of tooling. So by the time you get to the point where you need to roll it back, you have to roll back a lot to get back to that place.

Naber:  You're duct taped, and scotch taped, and glued everything together.

Jennifer Knight: Yep. So in order to do some data model work at Dropbox, it took me 12 months to rewrite a piece of code that was running on a python script under someone's desk, so that we could unlock it. There's that kind of work. The exercising the capability and the muscle around planning, planning your Systems change. You're often in an environment where everything is moving extremely rapidly, and on the process side you're iterating, and you're iterating and iterating. And then Systems don't always benefit from that rapid of iteration. There's a point where you have to be able to experiment outside the system. And when you get closer, you don't have to be perfect, but when you get closer to your ideal process, then you want to systematize it. So when a team like mine comes in, one of the big challenges we face is not actually a technical challenge. It's working with our partners to say, I know this feels like we're slowing down. We're not saying no, we're not saying stop, but we have to take a step back, and we have to once again put this in context, and figure out how we rationalize this within the system. And so that muscle, it's a challenge for everyone. It's a challenge everywhere. So that's one we face. These problems are very similar. And to your point when I'm making a decision now about where I want to go, you're living with this community and in this environment for a pretty significant portion of your day or your life, over the course of time that you're at that company. And everyone that has worked in tech knows it's not nine to five. If you've managed to pull 9-5, you're lucky. So you're probably spending most of your waking hours for several years, in that environment, and that being one that you feel supported in, feel excited to go to, that resonates with who you are. And where you are in that moment in your career and your life, I think is incredibly important. You can't always get it right, and you're going to find an environment that isn't the perfectly resonant one, but that's okay because then you learn aspects of that. And I think even there, you can take aspects of those environments, and take them with you going forward. But I agree. Especially the third or fourth time around. I think it's true. We always try to find a place where we feel might be a bit more like home.

Naber:  Cool. Good one. All right, Stripe. Two things - why don't we start first with an example of a major project you're working on, and maybe you could talk through as much as you can give us without giving confidential information obviously, but what are some of the really cool major projects or one major project even to give us an idea of the type of stuff you're doing at these different companies. So you've given really good examples so far. Give us a profile of Stripe and some of the things you're working on.

Jennifer Knight: Yeah, I'd say actually I'll do a little bit of a different answer than a systems answer because I always loved the technical stuff. The project that I'm working on at Stripe, and that's been the thing that's so top of mind for me over the last two years, is actually establishing the team. And establishing a team that is proactive and not reactive. Understanding what our actual needs are. So to give you a sense, my team when I joined, there were a few people in the organization who were part time working on Systems. And so the Systems were pretty underfunded, and that was one of the reasons they asked me to join. But putting language around what it actually looks like to manage these Systems well, putting language around the fact that we have huge gaps right now, and with that language also still keeping my team motivated, is that dance of being able to say we're here, we're growing, we're here to support you, and in the same breadth, I appreciate and understand that there is a laundry list of things that we were not able to do. And keeping that dialogue going, and figuring out how we grow up into Stripe as an organization, and how we try to close that, as rapidly as possible, close that gap. Which on the surface frequently looks like we aren't moving fast enough because some of these things, I mean they're around hiring, they're around team structures, they're around normalizing as a team. They're around that the thing that I just mentioned about learning how to partner with our partners, helping our partners understand planning processes. The big project that I've, there's a bunch of technical projects, there's a bunch of these kinds of negotiations, but actually the big project that I've been working on at Stripe is around that area. How do we understand how to best serve the organization? How are we getting out of this proactive mode? How do we become, I think we always are a value add, but how do we really drive that value forward? And how do we become a team that is not a handful of people who are just heads down executing, and trying to like scramble to the next thing, and are more laying the foundations and partnering to lay the foundations with our business partners? Knowing that we're a couple of, frankly, we're a couple of years behind, so we have a lot to lot to catch up on. That's really been, if I look at it across all of my teams, and what my function is doing right now. We are working on technical projects, we're delivering things every day, we're trying to move those forward. Kind of core things, core capabilities that I've discussed before are projects that we're working on. But really more than anything right now, we're focused on - how do we partner? How do we partner for success? How do we understand what we should be investing in with our partners? And how do we really surface their underlying needs versus the rapid fire day to day?

Naber:  So that is really interesting. I've got a question for that. So can you explain what the end result looks like? What does euphoria look like when you get to this place where...maybe not euphoria, you get what I'm saying though... you get to this place where you're being proactive, you're working with the business on the things you should be working on, and it is working like a smooth machine that is operating on all cylinders. What does that look like, and what do you guys accomplishing when that happens?

Jennifer Knight: Yeah. So maybe I'll start with what it doesn't look like. There's no world in which we're done, and there's no world in which there's no backlog, and there's actually no world in which we are doing everything the business wants you...all 10 items, every sprint. That just, that has never happened in the course of my career, regardless of the team size or anything like that. There will always be needs. There will always be needs that we can't serve immediately today. And part of that is actually the right investment model for the business overall. So we're always looking at prioritization. I think when it's smoothly, the factors that I look at are..We have transparent and clear communication with our partners. They know what they're getting, and we're delivering that in the way that we've committed to delivery. They are actively engaged and partnering, and feel good about the prioritization. They know why. They know the business impact, because they're defining it. But there's a lot of really clear communications there. And then on our side, like I said, we're delivering on time or delivering in a way that is thoughtful and accountable to the rest of the ecosystem. So we're not breaking each other, and we're not breaking the system. That actually gets quite difficult at scale. If you have five developers on a platform, and sometimes they have overlap, you have to make sure that they're all developing the Product that is your CRM or the Product that is your Marketing automation platform in a way that is conscientious. So, we are, when we're operating smoothly, we are not blowing up each other's work. That's a pretty obvious one in my mind. I think when we're operating smoothly, we are responding to the right things, with the right urgency, in the right SLA's. So this is one of the reasons we end up with a Run function. Not every ask has to be treated like a project, but not every ask can be treated like a quick win. So you want to have varying SLA's and varying approaches, and when we're running smoothly we have an intake process that allows us to triage those, and be very quickly responsive where it's appropriate, and be thoughtful and measured in our approach, where that's appropriate. But not trying to do a one size fits all. Those are the core tenants that I look to when I think about how my team is running smoothly. I think that maybe one that we don't talk about with the business as much, is we also spend some time thinking about the technical foundations, and how those potentially need to evolve because our SaaS partners are evolving different features, and giving us different capabilities. So maybe we set up an integration one way four years ago because that was what Zendesk allowed us to do. And that might be really difficult for us to maintain and manage. And on the business side, it may look like it just works. And on our side, it may be a ton of toil and work to keep it alive. And Zendesk releases a new feature that simplifies that. How do we also continuously bring technical, underlying improvements, infrastructure improvements, into our roadmap. And then when we're working really well, socializing those up with our partners so they really appreciate why us doing that work actually improves their world and makes us more efficient together. Those are the high level things that I look for when I think about my team operating well. And like I said though, the work will never stop. It will always be there. Which is the exciting and fun part. So really it's about transparency, and process, and prioritization.

Naber:  Nice. Awesome answer. Thanks so much, Jenn. So last question, and then we'll wrap. Okay. I've got one rapid fire question for you as well. So, one of your many superpowers, that you've alluded to a little bit, throughout your answers, but is...As you're going through every single one of these projects and all of your decisions, thinking as an end to end process thinker, where you're keeping the big picture in mind while you're able to zoom in and out of the details and the different requirements, and how do all these things stick together over an entire project over a sustained period of time. How do you bring stakeholders along with you in that journey? Because you're saying no a lot, you're saying yes a lot, you're saying no a lot more than you're saying yes. And you're also telling them, hey, please wait. Being a Sales and Marketing operator myself, I know that we could be inpatient every once in a while. So how do you bring stakeholders along in those conversations, and what are some of the best practices that you use for communicating with stakeholders? Because you're so good at that naturally, but that is not necessarily a Sales of Marketing operators forte as they're thinking about, just what they want to do for that quarter or that half of that year.

Jennifer Knight: Yeah. Yeah. So I've had a couple of different approaches. I think once again, this is an interesting one...That you say it's a strength that I can think that way. And sometimes one of my weaknesses of getting it out of my mind, and onto a piece of paper. And so what I've gotten better at over time is making sure...everyone who knows me knows I love a whiteboard. I actually don't think that most people in these complex scenarios, there's a few of them that can, if you describe it with words, actually can follow along. I'm someone that, if someone starts, if I focus extremely hard and someone is describing something, I can usually think that I've understood. But sometimes when they put it on the board, I realized actually I didn't. So one of the techniques that I use, and I actually encourage everyone on my team to do, and I encourage our partners to do, is write on the board. Write your process on the board. On our side we will write then the system on the board. And let's all look at it, and then talk about the areas that we don't understand, or talk about the areas where we want clarification. In our side, when I start to think, okay, here's our end to end process, now you have all these Systems. Helping people come along, part of it is by laying out, here's the areas that maybe we're gonna be able to accelerate quickly, and here's the areas where I either don't have complete control - I'm going to have to negotiate with a partner, or is technically complex. So let's look at the whole thing end to end. But starting that visual from the process. And it doesn't have to be elegant. It doesn't have to follow all the fancy flowchart, actual diagrams. I do love that stuff sometimes, but get a pen out, sit down together, and make sure that you both are actually speaking the same language. And then that your priorities align. So I might get really passionate about some part of the process that somewhere else I've seen be really interesting, and that might not really be what you're passionate about. Or I might be able to bring some insight because I've seen this at a larger company. I can say, hey, two years, we don't have to face it today, but two years from now we're gonna need these kinds of controls. I'm telling you that I want to build this foundation in today because I'm looking forward. Do we agree that that's an okay thing to do? But even to get it out of your mind, get it onto a board. That's a huge one. Then, like I said, on the transparency side for our team, we have milestones. We are sending out sometimes weekly or biweekly updates on how we're progressing against those phases of the project. We're checking back in what has changed. Have our priorities changed? Have some more micro points within the plan, do we need to adjust? Have we learned something new that's going to shift something out? Those are the muscles that we exercise. But I think the first and most important thing is - can we all get in a room, and can we look at this thing end to end, and do we actually, are we speaking the same language? And I'm not going to say it verbally to you. I'm going to show you. And then pull out a pen, and mark it up, and tell me where it's crazy, or tell me where it doesn't work, or tell me where your world is different. And that way we on my side of the house, have the context of where you're coming from. And you on the business side, can understand how we're thinking about the approach. And no one is surprised. That would be the tactic that I think about a lot.

Naber:  Man...I wish I could wrap that thought up and hug it because I loved it so much. You and I have a similar brain in some respects, and I'm loving that answer. Okay, last question. We're done with going through all these different examples, all this information. As you wearing like a tweed jacket and a hat right now, because you just professored everyone with all of your knowledge. So, one rapid fire question. So, I ask this to people on their birthdays every single year. It's not your birthday, but I'm asking anyways. Our audience has heard me say that a hundred times, apologies, but I'm explaining for the guests because they don't know. Maybe they've listened to all of them, nope they haven't. Most important learning or lesson you've acquired professionally in the last 12 months?

Jennifer Knight: I would say, I've always been a patient person. But in the last 12 months, I've actually gotten much better at learning how to be both patient and persistent. Which is kind of a weird abstract learning, I'll give it that. But in environments where a lot of changes driven by influence or cross team collaboration, and everybody is under a lot of strainm under resourced in their own way...Figuring out how to navigate that in a way that continuously feels constructive, is not something that I would say was my strength in the past. I am definitely someone who likes to get things done, and I'm a bit principled in my approach. But same thing happens to my team. People are coming to me and saying, Jenn, can you do this thing? Can you do this thing? And I'm saying, no, we have to put it in this roadmap. Learning how to be the customer on that side. And how do I navigate that? And how do I continue to emphasize the importance of something or being respectful and patient of the process that I'm in? And being okay with that patient. Part of it is with my partners, and part of it for me is actually with myself. It's knowing that when you're turning a really big ship, it's slow. And some months and quarters you have this moment where you're like, what did what have I accomplished? And those accomplishments are a bit abstract. They're maybe not, I delivered this project or made this great presentation. They're like I hired these people, and these people are ramping. That means in two quarters it's going to be awesome. Or I changed part of a culture around an approach. Or I encouraged another team and my team to participate together in a project. And yes, that project hasn't started, but the train is slowly leaving the station. That patience with myself, with my team, and with others, and really thinking about how to be persistent, but patient with the process, is something that I would say I've learned quite a bit about in the last 12 months...

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