Chalk Talk

Selling local, creating a sales playbook, and leveraging what's unique about your business.

There is no one-size-fits-all approach to multi-product go-to-market, but there are a few key elements related to product and go-to-market sequencing, buyer dynamics, incentive programs, and team structure to help guide your strategy and drive your multi-product flywheel.

Fundamental sales truths, JV's hiring tips, selling a value prop to employees, and measuring performance.

What markets are you overlooking? GTM teams often neglect pockets of TAM that can turn out to be true greenfield opportunities. JV walked through his quantitative approach to identifying pockets of growth and incentivizing teams to capture new segments.

Defining your TAM and allocating resources to the right markets is vital to most businesses and especially critical for SMB and VSaaS. JV provided a deep dive into best practices to optimize territory design and lead scoring.

Between the Covid-19 shutdowns in the past few years, and the uncertain market conditions today, maintaining growth can appear challenging. JV highlighted his approach: dig into the data, figure out how to maximize your resources and retain your strongest people, and then adjust your strategy and product offerings as needed.

In our Q1 2025 Chalk Talk session, Kevin Hamilton, Venture Partner at Tidemark and former CMO at Toast, shared valuable insights on implementing a Product-Led Growth (PLG) strategy within a traditional sales-led company. Drawing from his experience at Toast, where he helped grow ARR from $40M to $1.2B, Kevin discussed the process of testing into […]

In our Q2 Chalk Talk session, Ronnie Gurion—Chief Operating Officer at Clio, the leading legal-tech platform—shared a behind-the-scenes look at how embedded payments went from an experiment to a cornerstone of Clio’s growth strategy.  Head over to Ronnie’s detailed essay, “Payments That Perform: The Three Key Ingredients for Successfully Scaling Payments in Vertical SaaS,” for […]