Wingman and getting comfortable with discomfort

In 2018, three startup newbies came together to build and pitch a conversation intelligence company. As the founders searched for customers and tried to get them hooked on a brand new data point in sales, they fell many times but got up every time

The founders of Wingman had just started from scratch when they had to start from scratch again.

It was Shruti’s first startup. Murali and Srikar, both engineers, whom she had met in 2016 also had no founding experience. None of them had worked in SaaS, it had been years since the engineers had held a technical role in India. They had quit jobs in finance and tech around the world and teamed up to build Wingman in 2018.

Their idea was to launch a call recording and transcribing app specifically to help companies get sales insights from customer calls. The early Wingman team was very small. There was no one leading the design yet. Restless to launch the initial front end development on the app, they roped in a design agency.

It led to communication gaps. Not just on one design but pretty much the core of the early product. “The agency didn’t understand the problem and their interpretation of it ended up being very different. The trade off between speed versus actual quality was a bad one to make at that point,” Shruti says.

An expensive mistake too. They had to scrap all the work of the first three months. They were back where they had started.

“Recognise what your secret sauce or your meaty thing is, and try not to outsource it,” Shruti says in hindsight.

As they paid that price, the team realised that keeping core responsibilities in-house might have taken longer but it would have helped them delve deeper into product conversations.

Finding founders

As co-founder marriages go, the folks at Wingman had a mostly arranged one. They knew of each other and had mutual friends but all three met up only in 2016.

It was like moving in with strangers, and deciding to build a house with them. “And building a house together when none of you even know where the bricks will come from,” Shruti says with a laugh.

Shruti Kapoor had her start in Investment Banking, working with Morgan Stanley and then at Intellectual Ventures which invested in technology startups that came out of universities including IISc and the IITs. Over the course of taking these products to market and into the hands of users, the idea of end-to-end entrepreneurship began to excite her. But letting go of a salary is hard. To enjoy that and still get a taste of working in a startup, she moved to Payoneer which was selling its fintech product in India. There, she came across a problem.

Her sales team had some members performing well and others lagging despite being motivated. It was also proving a struggle to explain the needs of Indian customers to heads in Israel. Neither the customers nor the international bosses had time to get on more calls. This could be solved, Shruti realised, by recording the conversations. People needed to take notes and apply learnings from each other’s calls.

Muralidharan Venkatasubramanian, meanwhile, had already quit his job and moved from the US to India. He was sure that he wanted to start up. Shruti met him through a common friend. Srikar Yekollu knew Murali from their time working at Trilogy and Google earlier. He joined the team. Wingman took flight in May 2018.

They were so new to this, none of them even wanted a CXO title. But a startup has to have CXOs to ask for funding so they picked up a title each.

Being new and unknown also made hiring particularly difficult. The first 4–5 people they added were failed entrepreneurs, which was actually a stroke of fortune. “They had tried something of their own and already taken the big risk of leaving a large company. They recognised the struggle of trying to build something, and for them, the motivation was getting a seat on a very early stage journey,” Shruti says.

New and unknown as they were, the team still made it a point not to take on free customers. “Because without paying, they would not invest so much in giving us feedback.” Even after the blow of scrapping a design, success came early. By October 2018, they had their first paying customer.

Listening and learning

The founders felt inclined to keep that momentum going. Getting to the next 10 customers was tricky. They had a network in India but they soon realised the country was not a primary market. Call recording was a tough pitch here because of the barrier of language and budget. The team had to try its luck in the US.

While going to market from India to the US, be aware of availability bias, Shruti says. The founders had never done sales before and certainly not in the US. They built a product based on customer interactions they had had in India — because that is what was available. When they took their solution to the US, the reception was mixed.

Some said they should not be building this at all. Sales calls can be sensitive stuff. “There might be a kickback, there might be a discount, they might, you know, share part of the commission. No salesperson is ever going to want to record the calls and even if the salesperson agrees the customer will not agree to record that,” came the feedback.

The team had to contend with its priorities then. “We had to ask ourselves what we were betting on. Was it about being able to change that behaviour, or about finding pockets where there is already an interest in changing that behaviour?” It was the latter.

This led them to quarters from where a different kind of feedback came in. These were people who were excited about introducing them to companies but said most were already using competitor softwares such as Gong and Chorus. Wingman decided to embrace the competition and talk to users of those softwares anyway.

“We learnt a lot from those conversations,” Shruti says. Mainly, they became aware of how to articulate their differentiation. “In our case, it was real time coaching and feedback.”

They kept talking to the existing customers to determine how to take that differentiation ahead. People were happy to use and share their experience initially. But tracking the trends over a period gave the team a rude shock. Usage was dropping off.

The thrill of unlocking new data had kept customers active in the initial months. But as the element of surprise wore off, they used it less. To stay relevant, the product would have to become a part of the customer’s daily workflow. They built on the coaching capabilities. That way users would regularly come back to train representatives, save deals, etc.

More customers came. And, this time, they stayed.

Walking across uncomfortable territories

By 2019, Wingman won a ticket to YCombinator. Something you should know about the founders is that all three were easy-going and non-confrontational. At that point, although they had run a company together for more than a year, they had not quite opened up to each other. Fortunately, nothing helps fastrack bonding like staying together for three months during YC.

One of the insights that stint gave them was the fact that most companies shut because of co-founder disagreements. The Wingman founders realised they had formed parallel swimlanes and stayed out of each other’s responsibilities. “We would have some broad strategic discussions, but not about our own work.” As we know, avoiding conflict is not the same as dealing with it.

Dealing with it was actually a walk in the park. Literally. The team came back to Bengaluru and decided to go on no-agenda walks in HSR Layout’s parks 2–3 evenings a week. “This was our space to bring up anything, whether it was a large question about the business or a small tactical thing or a people issue.” A lot is said about walking the talk. Talking on the walk is just as important, in the founders’ experience. Their chats were more natural and candid, the ideas began flowing.

Shruti finds addressing conflict is not about telling someone they did something wrong. It is about how you can work together with them to arrive at an improved solution.

That is why the team now thinks in terms of versions. Always consider the current solution as Version 1. Articulating what version 2 needs to look like, why it even needs to exist, how we can get to that new version — that is a meaningful debate to have. And it is all in service to a better outcome. Not a criticism, just a point in the journey.

Tricky conversations, compromises, consensus, it is all part of the joy of starting up. “You just have to get comfortable with the uncomfortable territories that you will have to constantly come across.”

So when Srikar, who had a fear of public speaking, was told to deliver a talk at TEDx because it would help with hiring and funding — he did that.

The rest of the team contributed in different directions too. “We didn’t necessarily push people to do other things, but what we appreciated if they did other things. We wanted to give them the latitude to raise their hand and say, ‘I want to try this’. By not saying, ‘Hey, we didn’t hire you for this, so don’t do this’.”

And Shruti, who would much rather enjoy a quiet evening inside, began building her brand. She needed to put herself out there because the sales consultants they worked with in the US were not able to convert enough customers. “Even if a consultant did all the right things, the person on the other side knew that this was someone on a three month gig. They knew that they didn’t have skin in the game.”

From 2020 to 2022, she threw everything into that effort.

Getting funded vs Getting acquired

Even as they were building the business, the pandemic had thrown a spanner in the works. Sales teams had been downsized and that hurt the company’s revenue. The team used this time to understand how to make its product much quicker to adopt and get value from.

In 2022, Shruti travelled to the US to speak to investors and gather interest for the company’s Series A. Within a matter of weeks, something interesting happened. “I got three inbound expressions of interest from three different acquirers.” For a while, the word on the street had been that sales tech was going into consolidation.

Shruti’s first instinct was to prove them wrong but she knew the company had to give it serious thought too. She went about analysing those three and up to 15 more potential investors. Did they have the capacity to fund an acquisition, what were their strategic reasons for the acquisition, did their long term visions match, would everyone in the team have some value in the new ecosystem — these were things she was looking for. After some cold emailing and meetings, Wingman zeroed in on Clari. The acquisition went through in 2022.

It can be hard to switch off the founder button after acquisition, Shruti finds. But there are also parts that were a relief to give up. “I enjoy not having to do payroll every month,” for one. “And, having money in the bank is always better.”

Would the team want to start up again? “Three months ago, the answer would have been absolutely not,” she says from Dubai, where the three co-founders are currently growing Wingman. “Right now, I don’t know. Who knows, a year from now I might want to do it again.”

That is what happens when you get comfortable with the discomfort.