Scaling Smart: Bill Dillmeier on Building Sustainable Growth

Freddy D: 00:02:20

Today's guest is a seasoned financial strategist who thrives at the intersection of data growth and operational excellence. Bill Dillmeier helps companies raise capital, overcome challenges and accelerate their trajectory, especially in the fast paced world of SaaS.

Startups with over a decade of experience across Series A to unicorn stage companies, Bill specializes in turning financial data into clear, actionable strategies that drive real results.

Most recently he served as an interim finance leader, partnering directly with CEOs, boards and investors to bring both precision and innovation to high growth environments.

Before that, Bill was the Senior Director of Finance at Karat where he helped close a $100 million Series C round earning Carat the title of the first unicorn in the recruitment space. He's also led global FP&A and sales ops.

A Bill Gates owned media company and spent nearly 10 years in mortgage banking, trading securities and advising senior execs. Whether it's automating processes, scaling revenue engines or building KPI driven cultures, Bill brings a clear focus on sustainable scalable growth.

Currently he's helping early to mid stage startups scale smarter as an interim finance leader. Let's dive into the numbers, the growth playbooks and the lessons learned along the way.

Freddy D: 00:03:43

Welcome Bill Dillmeier to the Business Superfans podcast show. How are you this afternoon Bill?

Bill Dillmeier: 00:03:49

Great Freddie, super excited to be here.

Freddy D: 00:03:51

So tell us a little bit about what's your backstory of how did you get to where you're doing fractional CFO and helping funding businesses and all those kind of cool things to help businesses scale?

Bill Dillmeier: 00:04:03

Sure. No, that's a great question for me. I always think of my origin story as a little bit atypical. I started in large banking financial services.

So my first job was at Vanguard, the mutual fund company. From there I actually moved on to Morgan Stanley Institutional working for the president of a mutual fund company.

So my job was to go in and actually look at business of mutual funds, things like who invests the same way we do. What are those returns compared to other funds in the institutional space? From there I actually spent a large bit of time in mortgage banking.

I sometimes tell people it was I was in mortgage banking. While it was cool to be in mortgage banking, so I used to actually call Bear Stearns, Lehman Brothers and trade mortgage backed securities.

I was delivering about a billion dollars a month into the open market.

Freddy D: 00:04:52

Wow.

Bill Dillmeier: 00:04:53

And yes, it was a tremendous time. And then as that was starting to kind of wind down a little bit on the trade side, I joined a bank here in Seattle called Washington Mutual.

At one point the Sixth largest bank in the United States.

Freddy D: 00:05:06

I remember them.

Bill Dillmeier: 00:05:07

tgage market. So this is like: 2002

And as I always say, you put three or four finance guys in a room with a whiteboard.

the bank. So around about mid: 2008

He owns a media company here in Seattle, company called Corbis. We head to head against Getty Images in the stock photography space.

And this is actually a great pivotal point because this was a true digital transformation when you were going from negatives to digital imagery.

And at the time we had offices around the world and we were trying to figure out how to pivot the business to build a really engaging customer website, to be able to go ahead and sell images at sort of the same rate in which Amazon sells products on a minute by minute basis.

And part of my job was to run what we like to call a global transformation initiative in which we took a look at every part of the business, exited businesses that were no longer profitable, no longer driving revenue, and really continue to figure out how to double down on delivering the best digital experience for our customers. And so I ran global planning, global treasury, and then also then took on global sales operations in my role as well.

So kind of going from that back office of just looking at it numerically to really thinking about what our customers needed, how to really work with our sales teams in different regions around the world. And that was really a great pivot point for me to really think about how to manage a business, how to become a better operator.

And from there really started my next 10 years of my career, planning, strategy, operations, a number of different functions for venture capital backed or private equity backed SaaS startups, and along the way was able to go ahead and work with some tremendous leaders, raise capital, go ahead and scale operations from 20 million in ARR to over a billion dollars of an exit that actually happened just last year. Other companies was fortunate enough to raise $100 million Series C round to go ahead and get them to unicorn status.

And really the last two companies was an interim cfo. And these were series A, Series B companies. And that really is the genesis of where Aperture Advisors was created.

And right now I focus on working with everything from seed to Series B companies, helping them go ahead and holistically think about the organization to be able to go ahead and scale and and deliver the most amount of value to their customers.

Freddy D: 00:08:16

Very interesting story. And you obviously ran into and dealt with some very important people that have been instrumental.

I started in the SaaS industry when it first began like 45 years ago. I didn't come from a financial background, I came from an engineering background.

ld when it just began like in: 1980

I was an applications guy for several years and I had to really learn how to get out of my shell because as a financial guy you're back there with the numbers. As an engineer you're busy engineering and now you gotta talk to people and it's like, whoa, that's not me.

And so I can appreciate the transformation that you've gone through. And likewise with me, I transitions from an applications guide to sales.

And I also played on a global stage where I set up distribution channels and grew a product from zero to several million in the camp space.

Bill Dillmeier: 00:09:13

Oh, that's great. I'm actually right now I just took on a CEO role for a tech startup here in the Seattle area working with a very talented engineer who.

I think you'd appreciate this. As you think about, GitHub is synonymous with software engineers.

Now there's no platform for CAD people people or electrical or mechanical engineers to showcase all those great designs.

So imagine if you had a platform that could go ahead and through AI read the technical nuances of that, but then help bridge that when talking to a recruiter when looking for your next job.

Freddy D: 00:09:50

Right.

a because if you remember the: 1982

Pre robot days when they had guys on and you had the spot wall gu a gimbal had to go in there and make sure it was perpendicular to the metal to spot weld it.

And so I was doing a lot of geometry work and that's how I got into the CAD world is at the time they were looking for real engineers, not college boys and girls, but people that actually did stuff to legitimize the computer aided design and manufacturing world. And I don't have any of those things that'd Be really cool to still have.

There's some of my old design stuff and some of the things I did in the early days. I just got the plaques from top sales guy and all that kind of stuff. Not what you're talking about.

Which is really cool because then, you know, a picture's a thousand words. You get a story right there that people can look at.

Bill Dillmeier: 00:10:44

Exactly. And it's such a great way to break down just nuances. And we all know that hiring is incredibly challenging for engineers.

And you've got really smart people like yourself who know the engineering. But how do you talk to a recruiter? These are the things to look for on a resume. These are the questions to ask.

And this platform really is intended to be able to distill all that down and actually has a natural language AI.

And you can actually ask the question of like write me 300 words about Freddy's background or something technical down to what is the proper angle to which a weld would need to be made.

And it'll go through all of your technical documents and be able to surface that information to actually make it a much better enriching interview for you.

Freddy D: 00:11:27

Right? Yeah.

Because when I did it, the old school way was I would research the company and then when I was interviewing for a western regional manager position or things like that, managing half the US I would call in the interview and I would have a 90 day plan laid out of. So I would already assume I got the job. What that wasn't the assumption was it's my job, here's my plan.

And I usually blew away all the competitors because nobody approached it from that perspective to say not only am I qualified, but here's my plan of what I'm going to do in the next 90 days. And that usually took people back and that eliminated my competitive going for the same position.

Bill Dillmeier: 00:12:08

No, that's tremendous. I often come armed with something similar to that. But it's just so refreshing that you were almost a visionary at that point like that.

I think a lot of people think of table stakes as today, but no one, like you said, was doing that in the early days and just coming in with that forethought to be able to say in order to get up to speed. And we all know on the sales side, I always say it takes at least six months for a salesperson to come up to speed, three months to build pipe.

Those first six months are super pivotal. You don't have that 90 day, 100 day plan. You can really struggle and get frustrated as a sales leader.

Freddy D: 00:12:45

And so we're now busy. So it's already like, I've already got the job because now we're already tweaking. Here's the plan. Well, that's a good idea.

What if we did this and that and it was done. It was just a matter of making it formalized, but it was. The conversation was no longer about whether my qualified or not.

It's how are we going to implement the plan?

Bill Dillmeier: 00:13:03

Exactly. No, that's tremendous. And I think so many companies, when it comes to hiring, there's almost this beginning of like a larger disconnect.

I'm sure you see a lot of people using AI to go ahead and write resumes and tweak resumes.

And it's almost as if you're coming to this convergence zone where, like, your resume is simply an amalgamation of what an AI thinks it should be saying and every other AI is writing something in that similar vein. So resumes are just starting to stack up the same. There is no way to delineate unique experiences.

There's no way to really go ahead and find that right candidate because it's all just mishmash.

Freddy D: 00:13:43

Yeah. Unfortunately, today you're correct. This changed.

So share with our listeners a story of how you kind of transformed and got involved with the company and help them get funding and or change their bottom line. Because a lot of times businesses look at the revenue and they forget about net income. And we all get caught up in that.

Hey, Look, I remember $3 million, $50 million. Yeah, but you made no money.

Bill Dillmeier: 00:14:09

Oh, thank you. I mean, that's actually some of my favorite set of accomplishments that I look back at over my career.

And it's very odd when you hear a finance person wanting to partner with a sales leader. There's always that friction between finance and sales.

I'll always talk to my sales leaders and say, I want to make you the richest person in the room, but it's going to come at the price of efficiency. I'm not going to overpay for revenue.

I'm not going to go ahead and have any of these heroic actions to go ahead and just make that revenue number grow. And so probably one of the biggest transformations I did was one of my first startups, we were backed by Madrona Ventures here in Seattle.

And just really around the early part of the B round, I came in as the first finance hire, built the finance model, and then honestly became the finance business partner to the leadership team. So I would always say at any given moment, I had five different bosses who would weigh in on my performance review.

Head of marketing, head of sales, head of product, head of engineering. And it was my job to go ahead and make the rounds with each of them and really just be a good listener and hear what's going on in their business.

They're the domain experts.

I'm just there to kind of go ahead and put some tweaks around the edges and help them continue to optimize and then ultimately bring all that information back and distill it down in order to make an effective set of forecasts to be able to present to the investors. Present to the leadership team.

One of probably the biggest transformational things that I had done was I ended up running sort of like a shadow sales operations team. And that really came from the fact that, not that I didn't trust our sales leader, but the numbers that he was putting up were.

They were pretty lofty and I wasn't sure how we were going to go ahead and get there.

So I actually broke down the sales pipeline myself and then started writing an investment banking style report for the leadership team based on just simply looking at the data and you know what it's like.

You're looking at close date, you're looking at activity relative to close date and you really get a sense of this deal's really going to have to pick up a lot of speed to hit this close date. Or you're just simply putting this closed data in for a placeholder.

If your sales leader is saying, oh yeah, Q1, we're going to do 500 million in bookings, I would look at that number. I'm like, ooh, that feels more like a 420 or a 380.

And those numbers are so wide that if you put 500 in your finance model, you're going to get some potentially irrational numbers and you could over hire, you could set the wrong expectations with investors.

So by creating this sort of shadow organization, it was a way to be able to go ahead and create healthy debate at the leadership team level around what's the real number, what's our minimum number that we have to hit, what number do we feel comfortable going out to the investors at to continue to under promise and over deliver?

Freddy D: 00:17:03

That's an important part right there. Because even though you can have the lofty goal, yes, as sales guys, we always have to have a lofty goal. I mean, that's our target.

Because you shoot for Mars, you miss, you land on the moon, you shoot for the moon, you miss, you're out in space. So what you did though is you helped tweak proper expectations. So, okay, this is our lofty goal.

This is the realistic goal that we can present to the investors and everybody else. This is what we aspire to do.

But then you manage the expectations so you minimize conflict and all kinds of challenges that can pop up in that scenario.

Bill Dillmeier: 00:17:38

Exactly. And you remember from your SaaS phase, if you miss your bookings target for the quarter, you've just now shifted your cash flow for 36 months.

So for me, it's how am I going ahead and continuing to optimize my cash flow? And to your point earlier, I think gone are the days of revenue at all cost.

And every investor that I talk to these days is I want to see healthy ARR growth. I want to see good ratios when it comes to say, a CAC ratio or a CAC to ltv. And I want to know you're working the right unit economics to get there.

And revenue will come along if you can continue to hone and build an efficient machine.

Freddy D: 00:18:17

Right. What happened to that company?

Bill Dillmeier: 00:18:19

billion exit in mid: 2024

Freddy D: 00:18:32

Wow. So I'm sure that the owners of that company are super fans of you.

Bill Dillmeier: 00:18:36

Oh, yes, yes. Eric was a tremendous founder and the leadership team and I are still in contact.

As a matter of fact, the C has been my mentor for a number of years and he was always one to push me and he's always trying to think about how to squeeze that next mile out of any organization that he joins. But yes, that was just one of the examples where I was a super fan there.

Actually, at that same company, one of the things that we were running into was we're trying to think about how to go ahead and raise funds without diluting the shareholders and the investors. And the investors were completely on board.

time, these were say, Fortune: 2000

We had 130 NRR in any given year. So we knew the profile of our customers.

And really, for me, it was structuring a deal that allowed us to optimize how much we could borrow against this while at the same time trying to figure out the best ROI series of investments to maximize that return.

Freddy D: 00:19:59

So what was the final outcome in that case?

Bill Dillmeier: 00:20:01

We were able to draw down some funds, double down on engineering and continue to grow the product. This was a unique product and actually it was both a private cloud or on prem as well as a public cloud.

So depending on our customer profile and how they wanted to use the application, they could run either behind their firewall or on the public.

But we essentially had two engineering teams and we had to constantly figure out what was our investment return and were we getting that right degree of lift from having such a big engineering organization. You know, in theory could have cut our way to profitability if we didn't have to carry that large engineering team.

So really outcome was just a series of, okay, my customers are drifting more to say on premises. So therefore I need to make sure that I've got the right engineers to be able to go ahead and do this.

And ultimately it was a lot of very tactical conversations with investors and leadership team, but at the same time, you know, a lot of hard fought conversations about where we should go. And at the end, as I mentioned, huge exit and they're tremendous superfans of what I was able to help them do.

Freddy D: 00:21:10

Yeah, and that's really, at the end of the day, that's what it's about. Because now you've got those super fans promoting you and you can't buy that kind of priority.

Bill Dillmeier: 00:21:21

Oh no, no, not at all. I mean that is the ultimate PR stamp.

It's very much of the community that you were able to grow and support and knowing that you have their deepest respects for what your true skill set that you bring to the table are.

Freddy D: 00:21:36

Yeah, I still have friendships from some of the distributors I set in different countries years ago, about 25 years ago. I've been at some of their houses, stayed at their places when I visited them.

Those are the takeaways for me is I still have lifetime friendships of these relationships that I had built because I helped them taking on our CAM product that generated additional revenue from them. And then I helped them strategize and get their sales teams working and all that stuff to market the product.

And one of the things that I did, which is how I've got these relationships was I didn't just edify the top reseller or var, we call them value added reseller. I also recognized the sales rep that sold the most of our product within that agency. So what that did is it got everybody else to go, wow.

It's not just the company. He's appreciating the individual. So more people were interested in selling of our product. And that's how I got, you know, people got 12 watches.

They're an independent reseller, so they can market any products that they want. How do I get Mind Share? Well, that was my way of getting mindshare.

Bill Dillmeier: 00:22:47

Exactly.

Now that, that's tremendous because it's always about recognizing the individual on the team and because it does take that whole team to be able to go ahead and deliver against it. And I love the fact that you were shouting out that individual sales leader.

I mean, that just goes ahead and raises their stock across the entire space. And you've now made him the MVP in the league, who is probably now being highly sought after by other potential distributors in the space.

Freddy D: 00:23:13

And. Correct.

Bill Dillmeier: 00:23:14

Also raising the bar for competitors to be like, you need to be more like this individual.

Freddy D: 00:23:19

Yeah. One of the guys is actually went on to move to a vendor and he's been there for years and he's made bank with them.

And that was because he was one of the guys that I elevated and said he's a distributor, but look at him within that distributorship. So you mentioned that you've got another venture, so let's talk about that. What is that?

Bill Dillmeier: 00:23:40

Sure. So actually in late December, early January, I launched a company called Venture Fuel. And this is. I'm really excited about this.

This is very unique that when I go ahead and tell people, they're like, oh, that's such a great concept that no one's comfortable with yet. And really what it is, the pitch line is we know being a founder is hard.

And the first thing that I asked every founder that I meet is, what are you good at? Are you a sales founder? Are you an engineering founder? Are you a tech founder? Are you a podium speaker?

And once I have that, I can then begin to see where they need some additional support. And Venture Fuel comes in. And it's almost like founder services is what we provide. So for a flat rate retainer, we'll say $20,000.

You get a finite number of hours, but within that you get access to a CRO, a cpo, a cmo. Basically every major function is represented and you have a fractional leader with tremendous domain experience.

So that this way, as a founder, you don't have to interview five heads of marketing, look at eight different rate cards as you're trying to figure out how to build a bench.

This is basically a turnkey service that allows founders to go ahead and get the best in breed across every major discipline to help their business scale.

Freddy D: 00:24:58

That's a great idea.

Bill Dillmeier: 00:24:59

It really lets them go ahead and focus on what they're best at.

So for example, I'm working with a very talented people leader who has built an AI tool but he's right now struggling with marketing, he's struggling with financials. Venture Fuel has been able to come in and actually give him individuals to draw from to be able to help move his business forward.

Actually I recently introduced him to a CTO to actually help take his product on to the next level and he's now focused on doing founder led sales and continuing to evangelize the product in the HR space where he spent so many years.

Freddy D: 00:25:36

That's great. Should have ran into you 10 years ago. My now wife, we started a tech company and I never got funding, that was never one of my things.

But I figured out how to do it and I got some small investment, $100,000. We got to the point where we talked with Blackrock Group, met with them and I was like oh my God, I'm dealing with the big boys.

I didn't know what I was doing but I was still punting fake it till you make it. And unfortunately they liked the idea but I was asking too little money for them.

And then through her she I can't remember the gentleman's name but he invented Gas Station tv, those videos that play at the gas station pumps. And he sold that for 250 million and has been hanging out with Dan Gilbert, the founder of Quicken Loans. So I was actually emailing him directly.

She got his contact information through somebody she knew and he was like okay, I'm interested because we were applying for a patent on this thing and everything else and we were competing with YEX but YE wasn't as big as it is now. We never lost to them because we were pioneers in a couple areas. So he was intrigued, said meet with my team. So met with this individual.

I said ah, we like the idea.

I says in translation to where everybody can understand it was finish building your boat, show it that it can leave, dock the dock on its own power and we'll help you with money to scale. Like that's great, that's wonderful. I need money to finish building the boat.

Bill Dillmeier: 00:27:05

Yes.

That is often one of the innovators dilemmas right now is and that's exactly what I'm telling a lot of the companies that I'm with now is you need to get traction, you need to bootstrap this, you need to get some Lois under your belt and you need to find a series A investor that loves your idea, that's ready to write a term sheet but he's going to give you the criteria that you need to get to see him for series A.

That actually puts pressure on your pre seed investors to be able to go ahead and fund the company but also incense them to know that there is an exit path for them in the greater funding cap table.

Freddy D: 00:27:42

See, I didn't know any of that stuff. Should have met you years ago because it would be a different story. But anyway it was great learning experience and I don't regret it.

Bill Dillmeier: 00:27:52

For me that is as much half the battle is the learning. Actually I.

My father used to run an oil company so I actually came up through the ranks in on the east coast dragging a hose through the snow in the winter, doing inventory and really learning the business from the ground up. It's.

It's fascinating just all of the different moving parts and that each one of those lessons that you learn along the way are skills that you keep for a lifetime and it's amazing how they come back to you and how you can then begin to reapply those skills. And I remember and one of my very first jobs, I was actually working for the head of budgeting and planning for an international plastics company.

They used to make those little white creamers that you would get and they had a production line in Chicago and one in Pennsylvania. And for me it was kind of a hands on crash course in managerial accounting. And end of the day it was really just algebra.

I look back on that and it was still things that I apply today. And there's some tremendously smart people in the world and always appreciate the skills that they bring.

But for me, as long as you really understand algebra at its kind of basic level, you can do a lot of things in business because you're just constantly solving problems using various algebra, right?

Freddy D: 00:29:09

Yeah, it goes boils down to good old math.

Bill Dillmeier: 00:29:12

Yeah, it's just math. It's not just math.

Freddy D: 00:29:14

Yeah, that's one of the things that I helped recently with the interpreting and translation company. I stepped in as general manager for them for a little while and we put systems in place. They were averaging about a million.

It was a small company, a husband and wife, but they reached a level they didn't have a skillset to take it to another level. And so one of the things is we got the team going into the same direction, met with the team on a regular basis.

And then what I did is I brought in an external HR company that also had A CFO part of it. And so we went through the books and fixed the books because a lot of things, it's amazing how many things were improperly cataloged.

And I'm sure you've run into that more than once. So once we got the books corrected, then we can actually see where we were really at.

I did set a lofty goal, but at the same time we had a realistic goal and we hit the realistic goal. I had set a goal of 2 million, growing in a million, a little bit more than a million in a year.

And because we had a negative net income and I took it to 1.8 13, so grew by about a million dollars in a year's time.

But because we got the finances cleaned up, we had the right direction, we put the systems in place and we got everybody rowing in the rowboat in the same direction. Just like one of those racing boats. We had the four people and all in synchronization so that you're actually moving in the right direction.

And those were the differentiator.

Bill Dillmeier: 00:30:44

I completely agree, and I'm sure we've both seen this over time, is that the employee base that'll get you from zero to a million is very different than the folks that will get you from 1 to 5 and a very different set from 5 to 10. And it's really. You're always thinking about how to take people on that journey.

Once you get to that million dollar mark, it's like keeping that team engaged, but knowing that you're going to have to potentially bring someone in above them and they still have a role in the organization, but they may have just sort of capped out in terms of their skill set, continuing to help them learn, but knowing that you're going to need someone who has maybe that been there, done that experience to be able to then help them go on to the next level. But you're so bang on about getting everybody on the same page.

One of the analogies that I like to use with people is, you know, when you go to like a shopping mall, there's always that sort of big map and it says you are here. The story you're looking for could be off in another quadrant.

But just using that sort of approach of you are here, you can begin to see how you're all interconnected and then you can begin to see like, okay, if I make a change here, it's going to come back out someplace else. Coming at it from a finance perspective, one of the things that I was really looking forward was just listening to a marketing Leader.

And if they were saying like, oh, the marketing pipeline is slowing down, or we had a bad month generating pipe in the back of your head, you're like, hold on, it's not just going to hit marketing. This is going to come back and bite us.

So it's how do you go ahead and be thoughtful, to be able to be in front of the business, to go ahead and pick up those ripples and know where to plan, how to continue to maybe augment some expenses or continue to figure out how to double down and get your sales team to try to make something good out of a bad situation. But it always comes from rolling in the same direction.

Freddy D: 00:32:33

You're in tune with the business, so you can feel.

Feel is one word, but really you're looking at it technically, you know where it's at and you can pivot and tweak and adjust proactively versus being in a situation where it's all reactive now. All hands on deck. Because we're losing money and everything else, you keep it from going into that. All hands on deck.

Because we've both seen businesses where all of a sudden they go, wait a minute, we just lost this big account and we weren't proactive, and now 30% of our business is out the door. What do we do now?

Bill Dillmeier: 00:33:07

Exactly. That's where there's, yes, so much in de risking, which is always such a fun word to use in the business.

And you look at customer concentrations, you look at revenue concentrations, and you're always trying to figure out how stable is this customer or a series of customers that I need to continue to keep moving and happy.

One of the things that I actually use is a mechanism called keep, grow, react, where I'll take my entire customer base and I'll assign one of those three classifications to each one of my customers. So, for example, my keep customers are fully penetrated.

These are customers where, sure, I might be able to grow 1 to 3% just because of their natural business growth, but my churn rate isn't fairly low. So that could be like minus one and a half. My grow customers. These are my lend and expand customers.

These are customers where I've got a lot of opportunity to sell into this account. So that may actually have a 8 or 9% growth rate, maybe only like a 2 to 3% churn rate.

And then my react customers are those that have either signaled that they're going to leave or customers that are just not using the product to its fullest. You can get a sense that they're not true believers. And in that case, that's much more of at best 1% growth and -8, 9, 10% on the churn.

So very quickly, if you just apply that simple lens to your customer base, you can figure out where you need to continue to double down. And go ahead and think about it from a SaaS perspective. What is my NRR? What is that net recurring revenue number that I need to shoot at?

What's my upsell number that I need to generate to offset my churn? But just that simple lens is a great way to align the entire organization about who are my best customers.

How am I going to go ahead and focus to drive the greatest amount of revenue for my growth customers?

And I'm not one to advocate sort of say chucking a customer, but if I've got a customer that's in my react stage, maybe they don't have that much account size, that much ARR.

If they were to leave, I know my sales team's effective enough to bring in twice as much on a dollar basis because I've become much more mature from a sales organization. So I might be willing to let them leave more readily than trying to go ahead and fight.

Freddy D: 00:35:28

Well, that's excellent advice, really applicable to any business because yes, sometimes you do need to fire a customer, but you need to make it an educated decision because some of them can be a drain. And then you're always reacting with those customers and that's taken you away from being proactive with other customers.

Overall, I really liked your triple approach here because I never really looked at it from that perspective. I looked at it, but not the way you broke it down. And that really makes a lot of sense. And that's some really valuable insight for our listeners.

Bill Dillmeier: 00:36:02

Thank you.

I mean that's one of the things that I really and fortunate if I worked with some great customer success leaders and they really saw that and they thought that was the only limited. They were sort of thinking about the business themselves.

But once we opened that up and unsurfaced it to the entire leadership team, there were so many aha moments. The sales leader was immediately like lighting up and saying oh my gosh, thank you. Because I don't have to carry this much burden.

Freddy D: 00:36:28

It changes the whole conversation.

Bill Dillmeier: 00:36:30

That NRR ratio starts going up. The investors are much happier. You're starting to see numbers that help even the entire team, especially customer success.

Because for me, I always think of customer success in one of two very particular silos. It's are you selling or are you advocating? And it's hard to have a customer success team that does both.

And there's a lot to be said for playing either one of those two equations. But knowing where you stand from an organizational perspective is incredibly liberating.

Because not all customer success people can do both of those skills.

Freddy D: 00:37:07

No, but those skills are very important because the sale in my mind begins at the onboarding process. The signing of the paperwork is just a deal. The sale is everything after the deal. Because that's the whole experience.

Bill Dillmeier: 00:37:23

That's really well said. I'm sure there's a few salespeople who would take umbrage with that.

But you are correct that it begins with what is my first experience with the product. If I have a poor onboarding experience, that's going to put a bad taste in my mouth.

Freddy D: 00:37:37

But everything up front to that goes out the window just like that.

Bill Dillmeier: 00:37:41

Yes. And heaven forbid you find that you're not getting all of the functionality that you thought you were buying once you start to go love it.

Freddy D: 00:37:48

That whole experience is critical because it's either going to be very positive, energized, and it reinforces their buying decision, or it's going to make them question their buying decision.

Bill Dillmeier: 00:38:02

I completely agree.

And that is so much of what I think sometimes companies miss out on and you'll hear say, oh, they're product led growth or they're customer centric, but really how customer centric are they? And I think it all begins with the experience that you're outlining right there and going ahead and setting that right tenor from the beginning.

Freddy D: 00:38:23

Right. And that's how you create super fans. Because I look at it, as I mentioned before is I look at it as a total experience. Everybody's involved.

So you've got the customer success people, the salespeople, the customer, their people within that organization, you got to really incorporate all of that.

Bill Dillmeier: 00:38:40

Exactly. Yeah.

I was super fortunate to work for a company here in Seattle during COVID It was an interesting business model in that they interviewed software engineers on behalf of other companies. So, for example, say you wanted to work at Peloton.

You'd send them your resume as a software engineer and they'd say, freddy, we love your background. Now you need to take a three part knowledge test and a three part coding test.

So you call our company and schedule that you meet with one of our independent contractors who was an engineer and they would walk you through this and then we would give you a score of 1 to 5 based on how you completed the rubric.

And for me coming in, getting everybody to understand the dynamics of that business model was really as much of an education session because it was a two sided marketplace. And then I am selling to large tech companies needing software engineers.

y side of how do I get enough: 1099

And one of the things was how do you go ahead and keep that message fresh, to be able to keep the audience engaged?

It's easy for a finance person to kind of come in and wax philosophical standing in front of a PowerPoint slide, but how do you break that down to an engineering leader, to a marketing leader to really then help them grasp where you're going with that concept of what you're trying to achieve?

Freddy D: 00:40:14

No, exactly. Well, Bill, it's been a great conversation. You've got some great, great insights for our listeners. How can people find you?

Bill Dillmeier: 00:40:23

So the best way to find me would be through Venture Fuel. So it's going to be BillentureFuel XYZ. You can also find me on LinkedIn.

I post @ least daily and I'm always promoting ideas to go ahead and think about how to do business differently, how to be innovative and drive change, especially in this emergence of an AI marketplace.

Freddy D: 00:40:46

And do you have anything for our listeners?

Bill Dillmeier: 00:40:48

I would highly recommend is the role of mentorship. And seeking out a mentor is probably one of the best experiences that I've had throughout my career.

And I've been fortunate to have three to five really pivotal mentors in my life to help me actually go ahead and grow and experience and encourage me to do new things.

Freddy D: 00:41:07

I can't argue that at all because if you look at a sports team, they've got coaches for just about every position.

Bill Dillmeier: 00:41:15

It's true. Yeah. It is amazing just how many coaches and specialists and you have the ecosystem of nutritionalists, sleep study people.

Freddy D: 00:41:24

So getting a mentor is really an important step to transforming yourself and your business.

Bill Dillmeier: 00:41:31

Correct.

And if you are an early stage founder, think about working with an accelerator or an incubator, just making sure that it's on the right terms for your business. But that is another way to meet a group of diverse individuals who really are there to help grow your business and make you successful ultimately.

At the end of the day, Bill.

Freddy D: 00:41:52

It'S been great having you and we look forward to having you on the show down the road again.

Bill Dillmeier: 00:41:55

Thank you so much, Freddie. It was a great pleasure.