Core Partner Spotlight: Maria Loughlin, VP of Engineering at Toast

At Underscore VC, we believe it takes a community to build an enduring, iconic company. That’s where the Underscore Core and our Core Partners come in. In this series, we’re featuring a handful of our Core Partners, sharing their insights, and describing their impact. Read on to learn more.

With 25+ years of experience building products and scaling high-performing teams, Maria Loughlin is a highly respected leader known for her technical prowess, collaborative mindset, and sense of urgency. These skills make her a great Core Partner to Underscore portfolio company Mable, a B2B eCommerce marketplace that connects grocery store buyers, retailers, and brands.

What’s a Core Partner? Core Partners work closely with Underscore VC to help source investment opportunities and/or advise portfolio companies. In return, Core Partners receive “Core Allocations,” a portion of Underscore’s returns on the company via an interest grant in our Core Fund. That means incentives are aligned for productive relationships—at zero cost to our founders.

These partners provide tremendous value to portfolio companies. In this Q&A, Maria reflects on her career thus far and shares nuggets of wisdom that we can all learn from.

Active Evolution

Q: What’s something you’ve learned about building and scaling technical teams?

A: I’ve grown teams from the earliest days—a few experts finding product-market fit—to fully scaled operations, with hundreds of engineers delivering solutions to a mature customer base. Throughout these many transitions, I’ve learned that change is constant, and the team’s effectiveness depends on my readiness to evolve how we work.

The rule of three and ten proves true every time! What works for a team of three building an MVP must evolve when we grow to 10, then 30, and then 100.

When I find myself wondering how a team member didn’t know something “obvious” or why we’re experiencing new quality issues, I inevitably realize the gap is not with the employee. Rather there’s a process that doesn’t work anymore, such as how we communicate, hire and onboard, or balance our investment portfolio.

Not only must I embrace change, but I must also build a culture where everyone contributes to evolving our norms.

Investing in Leadership and Culture

Q: What’s one thing all startup founders should understand?

A: Founders are extraordinary people whose vision, courage, and resilience never fail to inspire! But they can magnify their impact by investing in a high-performing leadership team. This goes beyond hiring a top-notch team. It also requires engaging in the fun and messy process of building a culture of trust, healthy conflict, and a shared accountability for success (the Patrick Lencioni model).

My effectiveness as a VP of Engineering is amplified when I understand and fully buy into the top-level company OKRs, and when my peers openly share feedback, listen to my input, and hold me accountable. That’s the leadership culture that enables success.

Take Care of the Basics

Q: What has been one of the most important factors in the success of your career?

A: I spent time thinking about this question, searching for a sound byte or a stand-out characteristic that drove my success. And then I realized it’s not a stand-out thing—it’s not even an uncommon or surprising thing!

It’s taking care of the basics: setting clear expectations and following through on my commitments. By consistently taking ownership, being accountable, and delivering results, I’ve become known as a go-to person who is trusted to drive success for the short- and long-term.

Highlights as a Core Partner

Q: You were recently paired as a Core Partner to Mable. What are you most looking forward to in this work?

A: I’m excited about Mable’s vision—a platform that enables small groceries to stock their shelves with local and emerging brands. My experience at Toast opened my eyes to how technology can level the playing field in the restaurant ecosystem. I’m looking forward to seeing Mable make this impact within their food communities.

I also know I will enjoy working with Mable’s leadership team. Throughout my career, I’ve learned as much from advising and leading as I have from hands-on roles. I expect to gain new insights (and remember some I had forgotten) during Mable’s critical first few years.

Interested in our Core Partner program? Learn more about the Underscore Core and our programs here.