First and foremost, it was a pleasure to be Caitlin's first-ever podcast/show interview as a venture capitalist! So congrats to Caitlin there! But the congratulations doesn't end there just yet. Caitlin is engaged and will be celebrating her new marriage in a year or so... so you heard it here first! :)
I knew that our interview was going to be a great one from the moment she logged onto our zoom chat. I expected to see Caitlin in a gloomy Boston office room, but when she logged on it was clear she was somewhere sunny and warm: Palm Springs for her friend's bachelorette party! I hope it went very well!
In regards to how Caitlin got into venture capital, her story is a unique one. She graduated from college and went out to L.A. to work for a startup called Washio (on-demand laundry) that failed and washed out. What was nice is that this experience set the tone for the rest of Caitlin's career into B2B!
"I learned two big things from my first startup failure. First, I wanted to stay as far away from consumer apps as possible, and number 2, I really wanted to understand what makes a solid business at scale."Caitlin Bolnick | VC Hunting S2E3
From there she decided to gain more experience by joining other businesses and play multiple roles in those organizations, moving to Boston, finding a significant other and eventually joining OpenView Venture Partners.
Apparently the Caitlin drank the B2B Koolaid and enjoys the focus of only working with B2B software companies at a very specific stage: The Expansion Stage.
"Expansion Stage companies have a clear product-market-fit, repeatability, and go to market in place. We tend to look at a ton of businesses in the same verticals and provide tangible expertise. One of the best parts about that focus is you get to learn a lot about that one vertical, ours is B2B software."Cailin Bolnick | VC Hunting S2E3
I wanted to learn more about Product Led Growth, as I read a lot about it on the OpenView Venture Partners website. "PLG BABY!" What is it, and why is it so important?
Product Led Growth is a go-to-market strategy based on product usage as the primary driver of adoption, acquisition, conversion, and expansion. As Caitlin described it, most products can have sales teams behind them pushing the product along. In a PLG strategy, heavy usage of an application as an individual can lead to more adoption within a company because it's grass-roots, and not being forced upon people to use the app because it's a pet project or some sales guy sold the VP of Technology a SaaS system that everyone hates. I have particularly a lot of experience in this type of nonsense.
"What is Product Led Growth all about? It's all about creating an organic community and creating a product at a certain price point that an average employee at a company can use. Calendly is a great example of a bottoms-up approach because you or I can have a link in our email and we'd send it to one another and you'd say, 'hey, this is really interesting' and you'd adopt it and then the growth goes from there."Caitlin Bolnick | VC Hunting S2E3
Wanting to dig in a bit more about Product Led Growth, I wanted to understand what drove that decision for her firm to focus on these types of companies. Is it a de-risking methodology? Is it to ensure that companies have traction and some type of revenue-generating system that allows OpenView Venture Partners to ensure their investments have a higher chance of success?
Caitlin said it's simply because they don't believe in the Law of Large Numbers, or that simply having a lot of companies in the pipeline doesn't equate to portfolio success. They have about a billion under management, but they only invest in about 5 companies per year. This is because they hold a belief that they should invest in founders and companies and really help them grow and have a team of about 25 individuals where their full-time job is to do contract-based work with our companies.
"Once we invest we sit down with the entrepreneurs and really talk about their business with them, where there are real opportunities where we can provide tangible enterprise value very quickly or those areas where they are looking to hire someone or you don't have someone yet. Let us take that off their plate and work through it."Caitlin Bolnick | VC Hunting S2E3
Following up from this idea, I wondered what were the things that expansion-stage companies usually need and what are the patterns she's seen.
"A couple of things stand out. One is pricing and packaging. This is an extremely common thing that we work with our companies on. The idea is how do we either increase or decrease or change packaging so you can gain additional revenue without burn and churn. Another one is recruiting. Sometimes you just need an SDR (Sales Development Rep), and we have an internal recruiting team that can help companies fill these positions quickly. The last one is go-to-market. We have experts that we can connect the companies with to retune certain aspects of their go-to-market strategy."Caitlin Bolnick | VC Hunting S2E3
As we always do with VC Hunting, we dig up what people say and do online and keep them accountable. I had an interesting question that I wanted answering around 'scar tissue' of venture capitalists. What did she mean by this?
Her answer was great in that founders simply need to understand that venture capitalists have biases and preferences like everyone else!
"If you're in a space that the investor just doesn't like you're already barking up the wrong tree. There could be a variety of reasons why that investor doesn't like that space. You could have the best business in the world but it's going to be infinitely tougher for that investor to get comfortable with you as an entrepreneur versus another investor who has an affinity for that space more."Caitlin Bolnick | VC Hunting S2E3
Very sage advice that reminded me of what Bill Bryant said during our interview around how founders need to understand that investors have preferences and biases too. They have strategies and returns they need. As a founder, you have to ask the right questions to understand the person behind the money. This is another reason why we do these interviews! So that future founders know who to go to!
Finally, I wanted to know if Caitlin had figured out a better way to store passwords than a piece of paper. Apparently she's using 1Password for now (I use it too)!
I absolutely enjoyed this conversation with Caitlin Bolnick and I look forward to much more success! Make sure to follow her and if you're a B2B software founder with product-led growth, well, you know exactly where to go.
Enjoy my retrospective!
Och, ya cannae beat the smell of fresh pine in the breeze.
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