Core Partner Spotlight: Diane Randolph, Former CIO of Ulta Beauty

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.


Throughout decades of leading technical teams, “I saw how important it was to deeply understand cultural differences and life experiences,” says Diane Randolph, Board Member and Former CIO at Ulta Beauty. “I learned how to adapt my leadership style to develop a strong, trusting relationship with everyone in a different way.”

This is just one of many reasons Underscore is thrilled to have her as a Core Partner to portfolio company Moltin (now Elastic Path). “I don’t have enough thumbs to offer in support of Diane,” says Jamus Driscoll, CEO of Elastic Path. “She is an outstanding technical leader, advisor, and someone whose opinions I deeply respect.”

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 are tremendously valuable. In this brief Q&A, Diane shares insights from her experience as a technical leader. 

The Importance of Advocating for Yourself

Q: What’s something you had to learn the hard way?

A: When you have a technical background, it’s easy to assume that your successes and accomplishments will speak for themselves. However, many business leaders don’t fully understand the complexities of the work involved in delivering technical transformations—nor their broader business impact. 

To get the recognition you deserve as a technology professional, you need to develop marketing acumen and storytelling skills to effectively communicate the value you deliver and the effort involved in getting there.

The Digital Transformation of Commerce

Q: What’s an interesting trend you’re seeing in the digital transformation of commerce?

A: Over the last few years, there’s been a heavy focus on the “buy” part of the experience, with much attention to cart efficiency, pricing, and delivery communications. There’s always been a strong focus on leveraging product information to inform a purchase decision, but now there’s increased attention to discovery and exploration in the customer journey. The challenge is developing an experience that efficiently supports both.

Leading a Diverse Team

Q: What’s one important thing you have learned about leadership?

A: I was fortunate to have spent the early part of my career working at a high-growth tech startup based in Montreal. Canada has a very diverse population and a national commitment to multiculturalism, which was reflected in the employee base of my firm. 

I saw how important it was to deeply understand cultural differences and life experiences, and I learned how to adapt my leadership style to develop a strong, trusting relationship with everyone in a different way and to recognize the great value in truly diverse teams.

A Highlight as a Core Partner

Q: Can you share a memory of your work with Moltin?

A: Moltin’s CEO, Jamus Driscoll, and the engineering team were exceptional at communicating and pivoting in the moment, and it was fantastic to watch them interact. For example, in one meeting with a large enterprise, the Moltin team quickly realized how advanced its technical environment was. 

They transitioned seamlessly, shifting the discussion from building a technical foundation to specific add-ons that would complement the company’s existing infrastructure. This ability to pivot spoke to the intelligence, enterprise thinking, and adaptability of the entire team. 

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