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Wingman IRL: How Our Customers Coach and Train Reps With Wingman

Wingman IRL: How Our Customers Coach and Train Reps With Wingman

Chetna Sabharwal
Chetna Sabharwal
December 16, 2022
5 min read

As a sales manager, do you still feel like coaching or training reps regularly is a hard task? That there’s no way you can spend or spare enough time to sit with every rep and talk to them about what they are or aren’t doing right?!

You might have been right if it weren't for conversation intelligence (CI). CI platforms (like Wingman) pull all the important data from all your conversations and give you every bit of info you need to coach and train your reps. 

Want some pointers on what using CI for coaching and training looks like in practice? Here’s how our customers are using Wingman to coach and train their reps.

Propeller Aero

Propeller Aero wanted a tool that could capture all their sales conversations and data without having to remind their reps every time to make it happen. They wanted all the calls recorded so they could easily coach reps and analyze calls. 

“Wingman allows us to capture all the information, look back, and coach and analyze calls very easily.” - Drew Hultgren, Senior Manager Of Revenue Operations

With Wingman, sales managers at Propeller review calls regularly as part of their 1:1 meetings with their reps. 

“Every couple of weeks, we try to collect a few calls from each rep – a call that may have had a really good customer story, a call with a good snippet of competitor intel, or calls that bombed and could make for a good learning experience.” 


The folks at SafelyYou were starting to build out their training sales process when Wingman entered the scene. And Wingman fit right into the picture.

“We needed something to refer people to, to say to them that these are the calls where someone did a really good job of objection handling and you can learn from them. That’s where Wingman came in.” - Scott Porter, Sales Operations

Now SafelyYou has built topics (on Wingman) around the challenges that prospects face and they come back to the topics to see how their reps are performing:

  • Which reps are doing a really good job of asking discovery questions
  • If certain reps are asking for next steps more often than others
  • If a rep is doing a really good job of figuring out the needs of the prospect and is able to move the deal quicker because they're asking for follow-up meetings

Fidel API

Among the key challenges that Dan Plottner, Head of Global Sales, was looking to solve with a tool like Wingman was to have a way to go back to calls and coach individual reps.

“Being in multiple markets at the same time and being able to give feedback to both the SDR and the AE team asynchronously with Wingman has been really helpful. It doesn't matter what my schedule is. I can listen to a bunch of calls at 1.5x speed and provide actionable feedback to individuals. That is huge because it’s hard to get schedules across different time zones synced up.”


The folks at UXCam tried coaching with Zoom recordings but there wasn’t as much trust in the system as was needed for coaching and training. So they sought out Wingman. 

“Wingman captures everything. So, we can see the good, the bad, the ugly. It’s easier for me to see specific areas where a rep might need some upskilling or training.” - Maia Luke, Sales Development Manager

Also, Maia loves the fact that she can speed up the playback of the video and save a lot of time while reviewing calls. 

“When I actually go in and review the calls prior to the coaching session, I can search specifically for keywords around pricing and skip 20 minutes worth of conversation to really focus on the area that I want to train on. I listen to recordings normally at 1.5x or 2x speed.”


The main problem Ayyeka wanted to solve with a conversation intelligence tool was managing and coaching their team of SDRs. And Wingman’s transcription services really came in handy for this need.

“Transcribed calls obviously make searching for anything really easy. With Wingman, each rep would identify three to five calls and tag particular parts that they wanted help with. And we could easily pull up the sections of the calls that they wanted to discuss.” - Aryeh Samet Canter, Director of Sales Operations


“The biggest benefit of Wingman has been sales training for us. It’s about 90% of our usage.” - Jeremy Aaronson, Chief Revenue Officer

For UpSellit, having a CI tool meant having the ability to review calls and train individual reps easily.

“While reviewing calls, I see what reps are saying, how they’re saying it, or if they’re missing out on giving some information. A big part for me is also how comfortable a rep is on a sales call. If someone has been here for three years and they’re still as awkward and uncomfortable as somebody who just started, why is that?”

Annex Cloud

It was important for the quickly growing Annex Cloud team to see how their reps handled customer interactions. With Wingman, they are now able to capture everything that goes on during sales calls and train their reps better. 

“I have 1:1 calls with my team members every week. I speak more often to newer reps who need a little more guidance and support. If they have a call today, I’ll listen to it overnight and have a conversation with them the next day at the latest and coach them or provide guidance for the next call.” - Erin Raese, Global SVP


Holistics got a lot more visibility into their sales conversations with Wingman’s help. More visibility in turn meant better call reviews and more focused 1:1 coaching sessions. 

“I'm able to solve problems faster for my sales rep, uncover obstacles quickly and go over them with reps. In the past when reps came to me with the customer status, I would have to get on calls along with the reps to watch customer behavior – look at how they figure out the overall context from beginning to end – because the rep may or may not be experienced. Wingman gave me insights to address such issues quickly.” - Vincent Woon, CEO & Co-Founder


The process of scaling and adding more members to the sales team made it difficult for the management at Harness to identify the challenges that reps were going through. Sitting through every other demo call was not possible as the team grew. 

So, they brought in Wingman, which allowed them to look through recordings and see what reps were saying. 

“We use game tapes as part of the training process. It makes it easy to go over stuff. We can just tell the reps that here’s the script, the deck, or types of deals that they need to refer to. Game tapes also let us show reps the application of the scripts or the decks in a real life scenario versus only talking about it.” - Matt Weisman, Director of Strategic Operations

Alchemy Cloud

For Alchemy Cloud, sales training is a major benefit of Wingman. They wanted to capture relevant sales intelligence that could be leveraged later in the sales process. 

“We use both synchronous and asynchronous learning. We have certain game tapes that are cataloged and have all the information new hires need to consume. And then, there are ad hoc training use cases. For example, we have a game tape or a playlist comprising 75 different customer pains or customer objections. Whenever you're looking to go on a customer objection diet, you can dive in there and have a listen.” - Zachary Woods, Director, Sales & Client Development


The motto at Oktopost is Alway Be Learning! Every conversation, be it external or internal, for them is a learning moment. And Wingman fit right in with this mindset.

“With Wingman, we can check in on every conversation — a discovery call, a demo, onboarding, quarterly business review (QBR) and other discussions throughout the sales cycle. Wingman’s recordings maintain unbiased logs of all customer-facing conversations, making it possible for the senior leadership to gain insights on everything from product features to sales pitches.” - Colin Day/ Dave Kedzior, Managing Director (EMEA)/General Manager (North America)


“While call coaching was always part of the culture at Vendasta, it gets harder to do when you have more people, more value propositions, and more services and products to sell.” - George Leith, Chief Customer Officer

After experimenting with a few options to coach at scale, the leader at Vendasta came to the conclusion that they need some sort of technology to tackle this problem. And that’s how Wingman came into the picture for Vendasta. 

“With Wingman, we've really been able to make call reviews a habit. In a 1:1 or team meeting every week, there is the expectation that the manager is going to bring the game tape to review. And if they don't bring one, it's a little embarrassing! I think Wingman’s made it way easier for managers to get that information. This is the first time we’ve been able to make call coaching part of the daily cadence.


Since the sales team at Playbook was scaling rapidly, they were finding it hard to train the new folks coming in periodically. They tried out some tools that could help them overcome this challenge, but Wingman stood out for them. 

“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.”- Sal Grasso, Director of Sports Partnerships

So, there you have it. Our customers are clearly getting a lot out of Wingman - just look at how long this article is! :)

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