By Leigh Gallagher
March 21, 2018

The role of chief operating officer is famously hard to define—an oft-cited 2006 Harvard Business Review article calls it one of the most “misunderstood” roles in the C-suite. Perhaps for this reason, there haven’t been too many organizations or high-level peer groups bringing fellow COOs together, the way similar organizations exist for CFOs, CMOs, or CEOs.

Read more about COOs in our feature These Women Could Be the Tech Industry’s Next Great CEOs.

Of course, if anyone can pull off such an organizational feat, it’s COOs. That may be why a few such groups have recently gotten off the ground, to give this ultra-high-functioning, like-minded group a place to gather to share war stories, talk about best practices, and learn from their peers.

Lexi Reese, COO, Gusto; StacyBrown-philpot,
 CEO and former COO, Taskrabbit; Gillian Tans, CEO and former COO, Booking.com; Beth Ferreira, former COO, Fab
; Maëlle gavet, COO Compass

REESE: COURTESY OF GUSTO; BROWN-PHILPOT: BENJAMIN RASMUSSEN; TANS: COURTESY OF BOOKING HOLDINGS; FERREIRA: LISA HOULGRAVE; GAVET: COURTESY OF COMPASS

The role can be tricky for a number of reasons: Much of the work can be “unglamorous” and behind the scenes—overseeing functions like HR, legal and finance. There is no standard definition of the role—it varies widely from company to company and CEO to CEO. And, it’s a vague term to begin with. Minnie Ingersoll, now COO of Code for America and formerly COO of Shift, a platform for buying and selling used cars, says she held the title for almost two years before she finally asked her CEO what a COO does. (“I asked him, ‘Hey, what is this role supposed to be doing?’”) The lack of clarity can be as present in startups as it is in the Fortune 500 C-suite. “Unless it’s really clear what your accountabilities are and how success is going to be measured, it can be a terribly difficult role,” says Bonnie Gwin, vice chairman and co-managing partner of the global CEO and board practice at Heidrick & Struggles.

So the chance convene those in this role might be particularly useful, as these groups are finding. One such group was formed by Cameron Herold, a Canadian entrepreneurial coach and speaker and a former COO himself: Herold held the No. 2 position at franchise junk-removal firm 1-800-GOT-JUNK? for seven years, growing it from 14 employees to 3,100 during that time. Along the way, he built up a side business coaching and mentoring high-growth entrepreneurs and their seconds-in-command, and he eventually left to focus on that business full time.

COO event hosted by Performance COOs, Silicon Valley Bank and Bay Area Operators
Courtesy of Performance COO’s

As he did, he started to notice a gap in the market for high-profile peer groups for COOs. “Most of the CEOs ended up going to YPO (Young Presidents Organization, the membership group for chief executives), Fortune conferences, or Gazelles (an executive education and coaching organization) but they never fit in,” he says. “They needed somewhere to learn, but they didn’t have their tribe.” In late 2016, Herold started the COO Alliance, a membership organization intended for the “seconds-in-command” at entrepreneurial and mid-sized companies. (That could mean the COO, but, depending on the company, it could also be a general manager, vice president of operations, or other name for the operations chief).

For $20,000, alliance members gain access to three immersive two-day workshops with others of their kind (potential members can also “test drive” a single event for $6,740). Call it a COO “boot camp” of sorts: Herold, along with his own second-in-command, Rachyl Blank, gather the No. 2s in settings near their headquarters in Scottsdale, Arizona, for programs that include problem-solving exercises, “masterminding” breakout groups, and workshops with outside speakers. Workshops are capped at 25-35 members.

Herold knows his audience well: He collects their cell phones, and he and his team don’t share the agenda in advance (“COOs are very detail-oriented and like control—we like to take them out of that moment,” says Blank). Topics for discussion include building trust and communication with the CEO, and building a “decision filter,” a system to keep track of the entrepreneur’s ideas that assigns ROI, time spent and revenue projections all on a single page.

Another key topic: Giving the chief executive news that he or she may not want to hear. “[The CEO is] often the emperor that has no clothes, and no one’s telling them the truth,” says Herold. “Everyone is always trying to please them and to be political. And when [the COO] can be the only person who’s actually telling them, ‘dude, you stink,’ they love that.”

Almost more than learning new skills, Herold says his members derive some of the best value simply from the relief and recognition that comes with finally being among their own. In one of his first sessions, he says, “every second-in-command just started to laugh realizing that their entrepreneur isn’t crazy after all,” he says; “they’re just an entrepreneur.”

A similar effort had been gaining momentum in the tech world, where the need for strong seconds-in-command has become particularly acute in the current boom of high-growth tech startups. In 2015, John Kramer was one year into his role as COO of HoneyBook, a small business platform for creative entrepreneurs, when he came to the realization that the COO role in the tech world was “unmapped and undefined,” and yet no community existed for those in the position to share knowledge, the way it did for other C-suite functions. “My CEO, head of sales, head of marketing, head of people and product leaders all had robust ways to connect with their peers,” he says.

He started tracking down some fellow operations chiefs, including Tyler Palmer, VP of operations at Patreon, a payment platform for content creators, and a few others. Together, they approached some of their companies’ partners or investors for help getting a few gatherings off the ground; it didn’t take much for HoneyBook investor Norwest Venture Partners as well as Salesforce and Silicon Valley Bank–vendors to some of the COOs–to agree to sponsor the group’s first few events. Since then, the group, which calls itself Performance COOs, has grown into a self-funded, tight-knit community of about 30 members, hosting at least one event a month, usually dinners at one of the members’ homes or lunch at one of their companies’ offices.

COO Alliance founder and former COO Cameron Herold at one of the organization’s workshops in December 2017
Len Catalanotto

Because they are COOs, they have put some structures and processes in place: they developed a charter and implemented some rules (members should be willing to be vulnerable and not have egos; to invite another member, you have to have known him or her for a year). They start each event off by going around the group with each member sharing a new best practice.

Another Silicon Valley group, Bay Area Operators, has also emerged, a larger group with occasional happy hours. That group is quite useful, too, Palmer says; with its larger membership list, it’s helpful if a COO wants to throw out a question to a bigger group (“if you need a lot of data points”). But Palmer prefers the high-level intimacy of Performance COOs for deeper, more intimate relationship building and problem solving. “It’s a dream come true to show up to a dinner with people who do exactly what I do who I’ve come to know personally,” he says.

The founders of these groups tend to know their members very well—because they are or have been one of them. “They’re on time,” Herold says of his COO Alliance members. When he’s held sessions for entrepreneurs, if the event starts at 8, they’ll “stroll in between 7:45 and 8:30 and they’ll be on their phones,” he says. “Second in commands are all in their seats five minutes before.”

Says Palmer: “Because we’re COOs and hyper-focused on organization, we fill out a spreadsheet with each member’s name, company, and idea he or she wants to discuss.” And they rigorously track attendance, he notes. “Just because, of course we do.”

They have also amassed their fair share of advice for COOs. What advice does Herold give to those COOs—especially those who want to rise to become a CEO? Most important, he says, is to make a name for yourself that’s known beyond inside the organization, by speaking at conferences, at events, and in the media. “You don’t want to be the wizard of Oz,” he says. “You want to be a known entity for the brand you’re building.”

 

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