EP32 - Entrepreneurial Spirit Meets Marketing Excellence with Alison Osborne

In this episode of CMA Connect, Alison Simpson, the CEO of the CMA, speaks with Alison Osborne, the VP of Marketing at Quill Inc. Osborne shares her entrepreneurial journey, her company's acquisition, and winning the CMA's prestigious Achievement in Marketing (AIM) award. She also discusses the importance of self-advocacy and provides tips for young professionals striving to advance their careers. Watch the episode on YouTube.

00:00:00:00 - 00:00:20:18
Presenter
Welcome to CMA Connect, Canada's marketing podcast, where industry experts discuss how marketers must manage the tectonic shifts that will change how brands and businesses are built for tomorrow, while also delivering on today's business needs. With your host, CMA CEO Alison Simpson.

00:00:20:20 - 00:00:46:11
Alison S.
I'm very happy to welcome my guest today, Alison Osborne. Alison's a VP of Marketing at Quill Inc. and the most recent winner of our prestigious CMA Achievement in Marketing Award. This award honours a rising star who has shown outstanding performance and promise in the marketing profession early in their career. Before joining Quill, Allison founded Origins Media House. They're a company specializing in branded podcasts that was later acquired by Quill.

00:00:46:13 - 00:01:14:02
Alison S.
Her journey from young entrepreneur to now working in marketing at a larger organization is one filled with some valuable lessons, some challenges overcome, and also exciting opportunities seized. So in this episode, we'll explore Alison's entrepreneurial beginnings, the experience of having her company acquired, and also her thoughts on the future of content marketing. She'll share her motivation around the AIM Award, and also offer some great advice for young professionals who are looking to take charge of their careers.

00:01:14:04 - 00:01:19:03
Alison S.
So I would like to officially welcome my namesake, Alison, to the CMA Connect podcast today.
  00:01:19:05 - 00:01:24:12
Alison O.
Hello, Alison. Thank you so much for having me. And, what a nice intro.

00:01:24:14 - 00:01:40:01
Alison S.
We're going to try not to confuse each other with Alison. And it's even spelled the right way. So that's that's pretty unusual. To kick things off, can you share what led you to start Origins Media House, and also what motivated you to pursue the path of entrepreneurship?

00:01:40:03 - 00:02:04:20
Alison O.
Yeah, definitely. So Origins Media House, which I will shorten to OMH for speaking purposes because it is quite a lengthy name. It started out when I was in, I believe it was my second year of university where I was going to, Toronto Metropolitan University and myself, as well as a few friends in the program I was in, as well as some other production programs,

00:02:04:22 - 00:02:27:11
Alison O.
we wanted to get a better understanding of, how entrepreneurs were building their companies, what their journeys were looking like. We were young. We were, gung ho about starting our careers. The program that we were in was very entrepreneurial focused. And, a good friend of mine actually started with the idea of, well, let's see what others are doing where we're new to the space.
 
00:02:27:13 - 00:03:04:08
Alison O.
If we ever want to start our own thing, we kind of want the playbook of what others were doing. So we began with having conversations and networking and building almost a magazine. An online magazine about, these founders' experiences. And throughout that journey, we fell in love with the production side of speaking to these entrepreneurs. So we would develop a lot of creative assets around these interviews, like videos and photography and, in some cases audio, and realized that we had a bit of a knack for it as well.
00:03:04:08 - 00:03:40:19
Alison O.
And, from there, a lot of the founders and startups that we were speaking to were looking for production work themselves, and it was kind of a natural partnership from that point forward of, we're able to almost use our magazine as a lead generation piece to then get clients to do the production work for. So with that, I would say we didn't set out to become entrepreneurs in our mind. We set out to understand entrepreneurs, and then from there naturally fell into becoming entrepreneurs ourselves.

00:03:40:21 - 00:03:58:22
Alison O.
And it was, a really fun and creative journey for us to take. And I enjoyed that we kind of had these building blocks and knowledge to use of what we had learned from who we were speaking to, to then apply to our own company.
  00:03:59:02 - 00:04:16:17
Alison S.
I love that you started this almost as a school project and really taught yourself about entrepreneurship, and then decided, this is a pretty cool path. I'm going to pursue it. And to do that with a couple of people that you had gone to school with is an amazing experience. I've also been an entrepreneur and there's so much to love about it.
00:04:16:17 - 00:04:27:17
Alison S.
I will absolutely describe it as sort of a a real world way to get your MBA. It also comes with challenges. So I'd love to hear some of the challenges that you and your colleagues overcame.

00:04:27:19 - 00:04:59:08
Alison O.
Yeah, I would say, a couple challenges and and hard lessons. We were obviously very young, so we didn't have years of career experience prior to lean back on as knowledge when we would hit some more difficult situations or decisions to be made. So we failed fast and learned quickly and mistakes that we made were things like, the importance of lawyers when it comes to contracts and things like that,

00:04:59:08 - 00:05:31:12
Alison O.
and some of those mistakes cost a lot of money and really hurt. But we learned from them. And I think because we were, again, so young and excited with this experience and, fresh in the entrepreneurial landscape. Although those challenges were tough, we were very agile with them as well. And, we were able to move and pivot the company as we saw fit.

00:05:31:14 - 00:05:44:23
Alison O.
And, if something didn't work, we scrapped it.We moved forward. We didn't dwell on it. And, it was, I think the mindset that we had around the company was, was a good one to have at that time.  
00:05:45:01 - 00:05:56:15
Alison S.
That's amazing. And some of when I look back on my career, the painful lessons are absolutely the ones that you're never going to repeat and will stay with you decades from now.
  00:05:56:17 - 00:05:59:03
Alison O.
Yes, yes for sure.
  00:05:59:09 - 00:06:18:03
Alison S.
Now, I want you to walk us through the acquisition process. When Quill acquired OMH, what were some of the key considerations and challenges that you and your co-founders faced as you were deciding to sell your company? Because that's such a big decision. In many ways, this is your baby. you've worked hard together to build it, and then you think about when and are you ready to sell it?
  00:06:18:03 - 00:06:20:02
Alison S.
So I'd love to hear more about that.

00:06:20:04 - 00:06:45:21
Alison O.
Yeah, yeah. So we were about, I want to say, 4 or 5 years into, the growth of our company. So it was relatively well established. And at that point in time, we had noticed maybe about two years prior that there was starting to be a new medium taking the stand. And that was podcasts, and we had a knack for that audio piece, too.
 
00:06:45:21 - 00:07:09:16
Alison O.
And we were creating podcasts for ourselves, for the company, and then naturally had some of the companies that we were working with come to us and ask for a podcast for their company. And at this time, Branded Podcast was such a new term. It was very fresh for companies to start using this as a marketing tool. And we noticed that there weren't a lot of agencies in the space that were focusing on that audio piece.

00:07:09:16 - 00:07:46:11
Alison O.
So, we pivoted our company to become primarily just a branded podcast production agency. And, at that time, Quill was also coming to market, which they were a market, a digital marketplace first, and then also a podcast agency second. And we ended up partnering with them on a couple projects, with various clients. So we were lucky in the sense that we had already had a tester of knowing that the two companies worked well together and that we enjoyed their team, they enjoyed our team.

00:07:46:15 - 00:08:14:17
Alison O.
We brought a lot of the production and creativity background. They brought a lot of the, biz dev knowledge. So it was quite a natural partnership. And then in 2020, there was, final decision of they approached us with an offer for an acquisition. And at that time in our lives, we were all again, like I said, 4 or 5 years into this, it was a really great experience.

00:08:14:17 - 00:08:41:15
Alison O.
We we absolutely loved it. But we were also tired. And this was the only career experience to, to an extent that we had had. And we were ready to try something new. And, and as I'm sure we'll discuss as well, join a bit of a larger company and have more resources and also take a bit of a step down and enjoy being employees for once versus, creators and decided to, to make that decision.
  00:08:41:15 - 00:09:09:04
Alison O.
So but I would say the key things that we looked at were the synergy between our two companies, which again, we were lucky to know worked well. We looked at what all of our roles and futures were going to look like at that company. So where Quill saw us fitting in and what our departments would look like and the autonomy that we would have over those departments, that was a big piece as well.

00:09:09:09 - 00:09:33:04
Alison O.
And then also just the future of and the vision of Quill and where they saw the company going and did align with how we feel about content, how we feel about audio, do we feel excitement towards it? And we got to be a bit, I would say selfish in that, what do we want? And personally, what do we want our career paths to look like?

00:09:33:04 - 00:09:35:01
Alison O.
And will this support us?

00:09:35:01 - 00:09:58:22
Alison S.
It's amazing. It sounds like such a great coming together, two organizations and to your point, like being able to work with the people when you were two separate companies that immersed in their culture. Because often what will make for a very bad partnership is its very different cultures. If there's not complementary skill sets, and if you're not bringing something new, instead you're bringing more of what they're already doing,

00:09:58:22 - 00:10:26:06
Alison S.
and it sounds like, your business And Quill was highly complimentary from a cultural perspective or from a talent perspective and from a product offering perspective. So, very good. Yeah. As you mentioned, even with all of those things working to your advantage, going from your entire career, being an entrepreneur, in control of your own destiny to a large degree, to becoming an employee, it's a fascinating transition that's also rich with learning.
  00:10:26:08 - 00:10:29:17
Alison S.
So I'd love to hear you share some about that experience as well.
 
00:10:29:18 - 00:11:04:10
Alison O.
Yeah, I, I mentioned this before, but, we are all and to this day so very lucky that although now employees, we have a lot of autonomy over our departments. So rather than being co-founder and CMO, I now got to transition to just running the marketing department. So all those co-founder responsibilities and weight on me was lifted. And I got to feel as if I have this sense of entrepreneurship.

00:11:04:10 - 00:11:26:09
Alison O.
Still, with the autonomy of the department, I now get to run. But it's all focused on the area of my job that I love the most, which is marketing. And I again, to this day, still get to make a lot of the decisions of where are we going with this? What is this going to look like? What are our next steps?

00:11:26:15 - 00:12:09:01
Alison O.
And feel that entrepreneurial, creative spirit that is still alive. But now, just as an employee versus an owner. And of course, it was an adjustment, for myself as well as my co-founders and also an adjustment for the team members that we carried along with us through the acquisition, too. But I think that at that time and even now, it was a good decision for me to be able to hone in on my skill and marketing even more, because now that's where I got to place my emphasis and also be a bit more selfish in my own career.

00:12:09:07 - 00:12:34:09
Alison O.
And think about myself and what I want moving forward versus always having the worry of keeping the lights on and the employees happy, which of course, as a manager now, I still think about and I worry about, and I want to make sure my team members are happy, but it's to a different degree. And, and yeah, so I would say it was, an interesting transition, but a good one.

00:12:34:11 - 00:12:48:16
Alison S.
And to your point, you get to focus on the part of the job you love. And that way and I can totally relate to even when you said the word weight, there was a yeah, that's real. Like you're not just worried about paying your rent and your mortgage and your bills. You're worried about everyone that's working for you.

00:12:48:16 - 00:13:11:01
Alison S.
You feel an accountability for making sure the business is solid and thriving so that they also have that security. So I can totally relate to that weight being released and really being able to focus. Then you also called out like, this is a big decision for you and your co-founders. It's also a bit scary for the team at your organization who are now going to become part of a new organization.

00:13:11:06 - 00:13:14:21
Alison S.
So how did you help get that uncomfortable through the process?

00:13:14:23 - 00:13:56:04
Alison O.
Yeah, I, I think that, the early on, partnerships that we had with Quill from the beginning helped for sure, because now the team was familiar with the name, they were familiar with the leaders of the company, with the other types of team members that we would be working with. So that wasn't a surprise. I also think that because we were doing the same thing, it was now, it wasn't that they had to change the tasks that they were doing, and the even the types of companies that they were working with, it was just going to be under a new name and with a bigger team with more resources.

00:13:56:06 - 00:14:30:21
Alison O.
So of course, we had sit down conversations with our team and for some of them, that were primarily contractors versus full time, decided not to come along with the acquisition. And we had conversations with those, and that's okay. But for the team members that did decide to, to follow through with the acquisition as well, I think that because it was just such a natural partnership, it wasn't as big of a friction point because they got to do what they were doing under each.

00:14:30:21 - 00:14:31:20
Alison O.

 Anyways.
00:14:31:22 - 00:14:43:21
Alison S.
Yeah, so much about changes the unknown. And to your point, because you had a chance to work together as two teams coming together with a shared purpose that takes a lot of the unknown and the fear out of it for sure.

00:14:43:23 - 00:14:46:07
Alison O.
Yeah, yeah, exactly.
  00:14:46:09 - 00:15:00:22
Alison S.
Now, you've mentioned a couple times being selfish about your career, and I don't think you're being selfish about your career at all. I think what you're doing is managing your career, so I'd love to hear how the acquisition and your new role at Quill has opened new opportunities for your career growth.

00:15:00:22 - 00:15:35:20
Alison O.
Yeah. In many ways, the first I would say is they have dedicated a lot of resources and to, team members for our own personal growth, in our careers, for example, I worked with a, growth marketing advisor for about a year, and, he, I credit him to a lot of my perspective on growth, falling in love with data marketing.
 
00:15:35:20 - 00:16:12:20
Alison O.
And that piece of the puzzle was previously I was very much more content focused branding focused, didn't have that knack for the data piece, the data and growth and even product marketing piece, and he really honed that skill with me. So having resources like him on deck to be able to utilize and, leverage and shape the career path that I will be pursuing in the future, continuing to move forward as well as, we launched a analytics and, podcast insights product in 2022, and that has been an amazing experience.

00:16:12:20 - 00:16:44:17
Alison O.
And, previously I had never worked on any sort of product. So it's been an entirely new piece of the marketing puzzle for me that I've gotten to learn about and own and shape and refine my own skills and perspectives on. So I would say elements like that that just lend to a larger company where you can do a bit more, invest a bit more, play with bigger budget and have more people to utilize.
  00:16:44:22 - 00:16:50:19
Alison O.
It's opened the doors for where I see myself moving forward.

00:16:50:21 - 00:17:09:18
Alison S.
That's such great learning. So knowing that Quill specializes in branded podcasts, I'd love you to share your insights on the rise of this medium. You mentioned it a little bit earlier. It's still relatively new, but particularly on the Canadian market. What trends are you observing and what do you think has led to the rise of branded podcasts?

00:17:09:19 - 00:17:39:00
Alison O.
Yeah, I think that it's a pretty common opinion that typically the Canadian market is, quite a bit behind the US market when it comes to a variety of things, including media. And we felt that for sure over the past few years. And I would say it's been relatively recently that we're feeling a lot of growth and a lot of investment in the Canadian market when it comes to branded podcasts in particular.

00:17:39:01 - 00:18:11:08
Alison O.
And I would say a big reason for this being is that the medium is very effective for not just like awareness and reach and positively shifting brand perception. And those more top funnel activities. But I think that it does a great job at humanizing a brand because it's not common, especially for larger organizations, for customers to see the people behind the brand.

00:18:11:10 - 00:18:51:11
Alison O.
And podcasts do that really well at giving a voice and a face and a personality, to a company. And I think that piece of the puzzle is really powerful and what brands are leveraging the most. And from there, I think that it forms, relatively, deep and strong connection between brand and listener. But I will say that this means producing a piece of content that is actually valuable to the listener.  That is something they would want to listen to for 30 plus minutes.
00:18:51:17 - 00:19:17:05
Alison O.
And, not an extended infomercial for your company, because I don't want to listen to that. You don't want to listen to that, and no other listener will want to listen to that. So there's quite a fine line when it comes to branded podcasts of yes, it's by a brand, but it's not the content that your brand wants to create, it's the content that the audience actually wants to listen to.  Which there are some doing really well in the space.

00:19:17:05 - 00:19:49:10
Alison O.
For example, within the Canadian market, SickKids hospital has an amazing podcast called Sick Kids Versus. And, they take listeners to the frontline of the fight for child health. And you hear from doctors, hear from family members. It's a beautifully edited podcast. And, another one is even the, Team Canada with the Canadian Olympics. They put out a podcast called Momentum this year, hearing from female, athletes that were preparing for the Olympics, which was a really cool podcast as well.

00:19:49:13 - 00:19:59:18
Alison O.
So I think we're seeing more shows come to market and more brands get creative with the type of content that they're producing.

00:19:59:20 - 00:20:26:09
Alison S.
Those are great examples. And in an age where authenticity and consumers' desire to call BS on brands that aren't being truly themselves is at an all time high, podcasts really do create a great opportunity to have a very open and honest conversation when they're well done. There's an intimacy to it that you can't get another marketing and media vehicles that can be incredibly powerful.

00:20:26:11 - 00:20:53:01
Alison O.
I, I completely agree. And, I think that there, they're not to be slept on. They're a, a really impactful medium. And even with the clients that we are working with, we see benefits beyond what we all set out for when producing the podcast and even things with the guests that they invite on to the show. The relationships and partnerships that they get to build from there.

00:20:53:03 - 00:21:08:03
Alison O.
The feedback that they get from audiences of how it's helped them throughout their own careers or change their mindset when it comes to certain industry or topic. It's a really impactful content form. And, and I'm excited to see more Canadian brands are using it.

00:21:08:05 - 00:21:25:04
Alison S.
So looking ahead to 2025, which is shockingly a few short weeks away, what shifts and trends do you anticipate, and we'll broaden the conversation, in content creation and marketing. And then what recommendations would you give to marketers who are listening to effectively navigate these changes?

00:21:25:06 - 00:22:00:12
Alison O.
Yeah, I, this feels like a very generic answer, but I think it's still so important. And of course, as a content agency, we're going to say this, but, content. I think that content is so important. And if you don't have a strong content strategy, then you're going to be left behind, whether that involves podcasts or not. And with the rise of AI, I think we're seeing more content than ever before, but less content that's punching through the noise.

00:22:00:14 - 00:22:32:02
Alison O.
And I think that's where the sweet spot is, is not saying to not use AI in any capacity, but, more so focusing on creating content that, is well researched is, focused on thought leadership, is taking a unique perspective, is showcasing your brand's true opinions and ideas, and is just something different than what we see out there that, feels very repetitive and, cookie cutter.

00:22:32:08 - 00:23:11:22
Alison O.
So I think in 2025, we're going to see more brands getting creative with how they produce content. And of course, we're a podcast agency. So I primarily have podcast examples in my head. But, for example, another agency produced a really cool podcast called, Murder in HR, and it was a for an HR software, and they made a full, almost true crime style fiction series about, a, assassin, I believe that was in an HR department and had to uncover, like, who was committing these murders?

00:23:11:22 - 00:23:29:16
Alison O.
I don't know the exact storyline, but, it was a really cool idea and something that I don't think we see typically in B2B marketing especially. So I think we're going to see more of that of content that stands out, that catches attention, and that goes a bit against the grain.

00:23:29:18 - 00:23:31:22
Alison S.
That's a great example. I'm definitely intrigued to find

00:23:31:22 - 00:23:33:00
Alison O.
out, which HR

00:23:33:00 - 00:23:44:11
Alison S.
would be the of all the departments you want to be the most adhering of standards on the topic? Yeah, a murder mystery podcast is a very intriguing example, so thanks for sharing that.

00:23:44:13 - 00:23:46:01
Alison O.
Yeah. Of course.

00:23:46:03 - 00:24:07:19
Alison S.
Now, Allison, you nominated yourself for the AIM award, so I'd love for you to share what motivated you to put yourself forward for this recognition. I also want to applaud you for that because thank you. So few marketers of any age, especially that are newer in their or earlier in their profession, and certainly women. We don't tend to raise their hand and say, you know what, I deserve this.

00:24:07:19 - 00:24:22:00
Alison S.
I am going to nominate myself. So huge kudos to you for doing that, and I'd love to you to share your story on why you decided to do that. And what advice would you give to other young professionals, particularly women who may hesitate to seize such opportunities?

00:24:22:02 - 00:25:16:22
Alison O.
Yeah, I, thank you. First of all, and, I think that myself, as so many people in their careers, of course, struggle with imposter syndrome to some extent, incapacity. And I think for myself to overcome that, I really hone in on a practice of taking a step back and, observing my career at large. Or even if that's too large to look at, even the past quarter or six months or year and taking stock of what I have done, what I've supported other people and achieving, and where I plan on heading. And with that, it's helped me to feel more confident in my own role and, also my future of knowing if I managed to

00:25:16:22 - 00:25:37:14
Alison O.
get here, I'm excited for what the next years will look like and even, to put that into practice, something that I've started doing that has helped and I recommend for others to do as well, is usually on a if I can do it on a weekly basis, typically does not end up being this maybe a monthly basis.

00:25:37:16 - 00:26:06:00
Alison O.
I try to make a list of just the highlights of the month. These are the key things that I achieved. Or again, I supported someone else in achieving. And then at the end of the year, I end up having this master list of what the year looked like for me. And those are always a bit of a shock to look at at the end of the year of Wow, there is a lot on there because when you're in the day to day, it's hard to realize and take note of what you have done, especially in marketing.

00:26:06:00 - 00:26:40:17
Alison O.
When one thing's done and you're moving on to the next so you don't take the time to appreciate how far you've come and what you've done. So that has helped to combat that a bit for myself. And then I also think it's who you're. So you surround yourself with. I am really fortunate to not only have an amazing team and, amazing coworkers that, make me feel valued and highlight what I've achieved and encourage me for these types of awards to participate in and submit in, but also my community and network at large.

00:26:40:19 - 00:27:03:21
Alison O.
Which I spent a long time, trying to build a community of the type of people that I want on my side and around me. They have been a huge help to further my career, to hone in on the direction I would want to go in, and to make me feel confident when it comes to these types of awards.

00:27:03:22 - 00:27:19:07
Alison S.
That's outstanding advice. I really like the monthly highlights in particular, because even like no matter how much we all love our jobs, there are days and sometimes weeks where it's really not a lot of fun. So to be able to go back to that list and remind yourself of what you're capable of and what you've accomplished would be incredibly rewarding.

00:27:19:07 - 00:27:20:12
Alison S.
So well done.

00:27:20:14 - 00:27:31:20
Alison O.
Yeah, yeah, it I recommend it. It's sometimes it's hard to get myself to do or even you forget because if you're doing it on a monthly basis, a lot happens in a month. But I do recommend trying to do it.

00:27:31:22 - 00:28:01:12
Alison S.
That's great. Well, if you're not doing on a monthly basis, then at the end of the year you're trying to think about, yeah, what did I accomplish? I really want to do so I would love to close off by having you share one piece of advice for our listeners, knowing that we're primarily a marketing marketers tuning in today, as people are thinking about the Christmas holidays and Hanukkah and then kicking off 2025, what advice would you give them to set themselves up for a really spectacular 2025?

00:28:01:14 - 00:28:37:11
Alison O.
My advice would be to be really curious in 2025. I think there are so many new ways to use content new platforms out there, new, companies on the rise. And I think when we lose curiosity, especially as marketers, we, risk becoming stagnant. And that curiosity piece is what drives myself and, drives my own creativity. And I think that's something we can all have a little bit more of.

00:28:37:13 - 00:28:49:00
Alison S.
Alison, I have thoroughly enjoyed this conversation. I am very proud to share my name with you, and you're such a deserving recipient of our 2024 CMA Award. So congratulations again.
 
00:28:49:02 - 00:28:59:21
Alison O.
Thank you so much. And thank you for this call as well. It was a great chat.
  00:28:59:23 - 00:29:12:12
Presenter
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