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Building your C Level Team

team-justice-leagueBack when I was a seed stage VC I was always amazed to meet founding teams where every one of them had a C level title. CEO, CTO, etc. Now the beauty of having your own company is that you can call yourself whatever you want. But when dealing with institutional investors its important to be open and self aware enough to judge whether you truly have a C level team in their eyes.

I’ve been part of many startups now as either an investor or management team member. But FreshBooks is the biggest so far (Shopify is bigger but was much smaller when I was involved). We are at the growth stage, well beyond startup. And what we need in terms of leadership and management differs very much from what my past companies have needed.

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The Startup Treadmill

going-nowhere-fasterDo you know why startups fail? Because they run out of money. Yes, there are lots of root causes: wrong market, timing, team, product, execution. But you can get past these sins and keep fighting as long as you have cash.

Ironically, the reason why startups run out of money is because they raise capital too early. And they raise the wrong kind of capital too early.

As soon as you raise institutional capital of any kind you get on a treadmill where the VCs want you to run harder and burn faster. They want you to use their capital to accelerate – spend, hiring, marketing and ultimately growth. Acceleration is of course why you raise money and give up part of your company in the first place. But premature efforts to accelerate usually don’t work.

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Operation ‘Hire a VC’

A year ago today I started full time at FreshBooks, completing my transition out of VC. People often ask me if I miss it. The short answer is ‘no’. It’s been a great move for me on every dimension.

I was so positive my transition that a few months back I rescued another VC, hiring Russell Samuels away from Mantella Partners to come join our biz dev and corp dev team.  This has also gone really well. Russell is a happy camper and is kicking ass!

On the strength of these two moves, I realized that we need more of this. We need to rescue VCs and bring them back from the dark side. So, today, I am pleased to announce Operation Hire a VC. It’s a simple program really. Starting today, FreshBooks will give preference in all its current and future job openings to any applicants that have a VC background. The more experienced the better. We think General Partners bring a wealth of smarts and connections that can be applied to almost any role.

If you’re a VC and need rescuing, check out our careers page. And if you’re an employer and agree with me that VCs would make great team members then come join the cause and implement Operation Hire a VC at your company!


Conviction: This is a word we use a lot at FreshBooks. Why? Well, not because we like to hire ex-convicts, but because we are building a company for the long term and want to be a long term leader in our market.

When you look at the World through that lens it clarifies things.  You realize first of all how difficult it is to build an enduring market-leading technology company. CB Insights published some stats last week telling us that 2 out of 3 tech exits last year were startups selling at Series A or earlier. That’s just the companies that even get to exit. If you lump in outright failures on top then what you realize is very few companies get past series A and become true growth stage companies. Even fewer become profitable, stand alone market leaders.

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