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It’s Time to Pivot — Handshake’s Sales Playbook on Virtual Team Alignment, Pitch Certifications and Remote Training

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Nothing could have prepared Mark Riley for the challenges he’d encounter leading Handshake’s enablement function through the changes of the sales landscape in 2020. Luckily, Mark relied on his unique, human-centric approach to sales enablement to rewrite the new growth playbook for remote training and virtual selling.

At the beginning of March, Mark Riley was preparing to welcome a cohort of account executives from Handshake’s new New York City office for onboarding at the company’s headquarters in San Francisco. Within a week, their flights were canceled and Mark was grappling with the reality of leading his first entirely remote onboarding program. As time progressed and remote work became the norm, Mark found himself again adjusting his plans as he focused his efforts on re-training his team on a new selling methodology. 

As Handshake’s first sales enablement leader, Mark was able to guide both recent hires and tenured members of his team through the challenges of pivoting to a new, virtual sales landscape. Mark shares his insights and best practices in enabling sales teams.

Start Enabling During the Hiring Process

Since transitioning from the role of an Account Executive to Handshake’s first Sales Enablement Manager over a year ago, Mark has discovered what he believes to be the five must-haves for sales enablement. Along with cross-functional communication, a regular cadence to trainings and meetings, buy-in from senior management, and adaptability, Mark underscores the importance of being involved in the hiring process.

“Sales enablement starts the second I walk into an interview room,” says Mark. “The best interviews aren’t just about what that person is really good at and why we should hire them, but what that person needs to learn.” For Mark, interviews are a time to ask “ What are the weaknesses of that person? What can you train that person on?” With the insight that he’s able to gather as part of the hiring team, Mark knows exactly how he needs to personalize trainings to help a new hire build upon their skill set.  

Certify Your Reps to Maximize Training Impact

As Handshake pivoted to help customers master virtual university recruiting, Mark developed role-based certification paths in WorkRamp to help his revenue team sell virtually. In just three weeks, Mark rolled out over five training and certification workflows in WorkRamp to tackle topics around changing customer needs and Handshake’s new positioning in the market. From enterprise AEs to SDRs, personalized trainings aligned every member of the sales team on the new corporate messaging framework to deliver a more cohesive brand story that resonates in today’s market. 

In rolling out new certifications for the sales team, Mark makes sure to highlight the relevance of what the learner will take away. It’s a philosophy that Mark relies on in training new reps that he believes should extend to certifications. “You have to be able to say ‘here’s why you are going to be better at your job because of what you’re learning,’” says Mark. With pointed reasoning and relevant content, Mark is able to circumvent potential certification burnout or low completion rates.

Stay Interconnected While Apart

Like enablement managers at most companies, Mark has spent the last few months navigating his team through the transition to remote work. “There’s a natural level of osmosis that happens in the office,” says Mark, who truly discovered the power of lessons learned on the sales floor once that constant touchpoint was no longer an option.  Working from home, Mark is forced to find new ways to connect his team. “That’s one of the things I think about a lot,” says Mark. “How do I synthesize and make sure I know everything that’s going on, and then in turn ensure that my reps know it, too.”

Mark uses WorkRamp’s social challenges to create a virtual space for reps to learn from each other. This activity forces “learning by osmosis” that otherwise happens on the sales floor, as reps are able to watch peer submissions and learn how to personalize their own pitches. He also leads Whiteboard Wednesdays, a weekly open-agenda meeting with the sales team, to encourage collaboration by sharing best practices and brainstorming deal strategies together. He sets the tone by starting each meeting with upbeat intro music and taking advantage of interactive Zoom elements, like the poll and chat features. He also encourages the importance of providing breaks within and in between meetings, “give people room to think, give them time to think.” 

Measuring Success, Even When It’s Unconventional

As a trailblazer in sales enablement at his organization, Mark relies on clear metrics of his personal and team performance to highlight his impact on the company. An open dialogue about metrics and KPIs is especially important to Mark given his unconventional compensation structure, where his earnings are a direct reflection of new revenue brought in by the sales team. It’s a reward structure that is crucial to Mark’s entire philosophy around enablement. “The idea that my paycheck is a direct result of how our entire team is enabled is huge for me,” he says.  

While enablement at Handshake looks quite different from what it was a year ago, the fundamentals of Mark’s philosophy remain the same. By beginning enablement during the hiring process, building meaningful certifications, maintaining close team contact, and measuring all types of success, enablement managers can build a growth playbook that can handle adjustments along the way.

To hear Mark’s tips, watch the full webinar below.