Mar 02, 2018

Exploring Boston’s Startup Scene

By Sajeev Popat T’19

At the end of January, 20 Tuck students "ventured” out of Hanover into Boston to explore the startup scene in Boston. Over the course of two days, we visited four startups in marketing, health care, cloud infrastructure, and fintech as well as four VCs with differing cultures and investment philosophies.  By the end of the trek, we had learned about the challenges of growing and scaling businesses, how companies pivot multiples times before finding product market fit, and how different investors evaluate “winners” in the technology sector.


We started the trek at Drift, a marketing software company aiming to transform how businesses sell to each other. Will Collins T’16, head of business operations, spoke with us about the company’s story and introduced us to members of various teams across the business, including marketing, customer success, product marketing, and engineering. We learned about how, under the leadership of the former chief product officer of HubSpot, the company’s product and offering has evolved and pivoted, and is now finding its place in the marketing stack. Having honed in on its product market fit, Drift has begun scaling rapidly.

Tuck students visit Drift on career trek 

Bain Capital Venture

Our next stop was down the street in Copley Square at Bain Capital Ventures (BCV) where we met associates Akshay Agrawal and Aneesha Mehta, who shared with us BCV’s broad investment strategies across a variety of verticals. BCV differentiates itself from other firms by leveraging the broader Bain network, often times using contacts and intel from Bain Capital Private Equity during diligence and offering operating advice. 

CloudHealth Technologies

Next, we visited CloudHealth Technologies, a cloud infrastructure monitoring software company that helps clients better optimize the use of their cloud environments. We had the unique opportunity to be hosted by the first investor and current CFO, Larry Begley (also a proud father of a recent Tuck grad), and CTO and co-founder Joe Kinsella. Gaining each of their perspectives on the early evolution of the business was valuable for those in the room interested in VC and entrepreneurship. In addition, Joe provided advice that resonated with those aspiring entrepreneurs who were wondering when it’s the best time to start a business. In his view, to make the journey real, you need to “burn your boats” which could mean quitting a job or forgoing consulting or service contracts to commit to building a real product.


To end the first day, we visited Quantopian, a fintech startup that curates and licenses investment algorithms from users who get paid for performance. Josh Payne, the VP of Product and a D’96, shared with us his journey through the Boston-area tech scene, from feeling constricted working in a large corporate environment, to joining the HubSpot team during its growth stage—and now leading product at Quantopian.    

Tuck students visit Quantopian on career trek to Boston 

Openview Venture Partners

The next morning, we kicked off the day by visiting Openview Venture Partners, a venture capital firm founded by Insight Venture Partners alum, Steve Maxwell. Openview focuses on expansion stage B2B SaaS investing, with notable investments in companies like ExactTarget and Instructure. The firm differentiates itself by offering a robust portfolio support team that includes Sales and Marketing strategy support, Talent Recruiting, and Market Research. We were hosted by Brendan Deer (partner), Adam Marcus T’07 (managing partner), and John McCullough T’10 (VP of corporate development). All three had unique stories and perspectives on how they ended up in venture. However, what particularly stood out was Adam’s advice to really focus on building meaningful relationships across both classes during our Tuck experience and relentlessly pursue our career aspirations during our time in business school—things he managed to balance simultaneously when he worked fulltime for Battery Ventures during his time at Tuck.


Next, we went across the street to Wellframe, a digital health startup that partners with health-care plans and providers to deliver support and guidance from caregivers to patients through a mobile application. For many of us, health care was an unfamiliar industry, but our talks with members of the team from across the organization helped us better understand the complex challenges of delivering meaningful change in such a complex market. 

Tuck students visit Wellfram in Boston

Accomplice VC

We then made our way into Cambridge to visit Accomplice, an early stage investor focused on technology investments. Sarah Downey (principal) and TJ Mahony (partner) walked us through the firm’s history, starting with Atlas Venture, which spun off its technology practice into Accomplice, led by founding partners Ryan Moore and Jeff Fagnan. They also described the firm’s venture partner model, where entrepreneurs in their portfolio are given access to investable capital to deploy based on the idea that entrepreneurs have the ability to effectively source deals. From a career standpoint, TJ and Sarah maintained that for those of us seeking a career in venture, it is better to pursue peripheral careers in technology or entrepreneurship before considering the transition. Previously, TJ was a successful entrepreneur and Sarah had worked in startup leadership positions.

General Catalyst

To conclude the trek, we visited General Catalyst where we met with Holly Maloney McConnell (managing director) and Natalie Bartlett (associate). General Catalyst invests in early and growth stage technology companies in both B2B and B2C channels. Holly, who works on mainly on expansion stage investments, talked about her journey from investment banking and growth equity investing to her current role, where she enjoys partnering with companies to help them grow and scale. Natalie, in addition to her day-to-day work, works actively with Rough Draft Ventures, which funds student entrepreneurs across the country.