Gilt Groupe Co-Founder: The 5 Secrets of Super Successful Founder Relationships

Alexandra Wilkis Wilson, co-founder of Gilt Groupe and new beauty service app Glamsquad, reveals what it takes to build a productive and harmonious founding team.

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By Laura Entis • Oct 24, 2014

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Alexandra Wilkis Wilson knows a thing or two about successfully working as part of a co-founder team. Having helped launch Gilt Groupe in 2007, Wilkis Wilson worked alongside her four co-founders for seven years; together, the group not only got the flash-sale luxury site up and running but transformed the way many Americans shop.

In August, Wilkis Wilson announced that she was leaving her day-to-day duties at Gilt to join another team of co-founders. Alongside Jason Perri and Victoria Eisner, Wilkis Wilson launched Glamsquad, a mobile app that allows women in New York and Los Angeles book stylists who come to their house, office or gym for maximum beauty convenience. The company just announced that it has raised $7 million in Series A funding in a round led by SoftBank capital, and will be launching soon in Miami.

As any entrepreneur can tell you, building a business from the ground up is both exhilarating and enormously difficult. Having done it once, only to turn around and start the journey from the beginning, Wilkis Wilson understands the joys and pains of starting something. "There are always going to be good times and bad," she notes. "There are going to be the highest highs and the lowest lows."

Because of this, the relationships between co-founders are all-important -- it's no accident that most startups crumble not because of outside competition, but because of disagreements between founding members. More than any other factor, the team you build from the get-go has the power to make or break your enterprise.

Related: How a Couple Managed to Make It Work as Co-Founders

With that in mind, we asked Wilkis Wilson to share the lessons she's learned over the years on how to create and maintain a harmonious co-founder team.

1. Diverse skillsets and personalities. A large part of Gilt's success can be attributed to the fact that each founding member brought a unique area of expertise to the table – Wilkis Wilson (luxury goods), Alexis Maybank (ecommerce), Kevin Ryan (market strategy), Michael Bryzek (user-focused software), and Phong Nguyen (research and development) -- and as the company grew, this diversity of skillsets and experience was replicated in all subsequent hiring decisions. "We took the Myers-Briggs assessment very seriously at Gilt, whereby we brought in an executive coach to walk us through how to think about hiring diverse teams of people, with diverse ways of looking at problem solving," says.

2. Clearly defined roles. When each co-founder has his or her own domain of expertise, responsibilities are naturally divvied up, Wilkis Wilson finds. At Gilt, her co-founders' dramatically different skillsets was an asset. Not only did their range of abilities compensate for one another's knowledge blind spots, but "it was clear from the get-go who would be responsible for what. We didn't have any conflict in terms of overlapping roles and responsibilities."

3. A shared vision. While co-founders' roles and skillsets should differ, their views on the company's identity, purpose and overarching trajectory shouldn't. The realization that her vision for Glamsquad's future aligned perfectly with Perri and Eisner's is what ultimately convinced Wilkis Wilson to broaden her role from advisor to the fledgling company to its full-time CEO and co-founder. Each co-founder needs to share a sense of excitement and clear idea about where the company is headed, Wilkis Wilson says.

Related: 5 Ways to Have More Meaningful Exchanges

4. Trust. At Gilt, Wilkis Wilson came aboard as co-founder along with her best friend, Alexis Maybank. The two shared an inherent, built-in trust developed through years of shared experiences and mutual respect. In the beginning, Maybank was Gilt's CEO and Wilkis Wilson reported directly to her. "We had such a fantastic relationship and rapport," Wilkis Wilson says.

One of Wilkis Wilson's co-founders at Glamsquad is a friend from her days as an undergrad at Harvard University. "We have a history," she says. While it is often difficult for entrepreneurs to find the right co-founder organically -- thus the rise of entrepreneurial networking events and meet ups -- Wilkis Wilson recommends caution when considering bringing onboard a near-stranger. "Entering into a startup with co-founders, it's almost like entering into a marriage," she says.

As with any romantic relationship, before deciding to elevate things to the next step and make the partnership official, both parties should have a solid grasp of one another's background and personality. In other words, Wilkis Wilson advises, don't go the shot-gun wedding route. "You really have to go through a process of getting to know someone, doing your research, doing due-diligence, getting their references checked," she says. "A startup is a long journey. You want to know what that person is going to be like through the good times and the bad."

Related: The Survival Guide to Co-Founders Living Far Apart

5. Constant communication. "There is no such thing as over-communication," Wilkis Wilson says. Expressing any frustrations, confusion or strategy concerns as they arise, on a rolling basis, eliminates festering anger or resentment, and keeps the company running smoothly.

When Wilkis Wilson joined Glamsquad in August, she held a meeting with the company's entire executive team, and asked each member to answer the question: 'In order to have influence with me, here is what you need to know about me.' "It was a moment for each of our executive team members to go through their list, whether it be pet peeves in business, or things they respect, things they value and appreciate in their coworkers, whatever it is that was on their minds," Wilkis Wilson says.

At Gilt, and now at Glamsquad, Wilkis Wilson sets aside time each day for members of the executive team to communicate. "I think setting up safe environments for honest communication is really important and something that shouldn't be done once a year, it should be done on a regular basis."

Related: 5 Things to Do Before Saying 'I Do' to a Business Partner

Laura Entis
Laura Entis is a reporter for's Venture section.

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