Episode 10: Kris Rudeegraap and Amitabh Sinha

In our tenth episode, Gil talks about category creation with two people that are making waves in the desktop cloud computing and business gift giving categories.

Panelists for this episode include:

  • Kris Rudeegraap, CEO, Sendoso and one of the pioneers in creating the corporate gifting / direct mail automation categories
  • Amitabh Sinha, CEO, Workspot, and one of the pioneers in the remote desktop category

 

You’ll walk away from this episode with an understanding of:

  • The benefits of focusing on category creation from day one
  • How to pitch a new category to investors by using an anchor or proxy
  • The different metrics for measuring the success of a newly created category

 

BONUS!

Kris tells us why he decided to travel to 30 different countries while founding Sendoso.

TRANSCRIPT

Gil:
Cheers for the first one before we get started. Great to have you both. Awesome. All right, well, welcome to the Category Creators Podcast. This is I think the eighth or ninth episode. I’m very excited. I have two great folks here. Amitabh Sinha from Workspot and Kris Rudeegraap. Did I say it correctly?

Kris:
Yeah, you got it.

Gil:
From Sendoso. Very excited to have you both. I know both of your companies and I’m excited to get started. I’m the CEO and founder of Metadata. Maybe we’ll start with you, Amitabh, if you can give us a quick introduction about yourself.

Amitabh:
CEO and founder of Workspot. We started the company in 2012 and it’s nine years now, I guess. We’ve raised $80 million and going after enterprise customers for essentially enabling people to work from anywhere.

Gil:
Well, very relevant to today’s world. I hear great things about you and your company from Bill Portelli. It’s I think a mutual board member, so-

Amitabh:
Right.

Gil:
… very excited to learn more. Kris, you’re next?

Kris:
All right. So I’m the CEO and co-founder of Sendoso or a sending platform that helps other companies send out corporate gifts, promotional swag, fun, little quirky gifts, boos, you name it and we can send it. I started the company about four years ago, spent 10 years in software sales prior to that, and yeah, excited to be here and tell you more about my journey.

Gil:
Awesome. So that’s exactly what we’re going to talk about. We’re going to talk about a few subjects, but Category creation is one. What do you agree? Disagree. You have an opinion, I’d love to learn about it from your current experience, as well as previous ones and founder journey. That is also extremely interesting to me, to our listeners and let’s get started. So Category creation, it’s a big subject. It’s been talked about a lot. I think sometimes founders, we all read [inaudible] and other books that try to get you to think about that concept. Kris, maybe we can start with you. What is your thinking about category creation? Good idea. Bad idea. When is the good idea and what’s your personal experience deciding to go into it?

Kris:
Yeah, so I think it’s a great idea. I think category creation helps set you up for success long-term, it makes you really think about the category and it’s what also investors, if you’re going down the path of venture capital, they want to see category creators in most cases or fast followers of existing categories that you’re disrupting. But if you’re creating a category, that’s the type of company that can be lifelong and IPO and beyond. So a big believer in it. In our very early days, we thought about category creation from day one and we even tried to coin a category and recoined it after some different advisor feedback. Should I get into the weeds? You want to hear these stories?

Gil:
I think it’s the first time I hear of someone saying that you’re thinking about it from day one. I don’t think I’ve heard this before. Definitely not ever been true for me. I didn’t even know about category creation when I started the company, this concept. So yes, we’d love to hear that and hear [crosstalk].

Kris:
We’re lucky in that one of our early investors was David Sacks’ from Craft Ventures, and so David Sacks really focuses on the category creation talk track and investing category creators. He was a part of the PayPal founding crew. He founded Yammer, which was a category creation. So he really thought about category creation a decade ago, and so he really ingrained it in my brain early on. So with that, I really started to think about category creation. Our first thought was, actually we did some reading on Zuora and how they came up with the whole subscription economy theme.

Kris:
So I liked how they were positioning it as it’s more of like a trend, it’s something to be a part of. But our first stab at it was what we wanted to call our platform because we didn’t want to just call ourselves a direct mail platform because that was, had some old school connotations, perhaps and we didn’t want to be just a account-based marketing platform because that’s such a broad topic and we really wanted to be specific in our niche. So our first stab, we actually call ourselves an engagement delivery platform and thought engagement delivery was the category. We got shit on for that.

Kris:
Everyone thought it was terrible, our investors, everyone. But we used it for probably a couple of months in our deck. The thought was it was interested enough that it leads you in, but only it leads you in and you’re like, “What the heck does that mean even?” So we did some thought leadership brainstorming. We actually talked to this gentleman, Christopher Lochhead, who actually has a book called Play Bigger, which is all about category creation, which I’d recommend reading it, I think it’s a great book.

Kris:
We ended up switching our category to a sending platform, which I think it gives you enough context that you could get behind and it gives enough broadness that multiple people can end up falling in under this category. Since then it’s actually, we’ve seen other entrance into the category and other people that have popped up, raise money, and they’re talking about it in the same way we are, so to speak.

Gil:
Interesting. So you took one stab, got some feedback, not the best, not the most positive, and then went again and tried a different one. Amitabh, what has been your experience? What are your thoughts about that from day, one coming up with that category, starting to make that new name?

Amitabh:
Our stories [inaudible], we started in 2012 and we were trying to actually not to create a new category, which is creating a new category is so difficult. But when we talked about what we were doing to customers, they couldn’t understand what we were doing and they’re like, “This is a new category.” We’re trying to convince them, no, it’s actually not a new category, it’s a new way to think about the same problem.

Amitabh:
What we found was for customers, it was important that we anchor what we were doing to something they were already familiar with, because if you completely try to read, recenter and say, “This is a brand new idea,” it’s just really difficult for people to understand, right? So what we were able to do, it was anchor it to say, “Hey, it’s…” We use laptops to work from anywhere, but you only needed a windows laptop.

Amitabh:
Now you can actually work from anywhere and use your favorite device because the windows is running in the Cloud now. Anchoring it that way, made it easier for people to understand. So we ended up creating a new category, but we anchor it to an existing category so that people can actually draw the parallels between them and say, “Oh, okay, I understand that category. I can visualize how you get to this new category.” So try to not create a category, we created a category and then we said, “Okay, let’s make it anchor to something that people already understand, so we can actually explain how we are different from that old category.”

Kris:
Yeah. I think that’s really interesting, I’ve thought about that too, and when we were in the early days, when you think about selling into the enterprises too, and really these analysts out there, they’re not going to cover you per se, if it’s just some random category that no one’s ever heard of, but if you can anchor to an existing category, so we sometimes will talk about direct mail or we’ll talk about CRM or marketing automation and how this Venn diagram, where we exist amongst those. Then they’re like, “Got it.” So I think that’s one tip if you’re in the enterprise space and you’re trying to create a category. What are the analysts already covering? So you’re not a nomad.

Amitabh:
Right. I think the interesting thing for us is the analysts are now creating a new category, to say, “Hey, this is a new category, and now these are the players in this category.” It’s super confusing because now they have to go figure out what the attributes of that category are and help them define it because we defined it too expensively. It includes 50 people and then define it to narrowly just us. So how do you actually make it interesting, right?

Gil:
That’s a great point. How do you control the narrative? So you have a proxy or you were pushed to have an anchor or a proxy, and you said the same thing, Kris, because you didn’t want to be complaining in silo, but how do you also affect the narrative so that it is indeed something that you are, hopefully, I’m assuming the hope and the intent is to lead that category.

Amitabh:
Correct. I think it’s customer stories for us, which is, I think analysts don’t take you seriously until you start having them talk to your customers and the more customer stories they hear, then the more they believe that you actually are doing something different, which is, okay, you can’t with the old category because these people know the old category and they don’t think of the old category, right? So it’s your customers’ stories that have been the most effective for us. Our customers are mid to large enterprise customers.

Amitabh:
So for them and that’s an analyst, they talk to analysts quite often before deciding which vendors to even invite to the party, if you will. So for them to then tell their analysts, “Hey, we think this has got a completely different…” You don’t understand how they’re different. That is more effective than us telling them we’re different because that’s your point of view, but show me other people who believe you.

Gil:
It’s interesting. I think you mentioned a creator, David Sacks, and you just mentioned, Amitabh, no one’s going to listen to you, the customers are the ones who make the decision and the ones who are actually influencing. Deanna from Yammer told me in the episode ago, that both at Yammer and at… I forgot the name of the social media company. In one of those, if you remember the name, yeah. Please tell me.

Kris:
Well, I was going to say where she’s at now [inaudible] or the-

Gil:
No, the previous one, the social media platform to… It’s a very well known one. I I’ll look it up in a second. But both of them, the analyst didn’t really want to cover them or even pissed because at the Amor, customers could just start using the product, but it’s in an enterprise and the analysts were against it. So when it started covering them and saying, “This is not going to continue. It is not going to last,” she realized that the customer is calling on list and asking, “Is this safe? Should we use this platform?”

Gil:
Because the analyst really started taking them seriously to the extent where she realized, “Okay, I’m going to make a program out of it.” That’s exactly how she got the analyst from the Gardner enforcers of the world to create a category, agree with that name and put them in the right spot. How do you get your customers to do that for you? To say, “This is something new, you have no idea. This is not something that you’ve heard about before.” How do you get to that place where customers unsolicitedly or solicitedly go and be the voice for you?

Amitabh:
I think any mid to large enterprise customer that buys from you has gone through that exercise internally to justify why they’re buying you. Right? Which is you probably show up, there’s no budget for you. So they’re creating a budget for you. So they have to go explain to their bosses, the CFO, “I’m buying this, and I can’t buy the products from the other category or the previous category or another set of vendors, because this is just how these guys are different. I think most of our customers have very, very detailed research on why they’re buying us. It’s not a short-term process.

Amitabh:
They’re very detailed thought processes. So when you put them in front of an [inaudible], we didn’t do what you were saying that other person did, our analyst said, “Hey, we like your story, but do you have any customers? Okay, let’s introduce customers to you?” Then it was unfiltered conversation between the customer and the analyst and the customers would tell the analyst why they picked us.

Amitabh:
We don’t know what they said, but to the point, the analyst came back and said, “You know what, here’s what your customers are telling us about you, and here’s how you are different. Let’s talk about this to your next set of customers. So it’s interesting though, as the analysts, then come back and start giving you guidance on how to talk to your own next set of customers. So it’s super beneficial for all sides, because our customers educate the analysts, the analysts educate us, we educate the next set of customers and it goes [inaudible].

Kris:
Yeah. I would chime in there and I totally agree with that. A couple of things that we’ve done, one is just cultivating a community where we really try to drive. We have the Supercenter community where we try to empower our customers to be on a pedestal and celebrate their success, which in turn makes them more of these advocates in the market and then it makes it easier for them to outward share their success and then the analysts pick up on that. Have even taken it one step further too and I have some advisors who are customers too, that are one step closer to me than just a customer is and they’re even more inclined to talk ups and downs, so as well. So that has been successful over the last few years as well.

Gil:
Interesting. So for you, Kris, I hear, is this customer advisory board, or a similar-

Kris:
So [inaudible] advisory board, but this is actually more of like a personal advisory group where they’re closer to me than just a customer advisor. So I open up to them a little bit more. I give them highlights on the company, I might think about a Memorial as almost like an investor advisor where I’m confidently sharing updates and asking for miscellaneous things along our journey. Like, “Hey, do you know anyone that we’re hiring for this?” Or, “Hey, we’re doing this panel, do you want to talk?” So they’re one step closer than just a traditional customer advisory board.

Gil:
Fascinating. You’ll send them towards an analyst or get some of the feedback to understand how you can influence those analysts.

Kris:
I would say I don’t send them towards analysts. I think I let that happen on its own. But if an analyst comes to us and wants to talk to somebody, I have pools of customers that I can reach out to. Or we just recently did the Forrester TEI, the Total Economic Impact, where they go, first, it goes really in-depth and creates this huge report. So for some of those things, it’s helpful to have customers close by that you can call on that are willing to help out.

Gil:
This is really interesting. It’s really interesting to me. I started this podcast as a way to learn how to do this. This really is, it doesn’t get more organic than that. It became a podcast, but at first it was just to learn how to, how do we do this? Because to me, it seemed abstract at first because there’s analysts who make so much of the decision and the PR and the publishing around it, which is where customers go. But then you’re talking about the customers, making all, being the real important opinion, who are influencing those decisions.

Gil:
So Amitabh, when you’re talking about the feedback loop between customers, analysts and you, one is influencing the other, you’re talking to the customers, they call analysts and saying, “This is something new.” That we’re not using the old one because of ABC, and then they call you and telling you like, “Well, we had to discuss, someone’s calling us.” So you talk to your next customer, using those… What happens first? How does the process work when you’re actively trying to define and lead that category?

Amitabh:
I think you can’t be in category creation until you have found product market fit, it’s too early to do it. I think the first three and a half years, I think we were doing pretty much the same thing, trying to create a category, but we hadn’t found product market fit. So you could tell all your stories, but if you have no customers saying that is a valid story, it doesn’t work. We talked to analysts, they made a school vendor in 18 months after we started, had zero effect on customers. Analyst saying there’s a cool vendor.

Amitabh:
I didn’t change anything for people. But once we got customer stories back, real customer stories, we were able to then tell analysts, that’s when it really started. Right? So I would say first goal should be product market fit. Once you get that, then you actually can say, “Okay, this is actually a new category, let me now go create that category effectively.” Because I think if you start trying to create a category and you don’t have product market fit, it’s not going to be successful.

Kris:
Yeah, I totally agree.

Gil:
First of all, let’s drink to that, because I am asking you lots of questions. Thank you for that insight. Any of you think there is a critical mass? So let’s assume a customer or a company thinks they achieve product market fit for whatever reason, is there a critical mass, is like 50 customers, a 100 customers, is the revenue number? Is this a particular set of customer cohort and NRR number, a renewal that you certainly see that you say, “This is a critical mass that will be deployed with feedback to the analyst that will get us on that path where the analysts agree with us? We’re unique. We’re different.

Amitabh:
I think it’s either for us because our customers tend to be a little larger, right? So our average ACV is about $175,000 a year. So I think we started seeing it when we started getting our first large five digit customer, then our first large six digit customer, then our first large, seven digit customer. Then people said, “Oh, okay. I can see you guys growing.” So when we introduced the first five digit customer, they’re like, “Yeah, this is interesting. Six digit customer, okay, this is new.”

Amitabh:
The first seven digit customer, it was completely different for them at that point. So I don’t know whether it’s in terms of dollar amounts, but if you have the same size of customer, like $40,000 [inaudible] customers, maybe it’s volume then, but for us, it was not a volume thing, it was five digit, 6 digit, 7 digit and then it was like, “Okay, we trust you guys to be enterprise class now.”

Gil:
Very interesting.

Kris:
I was wondering maybe saying like in the total sales, maybe in the 10 to 20 million ARR, it starts to become real. Then I’d say, if you get to the 50 million ARR, then it’s like, okay, this is obviously a category, and obviously, get a 100 million and you’re public and you’re big and huge, everyone knows about you, but I’d say probably, maybe like 10 million is a threshold where it’s actually [inaudible] a business around it and you should have either enough, small customers, people, or enough big customers that is enough there.

Gil:
Thank you. That’s very interesting deck. Let’s change gears for a second and talk about some personal experiences. Kris, we’ll start with you. Tell me if you’re willing to share about the first big #fail moments that you had in category creation, because you had it in your mind from day one. So you’re aiming towards somewhere, and maybe, especially you were saying that you didn’t get the best feedback in the beginning, given that the #fail moments where you’re thinking, like, “I don’t know if this is working, this category creation part.” Or they don’t like this name, or maybe we’re not the category creator. How did that happen and what was it like?

Kris:
It was for sure when we tried to start pitching people on this delivery engagement platform category concept, that it was just like, “What are you saying?” So that was a fail for many months. So I think we were trying to be too creative and over I think the category. While I think it was we wanted to be thoughtful in the early days of category creation. I think you don’t want to overthink it and you shouldn’t spend all your thoughts on that. So that was a big fail. It didn’t help us, customers never used that word. No one thought about us is that, no one wanted to use that word. So once we changed it, it we had a good aha moment from there.

Gil:
I have two follow-up from that. First one is, thank you for sharing that, you said it was for a few months, how did you monitor that, that was a fail? How did you know? What do you monitor?

Kris:
Yeah. So we were doing a little bit of some focus groups, asking people, when we told people what we did, no one ever used that word or those phrases. When we saw people talking to us without us there, like in social or on review sites, that was never brought up, and investors never thought about it like that. So everyone, it was blatantly clear that that was a bad idea. So I think if you could get your customers using the vernacular or you can get investors or are other people using it while you’re not there, I think that’s a good sign of success.

Kris:
Even so we’ve seen larger companies have RFPs that mentioned the category now, which was a good pat on Iraq where we’ve seen people put in their resumes that we’ve had fun seeing that they’re skilled and they’re sending platform, blah, blah, blah. So some of that is good to start to see some momentum there where people are using this out in the world organically.

Gil:
Interesting. So skill sets, focus group, but mostly customers using it when you’re not in the room. How did you recover from that? What did you do? How did you say, “Okay, that didn’t work, this is what we’re doing next.”

Kris:
Yeah. It wasn’t too bad about the recovery because it was still early-ish in the days, so it was just updating a lot of our social posts, our slides, some of our internal collateral and stuff. So there’s still a few looming docs that I’ll see once in a while that pull up from the graveyard that mentioned that, but it was still in the early days. It was the first couple of years of our existence. So it didn’t hurt us.

Gil:
You are cool with just trial and error. You tried it, didn’t work, this is cool, find the next one. Is beautiful. Amitabh, tell us about [crosstalk].

Amitabh:
Ours was a little more painful than Kris’s experience, because… So just to give you a background. My previous job, I ran the product, which was the old category. So when we started this company, our tagline was the old category is dead, this is a new thing. We were doing that for about a year and a half and we had this one new sales leader come in and he joined us for the first call, one of the first calls we had with the large customer.

Amitabh:
He came back and said, “I don’t know what you guys are selling, but the customer really wants to buy the old category, because all I’m hearing is the old category.” We basically shut it down and said, “You guys, you know nothing about the old or the new category, so this is, like, stop.” Three months later, we had to actually pivot the whole company. We went from being the anti-old category to the next version of the old category company, like category ==, completely changed everything.

Amitabh:
It took us about three months to get there because we were fighting about it for three months, which is, how can we go from anti-category to category 2.0? That’s a big, big change. I think that was the beginning of when we started speaking the language of the customer, which is versus telling them what you want to buy is actually bad, we just said, “Okay, we are 2.0 version of that.” Then I think people naturally understood what we were doing. I was like, “Okay, that was much simpler.”

Gil:
One of you have concluded that. So really listening to the customer words and being quick about like, I think three months, one of you did it pretty fast? I think in a few months really being able to-

Amitabh:
No, that was after three months of knowing that. So the three months happened quickly, but it took us three years to get to the three months.

Gil:
Fair enough. That’s cool. Very interesting. I think that’s very insightful for companies to understand that. So try and error, listen to customers and try as best as you can [crosstalk].

Amitabh:
I wouldn’t [inaudible] what Kris did, which is if you have only collateral, then that’s easier, right? Versus you actually build a whole product and then you’re redoing everything that creates data. That’s much more painful.

Gil:
Kris, you’re very intentional about it, which I love, like from day one, you already had this in your mind for the end, which I’m sure your investors really appreciate. You give so much clarity because it’s one of your tenants.

Kris:
Yeah. I think you have to fail fast there if you can, because you’re going to invest resources into it and you need to do what you can do to make, just like a product market fit. I think maybe there’s a category scenario where you need to make sure that your product’s in the market, but is your product in the right category? Is it a new category, is it the 2.0 of an existing category and you need to know where you land and then double down on talking about it that way.

Gil:
Segue for this, you just coined a new term.

Kris:
Maybe. You heard it first.

Gil:
You heard it here first. That’s cool. All right. Let’s switch gears one more time. In your founder journey, as you’re creating a category, as you’re doing the product market fit, what’s a moment that you felt you are on the right path? You’re trying a bunch of things, you’re talking to an investor, they believe you or not, you’re raising some money. You may be even the chief [inaudible] market’s feet, but what’s a moment where you think this is going to be something really big, a signal that you wake up in the morning, you see something and you think, “I’m starting to believe in my own story. This is going to be a big deal.”

Kris:
There’s a couple of those. I thought it was going to be big day zero. So I think as a founder, you have to be crazy obsessed with what you’re doing and so I thought I was, day zero, I was thinking this is going to be the biggest thing in the world. I built this out of pain, so I was my first customer. So when I was in sales, I really wanted Sendoso to be an existence. So I knew that if I built it, people would come per se because I wanted it.

Kris:
But I think there’s other milestones along the way, like an ARR milestone, like a million or 10 million or 20 million, that feels good or headcount, thresholds are getting to a 100 or 500 employees or… The one recent one that I stumbled across on accident that made me just smile is that I was able to search through LinkedIn and see that there’s something like 600 people that put Sendoso in their profile and in their description of what they’re good at, next to Salesforce and stuff.

Kris:
So that was an aha moment too, where I’m like, “Wow, people are actually bragging that they know how to use Sendoso as they want to share about getting new jobs and stuff. So I don’t know, I think there’s a lot of different ways that you can look at it. But I think as founders, you have to be crazy that your idea is the best thing in the whole world day zero.

Gil:
Thank you. Amitabh?

Amitabh:
I think I agree with Kris. You always have to start with the conviction that this is a big market and you’re solving a big problem. So I think you’re challenged by your daily experience in terms of believing in that big market, if you will. For us, I think probably when we got our first large seven figure customer. The first phone call to us was, we have looked at everything that’s in the market and we believe you’re the only vendor we can work with. Are you ready to work with us?

Amitabh:
Because we will probably be your biggest customer and please tell us we are not, and we’re okay, we’ll be your biggest customer, but then you have to commit to being actually supporting us like your biggest customer. That was the first one call. They just called in and said, “This is it.” I think at that point was, okay, not only do we believe our story, somebody else actually reads the story, understands it, groks it and repeats it back and says, “I know why you are the best solution on the market.”

Gil:
Interesting. Seven figure deal, and the customer asking you to support it. Let’s talk about the future for a second versus the past experience or maybe it already happened, but what is the moment that you… I’m assuming both of you want to dominate your category, right? You want to be number one in your category. What is the proof point for you? If you’re monitoring it, Kris, you mentioned a bunch of things, Amitabh, you as well, what is the proof point that you say, “Yeah, we achieved it.” Or we are now the number one player in our category. Is it a wave report? Is it G2 report? Is it something completely different?

Kris:
I’ll chime in first and say, I think the Wave or the G2 or TrustRadius, those things are for sure, a good validation, it’s definitely something to strive for, I think, but it’s not maybe the end all be all, you want to keep shooting for the moon. I think another area that we look at as one of our PR agency looks like Share of Voice and I find that to be useful too, because it’s, who’s talking about us or what press we’re getting and that tends to be a little bit less controlled and it’s more of what the market’s saying.

Kris:
I think some of like the G2 sites, you ask your customers to do that. So maybe a competitor is vested in that and you could easily, I wanted to say [inaudible], but you can just have more of your customers doing more reviews. But the share of the voice is interesting to me because it’s completely uncontrollable. So I tend to like listening to that.

Amitabh:
Until you are private, it’s difficult to do it on objective measures, right? I think for us at least, it’s probably the analyst’s feedback to us, which is we think you are the best solution in the market for this category, and here are the reasons why, and the reasons actually makes sense to us. Because I think it’s difficult to measure the leader until… I think it’s fairly late in the process. Right? Especially in SAS businesses like ours, I think the compounding effect is so significant, that if you can keep that compounding effect going, what you can measure is how fast the company is growing.

Amitabh:
You might be able to measure based on LinkedIn, how many employees you have today and say, “Hey, we have…” But it’s the growth rate that changes everything, right? The growth rate is really not measurable by many of these external metrics in my opinion. So it feels to me, it’s, you want to make sure that the growth rate validation loop is in place for you, so that you think you’re growing fast and the analysts are claiming that, “Yeah. You know what, we have customers calling and asking about you more often now than they were before.”

Amitabh:
Or we talk about you more often now, because when they say we have the following requirements, we point them your way. Because I think that changes the growth trajectory, if you will. That’s one. I think two is we are working with a large public Cloud partners and they have also a bigger glass and window that they’re looking through and so their feedback is also very material, because when they come back and say, “We like you for the following reasons, and we’ll introduce you to our largest customers, because we think you’re the best solution in the category.”

Amitabh:
All of those are validating decisions, right? Which is, hey, you might be the same size as somebody else today. But if you can grow faster than you will, because the compounding effects will be significantly bigger, two, three, four, five years from now. Right? So for me, at least, I’m trying to measure the growth velocity more than the actual size right now and I think those are signals that are sending you about… If all of these people are saying, “Here are the reasons why you should grow faster, then you make sure that you actually can grow faster.”

Gil:
Interesting.

Kris:
I like that you validate it based on like a partner’s referrals too. I think that’s an interesting way to look at it. I know Gil you’ve had outreach on many on recently, I think Manny is a partner for us and how we generate referrals to get indication that who you’re going to refer is who is in the mind share of the [crosstalk].

Amitabh:
Yeah. Exactly.

Kris:
So that’s a good way to double check your triple check based on partner or else.

Gil:
It sounds like both of you, yeah, that is very interesting, the velocity, the feedback loop, the attributes that analysts confirming. These are new. I got to say, I haven’t heard those before. It sounds like both of you are pretty connected and friends with the analysts. Would that be a true statement?

Kris:
I would say I’m personally not like friends with the analyst, I’d say, maybe some people on my team are, like some on my product marketing team are more constantly talking to them. I get brought into those conversations at times, but I wouldn’t say I’m friends.

Gil:
That’s an important distinction. How often do you get brought into those discussion and influence them and join in our gender discussion?

Kris:
Maybe monthly, there’s some related conversation. I can’t really speak on behalf of my team though, on how much they’re working behind the scenes to make that happen or other conversations they’re having.

Gil:
The monthly polls. What about you, Amitabh?

Amitabh:
I think it’s less frequent than that, probably every three to four months and it’s really to go define that category really well, which is, because the definition of the category, the attributes of that category, change quite frequently, and you want to make sure that the analyst understands that change, because our understanding is changing on a daily, monthly basis. But because the analyst is not as closely connected to us, they don’t necessarily see that same degree of change. So I feel like it’s our job to make sure that they do.

Amitabh:
So to give that broad direction, which is, yes, we have everything the category is headed, and I find that the analyst scared about, if you tell them things they don’t know, then they pay more attention to you and then you have more influence with them and influence with customers as a result. So what I’m trying to do with the analysts is… Because for us, it’s a filter, right? The analyst says, “No.” Then you don’t get to the next level in the funnel. The yes is maybe less important, but the no is super important. Right?

Amitabh:
So we want to make sure that you allow the analyst to process all the new data points that’s coming into our field of view to… So that they’re able to constantly change their definition of the category, their analysis of the category, who should be in that category, et cetera. Because I think in current world, things are changing so frequently. We see change everyday, but you can’t do that to the analysts, they’re another time to come in every month. But at least every three months and a quarter, and definitely a big one before the end of the year, if you will.

Amitabh:
So we can’t afford to do it right now, but in the previous jobs, we would have the analyst in the office for a day or day and a half, where you actually spent quality time with them. So you don’t have that money to do that yet, but I think that’s where you had to write. If you want real mind share with the analyst, change the way the things make them understand how your customers are thinking, then you’ve got to do that and in our line of business, where we’re selling to enterprise customers, it becomes quite important.

Kris:
I think there’s also different tiers of analysts too, are different. So that’s another thing to take into account is, are you trying to talk with the tier, one analyst, which is the end goal, but there’s also in my mind, like take tier two analysts, I won’t get into names, but in some cases it’s easier to get meetings or talk to them and then they’ll start boiling the ocean and driving some awareness that then trickles up to the tier one analyst firms. So that’s a strategy that I was advised to also think about.

Gil:
Thank you. Yeah, that sounds like a good hack, and I will ask for those names later, when you can share those. That’s interesting. Let’s [inaudible] for a second. I want to ask some things about personal and entrepreneur journey and I want to refill my glass. So take a second to do yours as well.

Kris:
You’ve got a few more sips left.

Gil:
I’m good. Amitabh, what are you drinking today? I know that [crosstalk].

Amitabh:
I know it’s some Spanish wine, I don’t know. I don’t remember the name.

Gil:
Nice. Okay, cool. Are you in the Bay Area?

Amitabh:
Yep.

Gil:
Kris, you as well?

Kris:
Yep.

Gil:
Nice. Very cool. Well, cheers, happy Friday. Thank you for sharing your insights. I really appreciate it. This conversation is very insightful. I already took about 20 notes, so thank you.

Amitabh:
Thanks for organizing it.

Kris:
Yeah. This is fun. I love the topic. I was happy to see your email in my inbox. Talk about it.

Gil:
That’s really cool. One thing I want to hear from both of you, and I’ll give you the background, so an embarrassing, unrelated to category creation, even doesn’t have to be involved with a Plutonian company, but an embarrassing moment that you remember that these personal, that you’re willing to share. So I’ll give you an example, Mike Volpe, former CMO of HubSpot CEO of Lola shared how he vomited on a double date in a theme park and [inaudible] saying how he got arrested. Something that you’re willing to share about yourself that is a memory, that is still ringing a bell and something that is personal about you. Now, let’s start with you Kris.

Kris:
No, I’m trying to think about an embarrassing moment that still rings a bell. I tend to not get too embarrassed and I just shed things off or laugh a lot. What is an embarrassing moment?

Gil:
Cheers to that, first of all, that’s great. Laughing about those things is the best way to go. So that’s awesome.

Kris:
Amitabh, if you have one, while Kris is thinking, then-

Amitabh:
No, I can’t think of anything-

Gil:
Really?

Amitabh:
… that exciting to share.

Gil:
How about we’ll get back to that. I’ll try a similar one and adjacent one. Tell me about the worst moment you had as an entrepreneur, starting with you, Amitabh.

Amitabh:
Worst moment. North

Gil:
Worst moment. [crosstalk], there you go, you have it.

Amitabh:
I can’t share the worse moment, how’s that?

Gil:
Second worst. It’s okay if you don’t want to share.

Kris:
I think I have one top of mine that I can, to go on [crosstalk].

Amitabh:
Go for it Kris.

Kris:
This was pretty bad and I felt pretty bad about it, so when we were getting going, and me and my co-founder at Sendoso, our first hire we made, ended up not working out. So we ended up firing our first hire [inaudible] about three weeks in, and it was an introduction into the company. We didn’t really do a good… We just assumed it was going to be a good fit and it wasn’t in that.

Kris:
For that moment, it felt like we were going to fail. We were doomed. I was like, “We can’t even hire one person, we’re [inaudible].” So that felt really like it was like a gut check. Looking back, we almost have 400 employees now, so it’s funny to look at, but that was a holy heck moment where I thought we were going to fail. So that’s something that at least resonated with me today.

Gil:
That’s legit. First firing. Thank you for sharing that. Okay. Amitabh?

Amitabh:
No, I think this was early on, but we had one of our strategic partners ready to lead a series around and everybody was ready to do it. Final presentation was to the CEO, and they said it’s just a matter of, it’s just a formality. He never says no. And guess what, he said, no. That was pretty sad because you were already ready to go spend the money. It was, okay, this is a done decision, and this was after three months of dating, if you will. It was rejected and we had to start all over again, which was just not fun.

Gil:
That stuff, for sure. That’s a classic. Right? Thank you for sharing that.

Amitabh:
It’s not done, but it’s done, I guess.

Gil:
[inaudible] it’s done, right? Because none of you said, no, it was just a sad moment, but you got over it. I thank you for sharing those. Let’s switch to the best moment. Best moment you had as an entrepreneur. Amitabh, you first.

Amitabh:
I would still say it’s that one moment when we knew things were going well, which is when that customer called and said, “We’re going to be our biggest customer and we looked at everything else, and are you going to be able to support us as a big customer?” That was, I think you don’t get too many first calls like that, where they’re basically telling you they’re going to be your biggest customer and they still are our biggest customer.

Gil:
When was that?

Amitabh:
This was two years ago, two and a half, maybe even three years ago. No, maybe two years ago.

Gil:
That’s cool. Kris, what was your best moment as a founder?

Kris:
Yeah, I mean, I think it was probably back in as similarly related to customers, probably our very first customer back in 2017 is still a customer today, but it was the very first person that after we spent like a year in closed door building and getting everything ready and then we finally said, “Okay, who wants to buy? They’re the first ones to sign a contract and pay us money. That was just a really good moment.

Gil:
Validation.

Kris:
Yes.

Gil:
That’s awesome. Tell me, there are many entrepreneurs, many of our listeners and myself included, like VentureBeat, TechCrunch, [Sasta]. There are so many events, so many stories, so romantic, overnight success stories and all kinds of best practice for SAS founders and all kinds of absolute truth that they teach us in publications and events that some of them are true and many of them are bullshits. What are absolute truth, one or two that each of you have that are hidden? So something that, you know, to be absolutely true for yourself as the founder and CEO of a tech company that might be different than the common narrative that is public out there.

Kris:
One that comes to mind for me at least is like a Silicon Valley Tech CEO, our founder, is that you have to work 20 hour days in order to be successful and I would say, I don’t think that’s necessarily true. I like to travel and I probably been to 30 countries pre-COVID while founding Sendoso. So I think you can write the life you want to live and if it’s a balanced life, per se, that’s something that people can do. I tend to say, try to work smart, then work long is my mentality and I’ve tried to push that on my employees too, but I’d said maybe that’s one thing where some people look from the outside that every CEO and founder in Silicon Valley are working 20 hour days, and I don’t think that’s necessarily a 100% true.

Gil:
Insightful for sure. I think many would love to learn how you do that. That’s super cool, [inaudible]. Yeah. What about you, Amitabh?

Amitabh:
I think for me, it is the problems we’re solving are super important to the rest of the… It’s the problems the valley has, companies in the valley have, and the problems the rest of the world has. There might be some problems which are similar, but a lot of the problems are very different, right? In our early days, at least with the valley VC, is it was, we were trying to solve a problem and they would say, “But I don’t have a problem.” So it must not exist and it’s like, “Hey, just go outside the valley, there’s a lot of people who have this problem.”

Amitabh:
I just think people extrapolate from their own experiences a lot in the valley. For example, the way I think of it, Amazon web services is the value of the Cloud is the valley and Azure is probably the Cloud of the rest of the world right now and GCP, and all these guys are fighting for the rest of the world. But the value Cloud has been determined, it’s Amazon, right? Now we’re fighting over the rest of the world. So the problems, I think the valley has a blind spot to what the rest of the world actually is, right?

Amitabh:
Especially in the enterprise, which is in the valley, everybody’s running on using Macs and iPad pros and doing Google docs and the rest of the world, it’s still completely different, right? It’s just a completely different world out there. So I think that’s not obvious to a whole bunch of people, which is sometimes the problems the rest of the world has, is very different from the problems that the valley has then. I think the only time that intersects for us is when we talk to investors, used to happen, maybe six, seven years ago.

Amitabh:
It was difficult to explain to people that the problem we were solving was actually outside the valley, it was not in the valley. I think Sendoso, it might be easier because I think a lot of the valley people probably have the same problem, right? It should be easier to sell to valley companies for us, investors and valley companies find it more difficult to understand what we do, because, hey, you can just do this today by ourselves [inaudible].

Gil:
Both of them are big, right? It’s funny, I was just telling my wife yesterday, she was like, “The next company I’m thinking about B2C, I want to solve new kinds of things that are not just for all the tech companies out there.” So that resonates with me a lot. That’s very interesting. Traveling is something I want to do. I want to go back to it. So very jealous, Kris. Any last words before to entrepreneurs, to CMOs who are, I don’t know, [inaudible] and after they found product market fit, they think they have a new category or they’re not sure and they’re thinking, how do I tell the world that I’m different? Any advice there.

Kris:
I’d say my last advice to takeaway is probably two things. One is this really best in brand maybe earlier than you think. I think a brand helps you set yourself up. I think a lot of companies, it’s all about demand gen nearly days, and if you can afford to think what the long-term and invest a little bit more in brand that will help category. Then I think alongside that is content, I think you can create things like buyer’s guide for category or category maturity models or state of the category, data reports for that content that was painful to create, or it might be lots of pages and lots of brainpower. We’ll have some lasting affects and hopefully will drive long-term value.

Gil:
Thank you. Amitabh?

Amitabh:
For me, it’s just customers. The one thing that seems to drive everything else is customers, dollars and stories, right? Which is if people pay you money for something you’ve built, it’s worthwhile. If you can just focus on that and make sure that more people buy into that same story in dollars, I think that’s it, everything else drives off that. I think our most loyal customers, we don’t need to tell them to tell our stories, they tell them themselves. Right? So it’s keeping customers happy, drives everything else.

Gil:
I love it. Thank you for those last words and insight. It was really a pleasure to talk to both of you and you are full of insights. I learned a lot and I think our listeners will do as well. I really enjoyed the conversation. Thank you very much for spending time.

Amitabh:
Thanks, Gil. Thanks, Kris.

Gil:
Have a wonderful weekend.

Kris:
Cheers.

Gil:
Thank you both.

Amitabh:
You too. Bye.

Gil:
Thank you, Amitabh. Thank you, Kris. Cheers.

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