The Daily Briefing: May 5, 2020

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On Today’s Daily Briefing, Jim Benton was joined by Ray Carroll, the VP of Sales at Skilljar. They discussed how COVID-19 is impacting the way we motivate and coach our teams.

  • Meeting volume has been relatively steady, though down 8% this week
  • First and follow up meetings are both down this week. But there’s been a widening gap between first and second meetings

Before they dove into the data, Jim and Ray discussed the makeup of Skilljar’s revenue org, and the recent move to remote work.

“We’ve got about 25 people overall,” said Ray. And remote work is a new experience.

“I was known as ‘Butts in Seats Ray Carroll’. If you weren’t in your seat, you weren’t working,” he said about his philosophy in the past.

“But the world has changed,” he said. “I felt this coming before the pandemic. This just accelerated the inevitable. People like myself and team leaders, we are going to need to work differently.”

Right people and available leadership is the recipe for remote productivity


We’ve seen an 8% drop in meetings last week, but that was after a few weeks of steady increase. Jim and Ray explored what working from home means in terms of the overall productivity of sales teams.

“Productivity loss is not that significant, in fact, we’re seeing more productivity,” said Ray. “As long as you’re hiring the right people, and as long as you’re holding them accountable, then it’s just good management.”

Ultimately, the right hires will be more productive from home. “Great AEs can command working from home well,” said Ray. “If leadership doesn’t trust them, they’ll go somewhere else.”

The week to week dips and peaks doesn’t worry either of them. It could be that people are taking breaks, and Ray expects we’ll see a big dip in meetings once restrictions are lifted as many people will likely request to take vacations.

Inspire the next generation of great AEs


The next frontier of salespeople, the next wave of great AEs, will likely come out of this era. How you coach, motivate and inspire this next generation will be key.

Jim and Ray both acknowledged this shift and the difficulties presented to a salesperson who is still early in their career.

“When you’re early in your career,” said Ray, “you’re learning from everyone around you. It’s a bit harder from a distance. So, how do you get going? It’s about leadership. I felt this world coming. You need to be able to lead and manage teams wherever they are.”

Jim agreed. “A new group will figure out how to manage remotely that will blow us away.”

If you haven’t really thought through how you’re going to onboard people in this environment, you’re going to get burned.

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How is it affecting productivity for revenue teams?

Hiring is one part, onboarding and ramping is another.


“If you haven’t really thought through how you’re going to onboard people in this environment, you’re going to get burned,” said Ray.

Jim couldn’t agree more. He shared his personal experience of being onboarded remotely at Chorus.ai in March. “I’m a completely remote onboarded member of the Chorus team. But I’m learning you have to learn that everyone is a click or call away. I look forward to getting back to the in-person interaction, but it’s amazing how quickly we can adapt.”

Companies, leaders, reps, and AEs are all adapting as quickly as they can. But there’s one factor that seems to stand out to Ray as a sign of success: Mindset.

“Outbound teams really lost momentum in early March. They weren’t confident, they weren’t thinking about your product, they’re thinking about survival,” he said, “But reps with a great mindset - reps that are mentally tough - they’re going to make it.”

Relevant and personal outreach leads to better discovery


Chorus is reporting a dip in follow up meetings. There’s a slowly widening gap between first and second meetings. Jim and Ray explored why this is, and what can be done about it.

Do your research. Personalizing your outreach is always preferable, which can only happen if you have researched your prospect. The next step is applying that research to relevancy. Are you and your services still relevant to that company, that executive team? If not, pivot.

“You have to have been relevant before COVID-19 hit,” said Ray, and he added, “If I feel your emails aren’t written for me, then it’s blocked. I just move on.”

This is a priority for Ray and for Skilljar. “How do we get the awareness of the Skilljar name out there, so that even if they don’t know the name of the person reaching out to them, they will recognize the name of the company.”

Even with the personalization and brand awareness checked off the list, you must also be relevant. Ray is grateful that Skilljar has something to offer companies that they need right now.

“We have something to say right now,” he said. It’s critical that you use personalization, relevancy, and research to cut through the noise.

Companies are not buying software unless an executive has a problem and there’s a software with that solution.

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Layers of active discovery


You have to layer your discovery questions in a new way, for a new audience.

“Now what we’re coaching our team on is asking a few more layers of discovery questions,” said Ray. “Companies are not buying software unless an executive has a problem and there’s software with that solution.”

Which means you have to dig deeper to source the pain felt up top.

If a prospect mentions a problem, “The best reps will dig deeper. What exactly is the problem with that integration? Who else is impacted by that?” suggested Ray.

“You have to get to the executives,” he added. “Everyone should be thinking, who is the VP+ executive who would own the budget for this problem and solution.”

How is it affecting sales and customer success teams?

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