Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams. 

Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company. 

In this episode, Phil discusses these important topics.

• The five keys  to hiring your first head of sales to graduate from founder-led sales to a scalable sales team
• How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly
• How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth
• Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains

Quote from Phil Stern, Operating Principal at Mainsail Partners

“Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes. 

“You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you.

“If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them. 

“It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.”

Links

• Phil Stern on LinkedIn
• Mainsail Partners on LinkedIn
• Mainsail Partners website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

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Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial lifecycle. Sean and his co-founders had already started, grown, and sold a pro services organization before creating a PSA product and building a SaaS business. 

With a little funding from the founders and a few angel investors, Kimble started efficiently and grew steadily, eventually raising a practical minority funding round from private equity investors Accel-KKR in 2018. The company grew to $30M ARR before selling most of the company to Accel-KKR in 2021, which merged two PSA companies to create Kontata. 

In this episode, Sean discusses some of their deepest strategic opportunities:

• Learning to grow a SaaS business versus a professional services organization
• Building on the Salesforce platform and working in that ecosystem
• Starting in the UK and expanding to Germany and the US

Quote from Sean Hoban, former CEO and co-founder of Kimble Applications

“One of the most powerful ways I learned as a CEO is to find and talk to other founders in London who were in a similar situation. We would meet for beers, share ideas, and chat on WhatsApp. 

“If you have a specific problem, it was valuable to talk to other founders in the same growth stage. And these were founders, not hired CEOs.

“It's a lonely job as a CEO. And being able to talk to somebody else who is in a similar position can be cathartic and very helpful.”

Links

• Sean Hoban on LinkedIn
• Kantata on LinkedIn
• Kantata SX (formerly Kimble Applications) website
• Accel-KKR website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Josh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and dashboards, a tailored data warehouse, and detailed data models that leveraged the popular Power BI software.

Josh launched Satori, his second NetSuite solution, in 2019 and grew quickly in the NetSuite ecosystem, with a savvy team and no outside funding. Satori was sold it to private equity buyer Insight Partners in 2022 and combined with another NetSuite provider, Zone & Co.

In this episode, Josh talks about the benefits and challenges of building add-on solutions in the NetSuite ecosystem, their ROI of non-dilutive funding and strategic angel investors, selling two companies then getting bored and restless, and starting his third company, Cauzzy.ai to provide AI-powered automated financial analysis and insights.

Quote from Josh LaSov, founder of Satori Reports and Cauzzy.ai

“When you have a good exit, you can assume the lifestyle that you desire to live, you can slow down. So from 2022 until starting Cauzzy.ai in 2024, I did that, I worked out every day. I listened to more podcasts than any human should listen to. I educated myself, read every newspaper and news site. I took time for myself

“What I found was...it wasn't fulfilling. I needed more. I didn't want to be on the sidelines. I felt myself getting slower, like I was retiree. I appreciated the journey more than the destination. But there's a balance and I could achieve that balance.

“I needed to do something, but I didn't want to just jump into something just to do it. I was to be patient until I found something that I was passionate about and that's realizable. I thought, I can do this again, I want to do this again. Let's take our time and focus a bit more on balance this time, but let's get back in the game.”

• Josh LaSov on LinkedIn
• Zone Reporting (formerly Satori Reporting) on LinkedIn
• Zone Reporting (formerly Satori Reporting)
• Cauzzy.ai website
• NetSuite website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size.

Acquire.com has helped over 2000 entrepreneurs sell their software products for a combined value of more than $500 million. Acquire offers additional support to help founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for financial viability and identity confirmation before getting confidential details for any deal.

In this episode, Andrew describes their typical seller and buyer profiles, the typical process for a founder to sell a small and profitable SaaS company, typical multiples of profit that financial buyers offer, and founder transition periods.

Quote from Andrew Gazdecki, founder and CEO of Acquire.com

"There are three buckets of active buyers on Acquire.com. The first is below $100,000 net profit. That's going to be an individual buyer looking for something with maybe a little bit of product market fit. They want to take the product, grow it a little bit, see what they can do from there. They're buying a very, very early startup. So some buyers will actually start small and then work their way up.

"From $100,000 to $1 million in net profit in our middle range, the buyer will a blend of "micro PE firms" and holding companies that want to get their hands on a business where there's a lot more going on. And then a $1 million in profit and above is going to be for the more traditional private equity or strategic buyers."

• Andrew Gazdecki on LinkedIn
• Andrew Gazdecki on Twitter
• Acquire.com on LinkedIn
• Acquire.com website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies. 

Genius Monkey grew steadily as a bootstrapped company, with the founders and team working hard for years to improve their platform, prove results to clients, recruit agencies, and grow their team. Most ad tech peers took VC funding and are no longer around, but Genius Monkey is still growing and getting more profitable every year. 

In this episode, Seth and Clint talk about their unusual long-time partnership, the power of profits, competing with giants, building a strong company culture, and leveraging non-dilutive funding to grow faster.

Quote from Seth Hassell and Clint Ethington, co-founders of Genius Monkey

"Don't be afraid to fail with the smaller stuff. A lot of times, people don't take the chance of seeing, "What if we do it this way?" What happens? And all those little things that could become something big, they never pursue because they're comfortable with where they're at."

"Fail fast. Try stuff out. If you see it's not working, shelf it and go to the next thing. Move on until you find that one that's doing better than where you're at right now. Then, I will put the determination and the motivation behind it to see it through. Clint and I tried through lots of things that just didn't work out." 

"If it wasn't working, we were okay. We wouldn't say, "It's all over, close the doors." It wasn't like that. It was like, "Okay, we know that doesn't work. What's our next thing we're trying?" And we always had different ideas in the background."

• Genius Monkey on LinkedIn

• Genius Monkey website

• Cypress Growth Capital website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011.

HappyFox is a mid-market product that sells across industries and departments with an efficient product-led growth (PLG) approach. The product has matured with successful add-on products for live chat, AI support, business intelligence, and workflows.

The company has over 2200 customers, 110 employees, and now $20 million in revenue. Shalin plans to keep growing and leverage modern AI technology to become a much bigger company based on the disciplined product culture they have created.

Quote from Shalin Jain, founder and CEO of HappyFox

“I think software and its pricing need to be deflationary, just like hardware, where memory prices, hardware prices, and server prices have all been deflationary. But we are now going through a phase where software is actually getting more and more expensive.

“With the advent of AI and automation, software will become cheaper and more usage-driven. So, the best survivors in that phase would be the efficiently run companies that have not bloated themselves by charging more today to have more employees and spend more on ads.

“I believe software needs to get cheaper because it's getting cheaper to run software every day; it's getting cheaper to outsource to AI and build stuff with the help of AI as well. So software cost should not go up; it should go down.”

• Shalin Jain on LinkedIn

• HappyFox on LinkedIn

• HappyFox website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022.

Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls and savvy demos to busy compliance executives. They grew fast, were profitable in just over a year, and attracted attention from potential acquirers. 

In June 2024, Financial Recovery Technologies, a fintech legal software company, acquired Skematic for an undisclosed amount, including some cash and incentives. Brian and his cofounder still run Skematic and enjoy being part of a bigger software company owned by a private family office that is highly aligned with their culture and values.

Quote from Brian Kesselman, cofounder and CRO of Skematic

"My co-founder Charles and I had worked at a number of PE-backed software companies. And we had our own opinions about what it's like to work at a PE-backed company."

"The family office structure is very different from a private equity firm across the board. They're looking typically to build profitable cash-producing assets. And so that enables our team to think long-term, which benefits not only the founders and the people that are still participating in the upside of the business."

"That also means that the clients will benefit because you are going to do things that will benefit the clients every step of the way, one year, two years, five years, 10 years. And that was paramount to us, given that we've grown up in this very niche industry and our reputations to us are pretty much everything we have."

• Brian Kesselman on LinkedIn
• Skematic on LinkedIn
• Skematic website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. 

Six years later, Flodesk has over $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driven by great product design, the email footer “viral loop,” and referrals from customers and influencers. 

In this episode, Rebecca shares her insights on product design, their unlimited pricing model, working with her co-founder/CEO, Martha Bitar, why they haven’t taken outside funding, and where AI is showing usefulness in their products.

Quote from Rebecca Shostack, co-founder of Flodesk

“The reason you hire is never to solve a problem. You need to be sharp and figure out how to solve the problem on your own. Then, you hire people once you've proven something. 

“When you want to hire someone to run your paid ads, for example, you first need to figure out the basics. Then, you can hire someone to come in to own that so they can scale that operation. 

“But it doesn't work to hire someone to come in and figure out something that you can't figure out yourself. How can you hire someone to manage something you don't understand?”

• Rebecca Shostak on LinkedIn
• Flodesk on LinkedIn
• Flodesk website

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry.  

After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second company, Strety.  

Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company.

• Brian Dosal on LinkedIn

• BrightGauge website

• Strety on LinkedIn

• Strety website

• Entrepreneurial Operating System (EOS) website

• Traction book by Gino Wickman

• Anything You Want book by Derek Sivers

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. 

In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even extending through an industry ecosystem serving new markets. We also talk about the impact of AI on established vertical SaaS players and how it’s both an opportunity and a thre

Tidemark supports the global community of practical vertical SaaS founders by publishing their strategic growth frameworks, their annual Vertical SaaS Benchmarketing Report,  and they host the annual Vertical SaaS Collective Live conference for founders. 

Quote from Dave Yuan, founder at Tidemark

“Vertical SaaS founders should not be asleep with AI. You can wave it off, view it as a toy, and say that no one’s going to trust that outcome or use it. That may have been the case, but things are changing really quickly.

“Lots of smart people are making it better every month, and you have a massive opportunity to improve it with your data and workflow.

“Jump into it to control your destiny. Don’t get caught sleeping without AI in your product in a useful way.”

• Dave Yuan on LinkedIn
• Tidemark on LinkedIn
• Tidemark website
• Tidemark Vertical SaaS Knowledge Project 
• VSaaS Collective Live 2025 conference
• Vertical SaaS Benchmark Report 2024

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.