Mainsail Partners Product Workshop 2018

Kate Hopkins By: Kate Hopkins  |  October 4, 2018

In September, Mainsail hosted its first Product Workshop. Twenty-three product managers and product leaders from nine portfolio companies came to San Francisco for three days of product training and idea sharing. The workshop represents one of the many ways that Mainsail’s Operations Team seeks to bring best practices and resources to its portfolio companies.

Why product?

Product is at the heart of a company’s strategy, and it’s often an evolving function in bootstrapped software companies like those Mainsail invests in.  Early on, a founder usually acts as head of product, guiding development based on his or her knowledge of the industry and vision around the problem the company is solving.  But as the company grows, the demand on the founder’s time increases and the product becomes more complex.  It becomes useful to introduce more product people and processes.

Between $5M-$10M in revenue, we notice that companies begin to broaden the customers they work with, and the potential for distraction is amplified.  Without a true product team, companies run the risk of building more features, but delivering less value with each one.  At the beginning, the founding team knew what was needed, because they’d lived the problem.  As the company grows, gut isn’t enough, and it becomes necessary to research, test, and analyze to make sure product development hits the mark.  Strong product leadership can ensure that product development stays aligned with company strategy, and the right product management and design can increase the efficiency of scarce (and expensive) engineering resources.

Mainsail Product Workshop

Content and Community

During the first two days of the workshop, portfolio product leaders attended a product training with Marty Cagan, Founder of the Silicon Valley Product Group.  Topics included setting product objectives, tracking product analytics, and techniques for prototyping and testing.  As one Mainsail attendee explained, the training “did a great job at connecting the dots between discovery and delivery, and presenting a model that lets you do both effectively.”  A common goal coming out of the session was to move toward using Objectives and Key Results to guide product development.

Following the Silicon Valley Product Group Session, Mainsail invited portfolio attendees to a networking dinner and day of hands-on product coaching at Mainsail’s San Francisco office.  Barry O’Reilly led a series of exercises, in which the team from each company broke down product development challenges they were currently working on.  In between rounds of revisions, volunteer teams received feedback from fellow portfolio executives.  One attendee commented that “the opportunity to work on actual, specific problems in our organization with the help of outside experts was invaluable.”  The day finished with a conversation with Todd Olson, CEO of Pendo, on the ways product analytics shape product strategy.

The product workshop was also an important opportunity for operators to meet with and learn from each other. In their feedback, portfolio participants highlighted the value of the connections they made, “It was extremely helpful to talk with my Mainsail peers and hear their successes and challenges around product management. I am thrilled to have the list of contacts that I can reach out to in the future with follow up questions.”

“The opportunity to work on actual, specific problems in our organization with the help of outside experts was invaluable.”

Product on the Mainsail Operations Team

The product workshop is one component of Mainsail’s broader offering of resources to product executives at its portfolio companies.  Following the workshop, Mainsail’s operations team meets 1:1 with each portfolio product team to identify areas of focus where Mainsail can provide support.  In the past, Mainsail has gone onsite with portfolio companies to build user story maps, re-tool product roadmapping, and conduct week-long design sprints.  These efforts are supported by regular engagement through informal advising, a monthly product newsletter with relevant content, tools, and events, and quarterly conference calls for idea sharing between product leaders.


Kate Hopkins
Kate is a Vice President at Mainsail Partners, working with portfolio companies to accelerate growth. Her focus is in product and market strategy.
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