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A Winning Crew: How Rowing Together Made Our Virtual Sales Kickoff a Success


Mon Dec 21 2020

A Winning Crew: How Rowing Together Made Our Virtual Sales Kickoff a Success

When rowing on the water, every person in the boat needs to be in sync. It’s the ultimate teamwork sport, requiring all rowers to work in unison and be physically and technically exact in their movements. Success is defined through teamwork, and it often takes months of practice in mind, body, and soul to achieve the perfect balance of speed and strength.

When designing my company’s virtual kickoff this year, the goal was to put together an experience for our sales organization that would celebrate our successes, motivate and inspire, and improve our sales skills. Ultimately, we wanted to encompass purpose and momentum and create an experience that would feel unique to the year that we’ve all experienced. The COVID-19 pandemic has changed the education industry, transformed business strategy, shifted messaging, and heavily influenced buyer concerns and behaviors. We partner with K–12 and higher education institutions to provide education technology, and this pandemic has caused interruptions in learning, affected educators and communities, widened existing socioeconomic disparities, and deteriorated academic performance and development for students. Our virtual kickoff experience needed to creatively engage, motivate, and enhance the skills of our sales organization during these unprecedented times. We chose to anchor around the theme of crew, with us being in a boat together with our clients.


We set out by identifying the intended outcomes we wanted to achieve with a virtual kickoff experience. Similar to a crew team, we wanted to expand our understanding in how our roles internally and externally worked together with our clients. If we’re rowing better together, we help our clients drive a positive impact on their students. It was important to us that we kept our experience simplified, and we identified three themes to anchor our training around:

  • Virtual networking

  • Questioning strategies (the fear of loss and desire to gain)

  • Collaborative value propositioning

Once we had these anchors, we identified a cadence of learning that included two 90-minute sessions per day across a four-day period. Our focus for this cadence was on content and theme as well as on establishing an environment for this experience that would accommodate the needs of our sellers and avoid the dreaded Zoom fatigue. We built asynchronous participation into these 90-minute blocks, inclusive of discussion, role play, and self-reflection.

When executing logistics, it was important that our theme come to life, engaging and motivating our sales organization even when we weren’t energized in a room together. We partnered with our events team to send the agenda two months in advance of our virtual kickoff, allowing our sales organization to align to the timeline and properly prepare for activity prework and storytelling. From there, we sent a crew-themed gift box to every member of our sales organization that tied to our experience theme of “rowing together” and included a book by our keynote speaker.

Once our sales organization team had read the book, we hosted our keynote speaker, Arshay Cooper, at a sales organization internal team event four weeks from our virtual kickoff to speak and inspire about the strength that comes from overcoming odds and angst, leveraging the support of a team, seizing good and bad opportunities for learning and growth, and the importance of rowing together—a catalyst to salvation.

When we went live, our virtual kickoff also incorporated elements beyond sales skills. We hosted Hobson’s K–12 and higher education clients and internal stakeholders, speaking about business strategy, alignment, and goals for 2021. We felt it was important to harness the strong relationships we’ve built across the industry to speak to the continued impact we can drive together with our clients in the boat. Our internal stakeholders owned solution-specific, go-to-market training, which spoke to the formulation and formation of our “oars.” We also included smaller optional master class experiences across the week that taught our sales organization new hobbies and skills—cooking, mixology, feng shui, and more—tying into the importance of emotional, physical, and mental health and happiness. We know the pandemic will eventually end, but we wanted our virtual kickoff to weave in the perfect balance of mind, body, and soul to achieve speed and strength in the market.


The overall experience was well received. In fact, it was the highest-rated sales virtual kickoff we’ve hosted during the past four years. Our focus on rowing together and client empathy allowed our organization to evolve against the challenges that 2020 has given, especially as we row into 2021 and beyond.

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