The Story Behind our Investment in WorkRamp

Eugene Lee
Dec 9, 2020 · 7 min read
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Instead of the usual venture blog post on why WorkRamp is the next best thing, why it’s going to dominate the Learning Management System market, why we led the $17 million Series B, and all things you already know we’re going to say, we thought we’d do something a little different. What follows is a Q&A with CEO & Founder, Ted Blosser, on the fundraising process with OMERS Ventures, to give you the sort of insight you might not normally get.

This conversation was abbreviated and edited to include only the good parts.

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The start

Ted: We weren’t running a process and weren’t actually fundraising. Eugene just wired us some money.

Eugene: Sounds about right.

Ted: No really, we weren’t fundraising nor were we really thinking about it until next year sometime. But a mutual friend of ours asked if I’d be ok with an intro to Eugene. His email demonstrated that he understood what we were actually doing and had some knowledge of the space, so I took the intro. Honestly, each follow-on conversation we had became more intriguing, and I believe mutually beneficial. Instead of traditional pitching as in our Series A, these were conversations about the business, the ecosystem, the competition. I didn’t feel like I was pitching as these were discussions. And then all of a sudden, he tricked me and asked me for wiring instructions! Now, let me flip the script, why were you interested in getting in touch?

Eugene: I wasn’t, it was a bot we created internally to reach out to founders.

Ted: Sounds about right.

Eugene: I reached out because we take a very focused and targeted approach to where we want to spend our time. We call them themes and sub-themes. As digital transformation accelerated due to COVID, I became even more interested in how training as a category was impacting companies. This led me to a deep dive into the Learning Management System (LMS) market which ultimately led me to you.

Disruption in these large incumbent categories is somewhere we feel comfortable, as evidenced by our investments in ClearCover (four existing large auto carriers), WithMe Health (three existing large pharmacy benefit managers), and now WorkRamp with Learning Management Systems. It also fits the area that I focus on, which is vertical software companies for the modern workplace. So I had the bot get in touch with a former classmate of mine who was also a former colleague of Ted’s.

The why

Many of these legacy Learning Management System’s believe that training doesn’t extend outside the four walls of the company. Hence, our belief was that there was an opportunity for new entrants like WorkRamp, who have eschewed corporate training as a solely human resource use case and have exclusively staked their true north on providing the modern enterprise learning platform for all teams and departments, including those teams that are also focused on external customers.

We liked WorkRamp’s approach to seemingly act as a consumer company in terms of ease-of-use of its product, but built like an enterprise-grade product with its underlying complexity. This became more obvious from Ted’s background at Box and how they disrupted the exciting category of document management (Ted’s words, not mine). I’m a big believer in being product-led and WorkRamp ticked that box from an expansion perspective.

As for Ted, it’s not often you come across a founder who has been trained for multiple years on both product and sales and can relate to customers from both perspectives. He can apparently even write some code! Ted, you may or may not know this, but we chatted with many of your former colleagues and they had mostly incredible things to say about you. You should thank them, except some of them might still be upset with you for showing up too early to the office to be the first to take those round-robin calls!

Since I’ve said such nice things about you, what do you think about OV and me? No pressure, the wire already went through.

Ted: Next question! I alluded to this a little earlier when we talked about Eugene reaching out. After our initial Zoom, I talked to my co-founder Arsh and said “I think I just talked to an investor that knows more about the space than we do.” The corporate learning space definitely has its nuances and making sure you have a board member who understands the history of the segment and future potential is critical. From understanding why the larger incumbents are vulnerable, all the way to how the product should take advantage of how millennial employees like to learn, it was clear that Eugene knew what he was talking about. Add that on to his years of operating experience and it was a slam dunk in terms of a future partnership.

Building trust

Eugene: We’ve written a little bit about fundraising during a pandemic but I’d say we built trust pretty quickly and very early. It helped a lot that we have a mutual friend who could vouch for how great you are. I can honestly say, that allowed me to put my guard down a little as I felt that there was a sense of trust established already. As I was looking through my notes of our conversations, we were really communicating daily, multiple times a day via email or by Zoom. And I’ll echo what you said earlier, these were discussions and not selling one another directly on an idea, concept, or fund. You allowed me the opportunity to provide input on certain things very early on and then incorporated some of that into some of our follow-up conversations. That showed me that you were listening and cared about what we talked about which allowed me to reciprocate.

Ted: I’ll add on to that. I think our ability to understand one another quickly and the way each other thought was and is key. I never felt pressured or felt like I was being interrogated with diligence questions. They were all helpful questions that challenged me to think differently while also being supportive of what we had accomplished thus far. Eugene also introduced me to various members of the team, from other investment team members to the operations team, to see other aspects of the firm and how they may help in the future. I got a real sense of team and support.

Last, on a personal note, we are both fathers to two kids and we were able to bond on how to balance fatherhood with the fast-paced tech environment we run in. It’s one of the things our seed investor, Alexis Ohanian, blogs about frequently and it was great to relate to Eugene on the same level.

I mean, it was simple as all I had to do was check our account after he emailed me.

Eugene: Exactly.

The one

Eugene: I knew when we graduated our conversations and relationship from referral intro email, Zoom and more emails, to exchanging phone numbers and texting that there was something there. I’m sort of joking but I’m being serious too. When you feel like you can be reachable for someone at any time, that’s where you know it can be a partnership, a long-lasting relationship, that first call when you know what hits the fan. Oh and I know Ted likes steak, so we have that in common and can’t wait for a post-COVID get-together.

Ted: Well first off, I had my wife do some back channel references on Eugene because they both went to Vanderbilt and it’s not every day that you stumble across a Commodore here in Silicon Valley. Safe to say he checked out and I couldn’t find any dirt! But in all seriousness, I knew when Eugene switched from looking at WorkRamp from an investor lens to viewing us from a partner lens.

This happened after we started to dig into the detailed customer feedback, the team, and the future roadmap after our 4th or 5th meeting. It’s only after this switch where you can see someone’s true colors: they essentially go from an investor to a teammate who wants to succeed as badly as you do. When I saw this click for Eugene, his passion only grew more and I knew he was the one!

Eugene: Yeah I am! Go check your account, the money is still there, now let’s go do this!

OMERS Ventures

OMERS Ventures is the venture capital investment arm of…

Eugene Lee

Written by

Investor at OMERS Ventures.

OMERS Ventures

OMERS Ventures is the venture capital investment arm of OMERS, one of Canada's largest pension funds with over $100 billion in net assets. OMERS Ventures is a multi-stage investor in growth-oriented, disruptive technology companies across North America.

Eugene Lee

Written by

Investor at OMERS Ventures.

OMERS Ventures

OMERS Ventures is the venture capital investment arm of OMERS, one of Canada's largest pension funds with over $100 billion in net assets. OMERS Ventures is a multi-stage investor in growth-oriented, disruptive technology companies across North America.

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