An all-day workshop for Clipboard Health’s sales and operations teams grew into ongoing work on customer understanding, differentiated selling, and repeatable sales tools.
Clipboard Health sells into a healthcare staffing market with an established incumbent. Buyers already had a provider, already knew the category, and could not easily tell one platform from another. The sales team was fluent in the product and could explain what it did, but the pitch sounded close enough to the competition that deals came down to price and familiarity.
The company needed its salespeople to give facilities a concrete reason to switch, in language that came from the customer’s world rather than the product roadmap.
Before building anything I went and learned how Clipboard sells. I rode along with reps, sat in on live sales and support calls, talked with customers directly, and spent time with leadership and the people handling accounts day to day.
What came back was that the strongest reps were not leading with features. They were leading with what a director of nursing lives through when a shift goes unfilled at four in the morning. That knowledge sat with a handful of people and had never been written down anywhere the rest of the team could reach it.
The engagement began with a full day for the sales and operations teams, built on the material from that research instead of a stock curriculum. We worked on customer empathy as a practical sales skill: how to ask questions that surface what a facility is really dealing with, how to listen for the detail that matters, and how to turn it into something a buyer recognizes immediately.
The room then did the work itself. In breakouts, reps and operations staff pulled out real customer experiences they had witnessed, sharpened them into usable form, and organized them by the objections they answer. Teams practiced out loud and got live feedback.
The workshop output became an asset instead of a one-day memory. Those customer experiences were collected into a story bank, indexed by common objections, so the team could reach for the right example in a live conversation and new hires could learn from them during onboarding.
The work has continued since, including follow-up training sessions that reinforce the approach and keep the story bank current as the team learns more.
Clipboard’s CFO reported that customer conversations were connecting at a deeper level and that the company had seen movement in new customer close rates and existing customer lifetime value over the course of the engagement.
Commercial observations above are reported by Clipboard Health’s CFO. They have not been independently measured or attributed to this work alone.
“Matt took the time to deeply understand our sales process and our product, going on multiple ride-alongs, sales calls, and support calls with our team… We are seeing our customer conversations connect at far deeper levels than we ever had before, and we have seen a noticeable uptick in new customer close rates and existing customer lifetime value.”
“This will change the way you sell.”
“Incredibly helpful and engaging. It applies to every industry and role.”