Core Partner Spotlight: Allison MacLeod, CMO of Flywire

As a seasoned marketing executive, Allison MacLeod, CMO of Flywire, has deep experience across demand generation, brand, communications, content, customer advocacy, and business development. Yet some of the most important lessons she’s learned throughout her career have centered around leadership and team building. 

Great team building starts with hiring great people. “Once you hire strong, skilled leaders who can shoulder more responsibility, you’ll be able to take on so much more to truly lead the team and help your organization grow,” she says. 

This marketing know-how and commitment to leadership make Allison a great Core Partner to Mable.

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.

In this brief Q&A, Allison shares insights from her many years of marketing leadership experience.

Trust Your Team 

Q: What’s something you’ve learned about managing ambiguity as a leader?

A: In startups, high growth, and scaling companies, ambiguity is almost a guarantee. Personally, I think that’s what keeps it both exciting and challenging (in a good way!) at the same time. As a leader, however, I’ve learned two key lessons:

1) Empower your team through ambiguity: You need to continue to coach your team to let it fuel you, rather than hinder you. Empower your team to make decisions, adapt to change, learn how to deal with uncertainty and risk, and see ambiguity as an opportunity to problem-solve and build resiliency.

2) Lead with ambiguity: As a leader, you need to trust your team to provide you with enough data to make the best decisions, even when you don’t have the full scope of a problem. You also need to trust your team to make the right decisions. The best leaders don’t have all the answers, but they have enough knowledge and data to make a sound decision. 

Advocate for Yourself

Q: What’s the most important piece of career advice you’ve received, and why?

A: Always ask for what you want and communicate your vision and purpose. We often think that others see our hard work and know what we want in our careers. But if you aren’t communicating what you want in your career, your role, or your company, how are others to know? Speak up and advocate for yourself. Want to move into a new role or get promoted? Great! Ask for it.

Even if an opportunity isn’t currently available, ask questions and understand what it will take to get you there. In tandem, ensure others know your purpose and your ‘why’. Share your learnings, your failures, your accomplishments and goals, and ensure others understand your impact on your role, team, and organization. 

How to Build High-Performing Teams

Q: In advising startups, what are you asked most often? How do you answer?

A: Beyond aligning sales, marketing, and GTM teams and operations, I’m most often asked about leadership and coaching high-performing teams. One of the most common questions I get is about how leaders can develop themselves and their teams to continue to grow. 

My answer is to hire people smarter and better than you. On the face of it, that can seem intimidating, but it’s one of the best things a leader can do to grow their team, their company, and themselves. Once you hire strong, skilled leaders who can shoulder more responsibility, you’ll be able to take on so much more to truly lead the team and help your organization grow. 

A Highlight as a Core Partner

Q: Can you share a highlight from working with Mable?

A: Beyond being a super unique and innovative B2B marketplace in the retail space, the team is just amazing. I love their focus on developing talent across GTM functions—and really the entire company. A big highlight has been working with their head of marketing, Alex Temple. She is a star. She’s so open to feedback and seeks guidance and advice to build her org and drive revenue for Mable.

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