CFO Chronicles: The Secrets Behind Success

How Gamification Can Significantly Increase Client Retention with Bill Dillmeier

• James Donovan • Season 2 • Episode 23

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Unlock the secrets of financial success with our special guest, BIll Dillmeier, the mastermind behind Aperture Advisors. Journey with us as Bill shares his inspiring transformation from a traditional finance professional working with giants like Vanguard and Morgan Stanley, to a venture capitalist and private equity innovator. Discover how pivotal moments, including the 2008 financial crisis and his time with Bill Gates at Corbis, carved a new path for him, expanding his expertise beyond finance into the realms of global sales and the startup ecosystem.

Explore the fascinating world of gamification and its transformative impact on business engagement. Bill and I discuss the challenges faced by the stock photography industry and how digital adaptation was key to survival. We dive into the power of gamification not just as a buzzword, but as a real strategy deployed to enhance employee engagement and customer loyalty through innovative point systems and rewards. Even engineers at major space agencies find value in these strategies, proving gamification’s universal appeal and effectiveness in business interactions.

Get ready to elevate your professional game with insights on badging, credentialing, and data visualization. We break down the importance of platforms like Carrot and GitHub in recognizing talent and how visual tools can align and drive business momentum. Bill shares his strategies for leveraging LinkedIn to build a robust professional community and the shift from traditional SaaS pricing to more dynamic, usage-based models. Whether you're an entrepreneur or aspiring CFO, this episode is packed with valuable strategies for networking, branding, and business development in vibrant startup communities like Seattle.

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Speaker 1:

Welcome to CFO Chronicles the secrets behind success the go-to podcast for fractional CFOs and accounting firm owners who want to attract more high-paying clients and increase their revenue. Hosted by James Donovan from Nine Two Media, this podcast dives into marketing strategies specifically designed for lead generation and client acquisition. In each episode, you'll hear from industry leaders sharing their success stories and expert tactics to help you sign more lucrative clients and grow your business. Tune in and discover actionable insights to transform your marketing efforts and boost your bottom line to your bottom line.

Speaker 2:

We're joined today by Bill Dillmeyer, founder of Aperture Advisors. Bill specializes in helping venture capital and private equity portfolio companies navigate complex challenges with data-driven insights and strategic guidance, from improving operational efficiencies to driving measurable growth. He's here to share his expertise. Bill, thank you so much for joining us today.

Speaker 3:

I'm excited to be here. I've been looking forward to this for a while, awesome.

Speaker 2:

Awesome. So, bill, you were telling me just before we hopped on here, based out of Seattle. Tell me what it's like this time of year. I'm sure you know the weather's changing.

Speaker 3:

It's getting a little chilly there um, relative to the rest of the country right now it's actually. It's not that bad. It's probably, you know, in the upper 20s. We'll see swings from you know 20 to in the mid 40s today. And you know, the one thing I will tell people and this is a really well-kept secret is that it does not rain nearly as much as people think it does in Seattle. I tell people it's much more on a gray kind of sense from like. I always bookend it between sort of Halloween and like basketball season in March madness. That's when you're most apt to be gray and get some rain. But you know you come here in the summer you get 90 plus days, bluest of blue skies, no humidity. So it's one of the best places in the country to visit. Interesting.

Speaker 2:

Yeah, cause I've heard a lot about Vancouver, being Canadian, that it's always raining. Everyone says they love Vancouver, but it just always rains and I, I don't know, I couldn't, I couldn't do with that.

Speaker 3:

I will say that there are days where I feel like there's a degree of vertigo during the winter, where 10 o'clock feels like noon, feels like two o'clock. It's like I tell people, it's like you're trapped in a casino because you don't get any sense of like change of light pattern or like where you are in the day. So you know, my recommendation is you know a lot of vitamin D and you know, get out and exercise as much as possible.

Speaker 2:

Interesting. So, bill, tell me a little bit about how you got started in your background, leading into Aperture Advisors.

Speaker 3:

Sure, it's a great question. It's what I think is an atypical story. I came up through a very traditional financial services rank at large companies. So I started my career at Vanguard, the mutual fund company Trem. Tremendous experience, learned a ton, you know, went and got like my series seven, my series four, my series 63, and really was immersed in the financial capital markets for a long period of time. And then I actually transitioned over to Morgan Stanley Institutional on the fund management side of the business. So I was actually working for the president of the mutual fund company for a good bit of time doing a lot of analytics board reporting things like what's the investment thesis of our portfolio and how does it stack up to other people who have that same thesis and how does it stack up to other people who have that same thesis. So it was a nice way for the board to be able to go ahead and look at the efficacy and the returns that the portfolio managers were bringing back. And then we also flipped it to say who charges what we charge for an institutionally managed portfolio, to go ahead and make sure that we were competitive and allow us to deliver that most amount of value to our shareholders.

Speaker 3:

After that I actually spent a lot of time in mortgage banking. I tell people I was in mortgage banking when it was cool to be in mortgage banking. So I got to work for some really interesting companies. Actually, at one point I used to call Bear Stearns and Lehman Brothers and sell mortgage-backed securities. So at one point I used to call Bear Stearns and Lehman Brothers and sell mortgage backed securities. So at one point I was delivering about a billion dollars a month of securities into the open market. And then, kind of fast forward, I got recruited to come out to Seattle, worked for that bank, formerly known as Washington Mutual. So from the, you know, 2002 to 2008,. Worked for the CFO of the mortgage company running planning strategy, analytics. And from there around about June of 2008, you knew there was just something a little bit askew and, as I always say, it doesn't take more than three finance guys in a room with a whiteboard to kind of plot things out, and so we're like these numbers just don't continue to add up, and for me that was like the wake up call. So I jumped out of banking and went to work for Bill Gates for a number of years, worked for a media company that he owned here in Seattle called Corbis. So we would compete against companies like Getty Images in the stock photography space and there I was able to run global FP&A, global treasury and actually stretched my career into running global sales operations. So for me it was a nice way to move from being behind the numbers to being much more immersed in the business and that for me was probably one of the biggest transition points in my life. That sort of catapulted me to where I am today.

Speaker 3:

After working for Corbis and being able to travel to a number of different places around the world, see our offices, meet our customers, really then started to go into startup land. My first startup was actually a portfolio company from a venture capital firm here in Seattle called Madrona, and I joined relatively early. They had just done the B round and I was really the first finance hire, came in, built out a lot of models and helped them get from $8 million to $20 million in ARR in less than a year and from there set the path to future rounds of funding, going ahead and helping them scale, and you know they were very fortunate to have an exit this year for I want to say 1.5 billion to a private equity firm in San Francisco and after that was able to work for some other really cool startups. There's actually a company here in Seattle called Carrot. They actually interview software engineers on behalf of other companies. So it's an interesting market. It's honestly more like a two-sided market like Uber, because you have interviews coming one way and then you have people who are going to conduct these live interviews on the other side. So for me it was very much of that contextual switching back and forth about how to be able to go ahead and deliver the right number of interviews and have a balanced staff. And there we actually did a C round for 100 million and they actually hit unicorn status.

Speaker 3:

After that, and really my last two roles, I've been interim CFO for some interesting startups. One was based in Texas. I always say that they are the sort of the Khan Academy for med school students. It was a video platform that allowed medical students to go ahead and supplement their education and it was a B2B and a B2C play. So really got to see both sides led finance strategy operations partnered deeply with our investors to be able to go ahead and tell that story. And the last one was a rewards platform for hourly shift workers, which is sort of an interesting take on. You know, these are people who are traditionally like the lower end of the wage scale and it would be like James come to work, here's 10 points for coming to work. And these points were redeemable ultimately for gift cards, but it was a way to promote engagement and give these people sort of an opportunity to engage in some game theory, to go ahead and bring some enrichment to their careers. And really, after those two projects ended, I've been really building Aperture Advisors. So our focus is on going ahead and working with, you know, pre-seed, all the way through Series B companies and being very much of a financial partner through series B companies and being very much of a financial partner.

Speaker 3:

I think right now I would describe myself as a strategic growth architect and that I like to look at the entire span of the company and then be able to come in and help diagnose and then deliver that most amount of value. I've been super fortunate. I've actually run traditional finance sales operations. I can understand the marketing funnel, can talk to sales leaders. I actually enjoy talking to sales leaders a good bit because there's always that tension between finance and sales. Honestly, the first thing I say to my sales leaders are I want to make you the richest person in the room, but in order to get there, there we're going to have efficient growth. I'm not going to go ahead and buy my revenue. I'm not going to overpay in commissions to drive revenue. It's going to come at the proper degree of scale. So it's really coming in, looking at the big landscape and then adding the most amount of value to where that customer is in the journey.

Speaker 3:

That's a lot.

Speaker 2:

That's quite the resume. That's very cool. I have so many questions based off of what you were just explaining there. I definitely want to come back to what you're doing now with Aperture, but there's a name that stood out there Bill Gates. Did you ever have any one-on-one time with Bill when you were working for his company?

Speaker 3:

working for his company. I actually had the that's a great question. I actually had the distinct honor of building the finance presentation layer that he would read every other month, so I was fortunate enough to meet him a few times. I spent most of my time prepping my CFO, you know, literally writing out talk tracks. He was very old school, from like a public company where he had a prepared script, so we would spend hours looking at slide sorter and going ahead and building the story arc and getting that message just right. I always got tremendous feedback and I was always very grateful for what Bill Gates had to say about my work and it really was a pivotal time.

Speaker 3:

Corbis was what I think of was a true global transformation, but also a true digital transformation. This is, you know, 2008-ish, where commodity prices for stock photography are just falling and anybody with a digital camera could be in that space. Funny enough, by definition I'm a professional photographer because some of the images that I took were actually put up on a website and sold. So the barrier to entry was incredibly low, but we were trying to go from a film negative into a digital image. That I say usually is probably about the size of your palm and it's going to be on every newsfeed in America. So how do you create an Amazon level transaction velocity for an image that's super small, super transactional? So we had to really shift the mindset of our Salesforce from, you know, selling almost like a baseball card. You're like, hey, do you want this picture? Do you want this picture to this picture to opening up an entire catalog, to be able to go ahead and really serve our customers, which are books, magazines, newspapers, wire services, to get them the right image at the right time.

Speaker 2:

Interesting. That's so cool. You also spoke about I forget the name of the company, but you mentioned there was a gam gamification taking place a points system for just for coming into work, correct, here's points. You know you're still getting paid, but just a little bit of added incentive and here's some, some rewards in the the form of gift cards. I I've noticed that.

Speaker 2:

Um, I'm not sure if you're familiar with Alex Hermosi and the new platform he's backing with Sam Ovens called School. Anyways, they they're very big on gamification to get engagement inside your communities on school. So the more like and you can customize it, the more you like a post comment, et cetera, you maybe unlock access to other courses, whatever it is. I know a lot of companies use gamification as a huge retention play. I'm curious if you've seen that work elsewhere, if you've been a part of any other businesses or maybe firms you're working with now, if you even present that as a strategy to them of hey, let's use gamification to get more out of your customers, let's get more out of your customers, let's get more out of your employees, whatever that is. Can you speak a little bit to that?

Speaker 3:

Sure, yeah, I've seen a lot of companies, both internally and externally, try to use gamification. From an internal perspective, it's much more around employee engagement. You'll hear companies do kudos, rewards, and you can then give points to people who have done amazing things, have gone beyond and beyond and from there. Those are ways to go ahead and not only promote recognition across a team and create community, but also, you know, there is a little something at at the end. I was actually having dinner last night with um, some engineers from some really notable space agencies and they were talking about how that is a very common practice where, in order to promote all of the different disciplines in engineering, that you will be given an allotment of points to go ahead and be like hey, you're a hell of a mechanical engineer and you really helped me out on delivering X. And externally, I think a lot of companies mechanical engineer and he really helped me out on delivering X.

Speaker 3:

And externally, I think a lot of companies are seeing the benefits of gamification. Look at the role of badging and being able to go ahead and have some degree of credential. That was actually one of the things that we talked about at Carrot, because they were interviewing software engineers. You met the bar to work at Fortune 100 companies in technology and if you didn't get the job, but you were at least qualified, that could actually be something on your resume to say I am certified to do X or Y. And there's actually a project that I'm working on right now where we're thinking about a spin on github and thinking about github for a different audience as well yeah, the badging.

Speaker 2:

I mean, as soon as you mentioned that what stands out is, uh, meta, you know, giving people their their official badge on instagram and how it was so cool if you saw it was like, wow, that person's verified. And now it's at the point where I mean, you can just buy the badge or whatever it is, but, like now, they're even taking that gamification and modify and monetizing off of it. And I know there's a ton of other businesses out there where, like, credits are applied and it's just at the deeper level. It's really such a strong retention play and I not a lot of people, I think see it for what it is from, like that higher level business perspective, but it's such a strong form of retention.

Speaker 3:

Oh, exactly, and even like I'm a huge hiker runner and you know I have a garmin watch like most people do, and every week I'm in a competition for you know, a hundred thousand steps, 200,000 steps, and you know you just keep looking at your ranking. You're like, oh, all right, you know Sally in Michigan is kicking my butt today. You know like I got to get out and get on the trail or squeezing some miles and there's also some longer play rewards. It's like last year I walked the length of the Appalachian trail, so I walked over 2000 miles last year. But it was nice just to see my progress. And you know you get badges as you're unlocking, like different points and it's just a cool way to kind of keep you in tune within a community and you're ultimately competing against yourself, but it's always nice to see the support from others.

Speaker 2:

Yeah, that's really cool. I mean to see, yeah, how far you've walked in the year. But I think there's something to be said for a lot of businesses of where can they add in that gamification? Because, ultimately, what Garmin is doing, you're using their platform all the time and you're like I'm not going to switch off of Garmin because I want to compete. Like you said, sally, you know across the country, I want to see how far I've walked, but Garmin is keeping your attention on their product. I think there's so many different ways to get creative about gamifying your own product to keep your customer's eyeballs on your product, on your widget, whatever it is you're selling, and I think it can be done for any industry. It's just a matter of getting creative.

Speaker 3:

Oh for sure, and I'm also a big fan of data visualization. So, like so many people have different learning styles, but I've often found that a lot of people will drift towards visual. So I'm working internally with a team like I will go ahead and set up a full-blown data visualization and we'll harness API feeds from Salesforce NetSuite and bring it all together, and that is week to week. You're measuring the charts. You're seeing that gamification mindset of like. You know I killed it on SQLs last week. Our funnel is really moving in the right direction. And then it's all been about a momentum play and you know, some people think of themselves as like momentum investors, where you invest in a stock that has some legs to it, and I think that's a very common business mindset, and whatever way you can do to go ahead and create that visualization to gamification in your mind is such a great way to align management teams and leadership teams.

Speaker 2:

Yeah, absolutely. And leadership teams yeah, absolutely. Bill, tell me a little bit about how you're going out and finding new clients to work with at Aperture. How do you get new people to the door? What's been working well for you?

Speaker 3:

That's something that I will say is a work in progress For me. I start with thought leadership, so I post on LinkedIn Monday through Friday. Two weeks ago I did a five-part series on the fractional CFO revolution and so over the course of the week I wrote really nice leadership pieces about the different aspects of when to get a fractional CFO, what are some of the benefits of getting a CFO. The week after that, I did the importance of being a finance business partner. So for me, I've got a really strong community of people who really like and enjoy my content. That's actually spurred a lot of conversations.

Speaker 3:

The other way that I've been really doing biz dev is getting out into the community. Seattle's a really vibrant startup community. There's a group called Startup Grind. They're all over, you know, major cities in the US. It's a great way to meet young entrepreneurs, people with ideas, investors, bankers. The other way that I've been really doing it is bankers. The other way that I've been really doing it is working with an accelerator here in town and have met some talented folks. We actually had an all-day event a few weeks ago. It was a sort of little mini pitch competition, but there were also people who were angel investors looking for their next round, young companies that were pre-seed or just getting funded, that didn't really know what the next leg was in their financial journey to be able to go ahead and tell that story. So those are the primary places that I've been doing biz dev, but always appreciate feedback and opportunities to learn more.

Speaker 2:

Yeah, awesome. I love that you're publishing content on LinkedIn. I think it's an undervalued strategy that a lot of people aren't doing, and it's just a way to really get in front of the people who you want to be reading your content. And it's not even about the amount of engagement that's on it. It's just about the consistency that it's out there and that's going to continue to get recycled and and republished on LinkedIn for lack of better words. So it's not about, okay, I only got a couple likes or whatever the engagement was, doesn't matter. It's out there, it's going to help with your SEO as well, and it's just again showing you as that thought leader that you're speaking about. I hope you're putting this under the newsletter brand and not just individual articles.

Speaker 3:

I've been experimenting with that. I probably need to do a little bit more around that and there's sort of posts, like you said, versus blogs, versus newsletters. I've been sort of experimenting with a number of different formats to be able to get out and do that. And, you know, one of the best ways to actually drive content is to like and comment on other people's comment, and I've been able to meet some amazing investors, people who I never thought that I would ever have the opportunity to be in their same orbit. But, you know, just after some amazing LinkedIn integration, you're like they're, you know, coming back to me and I've started some amazing conversations as a byproduct of that as well.

Speaker 2:

That's awesome, yeah, commenting, liking, engaging in other people's things on LinkedIn, your newsfeed. It's always bringing your name and your profiling back into others, so you really get to tap into so many different circles by the smallest action. So we're always telling our clients hey, everything we're doing for you Awesome. But don't hesitate to jump in there Like a couple of posts throughout the week. Comment, give your feedback somewhere else. Provide value, because now you're selfishly, you're bringing traffic back to your brand on LinkedIn, which, in turn, if you have your sales funnel set up properly on LinkedIn, it's going to spark conversations for yourself. So lead with the value, but it is going to just put you back in front of everyone who you want to be in front of. So that's a great play.

Speaker 3:

Yeah, and don't ever underestimate the power of just a cold outreach. I mean, you know there's, sure there's. Maybe you know you put a little bit of lead magnet in there. But you know, lead with your authenticity and like talk about your pedigree and how you can think about collaborating.

Speaker 3:

You know you just can't go in and be like hey give me a job or hey, you know, let me send you a contract. It's about I have similar interests, similar experiences that I could help at a portfolio company level. I'm an operator. I can understand the pains that you go through. And from there, once they start to see you're not necessarily asking for something in the first round, it's a way to kind of go ahead and unlock that conversation to be able to say you know, this is someone whose thoughts you know could help augment where we're going and bring you a fresh perspective.

Speaker 3:

Because I mean for me right now, you probably see, like the move from traditional SaaS pricing where it was very linear, you know, $12,000 subscription and nearly $1,000 a month. So many people now are transitioning to usage-based pricing and that in and of itself is a bit of a mindset reset. So that how do companies now think about what revenue is really going to look like on a consumption basis? I tell people, if it's not consistent, it's going to look like an EKG meter. Because you're giving that customer that opportunity to be like I'm going to use your tool in January, I'm going to take a break until March and then I'm going to come back in December. It makes the financials look really, really wonky and it's sometimes a hard message to explain to investors.

Speaker 2:

That's so interesting that you bring that up. We use a tool called Zapier and there's. Are you familiar with Zapier? Oh, yes, yeah. So with Zapier they have a neat model where you're paying a flat fee per month up to a certain threshold of what your usage looks like, and then you're you're consistently re-upping. So for them, I would assume it helps with that fluctuation of, like you said, only using in January, taking a pause, where, if you still want to have access to all the things you've built, all right, at least you have to maintain at that certain level because you still have your tasks that are eating up your usage. So there's a lot of different ways to skin a cat, but that one I mean. They're getting our money every single month.

Speaker 3:

Oh yeah, I think from a retention play it makes so much sense. It makes it much easier to get into like a three tier pricing model, like a kind of a bronze gold, platinum type of thing, so that as you consume more, you're getting pushed organically into different price tiers that are lower. So you're getting rewarded for more usage with lower price, but you're just becoming more and more stickier and it's going to the unwind cost is just going to be absolutely brutal if you were to try to get out of it. Because, yeah, zapier for me has been a great way to move data super efficiently between platforms, get messaging out. No, I think it's a great connector tool.

Speaker 2:

And it's tying back into that gamification, like you were talking about the different levels of, like you know, bronze, silver, gold, platinum, and you're just you're moving up the ranks organically, whether you like it or not, and they don't even have a sales rep making all those sales.

Speaker 2:

It's just a natural upgrade by the click of a button which is powerful for some of those SaaS companies the click of a button which is helpful for some of those SaaS companies. We don't have a ton of time left here, Bill, but I got one last question for you. What would be your advice to anyone who's looking to get started in your field, or any aspiring entrepreneurs? What keeps you going on a day-to-day basis, as someone who you know if you, if you don't make sales, you're not eating, essentially Right. So what keeps you motivated? What's your advice to entrepreneurs?

Speaker 3:

Now that's a really thoughtful question for me, I would say. First of all, having a mentor is huge. You need a sounding board, having a super strong board of directors, as if it were to go ahead and help guide you and craft you. I've been super fortunate. I've had a mentor since 2008. And he and I have worked together at a number of companies and I still talk to him a couple of times a month, so he knows my work style and he kind of keeps my head in the game.

Speaker 3:

And you know from an entrepreneur, your motivation, I think, is innate. I would lean into what you're good at. So, personally, what I always talk to my founders about is I ask them one question what are you good at? Are you a sales founder? Are you a technology founder? Are you a podium speaker? Are you an evangelist? Identify what you're good at and be willing to raise your hand and fill in the gaps where you're not as strong, and that will just help you take so much pressure off yourself as a founder.

Speaker 3:

A lot of times. I think people need to feel like they're omnipotent and they need to do everything in the spectrum. No, focus on what you can do best. The founders that I had dinner with last night. They're engineers by training. They're scared to death about marketing. They're super worried about getting up on a stage and pitching their product. They really just want to focus on building a great new product that serves their community. And that's where I'm coming in and helping them fill in all of the other pieces. And I told them last night someone joking I'm like think of me as sort of like either your attack dog or the Rolodex of getting things done to able to enable your business to move forward.

Speaker 2:

That's so good. I love the doubling down on what you're good at, but being intentional to actually think about it, take a second and then run after it and then yeah, then I mean you can. You can do a ton of cool things with that. Bill, thank you so much for coming on today. This was an awesome conversation. Loved hearing about how you got started, your incredible resume, your thoughts on gamification, thoughts on using LinkedIn for prospecting, growing your business. I hope everyone who's listening really enjoys this, this episode we had with you. So again, thank you so much for coming on.

Speaker 3:

Thank you so much, James. It was a pleasure to join you.

Speaker 2:

Thanks for tuning into this episode of CFO Chronicles the secrets behind success. I hope you found value in today's conversation. As we wrap up, I'd love for you to do two things. First, make sure to subscribe to this podcast so you don't miss any future episodes. If you enjoyed today's discussion, please rate and review the show. It helps others discover the insights we share here. Second, if you're ready to take your business to the next level and attract the high-end clients you deserve, head over to accountingleadsnowcom or click the link in the show notes to book your strategy. Call it's time to position yourself as the advisor your clients need. And don't forget you can connect with me on LinkedIn to stay up to date on what's happening in the world of accounting and financial growth. We've got more exciting topics coming up, so stay tuned for the next episode of CFO Chronicles. Until then, keep pushing forward. Your growth is just one strategic move away.

Speaker 1:

Thanks for listening to CFO Chronicles the secrets behind success. We hope today's episode provided valuable strategies to help you attract more high paying clients. Be sure to subscribe, follow and share with fellow professionals. Connect with us on LinkedIn and leave a review or comment to join the conversation. Your feedback helps us bring you the best insights in finance and marketing. Until next time, keep striving for success and unlocking your business's potential.