“5 Things I Wish Someone Told Me Before I Became CEO of SentryOne,” with Bob Potter

Carly Martinetti
Nov 3 · 6 min read

Be humble. The troops like it when you admit when you’ve made a mistake. This last one I learned late in my career.


I had the pleasure to interview Bob Potter. Bob is the CEO of SentryOne, the leading provider of data DevOps and database performance monitoring capabilities for the Microsoft Data Platform. Bob’s career has included senior executive roles with leading Business Intelligence, Analytics and Data Management software companies. Prior to SentryOne, he was on the operating team of Alpine Investors, where he acquired and managed small SaaS companies. Before Alpine he was General Manager of the Business Intelligence/Analytics Business Unit of Rocket Software, a $340M enterprise infrastructure software company based in Waltham Massachusetts. Before Rocket Software he worked for QlikTech, a leading Business Intelligence software company. Expressor Software Corporation, a data integration software company he founded, was sold to QlikTech in 2013. Earlier in his career he worked for two very successful companies, Object Design and IONA Technologies, both of which had very successful IPO’s. Over his career, he has developed senior software executives, ten of which are CEO’s of successful software companies.


Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?

I’ve spent my whole career in the software industry. I started as a sales rep and did very well. In my very first tech company I was ranked the #1 rep out of 200 reps for two consecutive years. I ended up only spending 4 years total as a quota carrying rep. I became a sales manager, branch manager, area manager and then a director managing 100 people before I was 35 years old. I became a vice president at 36 and, after a few successful career moves, became the #2 executive in some pretty successful software companies. Object Design, a database company, was one of the most formative employers in my career. I was the Senior Vice President of Worldwide Sales and Services and I started before the product was released. The CEO took a real bet on me. I was 37 and didn’t know what I didn’t know, but he let me run hard and make mistakes. Like the rest of the management team, I took huge risks, like expanding into Japan when we were just $4M in annual revenue. We were the hottest company in the software industry, landing on the cover of Inc. Magazine as the fastest growing company in the US. I grew sales from $0 to $60M in 7 years, and we went public and got a $1B valuation. The CEO was Ken Marshall and he wasn’t afraid to hire the best and brightest. After Object Design I went to IONA Technologies and worked for another great CEO, Barry Morris, and we took that company to $180M. He was even more fearless then Ken, making huge gambles to establish market share. I never aspired to be a CEO because I love running field operations, but after IONA I said to myself, “ I think I can do this”.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

Leading SentryOne has been a blessing. I immediately got along with the founder and CTO, Greg Gonzalez. We had a shared vision of establishing a large company with a very big enterprise value, but doing it while supporting our customers with high quality software. I bought into the culture and the corporate values of agility, quality, and innovation. Mainsail Investors has been a very supportive partner and has backed all of the strategic initiatives we brought forward. My biggest early challenge was to grow my young management team from within. Five of my key executives were all promoted from Director to Vice President. They were all game to learn and grow, but I quickly realized that not only was it a challenge for them to evolve, it was hard for me to spend enough time with each one to provide the support they needed. Four of those executives are still with me, but I’ve also had to go on the outside and hire some veterans.

What are some of the factors that you believe led to your eventual success?

First and foremost I hire well. Secondly I mentor well. I am very proud of how many of my direct reports have gone on to become CEOs. I am always available and even though I don’t expect my staff to copy me, I am available 7 days a week at any hour. My family is not crazy about that factor but it works when you are scaling a business.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”?

#1, — Pick the right investors. Or, if they are picking you, make sure they are the ones you want to partner with. In a venture capital world make sure all investors have the right percentage of the company and let them determine valuation. The job of the CEO is to run the company not decide valuation. If you run it right, that takes care of itself.

#2 — Pick the right outside directors. Good ones want to help and make you a better CEO. Bad ones just want to impress the investors.

#3 — Do twice as many reference checks on executive hires as you’re used to. Wrong hires cost the company a lot of time and money.

#4 — Care about your employees. Invest in them and they will stay. They have choices and will leave if they aren’t motivated. They also know how to use Glassdoor.

#5 — Be humble. The troops like it when you admit when you’ve made a mistake. This last one I learned late in my career.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Work hard and play even harder. Do social events with your staff and become friends. You don’t burn out if you love the team and have a shared mission. You spend more hours working than anything else in your life. If you don’t love it and it is just a job, you burn out.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Those two CEO’s I mentioned were hugely responsible for where I am, but my maternal grandmother is the person I am most grateful for. Out of business school, with a fresh MBA I was recruited heavily and I went to the highest bidder, Ford Motor Company in Richmond Virginia, as a marketing analyst. I quickly realized I hated cars and trucks. I also didn’t care for the climate in that part of the country. I was miserable. I came up to Boston for a round of interviews and only one company asked me back, McDonnell Douglas Information Systems Company. I was despondent and was going to go back to Richmond without doing the follow up interview. She convinced me to go and put my best foot forward. I got hired by a guy named Steve Fisch, who took me under his wing, and I got promoted many times over a nine year period. I am grateful to him too.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

Professionally, Greg and I have the big hairy audacious goal of growing the company to a $1B valuation. We’ll need to get it to $100M+ in revenue to accomplish this. All SentryOne employees know about this BHAG. Personally, I want to be a great Nordic skier and cyclist. Being a lifelong alpine skier and golfer, I picked up these sports just a few years ago. Now depending on the season I do one of those almost every weekend. Of course I still golf and downhill ski.

What do you hope to leave as your lasting legacy?

That I’ve built some pretty great companies and I developed some amazing CEOs. On a personal level, I have 5 children who are very accomplished. I think of myself as a CEO and father, but not necessarily in that order.

If you could start a movement that would enhance people’s lives in some way, what would it be?

There is an organization in Boston called Youth Enrichment Services, which takes inner city youth and exposes them to winter sports, like skiing and ice skating. Imagine never seeing the mountains and then getting on skis for the first time after a fresh snow fall. I wish I started that movement. My wife is an adaptive ski coach and takes people with disabilities skiing. That is pretty cool too.

How can our readers follow you on social media?

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Carly Martinetti

Written by

2x pet tech founder, publicist, writer, and dog mom. I love learning about what makes CEOs tick.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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