Former Wayfair CFO and ex-Gartner CEO Michael Fleisher currently serves as a member on four boards, including his most recent appointment as chair of the audit committee for wholesale retail platform Faire — but simply being on a board to provide distant oversight and guidance is “not really that interesting,” he said.

While some professionals serving on boards may “show up four times a year, learn a little bit about the business, provide the right oversight and do all the things that you have to make sure are done, for me, that's not the engagement I want,” Fleisher told CFO Dive in an interview. “The engagement I want is, how can I really help this group of people make this business even better?”

Moving through the growth gates  

Fleisher has some “personal passion” surrounding the retail industry, he said of what inspired him to take his newest board seat with San Francisco, California-based Faire, which provides an online platform to foster connections between local retailers and brands.

Fleisher was also intrigued by Faire’s growth potential: The business is now recording annualized revenue of approximately $550 million, marking a 32% year-over-year jump, according to the March 11 press release announcing his board appointment.

Successfully seizing that opportunity requires some shifts on the part of leadership, however: Running a business that’s seeing $100 million in revenue is “quite different” than leading a business that’s seeing $250 million, which is then distinct from how to run a business at $500 million, he noted.

Having “been through some of those gates before, I think I can bring something to the table,” Fleisher said of Faire’s growth. “And the team is really open to wanting people on their board who are engaged that way. I think that's the part that was, for me, most exciting about it.”

An experienced retail executive, Fleisher’s resume includes a near-decade in the CFO seat for furniture retailer Wayfair beginning in 2013. During his tenure there, he helped to lead Wayfair’s initial public offering in 2014 which left the company valued at $2.3 billion, Industry Dive sister publication Retail Dive reported at the time.

Before Wayfair, his past roles included a six-year span at Warner Music Group including as vice chairman, strategy and operations for Warner Music Group and a six-year term at Gartner, including a five-year stretch as its CEO, according to his LinkedIn profile.

As well as Faire, he serves as a board member for restaurant chain First Watch Restaurants, website builder Squarespace, and technology and online sneaker and apparel business GOAT Group, according to his LinkedIn profile.  

Alongside other Faire board members, including DoorDash alum Christopher Payne, Fleisher will work to help strength the company’s operating discipline and financial planning as the business “sees substantial opportunity to expand its share of wallet over time, reinforcing its ambition to become the central operating system for wholesale,” according to the March 11 press release.

That means doing due diligence as the company’s audit chair: a role that is changing from simply overlooking financials to helping the company steer clear from risks, he said. During his first few months at Faire, Fleisher has also spent a lot of time conversing with Faire’s CFO Jason Lee, discussing key considerations surrounding capital allocation, talent needs and other critical points for the business to successfully execute its growth strategy.

Having those discussions with the finance chief is essential as “I do think the challenge of businesses that are at the stage that Faire is at is, there's too many good things to do,” Fleisher said.

That’s a good problem to have, but “it’s a real challenge, I think, for founders and teams to think about, where should I put my resources and what's my best bet, and more importantly, where should I decide, I'm actually not going to do that,” he said.

The board balancing act

Finding balance in his own role at Faire is also top of mind for Fleisher, he said: While there are some areas where he can step in right away and share his lived experience, there are others where “I need to understand the nuance of your business better before I tell you do this or don't do this, in my opinion,” he said.

In settling into his board seat, another area he’s focused on is ensuring key team members are comfortable approaching him. There’s often a perception that board members, while important figures, are not people to reach out to, which represents a “huge wasted opportunity” for Fleisher, he said.

“I want the people at Faire...thinking about, ‘oh how do we make sure the product gets to our customer the right way? And what's the opportunity there to think, oh, Fleisher is somebody we can reach out to for that and just gain that knowledge?’” he said.

Ensuring one can get along with key company leadership is not just important for ensuring the business can successfully meet its goals, but a crucial factor when considering an opportunity to join a board, he said.

Finance chiefs contemplating their first board opportunity may get caught up in the fact that their skills fill the appropriate niche: Oftentimes, CFOs get approached because a company is seeking an audit chair and are looking for a professional with the appropriate skillset. While it’s important to have those skills, and “you should care what the business is about, but you should really care about the people,” Fleisher advised.

“Do I get along with this CEO? Do I get along with the CFO? Do I think they want my input and my guidance? Do I think they are the kind of people I would want to spend time with and engage with?” Fleisher said. “I think those are really, really important and often under-looked [questions], particularly by CFOs joining their first board.”