Our First Year in Venture Capital: A Conversation with Kelly Jacques, Inovia Capital

A little over a year ago, I joined the world of venture capital. Prior, I’d served as CIO for four consecutive companies. It was a significant change for me, during a time of significant change for everyone.?

My story is not unique. In a world heavily influenced by COVID and shifting mindsets around work/life balance, more people than ever are uprooting their professional lives and taking on a new challenge. Not just new jobs, but new roles and industries entirely. Even within the world of VC, there are many more tales just like mine — people who made the transition within the last year, eager for a new challenge, but utterly brand new to the job.

A few months back, working on a mutual investment deal, I met a young VC named Kelly Jacques who had joined a firm called Inovia right around the time I signed on with Ridge. She and I connected (and commiserated) around the unique challenge of coming into such a complex and foundational space in the midst of so much social and political upheaval. Down the road, we even co-invested in a very cool company called Rewind.?

Kelly is based north of the border, in Montreal. After graduating from McGill University, she spent the early portion of her career in management consulting. But VC work always sparked her interest, and when the opportunity arose to make the jump, she did.?

I sat down with Kelly to compare notes on our respective first years in the industry. We talked about what made us decide to take on a new challenge when we did, and what it was like to onboard and become part of a team in the midst of a pandemic that made in-person meetings near impossible. We discussed early deals, what it was like to meet founders virtually and the most critical learnings we’ve each taken away from our first 12 months in the industry. Despite very different backgrounds and paths into the world of VC, we’ve shared a lot of common experiences — and learnings — throughout year one.?

What was it like to jump into a new and complex role, fully virtual??

Kelly: I think it was actually a blessing to be able to join fully virtual. It allows you to get a real sense for the company culture, because so many people associate company culture with a fun office space, happy hours, work events, etc. Those are important and fun, but they aren’t core cultural values — they’re add ons.?

When you have to cut away all the fluff, which the pandemic helped many of us do involuntarily, those core cultural components come to the forefront more readily. How do you want to make an employee or colleague feel day-to-day, when they’re not standing right there in front of you? How do you empower them, and vice versa? If you can communicate a strong culture virtually, you can certainly do it live.?

In tech, particularly, I think a lot of companies buy into this myth that culture is created around free snacks and whimsical beanbag chairs. In my first interview at Inovia, I was asked about my personal values. I think that is what has allowed us to build such a great team here. When you try to recruit for fit, you end up with people who have similar backgrounds and experiences. When you hire for values, it promotes diversity. You’re hiring a culture add rather than a culture fit.?

Yousuf: Well my onboarding process was very low key – it happened in my kitchen, with a cup of coffee and a donut! I’d only met a few of my new team members in the past, so while there was a little bit of familiarity I had certainly hoped to see everyone in-person. The transition from operating executive to venture investor takes time. I had to mentally make the switch from managing large teams and actively deploying technology to the mindset of an investor. Despite joining at a time when we were fully virtual, my incredible team members worked closely to guide me through my first few months in the business.?

When restrictions around COVID began to ease and we were able to meet in-person more often. I think the way we collaborate virtually was what allowed us to make such a smooth transition back to office life. One of the things I love about Ridge is that we operate as a unit, and truly work together on everything we do. This approach really helps people discover their strengths, and provides insight into the expertise and assets we have throughout our group, regardless of whether we’re meeting virtually or live.?

When was the first moment you felt like you’d “arrived,” or belonged?

Kelly: I don’t think a VC ever really feels that way. Part of the job is being a little bit uncomfortable all the time. You need to enjoy navigating unfamiliar waters, and be okay with the reality that you’re probably going to be the least knowledgeable person in every meeting you walk into. Think about it this way: Whenever I meet with a potential company, their leadership eats, sleeps and breathes their idea, their technology. I am an outsider, there to provide guidance and support, but I’m never going to be as dialed-in as they are. The ability to add strategic value regardless is critical.?

Yousuf: When I started actually working on deals, that’s when I at least began to feel like I belonged. Going through the process from start to finish — sourcing a company, bringing it to the partners for review and consideration, competing for the deal, issuing a term sheet, showing value and ultimately being selected — that’s when I really felt like I could contribute. I’ve always wanted to work in VC, so leading that first deal and ultimately becoming a board member was one of the most gratifying moments of my career.?

When you’re looking at making an investment, what’s your process? Where do you start? What is your upfront criteria, and what do you find out later??

Kelly: It goes without saying that there are a multitude of factors we look at when first evaluating a company — what problem they’re solving, the tech moat, the product itself. But one of the things we really care to dig deep on is the team itself. When you work with incredible founders consistently, you realize how important people are in those early days as they navigate product maps and pivots. VCs also really only benefit from investing in founders that share values similar to their own. At the end of the day, an investment is a partnership. If you’re not aligned on that front, it’s near impossible to help each other out. So that team aspect, holistically, is huge.?

Yousuf: At Ridge, we maintain a rigorous focus on B2B software, whether it’s SMB or enterprise, and that allows us to narrow our initial focus on product market fit. We spend a lot of time with the founding team, like Kelly mentioned, to get an idea for what they can do. We think about who within our organization partners best with those founders, who on our team can contribute the most value, who gets along best. Life is short, and you want to work with people you like and with whom you can achieve great things.?

What were the top lessons you each learned during your first year in VC??

Members of the tech ecosystem are wildly generous with their time.?

Kelly: There is a real sense of camaraderie, relative to other industries. It’s a unique dynamic — I’ve learned quickly not to be afraid to reach out to anyone, whether it be other funds or founders. People are interested in talking to others in a similar space. There’s so much passion in tech. I work in a building that houses all of the main VC funds in Canada. You might think that would create some awkward elevator rides, but it’s the complete opposite. It’s collaborative and friendly. You have to love what you do to be in this industry, and that leads to strong relationships that form within the ecosystem.?

Yousuf: I couldn’t agree more. I’ll just add that for me, collaborating with other VCs is one of the best parts of the job. Not only is the community a constant source of information about the business itself, the tech industry, trends we’re seeing across the board — it’s also a place where lasting friendships and partnerships are made.?

Curiosity is your best friend.?

Kelly: Hunger to learn is far more important than knowing everything. Founders and VCs are both learning, all the time. At the outset, I felt a lot of pressure to feel like I knew everything. Imposter syndrome is a very real enemy in this job, but there’s really no need to let it become a preoccupation. You’re always learning, everything is shifting every day, and there is always a need to adapt to something new. Being curious and eager to learn makes that roller coaster a lot more fun to ride. Early on someone said something that has stuck with me since: “If you don’t know the answer, that doesn’t matter — just find a way to find the answer.”??

Yousuf: Intellectual curiosity and a little bit of nerdiness go a really long way. Talking to founders, experiencing their work firsthand, hearing the stories behind how and why they built a product, how they succeeded and failed. Entering each situation from the vantage point of a historian and student has been really rewarding for me.?

Honesty and taking the time to give real feedback, whether to peers or to founders, is valued more than you can possibly imagine.?

Kelly: Giving people honest insight into why you made a decision, good or bad, is something founders especially care about. It’s easy to be generic, or to try to spare feelings, but it’s not productive. People who are putting blood, sweat and tears into something always want to know how to make it better. There’s an incredible openness to learning, to digesting new information, in this industry. People simply want to succeed.?

Yousuf: All founders need operational advice from experienced leaders. In my early conversations with founders, it became clear to me quickly that my real-world experience was what resonated with them most. Whether we decide to pass on a deal or make a funding offer, I always try to provide actionable feedback. The response is always positive. Founders are hungry for real guidance.?

Become hyper-aware of the biases you hold, and be patient.?

Kelly: VC is, in large part, pattern matching. But that comes with drawbacks. Founders that don’t fit the traditional mold might be left out of the equation, which negatively impacts diversity of thought and background. Learning to be aware of the biases you hold is important, and something I’ve caught myself on a few times. Because so much of VC work is pattern matching, there’s a degree of unlearning that has to happen.?

Yousuf: Company building is an incredibly long journey that requires patience on both the portfolio companies themselves, and the initial selection process. It takes a while to do it right, and doing it right is essential.?

The excitement that follows growth is infectious.?

Yousuf: My first experience working with a startup was moving boxes from one storage room to another, because the company had gone from five employees to 100 in three months. It always fascinated me, the concept of exponential and immediate growth that follows startups around, the idea of “overnight” success. That process of business building and creation from seemingly nothing is a truly incredible thing to watch first hand even once, doing it for a living is a source of constant inspiration.?

Even as a junior team member, you can really make an impact.?

Kelly: That was one of the most unexpected surprises for me, in that it really exceeded my expectations. VC still has progress to make on the diversity front, and one of the reasons I joined was to make an impact there. Incremental decisions and intentionality go a long way. I thought our overall impact could be improved by bringing in a partner to help us identify biases in our practice. The idea was received with open arms, and the outcomes have really changed the way we screen founders and look at investment decisions. It has widened the pool for us. It just goes to show that if everyone takes small actions, even folks at a junior level can make a difference.