Personalization and Contextualization in Sales Using Artificial Intelligence
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by Suraj Venkat
Personalization and Contextualization in Sales Using Artificial Intelligence

Suraj Venkat:

Hey, guys. Welcome to the second iteration of Decoding Venture. For those of you who are familiar, we bring the best startup entrepreneurs, founders, professionals changing the landscape of technology, sales, marketing, operations, name it. We have a very special guest from the Y Combinator cohort of 2019, Shruti Kapoor. She leads Wingman. I would leave the mic to Shruti to introduce herself.

Shruti Kapoor:

Hi, everyone. Really excited to be here. Like Suraj said, we were part of Y Combinator last year. Wingman is sales technology, so it's essentially a wingman for sales people during their sales calls. Sales is difficult, whether or not you're on the receiving end of it or you're on the giving end of it. And we want to make it a much better experience, both for sales people and for the buyers that they interact with.

Suraj Venkat:

Sure. Absolutely. I think one of the major themes that's highly discussed on LinkedIn, I'm sure most of the viewers tuning in have seen a million posts a day on what makes for a very, very good sales conversation, how do you produce very relevant conversations that add value to both the buyer and the seller? I think that's a very, very interesting challenge that you're trying to solve with Wingman.

Suraj Venkat:

How did you begin on the journey? What was that one specific event or a challenge that you encountered that pushed you to starting up Wingman, and building the amazing product that you have?

Shruti Kapoor:

Sure. I'm really new to sales. A couple of years back I was working at a fintech company called Payoneer. I'd spent a decade in finance already starting out with Morgan Stanley, and in this role I was working with them to help them figure out where to market in a new market. Very quickly that became about sales and basically that became about the friction between sales and marketing and product in some cases. Through that, what I realized in each case, one is sales people and sales as an organization within a company has a wealth of information on what the market is saying.

Shruti Kapoor:

They are the people who are directly interacting with the customers. And this wealth of information is relevant, not just for sales people, but it's also equally important for people in marketing and product. Basically an example was, we would get a lot of leads from marketing. 80-85% of them would get bucketed as not qualified. That will annoy marketing. That would mean that sales people aren't willing to follow up with those leads. That wasn't a good feedback. Who could tell marketing why we are getting so many unqualified leads?

Shruti Kapoor:

What I started thinking was, how can I tell marketing to get better? How can I give them this feedback? But of course that also doesn't exist in the CRM, right? Because no sales person in their right mind is going to spend five minutes taking detailed notes of why that last person put down the phone.

Shruti Kapoor:

What I started thinking about was, "Listen, there has to be a better way to do this. You can't fight human behavior, but what you can do is you can definitely learn from it and maybe get technology to replace some of that friction."

Shruti Kapoor:

I started thinking about what can you get out of a recording sales call, and not having somebody listen to them. And then the second part of it was also, bringing in new sales people was always a frustrating and time consuming process because it will take you five, six months to train each one of those.

Shruti Kapoor:

A large part of it was for them to just, in some sense, become familiar with tribal knowledge, which existed within the company, but slowly they would learn here, "Okay, what is the best way to handle his objection? What do you say when somebody brings pricing up?"

Shruti Kapoor:

Those things were what became another trigger points for me to say, "Listen, this can't be the only way to do this, where manually every time when a new person comes in, people have to sit down and maybe share with them what has happened in the past." And we started thinking about Wingman.

Suraj Venkat:

Could you go over maybe an example of a transformation using Wingman, where one of your customers was encountering a challenge and then they plugged Wingman in and then they saw a new increase, and all the magic that happens?

Shruti Kapoor:

Just a word of caution, not every magical story is true, but this one is. One of the things that we realized is that it takes long for people to learn, unlearn, and decode. When a customer says something, what does it actually-

Shruti Kapoor:

One of the company that I was working with, through the analysis of all of their calls, they realized that a lot of people who were buying, or not buying from them, had a question around trust. And it wasn't even very easy for them to decode that that question was about trust because the question would be phrased in many ways. The question could be phrased as, "Hey, do you have other customers in Arizona? Where are you based out of? Have you worked with another media and tech company? Have you done this particular thing?"

Shruti Kapoor:

All of those questions eventually boiled down to, "Listen, what will happen if I bring you on board? Will I get fired, or will I be applauded for making this decision?" Once we were able to show them that with the analysis of their sales calls, there were a couple of recommendations on what they could do and one of them was to preempt a question like this and build that into the opening script.

Shruti Kapoor:

The only change that they made was to go in and say, "Listen, we are going to add to our script in the opener," saying like, "If you are so and so, we have customers in these many countries. These are some of our top customers," and that's it. They just included that in that opener.

Shruti Kapoor:

And two things happened. One is the trust questions that they might encounter later in the funnel around, "Hey where are you based," et cetera, disappeared. And the second thing was that in that team of where they ran this and they coached their salespeople to adopt this new script, their conversion rates actually doubled.

Suraj Venkat:

Very interesting. Definitely I think as the world is getting more distributed, it makes a lot of sense to understand the context of some of these questions and how you build trust. I think that's the essence of any sales conversation and any successful one is you know how well you're able to establish trust. Very interesting case study.

Suraj Venkat:

Getting back into the broader topic that we wish to address to the audience, about personalization and sales using AI. A specific challenge that we are trying to solve in-house is, who to spend time on and who not to spend time on, from the start. Let's say you are given 1000 leads. How would you know, "I should reach out to these 500 and probably ignore the other 500 because they may not convert to a sale?"

Suraj Venkat:

That's something that we're working on the most. And especially because being in the services space at Tektorch, what I've noticed is it's a huge one. We have to send out outreaches to 1000 people, 2000 people a month. Maybe if I get on a call, because either a lot of people are building technology in-house or second is, they're not educated about the latest in technologies to know what kind of benefits AI, machine learning, and all these cool technologies could bring them.

Suraj Venkat:

We deducted that we should be able to optimize and reach out to this many people out of a list of 1000, 2000, and focus on them and solve them better. You're able to personalize the conversations more, instead of going in with an opener like, "Hey, if you sell XYZ, we have like 10 engineers. We've worked 25 years, written a million lines of code."

Suraj Venkat:

Instead, what we could of is very specifically look at, "These 500 people want to buy." So I'm going to go in. I'm going to say, "I noticed your business does this, this and this. These are the interesting transformations we can bring. This is the business impact that we can bring to your organization, and here's some insights, a one-pager insight. What do you think?"

Suraj Venkat:

Even if the customer is not converted, he's getting good value because he's getting information. He's getting more educated about the kinds of technologies out there in the market. You want to look at it as a pull effect, rather than a push effect, that we're pushing out our messages. It's almost like outbound, semi inbound where very targeted messages and then have people come in.

Suraj Venkat:

Able to take a list, let's say of 1000 people initially. They divide that list into let's say 800. We extract features. For example, "What's their personality like? What titles do they hold? What are their recent activities on publicly available resources." And come up with these features, you basically run them on the other 200 which becomes a validation sample.

Suraj Venkat:

We basically validate and come up with the model, and then each time you feed in more and more leads, the system just keeps getting better because it's a very tight feedback. Let's say, after three, four rounds, you feed them the next 1000, it becomes so good that you know with 80% accuracy it's able to give you 200 out of the 1000 that you should personalize your messages to. This is basically the essence of Growth Gravity and what we're developing in-house.

Shruti Kapoor:

Got it. That's very interesting because you're right, the conversations in the recent days has become more about personalization than automation. Honestly, people are beginning to realize that you can't do automation at scale. And so then the next wave of things is you have a very interesting approach to it, which is to say, "Listen, maybe you don't have to do it at as much scale if I can get you to the right people."

Shruti Kapoor:

"And the second approach to that is when you do have to do it at scale, can I help you figure out the signal as much?" I'll give you an example. Let me just share my screen. This is somewhat related to what we're talking about, only 1,050 implications that I've been there. If I want to quickly scroll through this, that's probably people who are trying to sell me something that I might be interested in.

Shruti Kapoor:

But one is, there is no way for me to get to the right conversations from here. Most people, like you can see, they don't even bother to put in personalization, because they are trying to play the numbers game that you described, which is, "Can I reach out to 1000 people every week?"

Shruti Kapoor:

When you have time to teach out to 1000 people every week, you're just going to put in some message. Or, you're going to send them a very generic introduction saying, "Hey, I'm so and so," and it's all about you. There's no personalization.

Shruti Kapoor:

This is the challenge. This is amplified in every aspect of sale. Whether you're thinking of it from outreach or you're thinking of the messaging when you're having that first conversation, when you're thinking of the messaging during the time of the call and the demo, at each of those times that personalization needs to be there.

Shruti Kapoor:

Part of that is, of course, being able to listen better. Listening doesn't always mean listening in the context of the conversation, but listening also in terms of understanding the signals from what they have been seeing on social media, or other places.

Shruti Kapoor:

I think the challenge is twofold. One is, can you personalize effectively? And the second part of it is, how do you personalize without infringing on someone's personal space? I can hyper-personalize something and make it all about you, the person that I'm selling to, but that still doesn't mean that it's relevant. I can say, "You have great black eyes and you're wearing a great V-neck T-shirt," but that doesn't say anything about why we should be talking.

Shruti Kapoor:

There are different things that people struggle with. Being part of conversations, that I've heard a customer complain that, "Listen, why did you go to my parent's Facebook profile and from my kids' photos [inaudible 00:14:27]." The thing is, at the same time I've heard [crosstalk 00:14:33] so much for sending me the ones when my kid was born because you saw something on Facebook.

Shruti Kapoor:

Both are parts of the same thing, which is you're trying to listen on social media about the context of your customer. But there is also a lot of subtlety to it.

Suraj Venkat:

Definitely. I've had people approach me with such, "Hey, we share a blue shirt in common. Let's connect." I mean it wasn't that personalized, but he was almost going to that level. I've seen people in sales trying to over personalize. I think there's no benefit in doing that either, especially if the other party does not want to be contacted, and the product you're selling has no relevance to the prospect or the lead that you're trying to reach out to. I think it's pointless to even make that effort.

Shruti Kapoor:

I think that's why perhaps contextualization is a better word, which is you're bringing it in the filter of what they think about or what they care about, rather than about them, but about their-

Suraj Venkat:

Basically selling to who wants to be sold to. I'd like to compare this to two scenarios. The McDonald's outlet or going to a Rolex store to buy a Rolex. Basically when you're selling B2C, you can afford to go for a more mass distribution, McDonald's tactic where, "We're giving away toys with the burgers you eat." It's pretty cheap, so we're not going to make a huge effort. We're just going to advertise a small toy, and we know you're going to come.

Suraj Venkat:

But B2B is not like that. You have to contextualize. If I'm a company that's in aviation, I might be more interested in meeting an embedded systems outsourcing company than a company that develops augmented reality for media. It doesn't make any sense for me to do that. I should be able to provide them value, show the value proposition better. Just as it is when you go to a Rolex store and they talk about, "Hey, this is all hand-crafted. It's going to look so good on you," et cetera, et cetera.

Suraj Venkat:

It's the higher value ticket that you're trying to sell for. It's not a $10 consumer product. Contextualization and a bit of personalization is very, very important in B2B. It's something that's escaping most organizations because they all think, "We have a bunch of tools that can do automated outreaches and we have all these beautiful tools that can give us 10,000, 20."

Suraj Venkat:

It's not so easy. I think that contextualization and personalization as you're able to engage your customers better, number one, resources aren't spent on yourself. Number two is, your customers are going to be happier. They're going to refer better. And B2B referrals matter a lot as I'm sure you've experienced too.

Shruti Kapoor:

Taking back a step further, or maybe just thinking of the different examples. I think you gave a great example in terms of the challenge of personalization, being partially, not knowing whom to personalize for and narrowing down that funnel.

Shruti Kapoor:

The other challenge is, I look at this as the asymmetry of listening versus talking. That's one part of it. The second part of it, everybody wants to broadcast. Everybody wants to put out videos. Everybody wants to put out content. Everybody wants to send out emails that nobody has the bandwidth to read. What it means is that you need to draw their attention. When you get their attention, you need to make sure that it's what they want, enough to get someone on a sales call.

Shruti Kapoor:

You've probably prospected across 1000 people. You've probably filtered out 900 of them. 100 are relevant to you. You've probably personalized and reached out to those 100 people. And then when you have maybe those five people on the call with you, you're making the mistake of giving them the most general message that you've put. And that's where personalization and contextualization plays an important part, which is two things.

Shruti Kapoor:

One is, understanding and contextualizing it to the problem that they have just mentioned to you. And two is, understanding what might be the problem, what might be the situation based on their size, their team, their stage in the company so that you give them the most relevant things.

Shruti Kapoor:

A very simple example that people love is storytelling. When I'm talking about a customer, if I'm pitching to you and say, "Listen, we have the most secure platform," and I say, "Amazon uses it," you might be like, "Yeah, okay," but you're probably not blown over by it because you're thinking, "I'm too small. Amazon is super. This is probably not going to work for me. I probably need engineers to deploy this," et cetera.

Shruti Kapoor:

But if I came and told you, "Listen, there are these three other companies in the same location as you that have been using us for the last six months and this is what they've seen," that's where it peaks your interest. That's where contextualization and personalization, plus great storytelling comes into the play.

Shruti Kapoor:

Then you know that the light goes off and you don't have to worry about, "Hey, what is it that needed to happen?" You don't need to put the pieces together. I can put the pieces together for you and contextualize that solution for exactly what you are facing.