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Moving from oDesk CEO to Polaris Venture Partner: My Decision DNA

By garyeswart on July 10, 2014

Hopefully in your career, you are lucky enough to find a job at the intersection of something you love doing and that you do well. Sometimes, that job also lets you work with great people. That mix of passion, aptitude, and culture is always what I look for in a job, and I am happy to say that I’ve found it at Polaris Partners.

After eight years as the CEO of oDesk, I decided to join Polaris Partners as a Venture Partner. When evaluating whether to move into venture instead of stepping into another operating role, I looked at the role in terms of the framework above, but also across the four dimensions that I believe matter to everyone in their work: impact, growth and development, financial reward, and balance. It is here that I found my answer to not only what I should do next – but with whom I should partner. Here’s a little bit of background on how I made that choice.

Impact:

As the CEO of oDesk, I was fortunate to be able to have an impact on more than a million businesses and 5 million freelancers. It was incredibly rewarding to not only help create opportunities for our customers around the world, but also to make a difference for our employees and investors by leading a successful company. At Polaris, I look forward to multiplying my impact by helping a greater number of companies (Polaris boasts more than 100 fast-growing companies in their portfolio) and their constituents, instead of focusing my energy on just one company.

I have also been fortunate to work with great entrepreneurs in the roles of coach, mentor, advisor, and investor. Nothing beats the feeling of recognizing a situation, pattern or strategy which I have experienced before that can be applied to a current business model. It’s like helping someone catch a wave I see coming our way. I realized how rewarding this experience was to me, so I’m eager to continue sharing all that I have learned in my career with entrepreneurs as a Venture Partner.

Growth and development:

At oDesk I enjoyed a tremendous amount of opportunity to grow and develop as a CEO, but that only makes me hungry for the next challenge. Meaningful personal and professional growth happens when you are out of your comfort zone, working in a new environment and through difficult situations. As CEO I gained a lot of experience from being the battlefield General, making decisions under fire (not all of them right), and adjusting when necessary. Those errors provided me a unique opportunity to learn what not to do again. But growth can slow when you spend a lot of time in the same role, so I look forward to embracing a whole new set of skills and experience from a different environment and responsibilities. My partners at Polaris have been together on the field for decades and I look forward to learning a great deal from them.

Financial reward:

You’ve probably heard stories about the wealth created for VCs who backed very successful companies. But what you typically don’t hear about are all the deals they’ve invested in that didn’t make it. Venture capital is not a get rich quick model; it is patient capital that requires a long term commitment. It takes time for companies to grow to the point that they can deliver a return and for those who have the mettle and dedication, the reward is worth the wait. It also requires putting skin in the game – both financial and sweat equity. This is a meritocracy model I can get behind.

Balance:

You may have heard people say that it’s lonely at the top — I can tell you from experience that it’s true. Most CEOs put every ounce of their energy into running the company, worrying about employees and customers and investors, at the expense of missing out on the rest of what’s important in life. I believe this venture role will allow me to achieve a bit more balance than when I was at the helm of a company.

Polaris has an investment approach where we all contribute to the success of the portfolio. We each bring skills and viewpoints to the table, which helps not only the companies, but ourselves as well. Being a member of a true partnership is being part of a team whose players support and learn from one another. Most of my partners have had incredible operating experiences and all of them have had successes in more than one field, which I find incredibly exciting. This is the kind of team I want to play on.

Of course, there are other factors to consider when accepting a new position. Here’s how I thought about those additional dimensions.

Mission and values:

I have always tried to create a great culture at all of my companies, leading by example with a strong work ethic and setting a high bar for bringing on the best talent. Polaris has a similar philosophy — building strong, enduring relationships with leading like-minded entrepreneurs, hiring curious, committed and intelligent people, and valuing fairness and true partnership as cornerstones of their community. It is here in this environment where I want to operate.

Strategy and opportunity:

For venture capital roles specifically, you have to align with the firm’s investment approach. Polaris ‘s long-term, diverse investment strategy has not only been extremely successful, but it also encompasses my sweet spot – early and expansion stage technology, SaaS companies and specifically people and marketplace businesses that leverage underutilized assets and excess capacity. Polaris has an extraordinary SaaS portfolio and a national franchise of more than 40 software companies. So while the firm enjoys success across the healthcare and technology industries as well as in all stages of investment, there is a significant opportunity to make a difference in an area which greatly interests me.

What’s more, I feel fortunate to join a great partnership with a fantastic track record. Polaris has a strong reputation on the East Coast, and though more than 20% of their investments are on the West Coast, they have a limited presence in the Bay Area. I view this as a huge opportunity for impact with tremendous potential for the future of the firm.

I am excited about this new chapter and look forward to achieving impact, growth and development, financial reward, and balance in my new role. I will share more about my journey along the way as I transition from CEO to Venture Partner beginning this Fall, so stay tuned.