Measuring, Celebrating & Course Correcting Sales Initiatives with Mark Wayland, CRO at Box

10/10 GTM Episode 25
Transparent sales process - working together
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders

Our guest for Episode 25 is Mark Wayland, CRO at Box. Before joining Box in 2019, Mark held leadership positions at Tanium, Salesforce, and Gartner, Inc. He brings more than three decades of experience to the conversation. 

In this episode, Ross and Mark discuss the importance of codifying deal excellence, partnering with frontline managers, and implementing effective strategies to measure, celebrate, and course correct sales initiatives. 

Listen to the episode here, and get the key takeaways from our conversation below.

Codify what excellence looks like for your biz

What does a perfect deal look like for your business? Take the time to codify what this means for your organization. Work with your team to identify the key characteristics, criteria, and outcomes that lead to success. 

“I started in sales before the internet. Back then, customers weren’t well informed about what the solutions were to their problem,” says Mark. “The perfect deal in those days was to get in first and set the buying criteria, then set traps for competitors. But that game doesn’t work anymore. Customers are too well informed now.” 

Once you determine the criteria, document it and make sure it’s easily accessible to your reps. Depending on your organization, you may opt to document using slides, recordings, presentations, or a combination of these. The purpose is to create a framework for your reps to work from so they spend their time and resources on deals that are most likely to close. 

Educate & partner with frontline managers

When you’re doing any sort of a change initiative, success starts and stops with the frontline sales managers. Your managers need to be educated and onboard with all your initiatives, otherwise they’re likely to fail. This begins with codifying what a perfect deal looks like (as discussed above), and getting your managers involved from the get-go so you have their buy-in. 

According to Mark, the most effective frontline managers are in the trenches with their reps: “When I lived in NYC, I would always see groups of union workers repairing potholes. And there would be four guys on the ground with shovels doing the work, and one guy standing around not lifting a shovel. That’s not the role of a sales leader. Managers are in the hole. They’re doing the work.”

In addition to frontline managers, revenue leaders must also be actively engaged. As a VP of sales or CRO, leading from a distance — whether behind a desk or through virtual meetings — isn't sufficient. It's essential to be present on the ground, interfacing directly with customers, and navigating deals to close. 

This provides insight into what works and what doesn’t, and allows you to balance the feedback you get from the teams. Then you take all that information from the reps, managers, and your experience and codify what the perfect deal looks like. From there, you educate everyone and get them on board. 

Measure it, celebrate it, and course correct 

To benchmark your team’s progress, measure what success looks like. Here are some key questions to consider: 

  • Who is your target audience?
  • Are you prospecting into the right roles within your target accounts?
  • Are your outreach efforts timely and well-tailored? 
  • Are you successfully scheduling meetings with prospects? 
  • How engaged are prospects in the sales process? 

As you measure your team’s effectiveness, celebrate their micro wins along the way. Whether it’s successful prospecting efforts, compelling pitches, or adept handling of objections, each achievement represents a component of that codified deal type. Recognizing these milestones boosts morale and reinforces the importance of consistency. 

This ongoing review process will also shed light on instances where things aren’t being done right. This represents an opportunity to course correct. Approach your frontline managers with specific examples of areas for improvement you’d like to address. 

The key is to remind everyone of what you’re doing and why. This requires ongoing repetition so it sticks. Most sellers have worked for someone in the past who was constantly running new strategies every month, creating fatigue and making adoption unlikely: “For many sales leaders, the adoption rate of new initiatives is similar to hot tubs and gym memberships. Upfront, it’s really good. But before long, everyone goes back to doing things the way they used to. They don’t go to the gym. They don’t use the hot tub. That’s why when you’re rolling out an initiative, you need to stick with it, explain why you’re doing it, be repetitive with the messaging, celebrate the successes, and course correct as you go,” says Mark. 

Rapid fire: Mark’s fast sales insights

In a rapid-fire Q&A session, Mark shares his insights with us on a wide range of topics: 

What’s the main reason most teams miss their ARR goals? They didn’t have a good enough portfolio of small, medium, and large deals.

What’s your favorite resource for revenue leaders? The Qualified Sales Leader: Proven Lessons from a Five Time CRO. 

SMB, Mid-market, or enterprise? I have three kids and I don’t have favorites. I also don’t have favorite segments either. 

Best way to unplug from the demands of leadership? Skiing. 

About Mark

Mark is a seasoned sales leader with more than 30 years of experience. Before joining Box as the CRO in 2019, he worked as the CRO at Tanium, SVP at Salesforce, and VP of Sales as Gartner, Inc.