Leadership Lab

Bringing Leadership Insight to VC at Pillar

I’ve got a new gig. I’m joining Pillar, a new venture capital fund in Boston, as a Partner.


Over the last few years, I’ve transitioned into a board member role at, and will continue to remain actively involved in this capacity. Gabriela McManus has been leading the charge, doubling the number of emerging leaders we’ve served in the last year, and expanding our reach to over 50 companies across Boston. couldn’t be in better hands.


Back in June, when I left Pluralsight, the last place I thought I’d end up was in venture capital. I was a lifelong builder, ready for a fresh start, but wasn’t sure what the future would hold. One thing I knew for certain was that I missed the community-building I’d experienced in the early days of - connecting entrepreneurs with each other, with team members, and with advice and expertise to help them scale. My new role at Pillar marks a transition back to my roots, to do just that.


As soon as I met Jamie Goldstein, I knew I’d found my home at Pillar. I was immediately struck by his vision for our fund, and knew I had to help bring it to life. We’ve invested in five companies to date, and over the last few months, I’ve experienced Jamie’s authentic commitment to supporting the interests of our entrepreneurs. Pillar is offering the option of common stock on any deal we lead, a radical move that aligns our interests with entrepreneurs. We’re collaborating with a team of 16 world-class CEOs, people like Ash Ashutosh (Actifio),Jeremy Hitchcock, Jason Robins (DraftKings), Tom Ebling (Demandware), Tom Erickson (Acquia), Steve Kokinos (Fuze), and Niraj Shah and Steve Conine (Wayfair), who are investors in our fund, and are mentors, advisors and board members to our companies. And we’re building a group of operators and resources to support our entrepreneurs as they scale — that’s where I come in.


As part of my new role, I’ll be making some investments on behalf of Pillar, but my primary focus, will be on building our Access program. We’ve been inspired by the unparalleled value Andreessen Horowitz provides to entrepreneurs on the west coast, and are taking a cue from the success of their model in developing our approach. While we don’t have billions under management, we think there’s a huge opportunity to bring the best elements of their framework to early-stage investing in Boston.


I’ve had the good fortune to work with a few exceptional teams over the last few years who have built standout companies. One thing was a constant across every one — we were hungry for customer introductions, experienced team members, and operational expertise. Pillar’s Access team will deliver on all three.


Our executive briefing team will curate a group of CSOs, CIOs, CTOs and tech executives from enterprise companies, providing direct access to our portfolio. Our talent team will cultivate a network of leaders in Boston who serve as executives, board members, mentors, and advisors to our companies. Our insight team will provide direct access to marketing and leadership guidance. As the co-founder of, I saw early on that there is a leadership and talent gap in high-growth companies; drawing on this experience uniquely positions Pillar to help our portfolio companies develop the skills and relationships they need as they scale.


One of the things that most excites me about being part of Pillar is the chance to learn about so many new emerging technologies. Every day brings an opportunity to meet with startups working with robotics, AI, IoT, machine learning — technologies that are transforming the way we live and work. With MIT nested right in our backyard, and a community of veteran entrepreneurs in our midst, there’s no better hub for innovation in these frontier technologies.


If you’re launching a company or want to get involved with one of our startups, I’d love to connect. Send me a note (, shoot me a tweet (@hodges), or follow me on Medium (Sarah Hodges).