Paddling Together with Dragonboat

Welcome to the first in a series examining the relationships and rationale behind our co-investments with our fund partners. Read on about “Why We Made This Deal” with Roble Ventures and Dragonboat.

Why We Made This Deal: GingerBread Capital + Roble Ventures + DragonBoat

A dragon boat [pictured, above] is a long, canoe-like boat, typically 40 feet long and 4 feet wide, that is decorated with a dragon’s head and tail. Dragon boaters paddle, rather than row, using paddles to propel the boat forward while facing the direction of travel.

What is Dragonboat the Platform?

Getting product development teams to effectively collaborate in fast-growing organizations can often seem like trying to steer a canoe without a paddle.

Dragonboat Founder and CEO Becky Flint had an intimate understanding of that dilemma in managing cross-functional product development teams. While building the product portfolio management operations for fast-growing companies like PayPal, Shutterfly, Bigcommerce and Feedzai, Becky worked with dozens of project portfolio management (PPM) tools. But none adequately supported the needs of these fast-paced, outcome-focused product organizations. So she built them herself, and helped fast-track many a new service and product offering for these leading industry disrupters.

In 2018, Becky set out on her own to create a platform that would enhance collaboration and efficiency in product management. She launched Dragonboat.io with a mission to help align an organization’s goals across various stakeholders and help product development leaders drive more business results, faster.

Today, Dragonboat offers an AI-powered platform for product operating models, including strategic portfolio management, customer-centric product management, and dynamic resource management. Dragonboat’s platform is now used across industries, with customers including large banks, broadcasters, auto manufacturers, IT and cyber security firms, and global human resources.

What Attracted Us to Dragonboat?

In 2021, GingerBread Capital Partner Ita Ekpoudom got a warm introduction through a mutual connection to Becky Flint.

Ita herself had experienced the complexities—and frustrations—of managing cross-functional product development teams early in her career, as a product manager at American Express and later at Travelclick, a global provider of data and revenue-generating solutions for hoteliers.

Ita recalled the over-reliance on manual systems—sometimes as rudimentary as emailing attachments of Powerpoint slides and Excel spreadsheets back and forth to track product development iterations, file histories, resource allocation and budget planning—that were rife with errors and inefficiencies. Yet there were no good software tools at the time for product developers to manage it all in one place.

Becky had raised a seed round to launch a pilot SaaS solution and her impressive background in product development management piqued Ita’s interest.

While it was too early for GingerBread to make an investment in Dragonboat (we typically invest at the Series A stage and beyond), Ita put in a call to our good friend Sergio Monsalve.

Sergio had recently launched his own firm, Roble Ventures, and was wrapping up raising Fund I. We were an early LP in Sergio’s Fund I, which focused on seed-stage investments in workplace productivity solutions.

Previously, Sergio had enjoyed a successful career in venture capital with a track record of big exits. Among them was a company called Adaptive Insights, a cloud-based, collaborative tool that helped finance leaders with planning, budgeting, forecasting, and financial reporting. What that company did for finance teams, Dragonboat was doing for product development teams.

Ita recognized a potential match and first investment for Roble and connected Sergio to Becky.

“When I met Becky, I knew she was building something special,” said Sergio. “Her first-hand expertise solving product scaling challenges is unparalleled. And her passion is infectious. You can’t find a better founder-market fit.”

The Deal We Made

In the Summer of 2021, GingerBread Capital joined Roble Ventures in a pre-emptive co-investment round in Dragonboat prior to the company’s $12M Series A.

“After doing our deep diligence together, it was the strength of Sergio’s conviction that got us over the edge and made us decide to invest. That conviction in a founder’s vision is exactly what we want to see when we partner with a fund.”

—Ita Ekpoudom

Sergio negotiated as the lead investor in the pre-Series A round in which we participated. The terms were structured in a way favorable to the founder, prior to a larger investor coming in for the next round.

Which is exactly what happened just six months later, when a much larger investor was the lead on Dragonboat’s $12M Series A raise, in late 2021. Read more.

In announcing the close, Becky stated:

“I’m more than thrilled to join a movement where a female immigrant founder can lead and grow a venture-backed company like Dragonboat. We decided to work with Sergio because of his ability to bring a wealth of domain experts as advisors. He is always my first and most valuable call.”

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