Sal Grasso


Director of Sports Partnerships at Playbook

We’ve transformed our sales rep training and onboarding process with Wingman

Hoboken, New Jersey, US
Sales training
Company Size


Hoboken, New Jersey, US




Sports Technology

Company Size


What we do at Playbook

At Playbook, we like to describe ourselves as a group of nerdy, sports-loving activity providers who believe that everyone deserves access to incredible sports and activity programs. We’re a fast-growing team with ambitious growth plans. As an account executive, I lead a team of 10 BDAs (business development associates) and counting.


The main problem we solve with Wingman

One of the main challenges that we were seeking to solve was that we have a lot of new sales people coming in periodically. I'd say we probably get a new person each month! You can only imagine the time and effort that I spend on training and onboarding them. So what we were trying to solve would be training them at scale.


How we found and chose Wingman

We began looking for solutions to help with sales onboarding and our CEO Josh Marcus found Wingman online via Capterra.

Incidentally, we also did a free trial with a different company, Gong.

But I know that Josh not only liked Wingman's product better, but he liked the people at Wingman better.

What stood out about Wingman was that it wasn't very salesy. Gong was very salesy and always trying to upsell, and charge us three times more in the next year, etc. Who wants that! Josh just liked the people at Wingman better and the product was just as good if not better.

Plus, as we’re a small business, one of the most obvious factors was price. But not at the cost of the tool and features itself. Like all customers, we wanted to have the best product at the best price. That’s where Wingman was a total fit.

Wingman vs Gong

Also read: Comparison of Wingman and Gong

How we train our reps with Wingman

Wingman has just made it so much easier for us to train and onboard our reps. We record all our calls with Wingman—the good, the bad and the ugly. I will usually go through the calls, especially for the newest reps, and leave notes for them to look back on. It's just an easier way to train people. That is really the main challenge that we’ve unlocked with Wingman.

How we now coach with recorded calls

We usually coach on calls just after our reps get off the call. They might say “I had a really good call with this person” and will look back and save it. Give it a name, pin it on our CRM or share it via slack. And then I share feedback.

With bad calls, I’ll usually Slack the Wingman link to the rep and say, “Hey, what were you doing here?”.

What I really like and use Wingman the most for….

When a BDA books a demo for me, I'll listen to the call to see what the prospect’s organization is all about, to see how it went, see if they're interested, and kind of gauge the temperature of that potential deal. Really helps me get a realistic picture of the sales pipeline and what the quarter is looking like.

Here’s how you can gain visibility into your sales pipeline


Also read: Deal Central for Powerful Sales Pipeline Visibility

I’ll also leave the rep notes on how they did, or what they did well, or what they should have done.

The impact of Wingman for us

One of the main benefits for me is that I don't have to be hands-on during the onboarding process for BDAs.

The last person that we hired as a BDA learned everything by listening to calls, watching demos, and reviewing the transcripts. I was able to onboard him much faster and more efficiently. Didn't have to put myself out of the game.

With Wingman, I can just say, “Here, listen to these calls.” And they can kind of do it on their own and listen and look at the notes themselves.

Also read: Now Playing—Game Tapes

You wouldn't have to spend your time as a manager sitting with your reps and training and playing the calls for them and looking at them. They can do it themselves. That’s the main benefit of having Wingman for sales training and onboarding. And it's definitely reduced that time.

How much shorter is the onboarding?

From the earlier week to 4-5 days, we now spend 1-2 days on BDA onboarding. It's definitely shorter and Wingman’s been successful for us.

So, would I recommend Wingman?

I would definitely recommend Wingman to any growing business that’s ramping up fast, both in terms of sales team members and revenue. For us, Wingman has been indispensable for training and onboarding new hires. And there are so many use cases! I would definitely recommend Wingman.


Make the switch to Wingman today.