This is part of our series on the inaugural inductees of Maestro Group’s Executive Hall of Fame. These 12 individuals have been honored for their dedication to advancing their employees from salespeople to sales professionals, holding their teams accountable, treating sales as a science, and modeling best practices within their organizations.
March 05, 2025
In the late 90s, Dean Gonsowski was an attorney in San Francisco, but he couldn’t help eyeing the startup world next door where many of his friends worked. Eventually, he caved and worked for a series of venture-backed startup companies. And then, says Dean—and as the story goes—the “bubble” burst. In his eyes, San Francisco seemed like a place you wanted to avoid if you could, “at least for a good long while.”
So, Dean and his fiancée moved to Denver, where Dean launched a computer-forensics firm with a friend—and then sold it to Fios (an early pioneer in the e-discovery space). From there, he spent the next decade in the e-discovery field and eventually became an executive at Clearwell Systems, a Sequia-backed software-development firm that the mammoth security company Symantec bought for a $400-million price tag in 2011.
This was a high point in his career trajectory, to be sure, and it took Dean a minute to realize it wasn’t the norm. “The rest of your career you chase [it] like, ‘Why don’t I just get those all the time…’ they all look like they have the same potential. You think they’re all gonna be that way. And then they’re not ….’”
In his next professional persona, Dean became a “semi-evangelist.” In addition to managing a professional services team, he developed himself as a business thought leader, “and fancied myself to be relatively good at it.”
He says, “It’s one of those [areas where] the more you do, the better you get. And then you realize, ‘Oh, [if] I want to do this, I’ve got to be really good. I’ve got to read all the legal cases, and I’ve got to follow all the other thought leaders…got to run around, shake hands, kiss babies,’ and it’s just sort of a full-time job if you really want to be good at it. Which is why I’m not great at it now, just because of the lack of time…”
At that point, Dean was a bit of a serial startup executive. A mentor of his, David Cowen, championed the idea of “getting closer to revenue.” To Dean, this meant chasing a chief-revenue officer position. “Twenty years ago, there weren’t really chief revenue officers that I knew of. It was all VP sales and chief sales officers.” These had never captured Dean’s interest as much as working on go-to-market strategies and launch plans. “To be honest, the pure, pure sales roles can be a bit tedious and aren’t as much of a challenge, philosophically, emotionally and intellectually…” The chief revenue officer role seemed to check the get-close-to-the-revenue box.
That advice brought him into the role of CRO (his first while at ActiveNav), but in so doing, it also raised the stakes of Dean’s success. “You have a good quarter, bad quarter, that’s terrifying. No one really wants that level of ‘nowhere to run, nowhere to hide’ accountability. It’s a certain level of insanity that takes getting used to.”
So, why do it? For Dean, it’s because revenue equals impact on a company in a way that, in his opinion, his webinars, talks, and thought leadership didn’t. And impact is how Dean judges his professional value. He’s also a fan of the freedom it gives him to fully steer his career. “If I mess up, it’s 100% on me, a hundred percent. And if I’m successful, I’m like, Okay, that’s because I hired the person who closed the big deal or made the right GTM pivot.”
It was also during this time that Dean met Will Fuentes and Maestro. He brought him into ActiveNav to run a few skills trainings. “Don’t tell him I said this, but he’s amazing in person.” Dean appreciated Will’s introduction of science-based sales insights, coupled with a high-energy presentation of best practices. “You have this visceral reaction: ‘Now this guy really knows what he’s doing.’ [It turned] my chaos into a process.” Dean found that guiding sales professionals didn’t have to be frenetic. “Once you go behind the scenes at a haunted house, and you’re like, ‘Oh. This is how the monster jumps out at you, and now it’s not scary anymore.’”
When Dean moved on to his current CRO role at the information governance software company Gimmal, he invited Maestro back for additional consulting. His reasoning was that it’d be more efficient to have the Maestro team create a playbook Dean could then use to train all his new hires than it would be to make hires without a preordained design. “Once we adopted [Maestro’s customized playbook] ‘The Way,’ the team has met or exceeded plan ever since.”
This is how Dean thinks about his responsibilities as a CRO. To some extent, this is especially important in private equity. One of the ways in which private equity is different from other outfits is the efficiency it demands, both in terms of time and cost. The goal, I learned from Dean, is not to pour endless amounts into a GTM plan and then hope you reap the benefits. Rather, he referenced the ”Rule of 40.” “The popular metric,” per McKinsey & Company, “says that a SaaS company’s growth rate when added to its free cash flow rate should equal 40 percent or higher.”
A private equity-backed company, says Dean, “wants you to grow a reasonable amount—call it 20–30% year over a year.” It also requires you to rationalize every spend. For example, it can take a new hire about a year to begin to bring in money. “And so that’s the hardest part of my job; I have to make the case for investments and have to build a business case to try new things…”
Dean likens it to farming: “You’ve got to spend the money tilling the soil, planting the seeds, before you can harvest. But if you don’t spend the time, then next year you’ve got no harvest.”
In times of yore, success was often measured by longevity at a company. These days, moving around might actually be seen as a boon. So, is mobility a model for the future? Or at least the present? To answer this question, Dean looks to the “T-shaped” philosophy. Rather than cultivating a deep knowledge in only one specific area, the T shape encourages both width and depth. “For me, this is not moving around. It’s sort of orthogonal.” Between law, professional services, thought leadership, and sales, Dean has gained that T shape. “Now, whether I did that at one place or different places [is] kind of independent…” He believes that the CRO role calls for that breadth. “Separately,” says Dean, “I think it’s really hard to stay anywhere for a long period of time now, anyway, just the way cultures are.”
Despite the complex responsibilities of a CRO position, Dean feels it’s vital to maintain perspective and keep calm—and he practices what he preaches. “I think it’s like watching the stock market. If you’re watching it by the second or the hour of the day…” that’s a recipe for anxiety. “If you look at it over a quarter in a year…all the little blips and beeps kind of [get] drowned out. And as long as it’s moving up and to the right, you’re kind of like, ‘Okay, we can do this.’”
This type of grounded approach helps Dean avoid over-fixating on minor setbacks that would distract him from seeing the “forest.” And no matter how many smaller issues need to be dealt with, the CRO must always keep an eye on the forest. This is not to say that he can ignore everyday to-dos, however small. It’s just important to distribute emotional energy according to long-term priorities. And in a business, the long-term priority is money. Which brings Dean right back to one of his favorite pieces of advice: “stay close to the revenue.”
You can learn more about Dean here. Be sure to congratulate him while you’re there!
February 27, 2025 Zoey Weinstein
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