One year in, reflections on going from bootstrapped to (heavily) funded

Written by: Noah Waisberg

September 10, 2019

4 minute read

A year ago this week we announced Kira Systems’ $50M Series A investment from Insight Venture Partners. It’s a good time to reflect on what its meant for our business and me.

If you’re not familiar with Kira Systems’ origin story, here’s some context. Dr. Alexander Hudek (our CTO) and I co-founded Kira Systems in 2011. We bootstrapped the company for the first 7.5 years as we were developing Kira, and getting traction with our early champions. Over that time we grew from 2 employees to over 100.

Why we did the raise.

There were a couple key reasons why we took the investment.

First, we believed outside capital would lower our risks (e.g., of an economic downturn) .

Second, we thought extra capital could help us be more aggressive seizing the huge opportunity we see in our market.

Third, we were really impressed with Insight’s knowledge of the contracts software space, as well as their exceptional track record helping growth stage companies grow. Bootstrapping from 35 to 110 employees in 20 months sounds more fun than it is. We felt Insight could help us grow more more systematically and gracefully.

What we’ve experienced in the last year.

By the time we took our funding, we were used to fast headcount growth, and spending significant amounts of money when we saw value in doing so. So the funding didn’t drive huge change to how we behaved.

That said, there are three key areas where the funding changed things.

It raised our profile. Our round was the largest legal AI funding round to date, and significant as Canadian VC rounds go. As a result, we’ve been able to continue building an amazing leadership team (and it has helped our leaders in the hiring of their teams as well). These new Kirans are helping drive the company forward. We have deliberately built a team with diverse experiences that is helping us think differently and better. It’s also worth calling out here that Insight has been a fantastic help with evaluating very senior hires. As a company manager, I will only hire a few heads of marketing over my career. Insight, on the other hand, participates in hiring lots every year across their large portfolio. They have given invaluable feedback on a few key candidates. Senior hires can make such a positive or negative difference in growth, and I feel they have helped us do better here.

Our raised profile has also helped our industry recognition. Kira Systems has been fortunate to be touted as one of Linkedin’s Top Five Canadian Startups. We’ve been identified as a “Market Shaper” by the Financial Times, and are well ranked amongst some impressive industry company. I suspect these kinds of recognition have helped Kira Systems’ brand awareness with prospective employees and customers.

Higher Expectations. Working with Insight has impacted how we think about success. Instead of benchmarking our results against legaltech or Toronto companies, we now think of success as meeting the performance marks set by the best Insight portfolio companies. There are some legaltech and Toronto companies that really impress us, but the Insight portfolio has a high number of stars, and it reminds us to keep aiming high.

Data Driven. We have become a more data-driven company. We still run our business, but we now have more of an obligation to explain to others why we are making the decisions we make. This is great, since it forces us to be more rigorous in our thought, and make decisions based on more extensive data (where we can). We like making evidence-based decisions, so we’re very happy with this evolution.

Our expanded teams are investing further in data tracking systems and bringing their expertise to them to help us better measure and report on performance. I see this driving better conversations across the company.

What I’ve personally learned.

Despite a busy schedule, I now make time for a regular set of conversations with several members of the Insight team. I’m constantly gaining new perspectives on items like the contract management space, enterprise sales, and partnership strategies. In particular, I’ve learned a ton from Peter Sobiloff. His experiences and stories from working with many leading enterprise software companies have been incredibly valuable for me.

One thing I love about my job—even on hard days—is how great of a learning experience it is. I think my learning has accelerated over the last year (though I still have a lot more to learn.)

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