In this episode, we’ve got Shruti Kapoor with us. Shruti is the Co-founder and CEO of Wingman, a company that helps salespeople make better decisions by bringing intelligence both into the conversations in real time and into the overall aggregation of data, so that people can close more deals. Join us for a deep conversation about the lessons Shruti has learned as she has built Wingman from the ground up.
If you missed episode #204, check it out here: How to Implement Effective Account-Based Marketing Strategies with Auseh Britt
What You’ll Learn
- Why data and activity metrics aren’t enough
- Key tips for starting a new company
- The difference between creators and sellers
- The importance of self-awareness and honesty for founders
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Show Agenda and Timestamps
- About Shruti Kapoor and Wingman [4:58]
- The keys to a successful startup [13:16]
- The difference between creators and sellers [15:31]
- Observations about selling to salespeople [17:56]
- The importance of self-awareness and honesty for founders [20:44]
- Paying it forward [22:02]
- Sam’s Corner [23:26]
About Shruti Kapoor and Wingman [4:58]
Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Today, on the show, we’ve got Shruti Kapoor, co-founder and CEO of a company called Wingman. Wingman is helping sales people make better decisions in the moment by bringing intelligence into both the conversations in real time and also into the overall aggregation of data, so that people could be better at closing deals, which is obviously important.
Before we get there, let’s listen to a word from our sponsors.
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Shruti, one of the things we like to do when we start is to give you an opportunity to tell us a little bit more about your company.
Shruti Kapoor: Wingman’s mission is to make the life of salespeople better. What we do is we help make revenue intelligence actionable. We bring in insights from different types of sales interactions across calls, emails, video meetings. And then not only do we analyze, find trends in them, but we try to take that intelligence, break it up into little nuggets that people can use, either while they’re actually speaking to the customer or while they’re preparing for that interaction or right afterwards.
I started the company almost four years back now. We are a team of nearly 50 people as we speak. And we mainly work with sales teams of all sizes and we have more than 200 sales teams that work with us today. The good thing with being a founder is, you’ll always feel unprepared, and the bad thing is that you’ll realize how much you don’t know. But in some sense that makes it, I would say, an equal playing field, because everybody who becomes a founder probably realizes that they’re unequipped to be one, because there are just so many different hats that you need to wear on any given day.
The keys to a successful startup [13:16]
Sam Jacobs: What are some of the key lessons that you’ve learned over the last four years building the company that you would share with a new founder or a new entrepreneur?
Shruti Kapoor: Every day in the startup world is a new lesson. So, I’m sure if you ask me this question a few months down the line, you might get a different answer. Early on, one thing that was really important was to believe in yourself and the idea, and that there will always be naysayers who will basically find a reason why this should fail. When we started out, a lot of people will be like, “But salespeople will not like that and their customers will not like that, and I don’t think this will work.” So, one is that.
The second part is that life is only that long or short to make all the mistakes. In the startup world, there are way too many of them that we can make. Go and find a person or maybe three people who’ve done the same thing that you’re about to do, and see if you can find out and learn from their mistakes.You don’t have to do it alone and you don’t have to feel shy asking for help. There are a lot of people who’ve gone through the pain who will be happy to reduce your pain.
The difference between creators and sellers [15:31]
Sam Jacobs: One of the things that you’ve talked about in the past is the difference between creators and sellers. Tell us a little bit about how you think about those two categories of people.
Shruti Kapoor: Mentally, the two categories of people are wired a little bit differently in terms of they need and seek gratification. I feel that a lot of times to be a good seller, you almost need to be somebody who is constantly impatient and quickly wants gratification and quickly wants results. From a creator perspective, sometimes that journey can be longer. Those people tend to get gratification and see success with a very, very different lens.
Sam Jacobs: And do you view yourself as a creator?
Shruti Kapoor: That’s a tough one. Yeah, I do.
Observations about selling to salespeople [17:56]
Sam Jacobs: Talk us through lessons that you’ve learned observing and selling into the sales profession.
Shruti Kapoor: If you’re doing outbound campaigns and you see that somebody has viewed your email eight times or 20 times, the chances are that it’s not because they’re about to buy from you, but that they just forwarded it to their own SDR team.
The second one is that you could be prepared to get on a cold call and then end the call. You might be on a cold call for five minutes and it wasn’t because they were setting up the meeting with you, but maybe they were giving the advice on your pitch. I think it’s basically an interesting mix of empathy and somebody who really understands how tough sales can be, how many nos a salesperson needs to deal with. But at the same time, it can also be a very challenging audience, because they’re not just looking at the product, but they’re also maybe evaluating the person for their sales skills and for their sales process. There are some good things, some bad things, but it’s a lot of fun.
You need to be a lot more on your toes and be innovative, because they know all the tricks in the book.
The importance of self-awareness and honesty for founders [20:44]
Sam Jacobs: One of the things that you’ve also said is that you’re not a big believer in this concept of fake it till you make it. How do you approach being a great founder?
Shruti Kapoor: The reason why “the fake it till you make it” philosophy doesn’t land well with me is it puts a lot of undue pressure on the founder. I don’t think it’s great for people’s mental health, because you literally are being told that you can never be honest. You can never let your head down in some sense and ask for help. That’s impractical and that’s probably counterproductive in some ways.
If you’re more self-aware and honest, you can have much better learning conversations and a much better learning journey. You can iterate much faster. But if you are always trying to fake it till you make it, you almost have to always sound like you’re on the top of the game, you believe everything is perfect, you’re super confident on what you are doing. Sometimes that closes the doors to feedback, to iteration and to improvement.
Paying it forward [22:02]
Sam Jacobs: Shruti, we’re almost at the end of our time together. When you think about people or ideas that have had a particularly large influence on you, tell us who comes to mind.
Shruti Kapoor: Some of the ideas from Yuval Noah Harari, the book Sapiens, especially the idea about the power of stories in terms of how our society has evolved. That’s been pretty foundational in terms of how I think the world operates today.
Sam’s Corner [23:26]
Sam Jacobs: Hey, folks. Sam’s corner. I enjoyed that conversation with Shruti Kapoor. She’s built a company that’s doing really important work because there’s so much data coming at all of us all the time. Making sense of that data and understanding exactly what you’re supposed to say and when you’re supposed to say, that’s the part of sales that we all need to be better at, because we have the information now, now we need to make sense of it.
We need to make sure that we are ourselves experts in the way that we communicate and the way that we interact with our buyers and our prospects. You have to be able to look at the business from a holistic perspective.
Don’t miss episode 206!
Now, before we go, we want to thank our sponsors.
- Pavilion, the key to getting more out of your career
- Outreach, find out why Outreach is the right solution
- Freshworks, developing digital customer journey maps with Freshscales
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