What Gong + Clearbanc Taught Me About Coaching Sales

sales coaching and enablement webinar with Gong and Clearbanc

Last week I was lucky enough to sit down and “moderate” (read: shoot the breeze with some cool people) a panel discussion between Matt Biggerstaff, CSM at Gong, Adriana Romero, Sales Enabler at Clearbanc, and our senior CSM here at LevelJump, Becca Shaffer.

It was an outrageous amount of fun.

But it was also super valuable. These three are not only a seriously good time, but they also seriously know their stuff when it comes to coaching sales.

Here’s what I took away from our hour-long chat.


PSST!! Video's are more fun. Watch the real deal right here.

1. You have to understand what to measure before you measure it

Enablers are often keen to immediately jump in with programs and training. Which is a superb impulse - but one that can get you into trouble when it comes to coaching sales. 

Our panel of experts recommended a different approach. 

Define what success looks like first. Figure out what sales metric you ultimately want to move. And don’t just make this up yourself. Go and ask your sales and revenue leaders what metric they care about and move that one.

Second, look past the dial you’re moving and focus on what activities are going to get you there. Because as Becca put it:

“everybody wants to have their team book, more meetings, close, more deals, build more pipelines, but specifically, what are those granular activities and those specific dials that actually need to be moved?”

Once you understand your revenue metric as well as the specific behaviours that are going to get you there, then you’re in a strong position to build out your program.

2. Enablement + sales managers should work hand-in-hand when it comes to coaching sales

Enablement and sales managers are often at odds. Even if they want the same thing, all too often enablement programs are seen as busy-work, and managers are viewed as blockers between reps and the training that will make them better. 

Obviously, neither of these extremes are true (I hope!) but friction between the two persists.

But Matt from Gong argues that both teams not only need to be working together, but it’s a situation of being greater than the sum of its parts.

Because enablers (especially at large organizations) are looking at sales productivity at a macro level, trying to answer the question: where can we spend our time to have the most substantial impact on the sales org?

In contrast, managers are extremely micro-focused on coaching sales – they care about their team, and their team only. 

It’s easy for these teams to become misaligned because the sales enablers are more likely to say one thing that doesn’t necessarily apply to every manager.

On the flipside, sales managers might bully and bluster to get enablement to build programs that lead, for  example, to better discovery, when in fact that might be a challenge only facing one team. 

The point is that they need each other. Sales enablers need to rely on sales managers to, as Adriana put it, “have a pulse on the sales floor.”

Sales enablers need to have a pulse on the sales floor.

Conversely, sales enablers are far better positioned to raise problems early across the organization, find coaching sales optimizations, and scale what’s working to other teams.

3. The way you get sales manager buy-in is proving enablement can impact the metrics they care about

Sales managers are truly the leaders on the front lines. And that’s a tough gig, often squeezed between projections and spreadsheet planning from above, and the reality of actually selling from their team below.

They don’t have time to care about coaching sales initiatives that don’t help them and their team achieve quota.

“The majority of your training [should] support sellers in their everyday role” Becca argues. 

The majority of your training [should] support sellers in their everyday role

Whenever you’re enabling or coaching sales, you have to prove that whatever time you’re asking for is a better use of sales hours than actually selling.

And to do that, you need to tie your programs to metrics that the sales managers are measured against. This means: 

  • Pipeline
  • Deal size
  • Win rate
  • Cycle length
  • Revenue generated

It’s also worth mentioning the early indoactos that sales managers look at to see if they’re going to hit their team quota, including activities, connect rates, meetings booked and held, etc... 

By zeroing in on those metrics and proving that you can make an impact that they can see, sales enablers can get a lot of trust and buy-in from managers. And as an added bonus, if you can prove out a few programs and tie them to impact, it gives you the trust to run programs that have perhaps less tangible results. 

4. Enablers should do Sales’ job for 30 days before your first program

“Understand the barriers your team has,” says Adriana. 

Enablers are often guilty of solving the problems they think the sales team has, without really walking a mile in a seller’s shoes.

Fortunately, there’s an easy fix.

Go do sales for a bit.

Adriana recommends 30 days. spend 30 days – either when you start, when you’re revamping your programs or even just when you feel sales and sales enablement alignment slipping – and actually do the job of being a seller. 


“When you're in those 30 days, not only shadow people and listen to them, but do the role. Sit down, pick up the phone, and make some calls, try to close some deals, and understand the barriers that your team has.”



Talk to BDRs, interview your AEs, sit in on calls, and of course, walk the walk and do the job.


“When you're in those 30 days, not only shadow people and listen to them, but do the role. Sit down, pick up the phone, and make some calls, try to close some deals, and understand the barriers that your team has.”


If you can do that, you’ll not only build credibility, but you’ll also get a ton of ideas for how you and your team can help.

5. Sales managers need to be coached (and enabled!)

Sales managers are often basically floated into management without a lot of help. They’re top-performing reps, and the assumption is that by promoting them, they’ll magically replicate their success. 

Turns out, that’s not the case. 

Sales enablement (and sales leaders!) need to include sales managers when they’re considering their constituents. Sales managers are so important to a functioning sales organization, and if you can make yours a little better, you’ll be in a good position to hit your number. 

Fortunately, our panelists had some ideas for sales manager training

  • Matt: enablement should provide the framework, processes, and automation that makes it easy for sales managers to coach their reps, so they can focus on the actual coaching. Enablement should also be helping senior sales leaders coach their managers, to help create a virtuous cycle that trickles down to better coaching of front-line sellers. Essentially, coach managers on how to coach.
  • Becca: enablement should be rolling out micro-programs for managers, both for their own enablement, but also that they can assign out to their team, so when they uncover a potential coaching problem, enablement can kickstart solving it (but managers still need to do 1:1 coaching).
  • Adriana: enablement needs to view sales managers as part of their mandate. They’re not just a stakeholder, but a group who can and should require dedicated attention and support.

Over to you

Our panelists had a lot of advice. So here are four sales coaching techniques you can use right now to make your enablement – and coaching – better starting now.

  • Sit down with your sales managers. Ask them what they’re working on, how they’re coaching sales teams, where the problems are, and what ONE metric they would move if they could. That should power your next program.

  • Don’t neglect your sales managers’ enablement. Ask senior leaders – how are they enabling and coaching sales managers who roll into them? What can you do to make that easier / better / improve coaching? And most importantly  - what revenue impact does improving coaching have? How will you define success?

  • Tie your programs to revenue. All the interviews, sit-downs, and shadowing won’t help you if you can’t prove you’re impacting the revenue metrics your managers care about. For your next enablement program, identify WHAT sellers care about, identify the early behaviours that lead to that outcome, and build a program to change those behaviours. Then, measure before and after to see if it actually worked.

  • Focus your programs on a single metric. Rome wasn’t built in a day. Focus your efforts on improving one metric with one program, and include your managers on deciding who needs to be enrolled. The more you can collaborate with front line leaders, the better your revenue team will perform.


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