We hit an important milestone recently.

As I sat and stared at my screen to let it all soak in, a million thoughts rushed through my mind. Here is my take on this journey, what we did right and wrong, as well as the emotional roller coaster that accompanied it.

Like a lot of things in life, you look at milestones as reasons to celebrate but also to compare yourself. I have been waiting for this day for some time now and it feels kinda numb.

Does it feel like anything else I have felt before?

• Getting into your dream college
• Getting married
• Seeing your child take that first step

Nah, none of those things can really compare. But with this milestone I know one thing — it is the start of something real and big.

You don’t know what you don’t know.

When I started Wingman, I had no idea of what I was getting into. I barely knew anything about my amazing co-founders (Murali and Srikar), SaaS or global sales. We had all worked at large and prestigious companies — perhaps the best way to leave ourselves least prepared for the startup journey.

Three years in, I have learned a lot about what I don’t know. It has been a journey as much in giving birth to a new version of myself, as it has been in giving birth to a company. #NewBeginnings

Pre-work: Ecstasy of ideation

Work: We had decided we wanted to start something before we knew what it would be. We brainstormed on many different problems that we had personally encountered. Our universe was more focussed on B2B. The idea for Wingman started brewing at my last job around 2017. I had been feeling this pain personally and I knew that there wasn’t a good solution in the market at that time. However, I was new to the world of sales and didn’t have a natural network to reach out to and validate the idea.

We started asking friends and friends’ friends if they knew anyone in sales or the startup world. We spoke to ~20 folks who were founders or sales leaders — primarily in India.

In 2018, we worked with an outsourced company to design the MVP of the product and give it some shape and form that would help us get more feedback.

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Learnings:

1. Get feedback from your ICP. Bucket feedback from different personas so you can see patterns to help shape the MVP more narrowly.
2. “If you don’t ask, the answer is always a no”. We were hesitant in asking for favors. In hindsight, I would have been more aggressive in getting intros to more people.
3. Speed >> perfection. While a lot of people will frown on outsourcing the initial version of your product, I think this depends on your team’s strengths. I would say go with whatever approach gets you to better customer feedback sooner. We chose a hybrid approach and worked with an external agency on design while development was in-house.

Personal: “I won’t get a salary this month”. The fear of giving up a well-paid job was real. Given our stage in life, backgrounds and risk appetite, we decided we’d build this as a venture-funded company.

0-6 months: Quagmire of paperwork

During this time in 2018, we:

• Set up the company (after a lot of research and conversations)
• Hired our first employees
• Built and launched the MVP
• Got our first paying customer(s)

Work: We were fortunate to have a term-sheet very early in our journey (before product or company incorporation). However, we had no idea of how complex it would be to figure out the company structure, shareholder agreements and actually get the money in the bank. We had the most frustrating six months, where most of my energy was spent on figuring out compliance and negotiating shareholder agreements for a small seed fundraise.

The term sheet gave us the confidence to go out and hire folks. We hired our first two full-time and two part-time folks during this period. As we started working from an office space, instead of Srikar’s home, things started to feel more ‘official’.

Personal: There was an edginess, excitement and anticipation of seeing the product grow screen by screen. Those initial customer feedback conversations were full of ups and downs. After those customer interviews, I’d sometimes feel validated and often it would feel like the product needed a lot more work before we could get it in the hands of customers. A lot of things felt out of my control and I didn’t know how to accelerate them. It was a lot of waiting and listening.

Learnings

1. Legal discussions can take their own time. Don’t fret everything — come to an overall understanding and framework and use that to negotiate. Work with a lawyer who understands the business perspective, not just the legal one.
2. Early customers can have a disproportionate impact on your product roadmap — be picky about who you work with.

6-12 months: Tech crunch of initiation

We had cultivated our initial users from our network and felt it was time to expand the pool.

• We spent a few weeks in the US interviewing potential users and understanding the competitive landscape.
• We focused on building a product with high engagement and innovating quickly to achieve it.

Work: We were a team of six at this point — three founders, two engineers, and two part-time folks working on design, marketing and everything else. The team was focused on constantly understanding how to improve product usage, while I was still spending a lot of time playing legal squid games. We held massive brainstorming sessions to educate everyone about the overall landscape, customer feedback, and what our competitors’ customers were saying.

We then went to the drawing board to come up with ideas on how to solve the biggest challenge at hand — conversation intelligence was still a ‘nice to have’ and its impact varied dramatically depending on the sales managers using the tool. Our aha moment was — “sales managers want to coach and love talking about it, but in reality don’t get or make time to do it regularly”.

We focused on trying to address this and that’s how the real-time sales coaching idea was born. We also tried to address other issues through this e.g. easily finding important moments in the call. In 2019, we were accepted into YCombinator on the back of this, got TechCrunched, and it felt like a strong validation.

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Personal: Those were heady times — we had a strong differentiation that solved a real pain point and delivered more closely on the promise than any other sales technology at that time. As founders, we were getting better aligned with each other and the overall mission of the company.

On the family front, this was a tough time. My 3-year-old son hadn’t taken well to the 3-week separation when I was in the US. Once I was back, he was super clingy. For the next 2–3 months, he wouldn’t let anyone else put him to bed and given my schedule of calls at night, it meant that he was crying himself to bed on most nights. #Adulthood

12-18 months: Wearing off of novelty

Three months and several meetings in the US later, we had raised a good seed round but hadn’t made much progress in addressing the go-to-market (GTM) question.

Work: Spending three months in Silicon Valley was exactly what the doctor ordered. We held ourselves accountable to ARR growth, had our first customer through cold outbound and had 50+ meetings with potential customers.

From a GTM perspective we:

• Launched on ProductHunt
• Re-branded to Wingman
• Got press coverage through YC
• Hired a sales consultant
• Worked with an outbound agency

Learnings: Despite the initiatives, the overall growth and response was lukewarm. We were beginning to realize that:

1. Educating the market about a new idea is HARD.
2. Trust is your biggest enemy as a startup — and a person with a rolodex doesn’t automatically transfer trust to you.
3. Don’t underestimate the friction in setting up and adopting a new tool. If you are expecting your customers to do a lot of work to be successful with your product, you are setting yourself up for failure.

Personal: Being part of YC and spending three months in Silicon Valley meeting people was surreal for me. It was exciting on paper but in reality, it was quite brutal. I was working 16-hour days and staying away from my child for three months took a toll on me emotionally. We decided to give ourselves a week-long break and came home to recharge our batteries before the fundraising madness began.

18-24 months: Trough of sorrow

We had reached a good place from a product standpoint, but GTM was slow. It was time to take a step back from the brute force approach of hard selling.

Work: We had analytics, a real-time engine and many more ideas on what we could build. But we weren’t seeing usage from existing users for a lot of these features. I decided to focus on two things:

1. Building trust — we started working with our existing users to voice their experience with the product more publicly on peer review sites. We were surprised by how quickly we got our first 30 reviews on G2 (we even wrote about it here) and how we started to see some inbound activity from that.
2. Customer success — I decided to spend time with all of our existing users to understand their workflows, KPIs and lastly their behaviour on Wingman.

It took some convincing internally to switch modes from our YC days of measuring ARR growth to chasing less tangible metrics. But I felt it was important for us to dig deeper and do some course correction to set ourselves up for success in the long term.

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.

Learnings:

1. Only one person knows your business and customers the best — you. Listen to everyone, but contextualize the advice and question the assumptions within each piece of advice.
2. Working harder isn’t always the best approach — sometimes taking a step back is important.
3. Choose metrics to help everyone understand and align with your new focus.

Personal: My professional circle expanded during this period. As everyone descended on LinkedIn (instead of in-person events), I got to meet and build relationships with many new folks in the sales world. I also spent time poring over data from sales calls and we were able to share some valuable insights with our customers on how things were changing during the pandemic.

24-36 months: Releases of improvements

By 2021, remote work became the norm and the economic downturn everyone had predicted showed no signs of surfacing. Technology became the substitute for in-person interactions and Wingman’s usage increased by 4 times!

We finally knew that teams were beginning to depend on our product, not just use it. We were getting constant feedback from customers, and changes in infrastructure were no longer going unnoticed. Suddenly, it felt like we could hardly keep things together and chugging — it was like changing the tires of a running car. #ExhaustingYetExhilarating

Work: We revised our:

• Positioning: We began to focus on the main challenge remote teams were facing — visibility into sales conversations. While real-time sales coaching was attractive, it wasn’t the poster child.
• Pricing: At the start of the pandemic, we announced aggressive discounts and freebies to support sales teams. While we got some adopters, a lot of companies wanted more stability in pricing. So we introduced pricing tiers catering to the needs of different teams.
• Product: We decided to improve sales pipeline visibility by bringing in emails (and email analysis) and providing a singular view for each account.

While the number of visitors to the website increased gradually, the number of leads shot up.

Learnings:

• Current vs Future: Many of our leads were SMBs but we knew the overall product we were building would be more valuable for larger teams with mature sales processes. So we decided to stay true to that segment.
• The lure of PLG: A lot of founders choose PLG because it means ‘not selling’. We evaluated PLG and for reasons specific to our unit economics, persona and product decided to stick to a sales-led motion.
• Run small experiments: As we tried to answer the question on self-serve, we thought about the simplest experiment we could run with zero engineering effort. We started allowing users to sign up for a free trial right from the website. The experiment told us that our ICP didn’t mind getting on a demo.

Personal: It was a period of confusion and soul-searching. Different functions were struggling with different types of problems and each one was trying to evolve and change. I would perhaps call this the painful side of metamorphosis.

Current: Wiggles of hope or the promised land

Over the past six months, we have tripled our team and our revenue. The speed of change has been increasing and perhaps the most reliable indicator of things is the growth in our brand recall and awareness. In August this year, we were recognised as a Gartner Cool Vendor™ for Conversation Intelligence for B2B sales and our work-of-mouth accelerated. 

We found our feet during COVID — most of the team hadn’t met each other until October! So while we innovated on the product and GTM, we also had to innovate on hiring and onboarding people.

We tried really hard to keep the pre-pandemic culture alive in the team through our weekly Show & Tell and frequent board game sessions. We had no formal onboarding structure when we went into lockdown.

But today, we have a well-structured 2-week onboarding program that introduces not just the industry and product but also the culture and vision. The result — while we met each other for the first time during the offsite in October, people felt like they already knew each other.

PS: We even did a 1:1 exercise during the offsite where each person had to find something in common with the other. It was surprisingly fun, efficient and effective. :)

Thankfully, we ignored some advice!

While I thrive on the advice I’ve gotten from my network, here are a few things we heard/read or were repeatedly told that we chose to ignore on our journey.

“You’ll have to start with SMB and scale up gradually”.

One of our first customers was Chargebee — a company with over 500 employees at the time. Overall, companies with more than 10 sales reps make up only 26% of our customers, but bring in 70% of our revenue. While SMBs are important for building a funnel for the future, they don’t have to be the bread and butter.

“Hire a VP of Sales and VP of Marketing to attain PMF”.

Listening to customers, and iterating on the product, messaging, pricing and positioning was crucial to getting to PMF. Once we had PMF, bringing in a marketing and sales leader helped with scaling things.

“You’ll have to go outbound to acquire mid-market customers”.

Today, 90% of our revenue is through inbound and 70% is from mid-market companies. While outbound can be an important channel, it is not the only way to access mid-market customers.

What's next?

As we gear ourselves for the next phase of growth, our challenges look different.

1. Innovating: In the early stages, innovation is a natural outcome of existence. But as the organization grows, people take on more specialized roles and metrics, and OKRs become the mainstay of our discussions. At this point, it is easy for innovation to take a back seat. Perhaps the only way is to focus on amplifying the voice of the customer to every employee.
2. Scaling: Paul Graham says “do things that don’t scale” and that’s the best advice early on. It helps with innovating, keeping ears on the ground and being bold. But it is time for us to switch gears or perhaps adopt another set of levers in our journey now.

Our people

It has been quite a ride and we have had a ton of fun and learning while doing it. The awesome team (employees, customers and investors) who has been the backbone of this journey deserves a lot of credit. I am grateful to them for their gumption, belief and for being our wingmates on this journey.

I am equally grateful for a circle of trusted advisors and friends who have so generously shared their experiences as operators so we could save on making all the mistakes on our own :) — Khadim Batti, Rajaraman Santhanam, Arun Verma, Siddharth Sharma, Sairam Krishnan, Varun Shoor, Vengat Krishnaraj and Germain Brion, among so many others.

Many thanks to our investors, especially Vishesh Rajaram of Speciale Invest, Rajiv Raghunandan of Arali Ventures, and Priya Mohan of Venture Highway, who have believed in our vision through the ups and downs.

As cliche as it sounds: The journey of a thousand miles starts beneath one's feet — aka with the right team! #WeAreWingman 💙