top of page
Phil Stern Headshot.jpg
Exec logo white transparent.png

Phil Stern

Vice President at Mainsail Partners

"I think there’s a misconception out there that once you’re a leader, you’re supposed to have all the answers. In my experience, nothing could be further from the truth.

I believe that really strong leaders are amazing listeners. And by doing that, they’re able to import the best ideas from the most diverse sources. "

Find Phil on Linkedin

More about Mainsail Partners

Phil Stern is a Vice President at Mainsail Partners, a growth equity firm that has raised over $1.2B and invested in over 50 growing companies. Phil is an expert in growing software companies and prior to his current role in leading the Sales Center of Excellence at Mainsail he was the Head of Payroll Sales at Gusto and General Manager at Zen Planner.


You had several leadership and growth roles before joining Mainsail; what drew you to that part of the business?


First and foremost, I am really drawn to things you can measure. So starting off in sales made a lot of sense to me. You can measure the impact of any unit of effort you put into your work. You could break a sales quota down to dollars booked per minute if you wanted to. I like to obsess over specific metrics and sales gave me that chance.


Apart from that, as I got my first leadership roles and took on more responsibility, I wanted to be a part of changing the way people were leading teams and doing sales. I love the idea of Servant Leadership and all of the work that Brene Brown does to help us create workplace relationships based on a foundation of trust. I wanted to use those ideas, invest really heavily in my people, make everyday fun, deliver the right experience to my prospects, support other teams within the businesses I worked at, and more. I had a vision for how I wanted my teams to operate and being able to see that play out and drive results drove me to continue seeking out new leadership roles.


Through those various roles and the one you’re in now, do you have a secret sauce for growth / sales? Is there a certain playbook you live by?


I think my secret sauce is that I do have structure and beliefs around leading teams and growing businesses, but really, I’m a learner. I come into each new role operating as a novice. I like to listen, observe and ask questions and see if anything matches prior patterns I’ve seen. If so, I might have a good solution or idea or playbook we can deploy quickly. If not, it’s just another opportunity to learn.


Apart from that, for every team I’ve led, I like to focus on four major categories:

  1. Culture

  2. People

  3. Strategy

  4. Operations

And within each of these categories, there are many sub-bullets to keep an eye on and playbooks I’ve developed over the years I like to bring to the table.


Why did you make the switch to Private Equity?


I didn’t intentionally move to Private Equity, though I do love what I get to do each day. Really, I have two basic requirements for any job: i.) The work has to be really interesting and intellectually challenging and ii.) I have to work with amazing people. If one of those two things is missing, then it’s time for me to look for something new.


When I accepted this role at Mainsail Partners, I didn’t think about it as moving to Private Equity, I thought about it as getting to do really interesting work every day with a team of people who are brilliant, passionate, fun and motivated. In that way, Private Equity has been a perfect fit for me.


Tell us about your role at Mainsail and what you’re focused on. 


I support all of our portfolio companies and their go-to-market teams. That can mean a lot of things. Primarily, I help our companies deploy sales best practices and develop critical infrastructure needed for the long-term scale and growth of their business. What it really means is that every day is different. We face different questions, challenges, and opportunities across a really interesting portfolio of businesses. And I get to partner with our amazing team and our amazing executives to drive change and help improve results. As I’m saying this, I’m realizing it’s a dream job and I’m very fortunate.


You’ve had a lot of success leading high growth teams; what’s the best leadership advice you can pass on?


Listen. One of my favorite quotes is, “Leaders are net importers of ideas.” From The Leadership Challenge by Kouzes and Posner. I think there’s a misconception out there – especially for new leaders – that once you’re a leader, you’re supposed to have all of the answers. In my experience, nothing could be further from the truth. I believe that really strong leaders are amazing listeners. They keep a pulse on their teams. Dig deep in their organizations for new and interesting ideas to test. Give everyone a venue for feedback. And by doing all of that listening, they’re able to import the best ideas from the most diverse sources and in turn, really help their teams and businesses innovate and grow.


As you look back at your career thus far, was there something you did, or routinely did that really set you up for success?


I mentioned that I like things you can measure. And for years, I’ve measured my personal life on a daily basis. To create new habits, achieve personal goals, and ensure I’m constantly learning, I track a number of items in my personal life every single day. It’s a big, complex spreadsheet that I’ve developed over the years and each year, when I refresh it, I add in new things I want to introduce into my daily rhythm and things that have become habit can be removed and no longer need to be tracked.


It’s been the greatest tool I’ve found to ensure that I never stop doing the things that bring me joy and fulfillment. And in turn, I’ve found that the more balance I have, the more personal fulfillment I experience, the better I perform at work.


I’ve met a few other leaders who also track their lives this way. And it’s been fun to share our spreadsheets and discuss tips and tricks for creating time to do the things we love most.


Favorite book that you love to recommend?


“Essentialism” by Greg McKeown


But I also keep a long, recommended reading list that I love to share with people when I get this question.


Favorite quote?


“Champions don’t do extraordinary things. They do ordinary things but they do them without thinking, too fast for the other team to react. They follow the habits they’ve learned.” – Charles Duhigg


Any parting advice?


I’m sort of sneaking in another quote here, but the founder of Reddit made a great point that “one of the most toxic, dangerous things in tech right now...[is] This idea that unless you are suffering, grinding, working every hour of every day, you’re not working hard enough.”


So with that in mind, my parting advice would be: Grit and hustle matter a lot. But so do balance, happiness, fulfillment, family, health, reflection, and passion. If you sacrifice most of that list in the name of “hustle” you’re shorting yourself.


Some of my most creative ideas, “ah ha” moments and honest self-reflections related to work and career come when I’m doing something that I absolutely love to do that has nothing to do with work. I make time for fulfilling, non-work activities every single day.

Thanks for reading. Check out more interviews here.

bottom of page