Help: There’s a Leak in My Pipeline!

Shruti Kapoor

July 15, 2022

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5 min read

The past few months have been quite the rollercoaster — to say the least.

Let’s break it down, shall we?

We sold our company to Clari.
I, along with every single Wingman employee, became an official Clari employee. Ahh, the joy of not being the last person standing. Just joking, Andy!
Our team and revenue growth in Q2 continued to be double-digit percentage points.
All of this in the middle of a looming — is it here, it is not here — sort of recession.

Not to be an alarmist, but make no mistake — all the signs of a recession are here. We’ve sadly seen layoffs, companies going under, and growth slowdowns overall. And while I will leave it to the economists to explain what and why, I can attest to seeing the signs and feeling the effects of the recession.

But it’s not the first slowdown I have experienced and sadly, won’t be the last.

Here’s my guide to surviving and with a bit (or a lot) of luck, thriving during a downturn. It’s what I call my LEAP framework but it’s more of a playbook to staying alive. Yeah, I like my Bee Gees references.

LEAP is an acronym that stands for listen, empathize, analyze and pivot.

*The LEAP framework to navigate choppy sales waters*

It’s what helped me (us) survive and thrive during a series of downturns during the past few years. That’s right — when times are tough, you need to take a leap. I did. Everyone at Wingman did. Here’s how:

Chapter 1: Listen deeply — to your customers

Back in March 2020, the world was thrown into a tizzy. We were standing at the edge of what seemed like a tough and uphill battle against the Coronavirus pandemic, which did play out as one of the toughest times humanity has ever faced.

As expected and predicted, the world economy took a hit. This you know.

But what was happening at Wingman at that point of time?

We were a young team — having raised a seed round of 2.3 million USD in 2018-19, which is our only capital raise to date. Here’s an excerpt from an article I wrote detailing our journey:

“This year was also 2020 and the pandemic had hit sales teams the hardest. Folks were getting fired everywhere, there was fear and uncertainty and we started to see some of our customers cut down their sales teams by as much as 70–80%. In hindsight though, the pandemic perhaps couldn’t have been better timed for us. It quickly became clear to us that it wasn’t the best time to be selling. This realization gave us some breathing space as we switched focus from selling to listening.”

As any seasoned salesperson will tell you, there’s only one thing better than selling. And that’s listening to your prospects.

Obviously, this was an easy task for us with Wingman. We didn't have to record calls via Zoom and download them. We didn’t have to transcribe them. We didn’t have to send them to Google Drive folders to die.

We made full use of Wingman’s capabilities to record, transcribe, analyze and share call recordings with the entire team. I know collaboration has become a buzzword now, but it really describes what we did with Wingman very well.

We were able to collaborate on early revenue signals and sentiment.

We understood that things would likely be turbulent for some time. The buying sentiment was low and sales tech wasn’t exactly on everyone’s do-or-die list.

But, we also realized:

Forward thinking companies were wondering how to weather the difficult times and we could help them move the needle. “How can we help them survive and thrive in a downturn?” became our rallying mantra.
We analyzed all our recordings and shared the analysis (Sales in the time of Covid) with sales teams to help them understand the macroeconomics at play. PS: It was interesting to see topics like parenting and kids come up often on sales calls. Not unexpected though.
The whole world was at home, and working online. In this environment, not listening to your customers was a cardinal sin that could mean the difference between heaven and hell for an early stage startup.
With our call data analysis, we were able to see that while some companies had the budget, they wanted to be assured of better “value” and ROI. These are all revenue signals that we discovered with Wingman.

*Topics like kids and parenting became mainstream on sales calls in mid-2020* — *also great icebreakers*

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But what trumps listening?

One word: Empathy.

Chapter 2: Empathize with your customers but also your team

My 7-year old reminds me daily that listening is ≠ empathizing. He may listen to me telling him that I’m too tired to read stories to him every night, but does that stop him from asking me to do so? 🙃

You can only imagine how pervasive the problem of developing empathy can be with your customers, but also within your own team.

Why do we need to make this tweak to this product feature?
Why does this little thing make a difference to our sales team?
Why does the customer success champion need this from me?

As product makers, we are sometimes too far removed from the customer. As an early stage founder or team member, however, you just don’t have that luxury. But understanding why something makes a lot of difference to your customer is a necessity, especially at a time when every deal counts.

Since the beginning, we listened to and shared call recordings on Wingman as a way to understand the customer (and know why our CSM was asking for that little button repeatedly). Empathy is not an inborn trait, and that’s why it’s important to make it super accessible and achievable to all.

*Customer Success <> Product: As easy as adding a comment*

Fun fact: Here are some of the features we built thanks to customer feedback:

Call scorecards: Multiple customers told us how it was so hard to create and maintain scorecards on spreadsheets!
Better organization features in Game Tapes: This in particular and many other improvements in Game Tapes v2 were built based on customer feedback.
On the go: The Wingman mobile app and recent enhancements like the ability to share a call via mobile, were developed in response to customer requests.
Management of shared call links: Reps love sharing calls from Wingman but they needed a better way to manage access to those links. So we built it.

Chapter 3: Analyze what’s said and what’s left unsaid

Sometimes what’s not said is just as important as what’s said — maybe even more.

The prospect said they wanted to go ahead but then they just ghosted me!
I sent them the contract like they asked and followed up. It’s been over 3 months.
I thought they were convinced when I told them how we’re better than X competitor.

Sound familiar?

Conversations can be a black box. When we began to build Wingman in 2018, we had one aim — to help sales teams win by unlocking insights from every sales interaction. While some sales teams were recording their calls even then, it certainly wasn't easy to unpack and get insights from those conversations. Unfortunately, this meant they were just leaving money on the table aka revenue leak. And how many missed opportunities or leaks can you afford?

As a founder who was also the most senior person on the sales team, here are some of the problem statements I solved personally and precisely with Wingman:

Which competitor is coming up most frequently on our sales calls?
Are the reps telling our story and value prop like we discussed?
How is our refreshed messaging landing with our prospects?
Why did we lose this deal?
Why did this customer churn and what early signals should we have been tracking?

Selling is not easy, especially not during a downturn. And if you don’t have that big enterprise energy, you have to stretch every dollar, make every lead count and maximize customer value.

Setting up and coaching your sales team for success is a big part of this. With Wingman, even as we grow fast, our sales managers are able to coach without taking themselves out of the game — they spend less time on reactive aka what-went-wrong-here coaching, and more time on deeper discussions and how-to-close-this-deal coaching.

Chapter 4: Pivot when needed — hard and fast

The only thing that’s more important than gathering insights is taking action. Sometimes this means responding promptly to customer queries on sales calls. And sometimes, this means reading revenue signals, forecasting accurately and course-correcting as needed.

Fact: Most of our sales enablement tactics and content live on Wingman. We have in-depth PDFs and docs to share with prospects, but everything our reps need to sell better lives on Wingman.

We’ve advertised this enough, but among our most helpful features are live on-call sales battlecards and alerts. All of our customers report, on record, that they now get new reps in the game faster with the power and flexibility of live battlecards.

Moving fast is a superpower and also a necessity for staying alive (I told you the Bee Gees are my jam). We have been able to pivot fast over the years because our sales playbook lives on Wingman. We are able to govern and stay on messaging for key topics like competitors, roadmap, pricing, etc. In the longer term, this helps us:

Set up new playbooks on Wingman, standardize and tweak them
Understand whether our reps are following the playbook
See what our A-players are doing right to share winning tactics

By keeping an eye on customer conversations, we were also able to understand that our prospects didn’t care as much about growing and onboarding sales reps as they did about maintaining pipeline conversions and picking up churn signals early. This directly led to us prioritizing functionalities like our Deal Central and adding useful alerts.

Sales is a team sport — you only win when everyone works together. Wingman has made this sport much easier for us and so many of our customers by creating one source of truth — with all conversations, metrics, dashboards and comments in one place.

And nothing makes us happier than seeing our customers grow. Here are some of the numbers our customers have posted in recent times, making us super proud.