Shruti Kapoor, Founder of Wingman – Conversations made Intelligent!

“It was 2012, and my husband took up a job all the way across the other side of the country. It was 2015, and I was a first-time manager and a new mother. It was 2017, and someone in the family was diagnosed with advanced cancer with poor chances of recovery. Either of these could have ended up as commas or full stops in my career, as they do for so many women.” But I choose otherwise.

This is a mere glimpse of Shruti Kapoor, a lady of strong will, grit, and perseverance! During her professional life, she found gaps in sales interactions in the industry, and decided to solve them! She is now the founder and CEO of Wingman – A Conversation Intelligence Software.

Let us read through her inspiring journey!

YC: Shruti, welcome to Yellow Chapter.  We would like to hear about your childhood. Can we start from those days?

Owe a lot to my parents!

Shruti: I was born in a small town called Mainpuri. We then moved to Lucknow where I did most of my schooling from Loreto Convent, Lucknow. My father is a doctor and he comes from a family of doctors. My mother is a Maths teacher and her family is packed with engineers. We had an interesting Maths-Bio divide at home.

Our parents ensured that all three of their daughters (two older twin sisters and I) received a good education. They were very particular about it. I still remember our dinner table conversations were very focused from an academic standpoint.

If I think of it now, I feel so proud of my parents. Taking into consideration how small a village we were born in and what the societal expectations were, they focused on providing their girl children with the best of education. It was nothing less than path-breaking. Our parents were truly thinking way ahead of their time. 

I went to Singapore, and it was there I completed my 11th and 12th.

New Horizons!

While in senior secondary, I was not sure of what to pursue next. I had three options, to study in the US, in Singapore or I could come back to India and attend JEE. I kept all three options open. The US was a bit expensive, and I was not able to appreciate the IIT culture although I gave the interview there. Singapore had a better gender ratio, more freedom for women and was a familiar place for me. So I decided to join a college there – National University of Singapore: NUS  – Bachelor of Science (BSc) (Hons), Life Sciences.

YC: How was graduation? What would you suggest to young minds to optimise their graduate years?

Shruti: 2001! I believe graduation is all about exploring. We usually choose a subject or a stream with minimal knowledge about the same and later realise otherwise. I think it’s ok and one should move on. I did my graduation in Life Sciences but later realised biotech, life sciences, research is something that I would not like to do for the rest of my life. So I went for an MBA- Indian Institute of Management, Ahmedabad

Regarding optimising the graduate years, so graduation is primarily about 2 things academic and extracurricular activities:

  1. Academically, I think it is very important to pick up courses outside your core curriculum. Basically, during our schooling we have a very limited vision, we just focus on getting good grades only. But college time is the right age to get a fuller context of the world. 

So I would suggest picking up a course of your interest, maybe philosophy, psychology, etc. If the university is not offering it, check out platforms like Coursera. These courses will help you in looking at things from a different perspective, which could be quite helpful in the years to come.

  1. Extra-curricular activities – This is the area where you will find your flawed state. You may also find some interesting people too. Extra-curricular activities you pick during your college days will help you learn how to maintain a work-life balance later in your life. You will find a lot of people saying, I used to play the guitar during my college days, or I was a good badminton or squash player back then.
  2. Internships and exposure – Do not do internships just for the sake of it. The internship scenario has changed a lot these days, there are great opportunities out there. Explore, research and pick something of your interest. Remember, an internship is all about exposure to real-life work.

Picking an internship has 2 parts:

  1. First, if you are interested in working for a company as you have read about them or you like the work culture or acquainted the employees there. You could try out the company by being an intern.
  2. Second, the nature of the work you are being exposed to. If you wish to excel in a particular niche, go for an internship in it.

The internship is an application of the theories you have learned in college. But if you feel you are not ready for it, it’s ok. I never went for an internship myself. I preferred to be at home, read, explore and reorient myself.

YC: What should someone out of college focus on?

Learning, Learning, Learning

Shruti: While picking a job, the very first thing you should look for is the learning out of it. For the first time in your career, you are making a huge jump from the schooling culture. You don’t have to optimise for the salary, the brand name, or the glamour. Instead, you should optimise for the learning potential you have in the company. A lot of times, it is determined by two things-

  • The agility of the organisation – A smaller place will provide you with exposure to a variety of tasks. You will also get to see the journey end-to-end. In a big organisation, you will only familiarise yourself with a part of it.
  • The type of work –  At times people would not even have the right understanding of what they like. Join a trainee programme with rotations in different departments so that you know to explore and figure out your true liking.

MBA v/s Job

If you are going for a post-graduation in business or an application based niche, spending some time doing real-life work and then pursuing the degree makes sense. I joined my MBA straight after my B.Sc (H) and I still remember in the very first lecture of HR, the professor was talking about labour laws and I was clueless. Initially, I could not internalise the concepts and ideas that were taught. This made me realise that first-hand experience with the industry helps a lot in relating the concepts thoroughly.

YC: Can we talk about your professional life and learnings?

Optimising Optionality!

Shruti: Post MBA I was not sure which role, industry I would like to work for. I was looking for something that would provide me with the maximum options in the future. The options were consulting or investment banking. I knew both the sectors will not slack me into a single industry. I also knew this would familiarise me with the end-to-end processes in a company, even if I’m not directly involved in those. 

2009 – I joined a fund called Intellectual Ventures – that centres on the development and licensing of intellectual property as an Associate, Business Development. My role involved developing the “Invention Capital” for IV, by forging relationships with inventors for accessing potential investment opportunities in their technologies; and technology companies that could licence and deploy the “Invention Capital” through their products. 

Learnings – 

1. Role of technology in every aspect of our lives – It is easy for us to think of technology playing a role in medical research or in developing new software and related experiences. However, being part of intellectual ventures I learnt about how we are still getting better at the stuff that is all around us. Making better adhesives that are greener, the coating for your reflectors on the road to keep them dust-free etc. I started observing more what around me needed improvement and what I had assumed couldn’t be improved.

2. Questioning the status-quo – what intellectual ventures’ Invention Development Fund was doing was a completely new approach to solving the problem of bringing technologies faster to the market. While it wasn’t obvious as a problem to an outsider, once I started speaking with researchers, it became clear that the gap between research and monetization can seem insurmountable.

2014 – I was promoted as Director Business Development & Leader India Office – My role was to lead the Invention Development Fund’s operations in India with a focus on bringing new innovative technologies to companies and startups in India. 

I am passionate about technology and was enjoying being at the cutting edge of the biz-tech interface in India. 


1. Error of omission versus errors of commission – In companies, we are assessed for what we did. In a lot of government settings, people are often more focussed on what they didn’t do (errors of omission). While errors of commission are more in the open, errors of omission are often hidden and hence it becomes hard to get folks in that frame of mind to take action.

2. Longer-term missions versus shorter-term goals – IV was found with a long term horizon and a lot of challenging problems and things that can fundamentally change the world, do need a longer outlook, funding and structures. However, being focussed on the long term without clear goals in the short term can lead to a whole set of perverse systems. It is important to keep thinking of structuring smaller term goals and iterating to help everyone stay aligned and focused.

2016 – In another leading role, I joined Payoneer – Financial services company that provides online money transfer, digital payment services and provides customers with working capital. I was part of Payoneer India’s founding team – contributed to various aspects of Go-To-Market for Payoneer in India including Sales, Product Launch, Customer Experience and Banking Relationships. Indian business grew 3X in this period.

Learning – B2B sales has three parts:

  • Figuring out your target audience
  • Arranging a meeting 
  • Pitching in your product. 

Only the sales team is involved with the client while pitching in the product. Usually, clients have a lot of questions about products like features, security, integration, customisation etc. I could see a lot of knowledge gaps in the sales team. 

The standard protocol is, other teams like the product team, strategy team, finance team usually ask the sales team for customer feedback, product features requirements, integration issues, gaps etc post client interaction. In most cases, the sales team will not be able to reproduce all the feedback they have received. Chances are, they might also fail to prioritise the areas of feedback as well.

I knew these conversations are way too valuable to deliver the right product. I saw an immense gap and a great opportunity.

2018 – Wingman – A tool to make sales conversations smarter and better, was born from my own struggles at Payoneer.

YC: How did you get your first few customers at Wingman?

Shruti: We (founding team members) knew we did not have the network that would buy us, customers. This meant that we had to start looking outside for our first customer. It was difficult, we had many conversations, trying to figure out the use cases and applications of the product, and get feedback. We were very clear on two things:

  1. We wanted a customer who was willing to give us feedback rather than someone who will walk away from the product if they don’t like it. So we knew we cannot start advertisements very early on. 
  2. Also, being at an early stage, we had no brand name and knew people would buy from us believing in us alone. So we even refrained from cold emailing and cold calling.

YC: Based on your journey so far, what would you suggest to fellow founders of SaaS startups?

Shruti: We still have a long way to go but based on my experience and learnings so far, I would like to talk about six points here:

1. Product market fit – I think in the early phase when you are trying to figure out the product-market fit, you need to figure out two things:

  • What to build
  • Who to sell

What to build – When you are trying to connect with people, it is important to think from their perspective, about how to reduce their investment and risk in your product. At Wingman, most of our conversations were like, “We just want to learn from you, can you give me your opinion on this?” These open conversations helped us a lot in understanding the customer and the shortcomings of the product. 

Who to sell – You will come across a section of people who will say a ‘no’. You quickly have to find a pattern of the people rejecting you, because part of finding the product-market fit is also learning what your market isn’t. You need to avoid some areas to avoid unnecessary attention to those unyielding areas. 

2. Marketing – One thing that worked for us was building the brand. We do the following quite religiously: 

  • Posting regularly on LinkedIn
  • Talking with a lot of sales influencers. Creating content-based on our conversations and promoting our content through them.
  • Sales communities – Silently observing and listening to conversations in these communities are quite insightful. Initially, we used to spend hours on such platforms. These conversations helped us a lot in identifying different use cases and tweaking our promotions accordingly.
  • We even made use of communities like Reddit and Quora. 

3. Sales –  Focus on selling to the right audience. Rejection in sales does not mean the product is not good, it can be that you have not picked the right set of audience. From the very start at Wingman, we knew our customers were people from an English speaking country, where sales was an expensive resource. We never targeted India for the same reason. We aimed at the US market from the beginning. 

4. Feedback – Identify your target audience, get access to them and their feedback as quickly as possible. Be selective of the feedback you take in too. Reception of unnecessary feedback can hinder your growth. 

5. Build Trust – Think of your go-to-market journey as a journey of building and finding trust. Start with finding who can trust you. Next, find ways to amplify the trust through testimonials and social influencers. 

6. Understand your competition – Competition is of two types:

1. Another product

2. People not doing anything about the issues they are facing

First, understand the competition and then speak to your customers. I think the best approach is to talk about the problem rather than pitching in the solution in the first place.

YC: What keeps you going on this journey?

Shruti: A perspective that you are not your start-up. A venture is a part of your life, and not your life. In my case, it is my kid who provides this reminder. He forces me to spend enough time away from work. Everybody should have some downtime for themselves, it is important in every sense. 

@ Family

As your team grows, you will find yourself surrounded by more people who trust you and stand with you on a tiresome journey. It helps in building a self-belief to say, “I have done a good job, I will take it further!”

Miles to go before I sleep…

As mentioned earlier we have a long way to go but I am really proud of the team at Wingman, here are some numbers: 

We have 200+companies as our clients and about 4,000 users for our platform. We aim to reach 10,000-12,000 users by the end of this year. We plan to raise our revenue 4x and also increase the number of companies that we work with. Our competitors are – and

YC: Lastly, anybody whom you would like to thank?

Shruti: I think for us, our early investors – YCombinator, Venture Highway, Speciale Invest, VentureSouq and Arali Ventures have been very important both as a resource and a helping hand. They gave us valuable advice on problems, provided a perspective on our journey, and connected us with the right people with expertise. 

SaaSBOOmi is an organisation that helped us a lot. I got a lot of fellow founders there, people whom I would reach out to for pieces of advice on specific things. That ecosystem is crucial for a founder because entrepreneurship is a journey of constant questions coming your way. It is always better to have people who have the experience to guide you. 

Of course, as I had mentioned, my parents. They are the ones I would thank the most in this journey. They moulded me into what I am today. I would also like to thank each and everyone who was instrumental in making this journey come true.

It was wonderful talking to you. Yellow Chapter wishes you all the very best for your future. 

Thank You!

Feel free to contribute