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.

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

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.