In today’s Daily Briefing, Jim Benton was joined by Conner Burt, President of Lessonly. They discussed how Sales Tech companies have been impacted by COVID-19 and how they can prepare for what's next.
Before launching into the data, Jim and Conner discussed how sales teams are coaching differently given the times. Conner shared that Lessonly tries to apply the philosophy touted by Brad Stevens, head coach of the Boston Celtics: Highlight the best. “Get better at the things you’re good at,” said Conner, “rather than try to be even across all skills.”
Here are the numbers:
- Meeting volume in Sales Tech: +6% WoW
- Prospecting Activity in Sales Tech: Cold calls are down 34% since March, but up 7% week over week. Relative Connect Rate is up 11% since last week
- Leadership Support in Meetings:
- Sales-side Directors are joining 59% more calls and Executives are joining 56% more calls compared to Pre-Covid levels
- Buying-side leadership is also joining calls at an unusually high rate. Over the past five weeks, leaders joining evaluations were up significantly
- Deal Risk Mentions:
- Timeline risk mentions are below peak, but still far above pre-COVID levels
- Employment risk mentions have increased week over week. Since the beginning of March, RIF is up almost 130% and “Not Hiring” is up almost 200%
Meeting volume is up overall, but key difference between inbound and outbound #
Chorus reported that meeting volume in Sales Tech is up 6% week over week.
Conner shared that while the data is similar, there were key differences between inbound and outbound. “Our inbound efforts have fully recovered, but our outbound hasn’t quite yet,” he said. “What we’ve seen is - I hope - lower volume but higher quality.”
Jim echoed that quality matters more than ever now, and he asked if there have been any changes in deal momentum.
Conner said that deal momentum is still there. “About 20% have completely sped up. Some have slowed down and the rest have continued as business as usual.”
At the deal level, there is more scrutiny from all points as companies determine their next steps.
“It’s been really important for us to shore up the business case that will get approved,” said Conner. “We have to align with our champions proactively. To set the deal up so as to get approved. And if now is, not the time that’s okay too.”
Honesty and transparency are key. Proactively bringing up deal based conversations is important, and the messaging has changed as well.
Conner shared how his team's messaging has shifted. “Our message and value prop before COVID-19 was around how creating excellent customer experiences has to do with who you’re putting on the phone, and how well trained they are. In today’s world, we’re saying: ‘Call volume is higher than ever. You have fewer agents. How do you get more time on the phone out of those agents?’”
Sales Tech prospecting activity is up week over week, indicating increased confidence #
In the Sales Tech segment, Cold calls are down 34% since March, but up 7% week over week. Relative Connect Rate is up 11% since last week.
“For two or three weeks,” Conner said, “there was a bit of fear around picking up the phone to talk to someone who is probably struggling.” Adapting to the current climate has likely taken a similar toll on most companies. “Took some time for us to build that confidence,” said Conner.
Like so many other companies, Lessonly was sending more emails. But, as has been reported in the past, inboxes are being inundated. “You have to go to other channels,” he said. “The things that we’ve seen working are quick video messages and crafting experiences. We’re helping people connect, which is driving engagement with the brand.”
Shifting outbounds teams to remote has been another universal challenge.
“These are tough jobs,” said Conner. “And when you’re not in the office, you lose a bunch of that energy. We’re trying to preserve that energy.”
Conner shared that they are expanding their hunters in the field, asking their closers to source more leads. “We’re sharing the responsibility on the SDR with the AEs around building pipeline. Let’s get creative; ask for referrals or talk to customers.”
Jim agreed. “Let’s try to engage the entire team in the sales motion,” he said.

Is it impacting initial conversations for sales tech companies?
Buyer-side leadership in meetings signals a need for over-preparedness #
Sales-side Directors are joining 59% more calls and Executives are joining 56% more calls compared to Pre-Covid levels.
And, more notably, buying-side leadership is also joining calls at an unusually high rate. Over the past five weeks, leaders joining evaluations were up significantly.
“I’m more surprised about the buying-side,” said Conner. “We’ve definitely seen a shift. There are two different types. One, the CFO gets on the phone with no context, just saying your prices are too high. And two, leaders want to make sure that the teams are prioritizing the right things.”
The second is a great conversation and the other, well: Conner suggests you get hyper-focused on making sure your deals are a financial team ready.
“This means deals are being scrutinized more,” said Jim. “Are there new types of coaching for these calls? It’s a different type of call when an executive joins.”
Conner had one word of advice: Preparation.
“It’s not really coaching,” said Conner. “It’s a practice. We’ve had to dial that up on larger deals, which has been a good side effect for us. A lot of these end in negotiation, so it’s about getting the levers right. Transparency is key.”
Deal level scrutiny is high. Be proactive, transparent, and prepared #
Timeline risk mentions are below peak, but still far above pre-COVID levels.
Employment risk mentions have increased week over week. Since the beginning of March, RIF is up almost 130% and “Not Hiring” is up almost 200%
Addressing these objections means being transparent and creative. Conner offered one lighthearted tactic: “We’re looking at how other people are selling to us right now to source ideas.”
In Lessonly’s Weekly Note, they reference the saying: “If it’s important, do it now.”
Conner shared that this is how they approach customers and help to establish value quickly. “We have used this to give our customers the perspective that ‘If this is important, let’s do it. If it’s not, then okay let’s talk later.’”

Are Sales processes changing in response to the crisis?
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