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Meet An Investor: Kelly Shaw - Principal Vestigo Ventures

Our goal of our newly launched series, “Meet an Investor,” here at Startup Boston, is to take you - the founder - behind-the-scenes of an investor’s website, social media handles, and portfolio, and breakdown how they operate and what they’re looking for in the companies they fund.For our first chat, Jody Robie, SVP of TalentWorks, sat down with Kelly Shaw, Principal at Vestigo Ventures.


Kelly is a passionate fintech investor and also a Harvard Business School MBA graduate with 8+ years of experience spanning finance, M&A, VC and entrepreneurship. Let’s learn more about her and Vestigo Ventures below!:

Startup Boston (SB): how did you get interested in investing?

Kelly Shaw (KS): I kind of fell into it. I joined Synchrony’s Corporate Development team shortly after its spinout. I was hired because of my M&A experience, but I was actually hired into a hybrid M&A and corporate VC role. This meant I was tasked with investing or acquiring startups of strategic relevance to Synchrony.


This was my first role within the world of VC. I really didn’t know much about it before that. I was very lucky to have a wonderful mentor who guided me through that and I absolutely fell in love with the work. I’m a curious person and I love learning new things. Within the role you’re constantly learning. I also loved being exposed to new innovations and getting to meet entrepreneurs who had such passion for their projects. This experience is what led me to join Vestigo Ventures after Business School.

SB: Are there any investments you made recently that you’re really excited about, and why?

KS: Asking for a specific investment I’m excited about is a bit like asking a parent to name their favorite child - it’s a little difficult to pick one! We’ve made five investments in the last nine months or so, and we’re very excited about all of them.

Vestigo’s most recent investment is a Boston-based startup called SaaSWorks. The company focuses on subscription analytics, essentially helping SaaS businesses get real-time visibility and analytics of their revenue. The co-founders, Vipul and Jim, have such incredible experience as operators and prior founders, so we are incredibly excited to be a part of their journey.

We’ve also recently invested in a company called Advocate. Advocate helps to automate and streamline complex insurance compliance processes for lenders. It also has a broader vision of using the data collected to build a central repository of truth across tens of thousands of brokers. This doesn’t exist in the industry today, where the information is highly fragmented, so we’re very excited by this vision.

SB: What is your firm’s team structure and how does this set you up for success?

KS: The Vestigo team consists of two GPs, two MDs , two Principals (where I sit), two associates, and an incredible COO, who ensures everything is running smoothly. We also have a couple of interns helping us out for the summer.

In terms of the structure, we are relatively flat and very collaborative. We meet as a team four times a week to discuss the deals we're working on, any portfolio company updates, and broader fund efforts. As such, we get this diversity of thought throughout the company, which is encouraged throughout the firm. We want our associates to speak up just as much as the senior leaders. Typically the entire team digs in to an investment opportunity. The benefits here are that you gain different viewpoints, experiences and networks too.

I would imagine this system is relatively unique to us. I do think that every VC has different models and some are relatively flat, while others are more hierarchical, but this collaborative effort is what we view as our secret sauce, on top of our proprietary data assets that we use for deal sourcing, diligence, and to help our portfolio companies.

SB: What does a typical week look like for you? Which types of activities are you spending most of your time on?

KS: One of the things I love most about VC is that there really is no typical week. While I have key responsibilities and activities, each week tends to vary. My week typically centers around networking, calls with founders, diligence, assisting portfolio companies, internal fund activities, and broader learning. Networking is fundamental – I’m often attending coffee chats, Zoom catch-ups, or events. I review pitch decks to decide if we want to take a call and, of course, talk to a lot of founders, diving into their start-ups.

If I’m in the middle of diligence on a deal like I am now, then I’m spending most of my time learning everything I can about that opportunity: diving into the data room, conducting research, talking to customer references and others in our network to better understand the market and how the company fits in.

We do a lot to help out our portfolio companies too. I might have board meetings or other calls to provide support, or I might be reaching out to other people on their behalf.

Then, of course, there's internal fund activities. That can range from our annual audit, DEI efforts, thematic research and thesis building.

Finally, I strive to be constantly learning. I'm always trying to read new books, listen to relevant podcasts and attend different seminars too. For instance, I'm attending a McKinsey early stage startup event this week, and I listened to an ESG seminar today.

SB: When you come across a product that you may invest in, what are you looking for? What qualities do you look for in the founding team that you invest?

KS: We're specifically focused on early-stage Fintech, where there's not necessarily a product market fit. Thus, on top of the usual TAM, Tech, and traction, we spend a lot of time focused on the founders and team. We see the potential of the team as one of the biggest factors for success

As such, we try to understand how well the founders know the space and assess whether they have prior entrepreneurial experience or success. Then of course, there's specific characteristics we look for. Do they have grit, resilience? Can they hire, motivate and lead a world-class team? We also assess whether there's a strong cultural fit within the company.

In terms of other factors, we look at market size, dynamics, competitive moat, among other factors. We're essentially trying to understand whether a company has a clear path to $100 million revenue.

SB: What is your biggest pet peeve in a pitch deck? / The big “don’t?”

KS: I have two. First, I often see comparisons to a successful company. They’ll say “We’re the Uber for X, or the Plaid for X.” Sometimes the comparison doesn't even necessarily make sense. While other investors may think differently, I prefer to see a company that feels like it's its own category and in its own class - to the point that they’ll be the reference point for somebody else.

The second is that people tend to exaggerate to make the start-up seem more successful. I get really excited by something, but then I find out that their pipeline, traction or the ARR numbers are stretching the truth. That’s why we always make sure we're doing proper due diligence.


SB: How do you support founders / add value to the companies that you invest in?

KS: At Vestigo Ventures, our ethos is to be as supportive as possible to our portfolio companies. It’s the reason we only have twenty portfolio companies per fund – we want to ensure we have the bandwidth to be as helpful as possible to generate great outcomes.

Of course, we provide assistance like other VCs for things like recruiting, strategy, go to market and distribution, and supporting fundraising. But we also strive to go beyond typical activities via our network and our data. For example, we often make introductions for portfolio companies to individuals and institutions within our network who can provide expertise or generate commercial opportunities.

We also carry out data driven projects. For instance, one of the data scientists on our team recently did a project with a CMO of one of our portfolio companies. This helped provide insights into their SEO, SEM and customer acquisition to identify new GTM opportunities.

Starting a company is a rollercoaster. So the last thing here is general support. We like to think of ourselves as the first person you call when you get bad news, but also the first when you receive the good news too. After all, we’re here to celebrate and support our portfolio companies.

SB: What is the best way for a founder to get in contact with you or your firm?

KS: The best way is through a warm introduction. Reaching out to me on LinkedIn is fine, but my LinkedIn inbox often gets clogged by many messages, mostly from founders asking to invest in their startup that is not in my strike zone. Before reaching out, you need to make sure that your startup fits our stage and our investment area. So, in essence, if you're a seed stage Fintech startup, please reach out to us. We also try to attend a lot of different events, especially within the Boston ecosystem.


About the author: Jody Robie is the SVP of North America at Talent Works, a talent attraction firm focusing specifically on recruiting and employer branding. If you have questions about your current talent strategy feel free to reach out directly to her on LinkedIn.


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