In Episode 156 of “The Trusted Advisor,” RSPA CEO Jim Roddy sits down with Shiv Sundar, the Co-Founder of ISV Esper, to discuss his journey leading a company from its startup phase to over $100 million in investments with hundreds of customers, partners, and team members.
“The Trusted Advisor,” powered by the Retail Solutions Providers Association (RSPA), is an award-winning content series designed specifically for retail IT VARs and software providers. Our goal is to educate you on the topics of leadership, management, hiring, sales, and other small business best practices. For more insights, visit the RSPA blog at www.GoRSPA.org.
Watch Episode 156 now:
“The Trusted Advisor” is also available on Amazon Audible, Apple Podcasts, YouTube Podcasts, and Spotify. Subscribe today!
Full episode transcript via Apple Podcasts:
00:00:01.280 –> 00:00:03.280
Roddy: Hi, Jim Roddy here from the RSPA.
00:00:03.420 –> 00:00:15.900
Roddy: Wanted to chat with you for a minute before we start today’s pod to make sure you’re aware that registration is now open for RetailNOW 2026, the Retail Technology Channel’s number one trade show, education conference and networking event.
00:00:16.040 –> 00:00:27.740
Roddy: Join RSPA and Retail IT Channel leaders live and in person July 26th through the 28th in Las Vegas at the new Caesars Forum Convention Center attached to Harrah’s and the Link hotels.
00:00:27.740 –> 00:00:35.880
Roddy: I have to say that again, Caesars Forum Convention Center, a lot of times when people hear Caesars, they think of Caesars Palace, which is where we’ve had RetailNOWs in the past.
00:00:35.880 –> 00:00:40.820
Roddy: It’s not Caesars Palace, the convention center is across the street from that.
00:00:40.860 –> 00:00:45.800
Roddy: Again, you hear Caesars Forum Convention Center, you’re like, must be by the Caesars Forum Shopping Center?
00:00:46.040 –> 00:00:48.580
Roddy: No, it’s across the street from that as well.
00:00:48.580 –> 00:00:57.600
Roddy: Again, across the street from Caesars Forum and from Caesars Palace is the Caesars Forum Convention Center attached to Harrah’s and The Link.
00:00:57.600 –> 00:01:10.120
Roddy: Again, I’m saying it should be changed to like the Liberace Convention Center or the Elvis Presley Convention Center, but either way, we want to make sure you end up in the right spot for RetailNOW, because we’re going to have nearly 200 exhibiting organizations.
00:01:10.200 –> 00:01:14.500
Roddy: That’s going to make RetailNOW one-stop shopping for VARS and ISVs.
00:01:14.500 –> 00:01:20.280
Roddy: With an expected 1,600 or more attendees, it’s the place for extreme industry connectivity.
00:01:20.460 –> 00:01:26.900
Roddy: Across just 48 hours, you’ll meet new partners and new solution providers who can accelerate the success of your business.
00:01:26.900 –> 00:01:31.700
Roddy: If you’re serious about the retail IT channel, you have to attend RetailNOW 2026.
00:01:31.980 –> 00:01:37.780
Roddy: Again, July 26th through the 28th in Las Vegas, retail now is where the industry meets.
00:01:37.780 –> 00:01:44.800
Roddy: I also got to make a note, maybe all of us can head over to City Council there and see if we can get the name change to the Liberace Convention Center.
00:01:44.800 –> 00:01:46.100
Roddy: People will be like, how was that event?
00:01:46.100 –> 00:01:46.700
Roddy: It was great.
00:01:46.700 –> 00:01:47.960
Roddy: I met a lot of new people.
00:01:47.980 –> 00:01:51.860
Roddy: I don’t know why there’s this big push to honor Liberace, but here we are.
00:01:51.860 –> 00:02:03.580
Roddy: So, well folks, for all the details and to register a discounted early bird rates that expire on June 15th, visit the RetailNOW website today at gorsp.org/retail now.
00:02:03.780 –> 00:02:07.220
Roddy: That’s gorsp.org/retail now.
00:02:07.280 –> 00:02:14.700
Roddy: Hope to see you there and I hope you enjoy this special episode of The Trusted Advisor featuring a RetailNOW breakout speaker.
00:02:22.662 –> 00:02:29.942
Roddy: Welcome to another episode of The Trusted Advisor podcast and video series, powered by the Retail Solutions Providers Association.
00:02:30.122 –> 00:02:35.462
Roddy: Our goal on the pod is to accelerate the success of today’s and tomorrow’s leaders in the retail IT industry.
00:02:35.742 –> 00:02:37.182
Roddy: I’m Jim Roddy back with you again.
00:02:37.182 –> 00:02:38.662
Roddy: Thank you so much for joining us.
00:02:39.042 –> 00:02:44.402
Roddy: As always, we talk with leaders in the Retail IT channel about their leadership journeys and what they’ve learned along the way.
00:02:44.902 –> 00:02:53.222
Roddy: In this episode, we’ll talk with Shiv Sundar, the co-founder of Esper, that’s a moldivite management software provider, he founded in 2018.
00:02:53.702 –> 00:02:58.282
Roddy: Shiv drove Esper’s fundraising effort, securing over $100 million in investments.
00:02:58.342 –> 00:03:14.022
Roddy: He also led the global revenue organization to sign over 700 customers, built and operationalized Esper’s global channel ecosystem, and developed Esper’s go-to-market strategies for several verticals, including restaurant, retail, healthcare, connected fitness, and payments.
00:03:14.122 –> 00:03:22.602
Roddy: Shiv will be one of several Retail IT channel industry experts, presenting at RetailNOW 2026, July 26th to 28th in Las Vegas.
00:03:22.602 –> 00:03:31.022
Roddy: His breakout is titled, From Chaos to Control, Mastering Device Lifecycle Management for VARS, ISVs, and ISOs.
00:03:31.022 –> 00:03:33.182
Roddy: Shiv, welcome to The Trusted Advisor.
00:03:33.742 –> 00:03:34.722
Sundar: Thank you so much, Jim.
00:03:34.722 –> 00:03:35.502
Sundar: It’s been an honor.
00:03:35.542 –> 00:03:37.342
Sundar: I’m a big fan of RSPA.
00:03:38.242 –> 00:03:43.142
Sundar: We started our Esper’s go-to-market journey with an RSPA conference in San Antonio.
00:03:43.402 –> 00:03:46.282
Sundar: So it’s been a good journey with RSPA so far.
00:03:46.862 –> 00:03:47.302
Roddy: Very good.
00:03:47.382 –> 00:03:48.262
Roddy: I’m thrilled to hear that.
00:03:48.262 –> 00:03:51.622
Roddy: Yeah, 2019 in San Antonio.
00:03:51.622 –> 00:03:55.842
Roddy: So I gave a very quick half a sentence on Esper.
00:03:56.022 –> 00:04:04.182
Roddy: Can you tell our listeners and our viewers about the genesis of Esper and then how the organizations morphed and adapted over the past nine years?
00:04:04.702 –> 00:04:05.022
Sundar: Yeah.
00:04:05.022 –> 00:04:13.342
Sundar: So I think when I found Esper in 2018, there are three companies that actually inspired me to actually go build Esper.
00:04:13.862 –> 00:04:16.922
Sundar: First was Square and Clover.
00:04:16.922 –> 00:04:24.962
Sundar: They were the first set of payment devices that were building Android-based touchscreen POS systems in the market.
00:04:25.502 –> 00:04:37.302
Sundar: Then DoorDash was actually deploying Android tablets or iPads across restaurants to accelerate the food delivery business.
00:04:37.342 –> 00:04:55.742
Sundar: I think the idea there was more and more businesses are going to deploy touchscreen devices across verticals as a point of interaction or a customer service or even just like point of commerce or point of payment, including your airport kiosks, clear kiosks, self-service checkouts.
00:04:57.122 –> 00:05:09.922
Sundar: We wanted to build a cloud platform that enables ISVs, VARs, and OEMs to go deploy at scale without having to have a field service.
00:05:09.982 –> 00:05:24.282
Sundar: Is there a scalable way to go build the devices, deploy the applications, manage and control those devices across the life cycle without having to actually go and install them or plug and play.
00:05:24.442 –> 00:05:25.902
Sundar: That was Genesis of Esper.
00:05:27.242 –> 00:05:29.242
Sundar: It’s been a phenomenal nine years.
00:05:29.442 –> 00:05:32.002
Sundar: Lot of success in both retail and restaurant industry.
00:05:33.922 –> 00:05:35.562
Sundar: I think our prediction was right.
00:05:35.562 –> 00:05:43.682
Sundar: I think our world has become full of devices for these applications both at home and at restaurants, retail and healthcare locations.
00:05:44.782 –> 00:05:45.502
Roddy: Interesting.
00:05:45.582 –> 00:05:53.442
Roddy: What I find most interesting about that is, I remember when tablets first came on the scene in the POS industry and it was met with all sorts of fear.
00:05:53.442 –> 00:05:55.782
Roddy: Oh my gosh, the point of sale era is over.
00:05:56.042 –> 00:05:57.662
Roddy: This is going to be terrible for us.
00:05:57.702 –> 00:06:04.122
Roddy: But it sounds like what you and a lot of other, your partners and a lot of other SP members, they turn that into an opportunity.
00:06:04.122 –> 00:06:08.502
Roddy: Hey, if there are going to be way more of these devices, how can we help with that?
00:06:08.502 –> 00:06:17.302
Roddy: I understand that whenever there’s fear, there’s always some part of the industry might go away, but then there’s another part of the industry that is going to improve.
00:06:17.902 –> 00:06:18.302
Sundar: No, 100%.
00:06:18.922 –> 00:06:24.942
Sundar: I think disruption obviously causes a fear.
00:06:24.942 –> 00:06:37.522
Sundar: I mean, we’re seeing the AI disruption right now, but then I would say, I would categorize every technology evolution that has 10% fear and 90% opportunity, and you have to decide whether you want to be on the side of fear or on the side of opportunity.
00:06:37.562 –> 00:06:41.762
Sundar: I mean, we saw the opportunity in devices and it’s been growing phenomenally well.
00:06:42.482 –> 00:06:43.142
Roddy: Very good.
00:06:43.142 –> 00:06:44.902
Roddy: How many employees do you have today at Esper?
00:06:44.902 –> 00:06:47.182
Sundar: Yeah, we have 170 employees.
00:06:47.742 –> 00:06:54.602
Sundar: Our headquarters is based in Bellevue, Seattle and we have a fairly large operation in Bangalore, India.
00:06:54.602 –> 00:06:56.722
Sundar: It’s two offices.
00:06:57.202 –> 00:06:59.502
Sundar: Everybody comes to the office every day.
00:06:59.842 –> 00:07:00.922
Sundar: That’s how we operate it.
00:07:00.922 –> 00:07:05.942
Sundar: I think we are a team of two locations running global operations.
00:07:06.962 –> 00:07:07.522
Roddy: Interesting.
00:07:07.522 –> 00:07:08.022
Roddy: Very good.
00:07:08.022 –> 00:07:15.322
Roddy: So looking back over these past several years since the founding of the company, what’s been the key to scaling Esper?
00:07:15.322 –> 00:07:17.982
Roddy: And so you’ve obviously grown significantly in that time.
00:07:17.982 –> 00:07:23.802
Roddy: And what leadership lessons have you learned from growing a company that you can share with our listeners and viewers today?
00:07:26.402 –> 00:07:27.742
Sundar: I mean, obviously a lot of lessons.
00:07:27.742 –> 00:07:29.102
Sundar: I mean, this is my first startup.
00:07:29.102 –> 00:07:30.162
Sundar: We make a lot of mistakes.
00:07:30.162 –> 00:07:31.702
Sundar: You learn from all those things.
00:07:33.762 –> 00:07:39.202
Sundar: To me, I mean, we realize that retail and restaurant is going to be a big vertical for us, all right?
00:07:39.282 –> 00:07:45.802
Sundar: When we came into RSPA, I would say nine years ago, we probably knew like one or two people in the ecosystem, right?
00:07:45.802 –> 00:07:48.402
Sundar: We probably had a meeting and we would introduce ourselves in Esper.
00:07:48.902 –> 00:08:01.782
Sundar: Now, this July, when we put RSPA, we pretty much, without exaggerating, I would say 70 percent of all the exhibitors in RSPA are either Esper’s customers or partners.
00:08:01.782 –> 00:08:03.282
Sundar: So that’s been the journey.
00:08:03.482 –> 00:08:07.922
Sundar: And the lesson there is like, you have to play nice in the ecosystem, right?
00:08:07.922 –> 00:08:10.262
Sundar: You have to, it’s a long game.
00:08:10.722 –> 00:08:25.282
Sundar: You have to respect everybody who’s involved, from the guy who’s manufacturing the hardware, from the research who’s distributing it, to the VAR who’s there, your distributors, your researchers, the VARs, the community, the conferences, the people who are involved.
00:08:27.522 –> 00:08:32.802
Sundar: Some of them will drive revenue towards you, some of them will be your champion, some of them will be even your competition.
00:08:32.802 –> 00:08:46.502
Sundar: But I truly believe that our success at Esper across eight years, across events, across all Western-region events, has been like respect the ecosystem, be kind, be nice, just do the right thing.
00:08:46.502 –> 00:08:48.202
Sundar: I mean, it just paid off immensely.
00:08:48.202 –> 00:08:58.642
Sundar: I mean, one thing that I’m very, very proud of when I actually go to events like be the blue stars of the world, seed of the world, they actually come to me and say, hey Shiv, you built a great company.
00:08:58.642 –> 00:09:02.842
Sundar: We love working with everybody from your team and we enjoy the partnership.
00:09:04.122 –> 00:09:08.682
Sundar: It could be the president of Bluestar, the CEO of Bluestar to CEOs of various OEMs.
00:09:08.682 –> 00:09:13.182
Sundar: That’s the feedback that I want to hear and I think it’s worked very well for us.
00:09:14.442 –> 00:09:14.982
Roddy: That is good.
00:09:14.982 –> 00:09:19.842
Roddy: I have a follow up question on what you said, but also just so you know, I have a note that I had is to share with you.
00:09:20.202 –> 00:09:28.502
Roddy: Along those same lines, you have everybody at Esper who I meet, they are all not just enthusiastic, but highly enthusiastic, tons of energy.
00:09:28.762 –> 00:09:30.262
Roddy: How have you made that happen?
00:09:30.262 –> 00:09:33.142
Roddy: Is it just finding out the right people or does it help or accelerate that?
00:09:33.302 –> 00:09:40.622
Roddy: Again, I have a follow up to what you said before, but I do have to ask since you brought it up, how do you have so many highly enthusiastic team members?
00:09:40.942 –> 00:09:45.162
Sundar: Yeah, I think I want to be very specific here.
00:09:46.102 –> 00:09:56.362
Sundar: Our VP of Partnerships and Revenue, Daniel Kretz, he was our first outbound sales person we hired eight years ago on an individual road.
00:09:56.482 –> 00:10:02.922
Sundar: He has grown from that to being the VP, and he’s probably one of the most phenomenal partner leaders there.
00:10:02.922 –> 00:10:08.042
Sundar: I think we’ve always hired and trusted and groomed people.
00:10:08.342 –> 00:10:31.402
Sundar: It’s always growing from within, growing from within the company, offering the management roles and leadership roles, offering people ability to move across disciplines from technical to sales, to technology and kind of every two years, we want to make sure that they are actually having a better opportunity within Esper than they would actually have if they change their jobs.
00:10:31.402 –> 00:10:38.942
Sundar: We really want to, if you make their careers and growth trajectory stronger and faster, I think the company grows.
00:10:39.542 –> 00:10:40.782
Sundar: That’s who it has always been.
00:10:40.782 –> 00:10:41.702
Sundar: I think it’s all about the people.
00:10:42.822 –> 00:10:48.182
Sundar: I think around 400 people have come and worked for Esper, 200 of them have left or are still there.
00:10:50.322 –> 00:10:51.682
Sundar: It’s always a positive experience.
00:10:51.682 –> 00:10:54.682
Sundar: Anybody who stays, anybody who leaves, it’s always been a positive experience.
00:10:54.682 –> 00:11:01.482
Sundar: Sometimes, we’ve had employees who leave our company and go to a different company, and they’ll actually come back and give us leads and opportunities because they discovered something else.
00:11:03.362 –> 00:11:04.542
Sundar: I think we’ve grown from within.
00:11:04.542 –> 00:11:07.922
Sundar: We’ve had a great talent both in India and Seattle.
00:11:10.402 –> 00:11:21.422
Sundar: Also, from a relationship principle, both me and my co-founder, we’ve always demonstrated doing the same sort of things that we ask them of employees.
00:11:21.422 –> 00:11:23.622
Sundar: For example, I actually come to every show.
00:11:24.102 –> 00:11:25.982
Sundar: I set up the booth, I tear down the booth.
00:11:26.282 –> 00:11:31.162
Sundar: I am selling, I am going for dinners, I’m setting up the POS system in every booth.
00:11:31.162 –> 00:11:33.782
Sundar: So just you have to show and tell that.
00:11:34.262 –> 00:11:39.082
Sundar: From laying the table cloth to connecting the thing, and having a CEO dinner rather you have to do it all.
00:11:40.262 –> 00:11:47.642
Sundar: That’s been our philosophy, I think, and that kind of translates to the energy of all the employees in general.
00:11:47.862 –> 00:11:48.502
Roddy: Yeah.
00:11:48.502 –> 00:11:51.182
Roddy: Everybody rolls up their sleeves for sure.
00:11:51.182 –> 00:11:54.482
Roddy: So now you talked about playing nice.
00:11:54.482 –> 00:12:08.982
Roddy: And so I guess one thing that I’ve observed in the years in this industry, short-term, you might be able to get over on some people doing something that’s only in your interest, but longer term, I’ve always said this industry, there’s, they say never burn a bridge.
00:12:09.242 –> 00:12:13.722
Roddy: There are so many bridges that are interconnected in this industry, and they’re all made out of wood.
00:12:13.782 –> 00:12:17.762
Roddy: So if you do burn one, it’s going to catch a whole bunch of other ones on fire.
00:12:17.762 –> 00:12:25.502
Roddy: I guess if you can talk about that again, building on your, it’s playing nice, not just to be nice, but it’s a long-term business strategy inside the retail IT channel.
00:12:25.502 –> 00:12:31.782
Roddy: If you do it the other way, you might get success for a few months or a few years, but then it’s going to get really ugly for you.
00:12:32.502 –> 00:12:42.102
Sundar: Yeah, I think one of the things like Adam Grant, there’s one book where he says like, the most successful people actually give first and take later, right?
00:12:42.102 –> 00:12:43.642
Sundar: I mean, that’s one of the philosophy.
00:12:43.642 –> 00:12:48.702
Sundar: I think I read it off of the fact, and we found that we’re very successful.
00:12:49.322 –> 00:13:01.002
Sundar: Oftentimes, when we go partner with a first-time bar or a first-time reseller, we’ll actually not go and come up with the most aggressive contract where we make most of our money.
00:13:01.002 –> 00:13:04.282
Sundar: We actually leave enough room for everybody to actually be profitable.
00:13:04.722 –> 00:13:12.542
Sundar: Yes, it’s like less money off the table, but eventually when they see that, hey, business is good, people are being enabled, partners are being enabled.
00:13:12.542 –> 00:13:17.602
Sundar: Even at the commercial contract, we make sure that there is the entire ecosystem benefits from this opportunity.
00:13:17.602 –> 00:13:23.582
Sundar: The OEM benefits, the reseller benefits, the distributor benefits, the VAR benefits, MSP benefits.
00:13:23.922 –> 00:13:26.562
Sundar: We make sure that it’s distributed.
00:13:26.562 –> 00:13:31.502
Sundar: Oftentimes, sometimes we’ll actually bring leads to our OEMs and partners.
00:13:31.682 –> 00:13:41.122
Sundar: Even though we might not have a contract with them, let us say if some restaurant or retailer is looking for a POS system, we’ll go and get our top OEM sales guys.
00:13:41.122 –> 00:13:43.042
Sundar: We’ll ping them, hey, this is an industry.
00:13:43.082 –> 00:13:44.862
Sundar: Let me know if I can help you get that.
00:13:44.862 –> 00:13:48.882
Sundar: I think it’s always helped massively.
00:13:50.082 –> 00:13:55.402
Sundar: Then they feel like, you know what, when we go in and we have a massive opportunity, we’re going to bring Esper first.
00:13:55.742 –> 00:14:14.182
Sundar: I think oftentimes, it’s been one of the interesting stories, is like when major RFPs happen across restaurant and retail, the CTO or the head of procurement will be like, hey, the funny thing about Esper is that all the three people who are leading up to win the RSPA, have actually brought Esper in.
00:14:14.182 –> 00:14:17.162
Sundar: So no matter who wins the RFP, Esper wins the RFP, right?
00:14:17.202 –> 00:14:29.562
Sundar: I mean, that is, I think for me, success is like, and the thing is that they know that we compete, sorry, we work with the competition, but they know that we always play fair, and I mean, just like an equal.
00:14:29.602 –> 00:14:31.722
Sundar: So that’s what success to me is like.
00:14:33.282 –> 00:14:38.142
Sundar: It’s also like the way we play the ecosystem is also very, very philosophical in terms of technology.
00:14:38.442 –> 00:14:53.922
Sundar: Our goal is to make sure that any CIO or head of operations or retail restaurant can deploy any OEM, any application, any configuration, any OS across vendors with Esper.
00:14:53.922 –> 00:14:55.582
Sundar: That’s why we want to maintain the ecosystem.
00:14:55.582 –> 00:15:01.622
Sundar: It could be like, it’s a hybrid deployment ecosystem, multiple form factors, multiple OS, multiple ISV.
00:15:01.622 –> 00:15:09.122
Sundar: So we always play neutral, we’re like, hey, whoever you choose, we’ll work well with them and deploy them at scale, making sure that’s outcomes are.
00:15:09.482 –> 00:15:17.762
Sundar: That is also the core of a product, like deploy any hardware, any OS, any application, any vertical without fear with Esper.
00:15:18.302 –> 00:15:18.802
Roddy: Yes.
00:15:19.242 –> 00:15:27.022
Roddy: In this industry, your marketing message is important, your sales efforts are important, but your reputation is exponentially important.
00:15:27.022 –> 00:15:32.022
Roddy: What do other people say about you because that’s going to either accelerate or slow you down in this industry.
00:15:32.022 –> 00:15:35.522
Roddy: So I want to talk about your leadership journey, but I just have a question.
00:15:35.522 –> 00:15:41.982
Roddy: I don’t even know how much your answer will apply to our members because a lot of them aren’t raising funds, but I’m just super curious.
00:15:41.982 –> 00:15:51.722
Roddy: So 25 years ago, I watched the documentary called startup.com, and it chronicled a company founder raising $60 million to try to get his startup off the ground.
00:15:51.762 –> 00:15:57.242
Roddy: And just remember from the documentary, the job is not glamorous at all, and it totally distracted from the organization’s core mission.
00:15:57.242 –> 00:16:01.862
Roddy: Like I cannot even remember what they did, but their CEO, he was just fundraising.
00:16:01.862 –> 00:16:03.262
Roddy: Like that’s all that he was doing.
00:16:03.582 –> 00:16:13.542
Roddy: I’m curious, can you share with our audience, how did you raise around $100 million for Esper while at the same time moving the company and the product forward?
00:16:13.542 –> 00:16:14.702
Roddy: I’m just curious about that.
00:16:15.082 –> 00:16:21.722
Sundar: Yeah, I think the early part of our fundraising journey was very, very, like I would say, centerpiece, right?
00:16:21.722 –> 00:16:24.562
Sundar: I think we actually had a problem that we wanted to solve.
00:16:25.142 –> 00:16:36.062
Sundar: We built a product, and then a lot of people in the Silicon Valley ecosystem actually had identified the problem already and said, hey, if anybody builds a company in that space, we’ll fund it.
00:16:36.062 –> 00:16:37.822
Sundar: So the first few million dollars came that way.
00:16:37.822 –> 00:16:39.762
Sundar: It’s very obvious.
00:16:40.382 –> 00:16:42.142
Sundar: It was also a hard problem to solve.
00:16:42.142 –> 00:16:45.442
Sundar: Not everybody could spin up a company and manage.
00:16:45.442 –> 00:16:51.202
Sundar: Today, we manage over thousand different kinds of hardware configurations globally.
00:16:51.322 –> 00:16:52.662
Sundar: It’s not a very trivial problem.
00:16:52.702 –> 00:16:55.702
Sundar: We can’t build a company in AI right now to go manage all this hardware complexity.
00:16:55.702 –> 00:17:13.982
Sundar: So I think, I would say, to put it in a framework, think of something that is unique, that’s something that both me and my co-founders, we were part of various device life cycles from Amazon Go to Samsung devices to Huawei devices.
00:17:13.982 –> 00:17:19.122
Sundar: So make sure that you are the most experienced person who can solve the problem.
00:17:19.262 –> 00:17:23.402
Sundar: Then I think go solve it for a bunch of customers.
00:17:23.402 –> 00:17:30.102
Sundar: Usually, what happens is like when I, the interesting thing is yesterday I actually went and met our first customer.
00:17:30.942 –> 00:17:35.262
Sundar: We ever sold to, he actually exited the company, sold the company and he was my first customer.
00:17:35.602 –> 00:17:40.722
Sundar: He took the reference calls from all the investors and he was like, hey, I know you were getting started.
00:17:40.722 –> 00:17:43.902
Sundar: I know you are just getting built, but someone knew you guys would do it.
00:17:43.902 –> 00:17:46.662
Sundar: So the customer, I think customers are very important.
00:17:46.802 –> 00:17:56.782
Sundar: I would say, inversions will always come, but I think if you can take care of your customers and make them successful, make their business outcomes happen, I think that translates into good investment.
00:17:56.782 –> 00:18:00.942
Sundar: I wouldn’t say like, hey, go make a great pitch and tell a big story.
00:18:00.942 –> 00:18:15.662
Sundar: All those are important, but at the end of the day, the final call before they write the check is they’re going to call 10 customers, both customers that you give them and they will do their own background research and they’ll say, hey, have they actually made their outcomes amazing?
00:18:15.682 –> 00:18:19.062
Sundar: I mean, Taco Bell was one of our very, very first customers.
00:18:19.062 –> 00:18:20.222
Sundar: We are 20 people employee.
00:18:20.222 –> 00:18:27.702
Sundar: The VP of IT actually took a bet on me and my co-foreman and said, yeah, I know you guys are building, but I think you can help us with deployment.
00:18:27.702 –> 00:18:37.942
Sundar: And then we pretty much flipped the entire Taco Bell deployment within North America to a new operating system remotely.
00:18:38.282 –> 00:18:40.482
Sundar: It’s never ever happened before.
00:18:41.222 –> 00:18:42.482
Sundar: And you have to follow through.
00:18:42.482 –> 00:18:57.042
Sundar: I think one thing this customer, I almost feel like, make sure, I think this is something that Nikesh Aura, the CEO of Palo Alto Networks says, if a company stops focusing on product and engineering, everything else falls apart.
00:18:57.042 –> 00:18:58.582
Sundar: I think fundraising is great.
00:18:58.942 –> 00:19:03.822
Sundar: But if you build really, really compelling products with the customers, everything else will just follow.
00:19:04.742 –> 00:19:09.122
Sundar: Oftentimes, we put engineering and product way below.
00:19:09.122 –> 00:19:17.302
Sundar: There is sales, there is glamorous fundraising announcements, there is happy hours they’re hosting, there’s social media posts, but the core is the product that you’re building.
00:19:17.302 –> 00:19:19.122
Sundar: It has to actually be.
00:19:19.622 –> 00:19:20.982
Sundar: So that is my framework.
00:19:20.982 –> 00:19:27.402
Sundar: I think a lot of people have done really well, but I would start with the product and customers first.
00:19:27.702 –> 00:19:28.462
Roddy: Interesting.
00:19:28.862 –> 00:19:29.662
Roddy: Thank you for sharing that.
00:19:29.662 –> 00:19:40.702
Roddy: So it’s funny because I’ve never done fundraising in that regard, but it all comes down to having a unique product that solves the problem of customers and have customers be raving fans about it.
00:19:41.162 –> 00:19:45.702
Roddy: That’s going to help you and sounds like fundraising and sales and attracting employees and everything.
00:19:45.882 –> 00:19:50.462
Roddy: If you get that part right, everything else is going to spin off if I’m understanding correctly.
00:19:50.502 –> 00:19:51.502
Sundar: Correct.
00:19:51.902 –> 00:19:52.542
Sundar: Exactly.
00:19:52.902 –> 00:19:53.522
Roddy: Very good.
00:19:54.102 –> 00:20:00.902
Roddy: So let’s go back a little bit even further and talk about specific experiences from early in your career that really shaped you as a leader.
00:20:00.902 –> 00:20:11.082
Roddy: Can you share with us one story maybe that has really stuck with you, shaped you as a leader, you draw from that on a regular basis in terms of how you behave, Shiv?
00:20:11.822 –> 00:20:12.082
Roddy: Yeah.
00:20:12.082 –> 00:20:16.342
Sundar: I think obviously spent my majority of my farming years at Microsoft.
00:20:16.342 –> 00:20:18.822
Sundar: That’s where I spent a lot of time.
00:20:19.082 –> 00:20:24.842
Sundar: Early employee, early first few years, I started off with an engineering discipline.
00:20:24.842 –> 00:20:26.642
Sundar: That’s where I met a co-founder also.
00:20:27.862 –> 00:20:31.322
Sundar: The way Microsoft did things in the early 2000 was phenomenal.
00:20:31.322 –> 00:20:35.282
Sundar: I mean, the opportunity that was presented to me was huge.
00:20:36.562 –> 00:20:39.802
Sundar: Even earlier in my career, I used to work with ecosystem players.
00:20:39.802 –> 00:20:42.222
Sundar: I used to work with Samsung, OEMs.
00:20:42.222 –> 00:20:43.702
Sundar: I used to work with Qualcomm.
00:20:44.982 –> 00:20:47.262
Sundar: That gave me a lot of confidence.
00:20:47.262 –> 00:20:56.782
Sundar: There was one point of time in my career where I actually was launching a smartphone for Microsoft, the biggest flagship device for Microsoft.
00:20:56.782 –> 00:21:00.602
Sundar: I was a program manager for the entire launch with AT&T.
00:21:03.022 –> 00:21:08.862
Sundar: Steve Barmer, the then CEO, would actually send his assistant to get this device flashed.
00:21:08.862 –> 00:21:17.302
Sundar: Basically, every day, he has a live status report of how the product is behaving.
00:21:17.302 –> 00:21:19.462
Sundar: That is why I was actually pulling fire.
00:21:20.342 –> 00:21:23.102
Sundar: And my manager would just sit back and let me actually run it.
00:21:23.102 –> 00:21:27.642
Sundar: She would never come in, her name was Lynn.
00:21:27.802 –> 00:21:32.462
Sundar: She would never come in and she would guide me, but she would be like, you got this, let’s just go.
00:21:34.562 –> 00:21:42.742
Sundar: They put me a lot of places where it was a little bit beyond my reach, but they let me experience that struggle a bit and succeed.
00:21:42.742 –> 00:21:44.742
Sundar: I mean, that shaped a lot of it.
00:21:44.742 –> 00:21:49.222
Sundar: And then I moved to Silicon Valley in 2012, and it’s been like 14 years.
00:21:49.742 –> 00:21:56.062
Sundar: The valley has a lot of people say a lot of things about how California is expensive, a lot of things is there and it’s a little hard.
00:21:56.062 –> 00:21:59.742
Sundar: But I think Silicon Valley is a very, very contagious place.
00:21:59.842 –> 00:22:07.622
Sundar: I mean, there are entrepreneurs who are actually dreaming up really big things, and you get a lot of support from the ecosystem.
00:22:07.622 –> 00:22:17.442
Sundar: For me, I think I would say the Microsoft experience was a turning point for me, and then Silicon Valley provided me the infrastructure to actually go on to build companies.
00:22:19.102 –> 00:22:20.722
Roddy: Can you talk about that genuine confidence?
00:22:20.922 –> 00:22:24.662
Roddy: It sounds like everybody talks about empowerment.
00:22:24.682 –> 00:22:26.962
Roddy: I would say you don’t want to do ignorant empowerment.
00:22:26.962 –> 00:22:31.622
Roddy: You don’t roll somebody into a surgery and go, here, grab a scalpel and do your best.
00:22:31.622 –> 00:22:39.222
Roddy: But it seems like you had support, but then there was also the opportunity that it wasn’t just so directive, if I’m understanding that correctly.
00:22:42.282 –> 00:22:44.282
Sundar: It was not directive, but a lot of coaching.
00:22:44.302 –> 00:22:52.562
Sundar: It’s more like, for example, that’s also philosophy applied in Microsoft and in Esper also.
00:22:52.622 –> 00:22:57.722
Sundar: I was provided opportunities and I was made to go lead in the front and be a friend.
00:22:57.722 –> 00:23:03.002
Sundar: My leaders, my VPs, they would actually sit back and make sure everything is aligned.
00:23:03.242 –> 00:23:04.842
Sundar: I have the resources that provide me.
00:23:05.242 –> 00:23:08.802
Sundar: They’re basically almost like, how can I help you kind of a scenario?
00:23:08.802 –> 00:23:12.702
Sundar: How can I help you was a philosophy and not like, let me tell you what to do.
00:23:12.822 –> 00:23:21.082
Sundar: I mean, it was a very, very different philosophy at Microsoft to encourage early leaders to go take big challenges and sit back and let them lead those initiatives.
00:23:21.082 –> 00:23:37.122
Sundar: And I think that to me was like, sometimes when I think about what I was doing, I get overwhelmed, but I would just do it the entire, I was probably 30 years old, probably it was almost a billion dollars of marketing behind a phone to be launched.
00:23:37.322 –> 00:23:41.282
Sundar: And I was leading it and the managers were like, what can I help you with?
00:23:41.662 –> 00:23:42.722
Sundar: That’s how they supported me.
00:23:42.722 –> 00:23:45.722
Sundar: And I think that gave me a lot of confidence.
00:23:46.522 –> 00:23:54.062
Sundar: I think once the product launched, I actually went to the AT&T store, purchased that phone and I don’t think there was a selfie back then.
00:23:54.362 –> 00:23:55.142
Sundar: Maybe it was.
00:23:56.022 –> 00:24:00.482
Sundar: I think I took a photo with that phone with my hand of the product that I really launched.
00:24:00.482 –> 00:24:02.142
Sundar: I think it was a novel moment for me.
00:24:02.142 –> 00:24:14.182
Sundar: And I think at that point of time, I felt like if I can actually achieve that, I think everything is from there is possible.
00:24:14.782 –> 00:24:15.022
Roddy: Yeah.
00:24:15.022 –> 00:24:16.102
Roddy: You got an early win.
00:24:16.102 –> 00:24:16.962
Roddy: So what now?
00:24:16.962 –> 00:24:22.302
Roddy: But also in that environment where they’re giving you coaching, they’re not holding your hand every step of the way.
00:24:22.302 –> 00:24:23.882
Roddy: Mistakes can happen.
00:24:23.882 –> 00:24:28.642
Roddy: Can you tell us about a mistake that you made as a leader and what you learned from it?
00:24:28.642 –> 00:24:36.282
Roddy: Again, this could be a recent example, could be from a long time ago, could be a colossal disaster just a time or maybe you fell short of your standards.
00:24:36.322 –> 00:24:38.682
Roddy: Share with our audience a mistake that you made as a leader.
00:24:39.662 –> 00:24:52.802
Sundar: Yeah, I think one thing I would say overall, and I suppose I’ve learned is that it’s very obvious but not obvious, it’s like more people doesn’t mean more productivity, right?
00:24:52.802 –> 00:24:55.202
Sundar: I mean, that’s been a mistake that I’ve actually made a lot, right?
00:24:55.202 –> 00:25:13.402
Sundar: It’s just like oftentimes when things, companies are scaling, when people are scaling, you think like, let’s add two more safety people, let’s add two more engineers, let’s add one more VP, let’s add more managers, let’s like, sometimes that doesn’t work like that, right?
00:25:13.402 –> 00:25:19.402
Sundar: So you have to really, really be smart about adding people to the organization.
00:25:19.402 –> 00:25:24.622
Sundar: Like even with limited number of people, you can achieve exponential growth, right?
00:25:25.982 –> 00:25:31.542
Sundar: That to me, I would say is probably biggest lesson.
00:25:31.802 –> 00:25:36.702
Sundar: Sometimes in media situations, sometimes I’ve actually said, you know what, I need to add more people because we’re going to scale.
00:25:36.782 –> 00:25:38.962
Sundar: Maybe the product was not ready for more scale, right?
00:25:39.062 –> 00:25:42.162
Sundar: If the market was not here, maybe we didn’t have enough partners.
00:25:42.162 –> 00:25:52.262
Sundar: I think hiring smartly, having very small nimble teams are actually much more beneficial than having large organization with a lot of layers.
00:25:52.262 –> 00:25:52.442
Sundar: Right?
00:25:52.802 –> 00:26:02.662
Sundar: I think for me, I felt like a couple of mistakes I’ve made was, I think we kind of scaled the sales team too fast for the product was ready in certain scenarios.
00:26:02.662 –> 00:26:09.802
Sundar: So we scaled, that was, I would say, is one of the biggest mistakes that we did, and we’re very, very careful about that right now.
00:26:10.522 –> 00:26:11.262
Roddy: Yeah.
00:26:11.262 –> 00:26:12.242
Roddy: So thank you for that.
00:26:12.242 –> 00:26:19.462
Roddy: The phrase that a couple of brothers that I work for, they’d always talk about independent standalone operating units, right?
00:26:19.462 –> 00:26:24.762
Roddy: Don’t build up some big borg and then there’s all this communication, like you said, the layers that need to happen.
00:26:24.762 –> 00:26:35.122
Roddy: So I guess, can you talk about how do you do that, that you keep, that you stay coordinated, that you keep people independent, that almost seems like it’s too conflicting thoughts there.
00:26:35.122 –> 00:26:39.142
Roddy: How do you scale without creating those layers in that bureaucracy?
00:26:39.762 –> 00:26:53.242
Sundar: So I think the way to scale organization is like basically, you have to make sure that everybody who can’t, sometimes I feel like everybody, they used to be the whole thing about hey, cross-group collaboration and work across teams.
00:26:53.242 –> 00:26:55.482
Sundar: I think it’s almost like going away.
00:26:55.482 –> 00:27:04.842
Sundar: It’s like you put everybody who’s on a mission in one team and one leader and give them the whole accountability to go do the trade.
00:27:05.182 –> 00:27:14.062
Sundar: I think if you look at a lot of philosophies coming out, in the AI, it’s something called AI-first organizations.
00:27:14.182 –> 00:27:17.642
Sundar: In AI-first organization, there are actually two roles, right?
00:27:18.502 –> 00:27:22.762
Sundar: It is basically people who are actually building and people who are actually selling.
00:27:22.842 –> 00:27:23.362
Sundar: That’s it.
00:27:23.362 –> 00:27:26.462
Sundar: There is no sales, there is no marketing, there is no product, there’s no engineering.
00:27:26.462 –> 00:27:27.462
Sundar: It’s all merged.
00:27:27.462 –> 00:27:31.702
Sundar: You’re either an AI engineer who develops or a go-to-market person who sells.
00:27:31.902 –> 00:27:32.662
Sundar: That’s about it.
00:27:32.782 –> 00:27:48.462
Sundar: Then the new organizations are such that, let’s say, you have a goal, you have a territory, your product, your engineering, your marketing and sales lives within that organization, and then you have one leader who’s going to be responsible for that.
00:27:51.022 –> 00:27:52.502
Sundar: Our structures are collapsing.
00:27:52.502 –> 00:27:56.622
Sundar: Pretty much everybody right now is having 50-60 reports.
00:27:56.622 –> 00:28:01.262
Sundar: There is no room for my middle management, there is no room for various hierarchies.
00:28:01.702 –> 00:28:09.482
Sundar: Pretty much many companies have actually gone on to say that, hey, probably CEO will be the only guy who will actually have management responsibility.
00:28:09.482 –> 00:28:11.862
Sundar: Everybody is actually going to roll up and do things.
00:28:12.442 –> 00:28:13.742
Roddy: Yeah.
00:28:13.742 –> 00:28:14.902
Roddy: Almost like a strike team.
00:28:14.982 –> 00:28:21.082
Roddy: So small strike teams don’t need a bunch of leaders and managers, everybody’s got a responsibility.
00:28:21.082 –> 00:28:28.902
Roddy: Like shared services, if you get so big and all these people are shared services, well, then they’re trying to serve all these different groups, and then that’s where it seems like you get into fights.
00:28:28.902 –> 00:28:29.822
Roddy: I see you nodding.
00:28:33.282 –> 00:28:39.182
Sundar: I think I would say self-contained AI first teams are the future.
00:28:39.182 –> 00:28:44.862
Sundar: They have the tools, they have the people, they have everything where they can go execute.
00:28:45.722 –> 00:28:53.702
Sundar: That’s about, I would say, that’s where the smaller teams with the power of AI are able to scale really well.
00:28:54.242 –> 00:28:58.822
Sundar: Everything from content to marketing to sales to code is all automated.
00:28:59.282 –> 00:29:01.162
Sundar: It’s all about how well you use the teams.
00:29:01.482 –> 00:29:01.662
Roddy: Yeah.
00:29:01.662 –> 00:29:03.982
Roddy: If you do it right, you get exponential productivity growth.
00:29:03.982 –> 00:29:08.622
Roddy: If you do it wrong, you’ll actually add more people, more expenses, and you’ll be less productive.
00:29:08.622 –> 00:29:10.462
Roddy: You get the worst of all worlds.
00:29:10.462 –> 00:29:16.002
Roddy: So we’re going to pause here quickly to let our listeners and viewers know about the Retail Solutions Providers Association.
00:29:16.242 –> 00:29:24.982
Roddy: RSPA is North America’s largest community of retail technology, VARs, software providers, vendors, and distributors in the retail, restaurant, and grocery verticals.
00:29:25.082 –> 00:29:30.782
Roddy: To accelerate your success through an RSPA membership, email membership at gorspa.org.
00:29:30.842 –> 00:29:37.422
Roddy: Also, we want to thank these channel-focused companies who support the RSPA community and make this podcast and video series possible.
00:29:37.522 –> 00:29:43.762
Roddy: Our gold sponsors are Bluestar, CoCard, Epson, Global Payments, and ScanSource.
00:29:44.002 –> 00:29:52.062
Roddy: Finally, registration is now open for RetailNOW 2026, the retail IT channel’s number one trade show, education conference, and networking event.
00:29:52.182 –> 00:29:58.502
Roddy: This year’s event is set for July 26th through 28th at the new Caesars Forum Conference Center in Las Vegas.
00:29:58.642 –> 00:30:00.962
Roddy: For more information, visit gorsp.org/retailnow.
00:30:03.342 –> 00:30:06.302
Roddy: RetailNOW is where the industry meets.
00:30:06.302 –> 00:30:10.442
Roddy: And my final question for you, Shiv, when we get to it is about your RetailNOW breakout.
00:30:10.442 –> 00:30:19.862
Roddy: But before that, can you talk about your leadership style and then some actions that you take when engaging with your team members to reinforce that approach?
00:30:20.482 –> 00:30:23.962
Sundar: Yeah, I think my leadership style is slightly unique.
00:30:24.002 –> 00:30:26.102
Sundar: I sit within the go-to-market organization.
00:30:26.102 –> 00:30:31.342
Sundar: I’ve been in the go-to-market org for the last nine years at ESPR.
00:30:32.602 –> 00:30:34.102
Sundar: My philosophy is very straightforward.
00:30:34.102 –> 00:30:35.542
Sundar: I actually sell, right?
00:30:36.002 –> 00:30:37.562
Sundar: I am actually the salesperson.
00:30:39.982 –> 00:30:54.882
Sundar: Like I want to know if it’s easy to sell or partner with customers on an every day, every week, every month basis, because unless you do it yourself, you do not know what a salesperson or go-to-market person is going through the company, right?
00:30:54.882 –> 00:31:03.102
Sundar: Even actively, you have to actively do, basically philosophy boils down to you have to actively do things that you ask your team to do, right?
00:31:03.102 –> 00:31:05.322
Sundar: I mean, if you’re a developer, you have to actively code.
00:31:05.322 –> 00:31:07.322
Sundar: If you’re a salesperson, you have to actively sell.
00:31:08.182 –> 00:31:09.922
Sundar: That’s the only way you will have empathy.
00:31:10.262 –> 00:31:11.982
Sundar: Otherwise, it’s very hard.
00:31:14.022 –> 00:31:17.302
Sundar: It’s like teaching somebody to drive without knowing to drive, right?
00:31:17.302 –> 00:31:20.462
Sundar: I mean, that’s how I put it.
00:31:21.022 –> 00:31:21.782
Sundar: That is my philosophy.
00:31:21.782 –> 00:31:24.522
Sundar: Only by doing things can you inspire.
00:31:24.582 –> 00:31:26.442
Sundar: Only by doing things can you motivate.
00:31:26.442 –> 00:31:28.022
Sundar: Only by doing things can you like.
00:31:28.162 –> 00:31:32.102
Sundar: When I close a deal or when I sign a partnership or when I build things, then it motivates.
00:31:32.102 –> 00:31:37.322
Sundar: Oh, if Shiv, with all the things that he has to go around, if he’s able to do this, then we should be able to do it.
00:31:37.542 –> 00:31:47.522
Sundar: If Shiv is able to travel and meet partners at conference, he’s able to book meetings, he’s able to outbound, e-mail and connect and bring some pipeline, I can do it.
00:31:47.582 –> 00:31:54.102
Sundar: I mean, that is how I have done it all my career, and I’m doing it at ESPR too.
00:31:54.102 –> 00:32:07.782
Sundar: I mean, it also gives me confidence that if nothing exists, if ESPR doesn’t exist, or if nothing happens, the whole thing is not there, I still have the skills to go do it, and it has to be that.
00:32:08.022 –> 00:32:15.822
Sundar: You can’t rely on a title or a leadership role or a company to be skillful.
00:32:15.882 –> 00:32:18.522
Sundar: You have to know how to do it ground up.
00:32:18.982 –> 00:32:21.922
Sundar: So that is my leadership style, and it’s always worked well.
00:32:22.742 –> 00:32:33.262
Roddy: So I’m curious, what percent of your job is sales, and then what percent is the leadership steering the company, if you’re able to put it into those two big buckets?
00:32:33.282 –> 00:32:34.842
Roddy: I was just curious.
00:32:34.842 –> 00:32:38.902
Sundar: I would say 50 percent is management, and 50 percent I would say is the LIC work.
00:32:40.562 –> 00:32:44.302
Sundar: I limit my management and all the other activities to 50 percent.
00:32:44.302 –> 00:32:57.682
Sundar: I actually go to individual meetings, build relationship, build pipeline, try and help with the closing, help with partners, show up at events, and those are my activities.
00:32:58.262 –> 00:33:01.582
Roddy: I bet you surprise some people in the sales process, like how long have you been with the company?
00:33:01.582 –> 00:33:02.442
Roddy: Well, I founded it.
00:33:02.442 –> 00:33:02.902
Roddy: What?
00:33:03.362 –> 00:33:04.802
Roddy: I’m guessing they’re surprised.
00:33:06.022 –> 00:33:06.742
Sundar: They are.
00:33:06.742 –> 00:33:07.782
Sundar: They’re very surprised.
00:33:07.842 –> 00:33:17.702
Sundar: They also like, oftentimes, they see that if the founder is motivated enough to be on the field and help sell the product, that means that there is something to it.
00:33:18.042 –> 00:33:18.942
Roddy: Yeah.
00:33:18.942 –> 00:33:19.622
Roddy: Very good.
00:33:19.622 –> 00:33:20.382
Roddy: I’m just reading the book.
00:33:20.382 –> 00:33:23.702
Roddy: I turned around and looked at it on my bookshelf by Dan Heath.
00:33:23.702 –> 00:33:27.502
Roddy: It’s called Reset, and it’s about how to get an organization back on track.
00:33:27.822 –> 00:33:31.342
Roddy: The number one thing he has is, go see the work.
00:33:31.382 –> 00:33:34.622
Roddy: You can’t be in a meeting and looking at reports and understanding.
00:33:34.822 –> 00:33:37.062
Roddy: You’ve got to get and be in the middle of it.
00:33:37.062 –> 00:33:39.742
Roddy: Like you said, if you were going to drive, you’ve got to be in the car.
00:33:39.742 –> 00:33:41.862
Roddy: You can’t just be watching from a distance.
00:33:41.862 –> 00:33:43.602
Roddy: It sounds like that’s a big thing for you.
00:33:43.682 –> 00:33:50.242
Roddy: Somebody told me one time, your job as a leader is there’s a way the business operates, and then there’s a gap between how you think it operates.
00:33:50.362 –> 00:33:51.962
Roddy: Your job is to minimize that gap.
00:33:51.962 –> 00:33:54.802
Roddy: It seems like you’ve got that gap, especially on the sales side.
00:33:55.282 –> 00:33:55.682
Sundar: Yeah.
00:33:55.702 –> 00:34:02.962
Sundar: I collect my information and data from the most junior and newest employees doing their tasks.
00:34:03.422 –> 00:34:05.002
Sundar: That is who I operate with.
00:34:06.482 –> 00:34:10.702
Sundar: Every time I go and say, hey, think of me as your teammate and let’s split the work.
00:34:11.102 –> 00:34:11.562
Sundar: Yeah.
00:34:11.562 –> 00:34:14.262
Sundar: That’s the only way you actually learn what’s happening at the company.
00:34:15.102 –> 00:34:16.182
Roddy: Very interesting.
00:34:16.442 –> 00:34:17.522
Roddy: Who just sit next to work?
00:34:17.522 –> 00:34:18.102
Roddy: Oh, the founder.
00:34:18.102 –> 00:34:19.542
Roddy: Wait, didn’t you just start at the company?
00:34:19.582 –> 00:34:19.922
Roddy: Here we go.
00:34:19.922 –> 00:34:20.602
Roddy: Yeah, sure.
00:34:20.602 –> 00:34:21.102
Roddy: That’s how we were.
00:34:21.102 –> 00:34:21.442
Sundar: Yeah.
00:34:22.322 –> 00:34:26.662
Sundar: I actually attend standups and I actually give my status report.
00:34:26.662 –> 00:34:31.422
Sundar: I actually tell what I did and how many calls I made, how many pipeline I booked.
00:34:31.422 –> 00:34:32.822
Sundar: I actually give them an update.
00:34:33.222 –> 00:34:34.362
Sundar: They are like, yeah.
00:34:35.002 –> 00:34:35.602
Roddy: I love it.
00:34:35.602 –> 00:34:36.262
Roddy: I love it.
00:34:37.122 –> 00:34:37.542
Roddy: Good.
00:34:37.542 –> 00:34:44.342
Roddy: I’m curious, who are some leaders that you look up to as mentors, and who are some folks who help shape you along the way?
00:34:44.342 –> 00:34:48.022
Roddy: You talked about your experience at Microsoft and how formative that was.
00:34:48.582 –> 00:34:52.202
Roddy: What did past leaders and mentors for you say and do that’s had a lasting impact?
00:34:52.922 –> 00:34:53.122
Sundar: Yeah.
00:34:53.122 –> 00:34:59.062
Sundar: I think fortunately being in Silicon Valley, you actually get to meet founders who actually do company public.
00:34:59.262 –> 00:35:03.742
Sundar: That is the level of peer group that you have here.
00:35:03.742 –> 00:35:07.802
Sundar: One of my biggest mentors, there are two people actually, one is called Suresh Vachu.
00:35:07.802 –> 00:35:12.042
Sundar: We actually do an MDM company, Mobile Iron Public.
00:35:12.962 –> 00:35:16.302
Sundar: When I was starting SPA, I went to him and I said, hey, I’m going to build something on the same lines.
00:35:16.302 –> 00:35:21.562
Sundar: He said, yeah, I built something that met IPO, but there’s a lot more opportunity and this is where you need to operate it.
00:35:21.942 –> 00:35:24.282
Sundar: He didn’t discourage me and say, I’ve already done it and built a company.
00:35:24.282 –> 00:35:26.062
Sundar: Why are you doing the same thing?
00:35:26.062 –> 00:35:27.362
Sundar: Again, I met him four months ago.
00:35:27.362 –> 00:35:28.002
Sundar: He was like, great.
00:35:28.862 –> 00:35:30.562
Sundar: I love how far you have come.
00:35:30.902 –> 00:35:34.662
Sundar: There’s one more mentor of mine, his name is Suresh.
00:35:34.722 –> 00:35:44.202
Sundar: He’s like, I would say mid-50s and on his fourth startup, and he pretty much sold all three startups to SAP and Salesforce.
00:35:44.202 –> 00:35:45.782
Sundar: This is his fourth company.
00:35:46.462 –> 00:35:50.502
Sundar: The guy has the energy of a 20-year-old founder, the energy and enthusiasm.
00:35:50.502 –> 00:35:55.202
Sundar: You see him in conferences in Vegas, you’ll be like, he’s selling payment solutions to construction workers.
00:35:55.862 –> 00:36:01.942
Sundar: It’s his fourth startup, but he tells me, hey, Shiv, can you help me on this thing?
00:36:01.942 –> 00:36:03.942
Sundar: I’m like, why are you asking me for help?
00:36:04.142 –> 00:36:10.682
Sundar: No, I always ask for feedback from up-and-coming founders because you may have a playbook that I don’t have.
00:36:10.682 –> 00:36:11.862
Sundar: He’s willing to learn.
00:36:13.382 –> 00:36:15.422
Sundar: I think he’s my mentor, but he asked me for questions.
00:36:15.422 –> 00:36:19.222
Sundar: I’m like, give me feedback, give me how I do.
00:36:19.562 –> 00:36:21.562
Sundar: His company is called Lumberfi.
00:36:21.562 –> 00:36:28.602
Sundar: He completely went from Silicon Valley to build payments in construction industry, and he just figured it out all the way.
00:36:29.882 –> 00:36:41.162
Sundar: I think it’s all about learning mentality, and I think those two mentors have told me, you have to learn, you have to learn always, and that’s what I felt was the biggest mentorship that I get from all those folks.
00:36:41.762 –> 00:36:42.582
Roddy: Very interesting.
00:36:42.582 –> 00:36:51.282
Roddy: Again, I guess to our audience, what you’re hearing from Shiv is mentoring doesn’t have to be, I’m the mentor, you’re the mentee, and it’s all directional.
00:36:51.462 –> 00:36:58.482
Roddy: It can be the whole iron sharpens iron kind of thing, it just exchanging ideas and problems and opportunities back and forth.
00:36:58.482 –> 00:37:01.982
Roddy: That’s what it sounds like the relationship that you have with those folks.
00:37:02.702 –> 00:37:08.202
Sundar: It is like they tell you things and they’ll ask for things from you, and it’s just like, it also happens to me.
00:37:08.202 –> 00:37:15.882
Sundar: Oftentimes, I mentor, like we talked about fundraisers, oftentimes I mentor people who are actually starting the company, who were eight years before my journey.
00:37:16.942 –> 00:37:22.222
Sundar: In that one-hour conversation, I actually walk away from something very, very unique that they’re doing that I’ve actually learned.
00:37:23.622 –> 00:37:27.402
Sundar: So mentorship is never a one-way thing.
00:37:27.462 –> 00:37:36.542
Sundar: You’re always going to learn, and especially from young founders, you learn a lot from them because they are trying to invent something or trying to make something happen with very, very limited resources.
00:37:36.542 –> 00:37:37.802
Sundar: They’re very, very creative.
00:37:38.402 –> 00:37:42.002
Sundar: So it’s a very good learning experience in general.
00:37:42.142 –> 00:37:45.782
Roddy: Yeah, they’re very, very resourceful for sure.
00:37:45.842 –> 00:37:46.622
Roddy: So yeah.
00:37:47.202 –> 00:37:47.722
Roddy: No, good.
00:37:47.722 –> 00:37:48.362
Roddy: No, thank you.
00:37:48.362 –> 00:37:52.702
Roddy: I think that I guess there’s also in the backdrop of that, there’s humility, right?
00:37:52.702 –> 00:37:59.522
Roddy: You have to have some humility that you can learn from that other person as opposed to, hey, I’ve done four startups.
00:37:59.522 –> 00:38:01.862
Roddy: Let me just tell you Shiv, what it’s all about.
00:38:01.862 –> 00:38:07.522
Roddy: That seems like it’s an important part of you as a leader as well, being humble, if I’m understanding that correctly.
00:38:07.862 –> 00:38:08.362
Sundar: That is true.
00:38:08.622 –> 00:38:13.462
Sundar: He used to tell me like, hey, every time I need energy, I’ll call you because I need to meet with young founders.
00:38:13.462 –> 00:38:15.142
Sundar: I always want to meet with young founders.
00:38:17.522 –> 00:38:19.402
Sundar: He’s the guiding force for a lot of people.
00:38:19.402 –> 00:38:24.402
Sundar: He himself has invested in 10 startups, but he’s always like, hey, I need some feedback on this.
00:38:24.402 –> 00:38:26.222
Sundar: I’m like, really?
00:38:26.422 –> 00:38:29.202
Sundar: It took me a while, but he was very genuine that he wants to learn.
00:38:29.422 –> 00:38:29.842
Sundar: Yeah.
00:38:30.122 –> 00:38:30.782
Roddy: Excellent.
00:38:31.502 –> 00:38:33.902
Roddy: Last question for you, Shiv, and just the time we have left.
00:38:33.922 –> 00:38:36.422
Roddy: Can you give us a preview of your RetailNOW talk?
00:38:36.422 –> 00:38:43.142
Roddy: Again, the title is, From Chaos to Control, Mastering Device Lifecycle for Vars, ISVs, and ISOs.
00:38:43.142 –> 00:38:45.562
Roddy: What are you going to talk about in Vegas?
00:38:47.382 –> 00:39:04.722
Sundar: Right now, if you look at it, if you look at hardware as a large part of the journey, you are deploying millions and millions of devices from the manufacturer does it, then it goes to a distributor, then it goes to a researcher, then to a customer.
00:39:05.102 –> 00:39:11.062
Sundar: A lot of money is actually being spent in the hardware, but the question is, whole life cycle is expensive.
00:39:11.082 –> 00:39:12.002
Sundar: When do you ship the devices?
00:39:12.002 –> 00:39:12.842
Sundar: When do they arrive?
00:39:12.842 –> 00:39:14.262
Sundar: How do they get configured?
00:39:14.422 –> 00:39:17.642
Sundar: Who opens up the packaging and puts the printer back on board?
00:39:17.882 –> 00:39:19.682
Sundar: And when does it reach the customer?
00:39:19.682 –> 00:39:21.702
Sundar: And what happens when it gets deployed?
00:39:24.222 –> 00:39:27.902
Sundar: The CAPEX and OPEX for devices are actually very, very critical.
00:39:27.902 –> 00:39:31.682
Sundar: Sometimes you think that the hardware costs are the biggest cost, but it’s actually not.
00:39:31.942 –> 00:39:37.562
Sundar: Eventually, the management costs of the hardware, configuration costs, shipping costs, it all adds up.
00:39:38.422 –> 00:39:47.542
Sundar: I think where we are going at ESPA is like, we want to go in as The Trusted Advisor for all our big partners and say, what hardware are you buying?
00:39:47.542 –> 00:39:48.562
Sundar: Where are you buying it from?
00:39:48.562 –> 00:39:51.102
Sundar: How does the configuration look?
00:39:51.102 –> 00:39:56.242
Sundar: Is there any steps that you can actually automate at the manufacturing process that can be plugged and played?
00:39:56.482 –> 00:40:02.142
Sundar: Can you actually ship the device from a factory to a restaurant without actually configuring it?
00:40:02.142 –> 00:40:05.222
Sundar: So that is where I would say it’s like, and how do you maintain it for five years?
00:40:05.222 –> 00:40:06.222
Sundar: How do you update it?
00:40:06.722 –> 00:40:16.002
Sundar: So I think our goal is like, how do you deploy millions of devices with the least amount of operational expense positive?
00:40:16.002 –> 00:40:18.202
Sundar: That is where Esper is going.
00:40:18.202 –> 00:40:24.362
Sundar: That is where it’s a philosophy that we actually want our partners and ecosystem partners to think about.
00:40:24.622 –> 00:40:25.582
Sundar: What are the steps?
00:40:25.582 –> 00:40:27.002
Sundar: Is there a way to minimize the steps?
00:40:27.002 –> 00:40:31.282
Sundar: That’s what my RetailNOW roundtable is about.
00:40:31.322 –> 00:40:40.302
Sundar: We’re going to have a few VARs who will join us in the roundtable to share their experiences, and that is what I’m going to be talking about at the CSIS forum in RetailNOW.
00:40:40.902 –> 00:40:41.702
Roddy: Excellent.
00:40:41.702 –> 00:40:42.882
Roddy: I’m looking forward to that.
00:40:42.882 –> 00:40:46.062
Roddy: It almost seems like there’s that trend of where folks are talking about.
00:40:46.542 –> 00:40:55.742
Roddy: A lot of hardware is lasting longer and it’s getting better and stronger, but tracking it and being able to manage it, seems like that is now a new opportunity for VARs.
00:40:55.742 –> 00:41:01.042
Roddy: They might not be making a ton of money on the hardware sales, but it sounds like there’s an opportunity for managing it.
00:41:01.042 –> 00:41:02.722
Roddy: I think you said doing it, it’s a little overhead.
00:41:02.722 –> 00:41:04.982
Roddy: Am I understanding that trend correctly?
00:41:04.982 –> 00:41:06.222
Sundar: That is correct, yeah.
00:41:06.222 –> 00:41:06.842
Roddy: Excellent.
00:41:07.342 –> 00:41:07.762
Roddy: Very good.
00:41:07.762 –> 00:41:10.022
Roddy: Well, that does it for this episode of The Trusted Advisor.
00:41:10.022 –> 00:41:17.422
Roddy: If you enjoyed our discussion, be sure to subscribe to the RSPA YouTube channel and The Trusted Advisor podcast so you never miss an episode.
00:41:17.422 –> 00:41:21.522
Roddy: Before we go, a big thanks again to Shiv Sundar for sharing his wisdom with us today.
00:41:21.682 –> 00:41:29.782
Roddy: Thanks also to RSPA Marketing Director Chris Arnold for his production work, Joseph McDade for our music, and last but not least, thanks so much to you for listening.
00:41:29.942 –> 00:41:36.982
Roddy: Our goal at the RSPA is to excite the success of our members in the retail technology ecosystem by providing knowledge and connections.
00:41:36.982 –> 00:41:40.722
Roddy: For more information, please visit our website at gorspa.org.
00:41:40.822 –> 00:41:44.442
Roddy: Thanks for listening and goodbye everybody.
