The Lessons I’ve Learned From My CEOs

Frank Caron
9 min readMar 19, 2018

In this weekly series, I opine on how words affect the way we understand the products and services around us. I do this for your entertainment and education (and, of course, to remind you that if you’re looking for a freelance copy, content, product, or technical writer… yada yada, hire me.

Last week, I participated in a rare and personal interview of sorts with my good friend and well-respected teacher Allen Lee.

As a way for him to connect to those he’s distant from while continuing to learn, Allen began hosting a weekly talk show. A humble and curious guy, Allen is always interesting to talk to and eternally grateful for what he’s able to learn from others.

We had a great chat about tech and leadership, but in its wake, I felt acutely aware that I haven’t been as grateful to those who I’ve learned from as Allen was to me.

So much of my perspective and professional success can be traced back to the wisdom shared with me by the people I’ve been lucky enough to work for over the last ten years.

Ergo, with this week’s post, I thought I’d do something a little different. I’d like to share the single most important lesson I’ve learned from each of the CEOs I’ve worked for in the past as a way of expressing my gratitude for their contribution to my career.

Yes, this is off-brand and potentially a bit corny. However, this momentary respite from my usual writing is my honest attempt to be grateful, which isn’t my strongest suit — so please bear with me.

Mostly chosen for effect. Mostly.

Lesson #1: Know and own your niche.

Ken Fisher, Editor-In-Chief at Ars Technica

Nearly as old as the commercial internet itself, Ars Technica is a tech news institution. Its success can be attributed entirely to the contributions of its incredible staff and the vision of its editor-in-chief Ken Fisher, who, alongside co-founder Jon Stokes, built a resilient media business which flourished as its aging competitors faltered.

From Ken, I learned that great companies know, and own, their niche.

Thanks to its coverage of topics like tech law & politics, as well as its incredible long-form content, Ars provided its niche enthusiast audience with content they would pay to pore over for days rather than pandering to a mainstream readership who would freely gloss it over in seconds.

Ars prioritized long-form value over ads, and, in doing so, paved the way for modern web media — a strategy that contributed to the company’s acquisition by Wired parent Condé Nast in 2008.

Lesson #2: Let your team take you way outside your comfort zone.

Howard Ganz, President and CEO of Ganz Studios

Few people know the Ganz family dynasty or its reclusive owner Howard. Yet, there are millions of kids around the world for whom the company’s products will forever have a place in their hearts.

As a family business owner, Howard had to balance being true to the traditions the business was built upon while forgoing those traditions to “innovate or die”.

Seeing the rise of the internet and aware that his company may be in peril if it couldn’t adapt to the trends, Howard entrusted a young group of digital dreamers to transform his physical product company into a video game company.

So was born Webkinz, one of the biggest success stories in the history of kids’ toys and a game property still generating ample revenue more than 10 years later.

From Howard, I learned that great leaders must let their people go outside their comfort zone in order to succeed — and given that Webkinz was, at its peak, earning $100M in ARR before “ARR” was a common metric is proof positive that discomfort can pay off for founders.

Lesson #3: If your employees love your company, so too will your customers.

Razor Suleman, CEO of Elevate (formerly CEO of Achievers)

Among the most inspiring leaders I’ve worked for is Razor Sulemen, whose small employee rewards company I Love Rewards became the successful, large employee recognition company Achievers.

Achievers was widely known for its incredible company culture, and that culture is almost entirely attributable to the way that Razor prioritized making employees happy.

Few leaders out there are bold enough to host a company roast of the senior leadership let alone insist that, even at 300 people, the entire company meet every single day for 9 minutes to share wins, mourn losses, and celebrate progress towards a well-articulated vision.

From Razor, I learned that if your people love what they do and who they do it with on a daily basis, they will make your customers love your company — and that strategy is why Achievers counts great companies like KPMG, PwC, Samsung, Rogers, BP, and Microsoft among its many customers and raving fans.

Lesson #4: Be persistent in solving a hard problem.

Gemini Waghmare, CEO at UXP Systems

Telecom companies are notoriously siloed, slow-moving, and stubborn. The idea of creating a company to disrupt that, then, could be easily construed as lunacy.

Yet, that’s precisely what UXP Systems’ CEO Gemini Waghmare did. Seeing the emerging trend of personalization and device-agnosticism coming, Gemini knew that operators wouldn’t be able to evolve their infrastructure fast enough to catch the likes of Netflix.

From Gemini, I learned that persistence can pay huge dividends if you believe in yourself and the problem you’re solving.

Despite an extremely long sales cycle and an incredible set of hurdles technical, legal, and logistical, Gemini’s user lifecycle management platform has found success — so much so that it was recently acquired by Amdocs.

Lesson #5: It takes more than tech to build a great tech company.

Alex Salazar, VP Product at Okta (former CEO of Stormpath)

Perhaps the most humble and human C-level executive I’ve ever had the privilege to work with, former CEO of Stormpath Alex Salazar pairs a strong business sense and product acumen with ample EQ and charisma.

From Alex, I learned that you need more than tech to build a truly successful tech company.

He hammered home in me the understanding that customers care much more about the problems your product can solve than the elegant design or ingenious implementation of your solution.

This was a lesson he learned during the years his company was embattled with its competition in an arms race for marketshare. Winning the race ultimately meant building features that weren’t quite as tech sexy but functionally required to the solve meaningful business problems of the customers who were willing to pay.

Thankfully, Alex was able to find a great partner in Okta (who acquired his company Stormpath in 2017) to bring the amazing tech his team built to a broader base of customers.

Lesson #6: Manage with metrics, not man-handling.

Rob MacLean, CEO of Points

By far the most seasoned CEO I’ve ever worked for, Points’ Rob MacLean founded and took a fledgling Canadian startup from no revenue to the TSX and well beyond over the last two decades.

His $203M company has found success with virtually every major airline company and hotel group in the world.

While I didn’t spend a lot of time with Rob personally, I drew lessons from his leadership via the team of C- and VP-level talent that he hired, including former CTO Dave Simons, former VP of Marketing Danielle Brown, and current SVP of Product Peter Doulas.

From Rob and his leaders, who largely trusted their teams in the trenches to get the job done, I learned that managing with and carefully monitoring key metrics can make a huge difference in your company’s ability to accomplish big things.

During my time at Points, we underwent a major re-platforming of the company’s biggest product and most significant line of business. The focus on metrics helped us build a modern, multi-million dollar product that ultimately improved conversion and top-line revenue — all while maintaining steady year-over-year growth.

Lesson #7: Building great partnerships requires great humility, loyalty, and sacrifice.

Alex Barrotti, CEO of TouchBistro

Above all others, I worked most closely with TouchBistro CEO Alex Barrotti.

Alex afforded me a tremendous amount of his time to discuss all manner of product, rev share, and strategy. He gave me the opportunity to present our roadmap to the board, to directly address our company on numerous occasions, and even to speak to the media on his behalf at off-sites and events.

Yet, it was our business trips together that taught me the most important lesson I would learn from him. I was witness to the man’s unyielding commitment to his business partners, and no matter how glamorous the life of a CEO may seem, the gruelling circuit of travel and shop talk can and will wear down even the most steadfast founder’s fortitude.

Among other things, Alex taught me that building great relationships that can drive long-term value requires great humility, loyalty, and sacrifice.

Alex remains convicted in his pursuit of delivering to and with his partners, and as a result, TouchBistro has now teamed up with Chase among many others to provide the #1 point-of-sale for restaurants.

Lesson #8: Be your own competitor.

Mike McDerment, CEO of FreshBooks

While I haven’t spent much time with Mike yet, I was drawn to work with FreshBooks after I read the story of Billspring and became a customer.

With a technology solution that was largely stagnating and a set of entrenched incumbent competitors narrowing their sights on his first company, Mike made the bold decision to found a second: his own competitor.

So was born the New FreshBooks and, in the process, one of the most interesting displays of product strategy that I’ve ever seen — as well as a clear lesson: even if it means becoming your own competitor, never believe that the product you have today is all you need to stay in business beyond tomorrow.


I would be remiss if I didn’t mention three more CEOs who I haven’t had the luxury of working with directly but from whom I’ve drawn at least one great lesson.

Lesson #9: Don’t hire in a hurry.

Brian de Haaff, CEO of Aha!

I had the good fortune to spend some time talking to Aha! CEO and co-founder Brian de Haaff recently, and in our short conversation, I learned that it’s incredibly important to hire with your gut, even when that means saying no to someone that on paper should be a perfect match.

In building Aha!, Brian has bootstrapped an incredible (and under-the-radar) growth company without falling for any of the major trappings of today’s modern rickety Valley rocket ships.

He’s accomplished this largely by being exceedingly careful with who he and his teams hire, and as a result, he’s enjoyed virtually no major employee turnover and his company shows no signs of slowing down as Aha! continues to transform product enterprises.

Lesson #10: Know thy landscape.

Daniel Debow, CEO of (formerly co-CEO of Rypple)

While I only met Daniel Debow once, when he was the CEO of Rypple (a then-competitor to Achievers), his words and actions have stayed with me to this day.

Daniel paid very close attention to the competitive market and understood better than anyone the landscape he found himself at war upon.

That’s how we met. In his market monitoring, he’d found a critical article I’d written about Rypple’s product while I was working on gamification features for Achievers’ platform.

He was acutely aware of the landscape and where the various players in our employee recognition space fit, and he spoke confidently about his direction relative to ours when he took for a coffee to confront me over what I’d written.

His commentary proved prophetic, and as a result of his market-mindedness and networking savvy, he was able to create the circumstances for the strategic (and timely) acquisition of Rypple by SalesForce in 2012.

Lesson #11: Pick great cofounders.

Zak Hemraj, CEO of Loopio

Last but certainly not least, Zak Hemraj and I previously worked together at Achievers before he went on to found the award-winning RFP response platform Loopio.

From Zak, I learned the value of picking great co-founders.

Zak is one of the smartest people I know; his insatiable curiosity and intelligence allow him to excel at just about anything he decides to pursue.

However, Zak knew that he couldn’t build a great company by himself, so he chose two equally-talented cofounders in his friends and former coworkers Matt York and Jafar Owainati — and the three have been enjoying great success since.

What Have You Learned?

As I look back on the last ten years, I find myself tremendously grateful to those outlined above and the lessons I’ve learned from each of them.

Of course, these CEOs are just a small subset of the many leaders I’ve worked with over the years. I’ve also learned a ton from others—leaders with and without title—and I look forward to celebrating the lessons learned from them in a future post, too.

For now, though, I would pose a challenge to each of you before I return to the regularly-scheduled weekly shenanngains of my typically-sassy product posts.

Forget about your company in-fighting and your personality clashes and your various day-to-day dramas. Forget about appearing to be a “suck up”. Take some time to try to do this exercise and to be grateful to those you’ve worked for and with. It’s not easy, but it’s immensely rewarding.

Oh, and thank you for reading, too. See? Gratitude is awesome, amirite?

Have your own CEO lessons to share from a great CEO you’ve worked for? I want to hear them. And if you’d like to learn more about me or my business, visit