[00:00:00] 

Rob Balena: There needs to be a willingness and intestinal fortitude to weather the long journey to enterprise success.

Finding good salespeople is one of the [00:00:10] hardest things in the world. Do you have the runway and the stomach to play long ball?

That's the only way to do large strategic [00:00:20] deals.

When you take a message that resonates with a VC, it's going to potentially scare some risk minded folks at large enterprises. 

Show me how it hits the P&L of the site. That's [00:00:30] interesting. That's something that I can take to operational leaders.

Your job is to convince them that you are the safest place for their destiny. And the reason is not because of your [00:00:40] size, but it's because you can get them to the other side, to what you're promising for them.

The end state is not the close of business. 

The end state is whatever [00:00:50] implementation goal you've promised to them is achieved.

Andrew Kazlow: Welcome to the Diligent Observer, the first podcast exclusively focused on helping angel [00:01:00] investors make better bets. I'm your host, Andrew, and every week we explore what works, what doesn't, and why through conversations with experienced startup [00:01:10] investors and operators. 

Andrew Kazlow: My guest today is Rob Balena, a master at helping startups land and expand enterprise accounts. [00:01:20] After selling for multiple venture backed companies into Fortune 500 clients, Rob now leads strategic accounts at TeamSense, where he's helping transform how [00:01:30] manufacturing giants engage their workforce. In this episode, we explore his strategies for building credibility as a small company, avoiding common enterprise [00:01:40] sales pitfalls and connecting startup products to metrics that actually matter to big company executives. I hope you enjoy learning from Rob as [00:01:50] much as I did.

Andrew Kazlow: Rob, thanks for being with me today.

Rob Balena: So excited to be here. Thanks for having me.

Andrew Kazlow: Okay. So Rob, I'd love to start with just what's exciting [00:02:00] in your world right now, either at TeamSense or things happening in the broader kind of sales ecosystem that you find exciting?

Rob Balena: My [00:02:10] passion has always been, walking alongside customers and helping them transform. I love finding people that are, trying to solve problems on the ground level, building a story with [00:02:20] them, and then taking that to corporate executives. And in my role at TeamSense, I get to do that more and in a different way than I ever really have before.

Rob Balena: We sell primarily to [00:02:30] manufacturing companies, which is a new industry for me. And so, I've sort of traded my wingtips in for steel-toe boots and instead of spending [00:02:40] time touring data centers, I now am touring manufacturing facilities, which is really interesting.

Rob Balena: You feel like a little kid when you're in there watching trucks get built or engines put together. But then [00:02:50] also really getting to hear the ways that software can improve the lives of people that a lot of the tech industry has ignored for a very [00:03:00] long time, right? The hourly workers in factories.

Rob Balena: And so that's really exciting to me here at TeamSense. I think broadly what I'm seeing is there really seems to be a [00:03:10] shift. I wonder if it's, you know, post COVID. COVID everybody went remote. Everything was very much done over Zoom. And I think there's still sort of a, a reticence [00:03:20] among sellers to get out in person and to be face to face with customers.

Rob Balena: And so, That's unfortunate. I mean, that being Being in person is such a force [00:03:30] multiplier in the go-to market world. But for someone like me that loves to be in person it's actually an advantage because it does set us apart. In fact, I've had customers tell me and tell [00:03:40] folks on my team like, we went with you because you're real people and you came to visit us and we've we had this previous vendor and we'd never met anybody in person and so I do see that as a shift as maybe a swing [00:03:50] back to the traditional field sales of being in person and seeing the tangible impact that makes on outcomes for sellers.

Andrew Kazlow: What's old is new [00:04:00] again.

Rob Balena: Yeah

Andrew Kazlow: So you said something interesting just now. It sounds like this transition from large data center [00:04:10] focus to manufacturing has been quite a transformation in terms of target market. What are some of the things you've seen that are consistent in terms [00:04:20] of your sales motions and the way you go to market?

Andrew Kazlow: And what are some of the nuances that you've found between those two markets?

Rob Balena: The way that large [00:04:30] organizations buy is pretty consistent, right? There's a huge focus on reducing risk. There's a huge focus on [00:04:40] understanding outcomes. One of my favorite go-to market people in the world is Todd Caponi the author of "The Transparency Sale". And he's famous for saying that, "People buy when they have certainty, [00:04:50] when they know what the outcome will be. Even if they like, they need to understand what the potential downsides are before they're willing to buy." 

Rob Balena: That's pretty consistent. And so, building a business case and [00:05:00] helping all of the stakeholders in a large organization understand not just the pie in the sky vision of the software, but how do we help you get from where you are today [00:05:10] to where you're going to go next. That's pretty consistent.

Rob Balena: I think that's just buying behavior in general. Building consensus across multiple stakeholders. Understanding the pains and the [00:05:20] potential benefits for different stakeholders is all pretty consistent. What's really unique about the manufacturing industry, I think what surprised me initially coming to TeamSense is [00:05:30] how independent some of these facilities are and in fact one of the first things that I did when I came in as head of sales was I looked at, okay, we've got [00:05:40] fantastic logos, but it's typically at a single site. We've got a single site where we're covering their hourly workforce.

Rob Balena: How do we expand other sites? And I was surprised [00:05:50] to find that many times our contracts were not with the corporate entity, but with a wholly owned subsidiary that had the corporate name plus the site [00:06:00] name with it. And so, in many cases going to a different site or trying to do a corporate level expansion meant starting from scratch from a legal and procurement [00:06:10] perspective, which was a big lift.

Rob Balena: And so. That's been surprising to me. The world that I previously come from, I was at Cloudera where I sold mostly to either tech companies or to [00:06:20] you know, I.T within large companies. And they're pretty well enmeshed in the corporate structure. And so, what you see is what you get.

Rob Balena: The last thing that I'll say too is, this is the first role [00:06:30] for me where I'm selling primarily to HR and then tangentially into operations at the site level when we're starting there and compared to selling to folks in I.T. [00:06:40] who buy a lot of software, run a lot of projects.

Rob Balena: Know kind of where the bodies are buried and how to navigate the structure. Folks that are at an operating facility in [00:06:50] HR, many times they're buying software for the first time or they're running a project for the first time. And so, my role takes on an additional layer of [00:07:00] project management, almost helping them kind of think through.

Rob Balena: How do we get this purchase done? And then what do we need to do post purchase to prove the value that we've promised to the [00:07:10] organization and show that to them? 

Andrew Kazlow: That's an interesting point on the kind of isolation of different nodes within a broader organization. Do you think that's [00:07:20] consistent across other heavily physical enterprises as well, like healthcare companies or hospitals. Help me draw the distinction between [00:07:30] that highly individualized client base within a broader corporate umbrella?

Andrew Kazlow: Like, is that multi industry or you think that's unique to manufacturing?

Rob Balena: I think what's [00:07:40] unique about manufacturing and I'm painting with broad strokes here, but these facilities and the plant leadership. It's usually a plant manager, a general manager, [00:07:50] they are running a P&L for that facility as if it's its own business. And sometimes legally it is right.

Rob Balena: It's legally its own business. And so, there is more [00:08:00] isolation. There's like a shared services model that comes from corporate, but in the day-to-day operations and how they run and manage their business, a lot of that is left up [00:08:10] to them. And I do believe that has to do with the physical nature of the manufacturing industry and the fact that there is so much P&L focus site by site.

Rob Balena: One [00:08:20] of the most interesting examples of that is we had a great relationship with a general manager at it was a logistics company and they had this great story about [00:08:30] how TeamSense had saved them all kinds of money in overtime costs. And we're like, okay, well, we want to take this story to another plant. To the plant that's across state lines.

Rob Balena: In my [00:08:40] experience, when I've had experience with folks in I.T. or, or you know, a sub team within I.T. and they have a big win, they want to share that with everybody and show everybody, hey, look what we [00:08:50] did. In this case though, there was hesitation. It was like, In some ways that plant leader is competing with his peers that are at the other plants. If he's found an [00:09:00] unlock that helps him save a bunch of money or lower his cost of labor there's this tension of well I want to do right by the company and I want to bring the tide up and raise all ships, but at the same time like you've given me an [00:09:10] edge here and this is there's a friendly level of competition.

Rob Balena: And so that was something I'd never experienced and was a little bit surprised to see that level of [00:09:20] isolation.

Andrew Kazlow: It's Charlie Munger, "Show me the incentive and I'll show you the outcome". There it is. Pure and simple. That's fascinating. Okay, Rob. So I want to double [00:09:30] click on your framework, your mental model for assessing go-to market strategy. You have worked with [00:09:40] multiple small companies selling to big companies. That's not an easy thing to do, but you've love it.

Andrew Kazlow: And that is a pitch that many, an entrepreneur makes [00:09:50] to an investor.

Andrew Kazlow: Probably half of the software companies that we look at, at the early stages are painting this corporate sales customer, they're [00:10:00] showing these cool logos, like you just mentioned. 

Andrew Kazlow: I'm curious to understand what is your framework?

Andrew Kazlow: What are the key questions that you would ask if you sat down with a new [00:10:10] entrepreneur, small team, sub-five people aiming to go to market with some of these large enterprise clients. What are the questions you would ask? How [00:10:20] would you deconstruct their pitch deck?

Rob Balena: I mean, they have picked potentially the hardest path. Right. So, For me, there needs to be a really good [00:10:30] product reason why that is the direction, why that's the fit. Why we're going to go after large enterprises and we're going to go after long sales cycle, large [00:10:40] dollar deals off the bat.

Rob Balena: When I ran my coaching business and I would interact with very small startups. And one of the biggest challenges I saw with them is that [00:10:50] they would oftentimes pitch to large enterprises the same way that they pitched to their VCs. And so the same story that got them [00:11:00] funded makes sense is, well, that, that should get us a sale at this large company.

Rob Balena: And one of the unlocks, I think for them was realizing very different organizations, very [00:11:10] different group of people, typically VCs, much smaller group of people, fewer stakeholders, and it's people that are literally in the business of taking risk. They [00:11:20] are looking for high stakes, high return types of ventures.

Rob Balena: A large enterprise is, for the most part, very very different. They are, [00:11:30] by their very nature, risk averse. A publicly traded company has organizational institution and structure to avoid risk. There are risk departments. And [00:11:40] so, when you take a message that resonates with a VC, something about we're the very bleeding edge of a particular technology or, we're doing something that nobody's ever [00:11:50] done before.

Rob Balena: That may get some VCs very frothed up, but it's going to potentially scare some risk minded folks at large enterprises. And so, the [00:12:00] pitch needs to be tailored to the enterprises. I think what I would peel apart too is, do you have the runway and the stomach [00:12:10] to play long ball?

Rob Balena: That's the only way to do large strategic deals. And it can be very easy at the beginning stages to say, yeah, you know, we're going to do the [00:12:20] right thing. We're going to build these relationships over time. We're going to build a business case that's locked tight, we're willing to put in the time and the effort to do that.

Rob Balena: But then as quarters go [00:12:30] differently than you expected and as pressures from the board mount, suddenly there's a very large temptation to do some short sighted things. And in [00:12:40] the course of working towards a strategic relationship with a large enterprise, there are absolutely opportunities where you can pull a string or, or yank on some leverage to [00:12:50] try to get a quick deal.

Rob Balena: You're going to do that with that customer exactly once, and you're mortgaging your future with that customer. There needs to be a willingness and intestinal [00:13:00] fortitude to weather the long journey to enterprise success. And then they also would need to show me a very clear plan of how you're going to find [00:13:10] sellers that are going to come sell for you.

Rob Balena: When I think about the reasons why a seller who knows how to operate at a VP or C-level, why would [00:13:20] that type of person go work for a startup? Enterprise sales is already very very risky, right? An enterprise seller has fewer accounts. Each deal they close is a [00:13:30] large proportion of their quota and thereby their earnings.

Rob Balena: And so, why layer on an additional set of risk of going to a startup that's unproven [00:13:40] that maybe there's not even good product-market fit. Maybe there's not a history of success yet. And usually the answer is a small [00:13:50] startup gives them an ability to do a broader set of things.

Rob Balena: They're not quite so much a cog in the wheel, right? They're able to wear more hats. They want [00:14:00] more of that autonomy and freedom that they're not going to get at a larger organization. I also hear sellers say things like, if I can find an organization and ride the hockey [00:14:10] stick then that's a way to earn 

Rob Balena: a lot of commissions. When a startup hockey sticks, necessarily the quotas have to grow very quickly, which means that there's a [00:14:20] period of time where the high performing sellers are going to be massively outperforming their quota and have huge earning potential. And then equity, of course is a big one.

Rob Balena: And [00:14:30] so, that has to be part of the picture. If you're looking to attract top sales talent especially at the enterprise level, because they're going to be playing long ball. They're going to be investing a lot of time with very [00:14:40] little return until those come to fruition. I think a lot of founders over rotate on the vision or the mission which of course they do, right?

Rob Balena: It's their baby. They created it, [00:14:50] they're the ones that believe it most deeply but I often see folks say, well, we're gonna attract the best talent because we're doing something really amazing and people are gonna drink the cooling they're just gonna want to be [00:15:00] here. The hard truth is like while belief I think is maybe one of the most important parts of, of sales for me in particular, and for sellers in general, you've got to believe [00:15:10] in what you're selling.

Rob Balena: No one is going to believe in the mission or vision of your product or your company as much as you, the founder. And that can't be used [00:15:20] as leverage to manipulate lower comp or lack of equity for a seller when if they're worth their salt, they could probably earn [00:15:30] much more dependable revenue at a larger company.

Andrew Kazlow:  I want to poke on something you said about these quick wins, kind of pulling leverage and [00:15:40] getting a logo all of a sudden, but that you can do that exactly once. If I'm an investor and I see a couple of impressive logos on that pitch deck, how do I suss out if that's [00:15:50] a quick win?

Andrew Kazlow: They pulled the strings and this may or may not happen again, or there's real potential there. What are the follow up questions you ask to discern that without [00:16:00] really being able to know?

Rob Balena: It's tell me the story, right? And that's the same thing I do when I interview salespeople is you can suss out very quickly if someone was intimately involved in the [00:16:10] transaction when they tell you the story and if you know, pull a particular logo and you ask them to tell you the story and it's generalities, you either need to dig deeper or you need to be really concerned.

Rob Balena:  [00:16:20] I joined Cloudera, which is a big data great great successful company IPOed. I joined as part of an acquisition and came into an underperforming [00:16:30] territory, post acquisition, which was a little bit of a culture shock because I'd been on this wild rocket ship ride at Gazzang and we were acquired and then I was like, oh, here's this terrible territory.

Rob Balena: But I was in Central [00:16:40] Texas and one of the accounts that they gave me was Dell which sounds like a great account, but they were exclusively using our competitor and there was like, there was not a lot of opportunity there. But at the [00:16:50] time, I had a Sales Engineer and a boss who were both willing to walk the long road with me.

Rob Balena: The mission there was, [00:17:00] let's get a beachhead. Let's plant our flag in whatever way we can. And then, shout that story from the rooftops. Make those people so wildly [00:17:10] successful that everybody has to look and see what we're doing. So that's an example of yeah, we did get a small, quick win by design.

Rob Balena: We went and found some people that were doing some very [00:17:20] disruptive things that wanted to try something new. They needed a lot of hands on in-person support and I was not far from the Round Rock headquarters and so I was like, great, we'll be here every [00:17:30] Tuesday and Thursday. We'll just kind of hang out with you and help make this happen.

Rob Balena: But that was all in service. And even the customer knew this. We are building a story and we're tracking our progress [00:17:40] because we want to share this not just with your peers, but with your superiors and their superiors. Over the course of what ended up being about three years [00:17:50] unseating that competitor to take over the account.

Rob Balena: That would be the story I'm looking for. If I'm an investor and a startup comes in and they've got big logos with little implementations, I want to know, [00:18:00] are you strategically working with whoever it was that took a very big chance on you to craft a story to go get more from that customer and make them [00:18:10] successful?

Rob Balena: Or did you have an executive relationship that you leaned on? Was there a larger opportunity and you pulled a string, you threw a big discount at them to get them in the [00:18:20] door? Because you just wanted to take it off the table. That's a very different story than we have a strategic plan that's months or years long to take over this account.

Andrew Kazlow: One of the other [00:18:30] things that related to this that I find myself asking when speaking to these entrepreneurs that are going after these large enterprise accounts is, what happens if they say yes? [00:18:40] What happens if they hit go?

Andrew Kazlow: How do you think about positioning for scale and positioning for rapid growth in fulfillment and all [00:18:50] of that?

Andrew Kazlow: Because if a bigger enterprise in theory, right? And gets to the full scope. It's okay. I need 10,000 units tomorrow. Can you make it happen? 

Andrew Kazlow: The answer is always, uh, [00:19:00] yes. Am I thinking about it the right way? Or is it usually more of a slow roll?

Rob Balena: Let me start by saying, and I've even seen this at TeamSense. I think there's this [00:19:10] desire amongst many people to not share your size when you're a tiny startup trying to sell to a big company. It's like, well, we have to make ourselves look [00:19:20] bigger than we are. I don't believe that's true.

Rob Balena: At best, it's like you're throwing some smoke. At worst, you're outright lying to people. I think what you do [00:19:30] want to show them is competence. You want there to be no question in their mind that their future is best suited with you. [00:19:40] 

Rob Balena: Many times for many large enterprises, that means they want to work with a large market leader because the risk is lower. And so your job as the founder, [00:19:50] the enterprise salesperson, whatever, is to convince them that you are the safest place for their destiny. And the reason is not because of your size, but it's because you're competent because [00:20:00] you know the path because you can get them to the other side, to what you're promising for them.

Rob Balena: And then through the sales process, that's a big part of qualification. And I've heard [00:20:10] the definition of qualification being like, knowing how you lose and uncovering it as early as possible. Well, if you're a tiny startup, one way you potentially lose is you [00:20:20] cast a big vision and you get a whole bunch of people really excited.

Rob Balena: And then you can't deliver because your product doesn't scale or you don't have the means to fulfill it. [00:20:30] And so part of qualification during the process is putting the customer in the mind of post implementation and having them with you [00:20:40] craft what that world looks like so that you and they both have a very clear understanding of what's happening.

Rob Balena: It's just sort of like a sales tool that I've always used throughout my career is a mutual action plan, and [00:20:50] there's mutual close plans and all these different versions of it. I think what I've found most effective is when you have a plan that is collaborative with the customer. It's something that you [00:21:00] pull up on the Zoom or you put up on the whiteboard with them together and you're both editing it in real time and that the end state is not the close of business because that really doesn't matter to the [00:21:10] customer.

Rob Balena: The end state is whatever implementation goal you've promised to them is achieved. And so, in my case at [00:21:20] TeamSense, we say, we reduce absenteeism and that reduction in absenteeism in your hourly workforce results in lower overtime costs, lower labor costs. The end goal is [00:21:30] that it's the seeing the costs of labor come down, it's seeing that crest and start to come down.

Rob Balena: That's the end goal. And that's what you want to track towards with the customer. If as early as [00:21:40] possible, you can start getting them in the mindset of what's the one gonna look like post implementation, they're gonna uncover for you very quickly. First we'll roll out to North America and then it'll be [00:21:50] the EU

Rob Balena: and you're like, Oh, whoa, whoa, whoa. We've never done business in the EU. Do we need to be GDPR certified? What are the things that we need to be aware of? And that will help you uncover the potential [00:22:00] pitfalls.

Andrew Kazlow: Where do you see inexperienced salespeople and, or entrepreneurs screw up in this process of casting that vision and [00:22:10] focusing on the outcome. What are some of the more common pitfalls? Maybe this pull the strings and get the quick win rather than focus on the long outcome like you talked about earlier. What are the common mistakes [00:22:20] that you see?

Rob Balena: I think being too short sighted and judging short or long sightedness on your customer's scale, not yours. The life [00:22:30] cycle of a VC backed startup is short and fast and furious and things happen very very slowly at large enterprises. And so when you say I'm playing long ball to [00:22:40] a large company that's 100 years old, that could mean a couple of years.

Rob Balena: So that's certainly one. I think, tailoring your pitch to that audience, making sure that [00:22:50] you are attaching what you do to a tangible impact and that those tangible impacts are impacts that matter to that customer. My favorite example of this at [00:23:00] TeamSense is we were working with a company called Kenco Logistics, their big third-party logistics company.

Rob Balena: We had deployed at a single site, just north of Atlanta. Very [00:23:10] successful initial deployment and we saw their absenteeism rates go down. They were struggling with absenteeism. Their absenteeism rates came down by 39%. And so we were like, Oh my [00:23:20] gosh, this is amazing. And so the seller and I, we went to the general manager and we said, Hey, will you broker a meeting for us with who is it on the executive team that cares?

Rob Balena: The VP of [00:23:30] HR? Is it VP of Ops? Who cares? And so he was willing to do that. He got us a meeting and we walked in with like some swagger because it's like, Oh my God, we had this amazing implementation. [00:23:40] We've got the GM and the head of HR for the plan just like singing our praises. And we have this measured impact.

Rob Balena: With the absenteeism dropped by 39%. Look at this beautiful chart. [00:23:50] And I remember the moment very clearly the VP of HR, she looks at me and says, uh, yeah, that doesn't matter. What do you [00:24:00] mean that doesn't matter? And she's like, well, it's, I need to understand the tangible impact. Like tangible?

Rob Balena: It's tangible. It's right there on the screen in front of you. More people are coming to work. It's a reduction in [00:24:10] absenteeism. It's not tangible unless I understand how it hits the P&L of that site. Show me that. Show me how it hits the P&L of the site. That's interesting. That's something that I [00:24:20] can take to operational leaders.

Rob Balena: But if we have the same throughput efficiency, and we're moving the same number of pallets from one side of the facility to the other, when absenteeism [00:24:30] is X percent versus Y percent, it doesn't matter unless it's affecting that outcome. So go show me that connection. Draw that line. So that's what we did.

Rob Balena: We went back, crunched the [00:24:40] numbers, and we found this deep connection between absenteeism and overtime costs. And then in their particular case, they were actually overstaffing [00:24:50] shifts to account for unplanned absences. So if the shift called for 100 people, they would staff 103, expecting that three people wouldn't show up unexpectedly, and then they've got a full shift.

Rob Balena: [00:25:00] Well, that resulted in a whole bunch of wasted money. Because if everybody did show up for the shift. Then you're having to pay usually a half day's wage to those folks and send them home or they're going to stay on your, and you're [00:25:10] paying them anyway. And so, we were able to show the reduction in those costs because of the reduction in absenteeism and that's what unlocked Kenco for [00:25:20] us.

Rob Balena: Then it was hair on fire. How do we roll this out to as many of our sites as we can? Because look it's a huge tangible impact to the P&L.

Andrew Kazlow: That's an amazing story. So [00:25:30] basically this completing the circuit, essentially. You guys had most of it, but you didn't take it to its final conclusion into what actually bottom line mattered

Rob Balena: If I can even put another turn on [00:25:40] it. Since then, and what do we do as a small startup? We're like, Hey, that worked once, boom, stamp it and let's do it everywhere. Well, not every company has the same labor practices that Kenco [00:25:50] has. Not every company cares about overtime the same way that Kenco did.

Rob Balena: Some companies are unionized and they're controlled by a CBA. And so they're, have requirements around [00:26:00] overtime or overstaffing that are independent of absence rates. And so, it's not just completing the circuit  and drawing that very clear line to a tangible impact, [00:26:10] but it's gotta be a tangible impact that matters to the customer.

Rob Balena: You can't just throw this into a white paper and blast it out to everybody and be like, all right, I'm ready to receive your deals. I'm [00:26:20] working with another customer and I won't mention their names. They're not a referenceable customer quite yet, but, they make household items and they have a goal [00:26:30] for each shift and it's called their million thing incentive, this thing that they make. They want to see if they can make a million per shift. And if they [00:26:40] make a million per shift, then that shift gets an incentive, right? And as I'm speaking with the leaders at this site, and I'm trying to understand what are the [00:26:50] metrics that matter to you?

Rob Balena: What are KPIs that we might affect that are going to resonate with folks? And I tried on the overtime thing. I tried on the overstaffing thing. And they're like, well, you know what? It really is. We [00:27:00] haven't hit the million thing incentive in months. Like we used to do it consistently all the time, but since absenteeism went up, we're having trouble.

Rob Balena: And I was like, guys, [00:27:10] that's the thing. If we can implement TeamSense, reduce absenteeism, show better engagement with the workforce. But if that then results in you hitting [00:27:20] that incentive more consistently, if I go tell that story to corporate, are they going to know what that is? Like, Oh yeah, that's their thing.

Rob Balena: They say that all the time. The million thing incentive, right? Great. That's the story I want to [00:27:30] tell.

Andrew Kazlow: As you're talking, it sounds like finding message, the actual thing that's important that top to bottom people care about, like CEOs, all their [00:27:40] broad messaging. But what's the thing that actually filters all the way through the organization. That's what you have to connect the sales message to in order to really get top to bottom buy [00:27:50] in

Rob Balena: What's the thing that when you say it out loud, everybody rolls their eyes because they hear it at every all hands. If you can connect to that. An example of this is we did this at Dell at Cloudera, we [00:28:00] found a series of blogs by their CIO and it was called Dell on Dell and he would on a regular basis share stories about how [00:28:10] the finest examples of the use of Dell hardware and Dell products was inside of Dell IT.

Rob Balena: They wanted to be the lighthouse customer for all the products that they sold. And they said, Hey, [00:28:20] customers, Dell customers, do you want to see what great looks like? Look at how we use our own stuff internally. Dell on Dell was his thing. And so we found that and we started saying that around [00:28:30] the office at round rock too.

Rob Balena: And everything right. Dell on Dell, people would roll their eyes, people would roll their eyes. But that was how I got my initial beachhead was because I got into a room with some [00:28:40] detractors and I said, you know, I've been reading this blog, Dell on Dell. And I got to ask you. I know because there's a partnership between our companies that you recommend to your [00:28:50] customers that they use Cloudera on Dell machines, but you're not doing that internally.

Rob Balena: So help me understand why we're not doing Dell on Dell here. [00:29:00] Shouldn't we be able to tell your customers that the largest, most successful deployment of Cloudera on Dell hardware is inside Dell IT. And that was that was the the [00:29:10] the banner that got folks charged up enough to take a shot at putting up putting us in in spite of it being a competitive account

Andrew Kazlow: Rob, I'm listening to you. I'm [00:29:20] a founder. I'm like, Oh my God, I need this guy. Okay. Or somebody like him on my team, because that was amazing. Like those stories, let's say I'm a technical founder or [00:29:30] I'm just not a great communicator. I don't see myself in the sales seat long term. You talked a little bit about this earlier.

Andrew Kazlow: How do I convince somebody like you to come work for me?

Rob Balena: [00:29:40] The vision is important right the story that you're telling is important don't over rotate on that Um, don't don't believe that that will necessarily get someone on board that [00:29:50] also has financial goals for themselves and career goals. I think finding good salespeople is one of the hardest things in the world.

Rob Balena: Sellers are notoriously [00:30:00] great in interviews, right? They're good at selling themselves. And I know many sales leaders that have just been so excited about a new person on their team and the [00:30:10] person gets in to see. And for whatever reason sometimes it's not even that they're they're bad salespeople.

Rob Balena: It's just maybe, it's not a fit. There has to be a fit between the seller and who you're selling [00:30:20] to. I think if I can offer a couple of things I would say, look for someone that either has some history being at smaller companies [00:30:30] because they've got that experience of wearing different hats and trying different things and being disruptive or look for someone that's been at a larger company.

Rob Balena: Nothing wrong with larger companies. In fact, the enablement [00:30:40] and training at a large company is amazing. Especially, if someone's right out of school, right out of college. I went to work for a startup in sales. I didn't know what the heck I was doing. They tossed me into a [00:30:50] territory and that was it.

Rob Balena: Like I had to figure it out. There is fantastic training and enablement at larger, more established companies. But you need to find somebody that has that [00:31:00] entrepreneurial mind and hat wants to be innovative and disruptive. And maybe probably chafes a little bit at the organizational structure and the red tape because they want to do things that [00:31:10] are new and different.

Rob Balena: One of the biggest challenges for me going from Gazzang, which I think at the time of acquisition, we were 65 people or something to Cloudera and at the time it was [00:31:20] when they acquired us, we were 600 and then I stayed with them. I don't know how big we got, but thousands. At Gazzang, I'd be working on a deal and put the phone on mute [00:31:30] and bang on the wall to Larry Warnock, my CEO, or Patty Sock, my CFO, and be like, Hey, what about this?

Rob Balena: Can we do this? Yes, go for it. Right? Um, and, And here at TeamSense, [00:31:40] I'm blessed with a leadership team that they trust me to find the balance between advocating for my customer and protecting the company. And they give me [00:31:50] a lot of leeway to find a path forward within that. You don't get that freedom and autonomy at a large company.

Rob Balena: And so if you find someone that enjoys that and can do [00:32:00] it responsibly that's a great thing to do. I think that the absolute best thing to do when you're evaluating sellers though is get them to tell you stories because storytelling is such an [00:32:10] essential part of sales. You want to understand if they can succinctly tell you a story that's compelling, that has a moral at the end or a lesson that they [00:32:20] learned.

Rob Balena: You want to know that they have intimate knowledge of the inner workings of a deal. How they got in, how they pitched, what was the vision that they cast for the customer? And then what was the [00:32:30] nuance of contract negotiations and pricing negotiations and how did you do that? I don't want somebody that's never been through that, right?

Rob Balena: If I'm doing that for the first time at a startup. And then another question [00:32:40] that I like to ask is tell me who the best salesperson you've ever met is, who's the best salesperson you've ever met? And that will illuminate for you what this [00:32:50] person values and who they want to be like.

Rob Balena: So if you say, who's the best salesperson you've ever met? And they say, well, I want to be like Rob, because he was the top [00:33:00] salesperson and he made the most money. Okay, fair, fair answer, but that lets me know that you value like your own performance and earnings [00:33:10] above everything else. I asked that question one time and the person literally answered me,

Rob Balena: I'm the best salesperson I've ever met. I was like, all right, this conversation is pretty much over. I don't need to hear anymore. I don't [00:33:20] think. I also asked that question one time to a candidate and they said I forget her name, mrs. Smith. And I said, who is Mrs. Smith? And they said, my third grade teacher.

Rob Balena: Why [00:33:30] is she the best salesperson you've ever met? Well, she got me excited about school. Up until third grade, I couldn't care less. And she was the one that convinced me that it was  to apply myself in school. And I was [00:33:40] like, Oh my gosh, what a cool answer. And what does that tell me about that individual?

Rob Balena: That's the kind of person I want on my team. Somebody that sells through inspiration and because they truly [00:33:50] want their customer's lives to be better. And they believe that that can happen through software.

Andrew Kazlow: Let's flip that around. What are some of the questions that you would ask the CEO [00:34:00] that you're interviewing with? If let's say you're a sales killer, you've got all the chops, all the right options. What are some of the key burning questions that you'd actually be focused on [00:34:10] asking of the CEO?

Rob Balena: I need to know what stage the company is in truly. Do you have product-market fit? Is this a, okay, we've figured it out and we're scaling kind [00:34:20] of motion. Or is this a, we don't have it. like we, we, We need to figure out even what resonates with customers and there's going to be a ton of experimentation.

Rob Balena: [00:34:30] That matters. It's going to be a very different experience for a seller. If you're handed a playbook that you have relative faith is going to work and your job is [00:34:40] simply to execute at a high level. That's a very different role than, hey Rob, come help us figure out how to sell this thing.

Rob Balena: We've got this thing. We know there's something there. It's [00:34:50] investable, but - we haven't quite cracked the nut on how to get companies in on it. That's not a bad thing, but as a seller I need to know that. I need to know what I'm walking into because that's a very different [00:35:00] role. In a lot of experimentation and figuring things out, I would want to know. I think there's some logistical basics.

Rob Balena: How is the product licensed? What does the [00:35:10] contract look like? I want to know that I'm going to be representing something that's easy to do business with. That we're just the buying process is not a hindrance to me making sales. [00:35:20] It's hard enough for a startup to get deals done.

Rob Balena: But when you have an onerous contract or a licensing structure that just doesn't make sense, not aligned with how people buy. That can be [00:35:30] challenging. And then, I think I also want to know what's coming next? The advantages of going with a startup if I'm [00:35:40] a large enterprise is innovation. It's potentially getting to influence or be part of where that company goes. It's [00:35:50] getting a competitive edge that I can't get somewhere else.

Rob Balena: And so me as the seller, if I'm going to be selling that message to a large enterprise, I [00:36:00] need to have confidence that the company is aligned to that. That we've got a technical organization that is going to be listening to the market. They're not creating things [00:36:10] just for the sake of creating them or because they think they sound cool.

Rob Balena: They create things that customers want to buy, that they're listening to customers. One of the very first things I did when I got to TeamSense [00:36:20] was I had what I called "sell to me" sessions and so I had our CEO, our CTO various folks that I would bring into [00:36:30] deals to drive consensus and create executive alignment. I wanted to see how they would do in front of a customer and if you've been selling for any period of time for startups, you know that [00:36:40] there's some folks that aren't great in front of customers and that's okay.

Rob Balena: Like they have other value to the organization, but as a customer representative, I want to know exactly who I'm bringing into my customer. I want to know exactly what [00:36:50] kind of experience it's going to be for them. And so, I would attempt to suss some of that out even in the interview is, is this an executive team?

Rob Balena: Is this a team of [00:37:00] leaders that I know I can put in front of a customer and it's going to increase credibility and it's going to add to my chances of winning? Rather [00:37:10] than make the customer kind of look sideways and think, Oh, like, are these folks for real? Can we trust them? It's so much of selling to a large enterprise from a startup is proving credibility and trust.

Rob Balena: And [00:37:20] so that, that would be a big part of it.

Andrew Kazlow: Love it. Super helpful. Rob, I want to ask about the season of life post Cloudera, but before your next thing, I [00:37:30] was reviewing your background and noticed you took a season of sabbatical. I'd love to just unpack that. A little bit. I don't see leaders often do that. But I have a lot of [00:37:40] respect for it because, and we only get one life and taking time off to highlight like what's important and reorient, I think is just such a wise thing to do [00:37:50] seasonally.

Andrew Kazlow: So I wonder if you could just tell us more about that season. Why did you do that? And what stood out to you during those months?

Rob Balena: We could have [00:38:00] several podcasts about that. I will attempt to give you a succinct answer. The shortest way to share it is, Cloudera took a very large investment from Intel and [00:38:10] Intel was a very important part of our investment team. There was a policy at Intel and I believe I'm getting this right.

Rob Balena: If you had been at Intel for seven years, you were able to take a seven week paid [00:38:20] sabbatical. And so when we took the investment, one of our founders, Mike Olson said, this is a great idea. Let's do this same thing at Cloudera. And so if you've been at Cloudera for [00:38:30] seven years, you can take a seven-week sabbatical.

Rob Balena: And, you know, They had backdated my start date to when I had started at Gazzang pre- acquisition. And so, I've got this sabbatical coming up. I wonder what I'm going to do with it. And then [00:38:40] as chance would have it, I have four children. During the birth of my fourth, there was a complication and my wife had a medical emergency that required a lot of care.

Rob Balena: [00:38:50] And so, I ended up using my, my seven-week sabbatical mostly to care for her. It wasn't quite the you know, trip to Europe kind of thing that we were hoping [00:39:00] for. Which was great. What a cool thing that like, the company allowed me time and space to do that and everything but the sabbatical wasn't what we expected so when it came time [00:39:10] for me to leave Cloudera, Cloudera had changed a lot.

Rob Balena: It had grown we had merged with a competitor. We were headed for PE and so I decided okay, I think I think i'm gonna go find something different but I'm not sure what to do next and [00:39:20] oh I said, well, you know, we never got our sabbatical. Maybe we take a sabbatical and I said, okay Let's do it.

Rob Balena: So that was I think it was November of 19. We decided to take a [00:39:30] sabbatical that would kind of take us into the new year. Once the new year starts, then I'll go find a new job. And so it was great. I checked a whole bunch of things off my list. I [00:39:40] invested in time with friends, I got to be with my four children and my wife and I did a lot of focused time on our marriage and just making sure that we were headed in the direction that we [00:39:50] wanted to be both like professionally and as a family.

Rob Balena: That those were the inklings of things that started that eventually led to me relocating to rural Tennessee, [00:40:00] which is another interesting story. But get into the new year, it's 2020 then COVID hits and suddenly all four of my kids are at home. And I'm like, okay, I gotta, like, I can help out [00:40:10] with this.

Rob Balena: I've still got a little runway left. And so I was educating my four children in the spring. And then it was that late that spring when I started sort of moonlighting doing some [00:40:20] individual coaching, some connections that I had in the Austin area had asked me like, Hey, would you do this on the side?

Rob Balena: I know you're taking time off and found I really enjoyed it. And eventually led to me starting a business [00:40:30] around it.

Andrew Kazlow: Amazing. And when we spoke previously, you mentioned that after a while, you just realized you kind of missed being in the game a little [00:40:40] bit. And I wonder if you could say more about kind of that self-awareness exercise during that season. And as you got into the coaching world, talk to me about [00:40:50] your mental process of just realizing that about yourself and what led to your ultimate decision to sit in the seat you're at now.

Rob Balena: My wife and I have a concept of [00:41:00] checkpoints and the idea is whenever we make a major decision, we set a checkpoint in the future. And we agree that at that checkpoint we are going to like [00:41:10] from the foundation soup to nuts assess is this the right decision? Is this where we want to go?

Rob Balena: But until then we will not doubt our decision unless there's, you know, some sort of catastrophe or [00:41:20] something. And that very simple system has like allowed me to weather some really big, professional and personal storms that have ended in really [00:41:30] good things on the back end. Gazzang was a great success story.

Rob Balena: You had Larry Warnock on the podcast a few weeks ago He was the CEO at Gazzang. It was not all sunshine and lollipops. like we We did you know market [00:41:40] pivots and there were changes in sales leadership and all kinds of goofy stuff that any wiser man probably would have jumped ship at some point.

Rob Balena: But I had a checkpoint where I was like, I'm sticking with this thing until [00:41:50] they fire me or until we hit the checkpoint. So, started the business, loved doing Differential selling. That was the name of my business. And it was individual sales coaching for [00:42:00] enterprise sellers selling from startups to large enterprises. And then I did, you know, workshops for, for sales kickoffs and things like that on the side. Amazing, fun, very [00:42:10] stimulating. It was a lot of thought work and very creative process. But as I finished my second year rounding into the third, our checkpoint was at the end of the year.

Rob Balena: And so we were [00:42:20] sitting down to talk about it and I was like, ah, I'm a little antsy because I spend all my time talking about doing this thing that I love and I don't really spend any time doing [00:42:30] it. I wasn't selling giant enterprise deals of enterprise selling. I was selling, relatively small deals of these engagements for coaching

Rob Balena: and it was usually with one stakeholder, the sales leader or the [00:42:40] CEO of the startup I was working for. I was like, I spent a lot of time talking about what I'm doing, but I don't actually do it. And then quite frankly, I hope I don't embarrass him, but Adam St clair, who's here at [00:42:50] TeamSense, he was one of my coaching clients, and our engagement when I was at Differential was I loved all my coaching clients.

Rob Balena: He was special. We built a really [00:43:00] special relationship and I found myself as we were sort of nearing the end of that engagement being like, Oh man, like I want to spend more time with Adam. I want to go watch him put [00:43:10] into practice the things that we've done and I want to see the fruits of his labor.

Rob Balena: In my coaching, I did a lot of hands on stuff with folks and we listened to calls together and we would spend time, but it wasn't appropriate [00:43:20] for me to like go on site to a customer with my clients. And so I was like, man, I want to go with Adam. I want to see him in action on a customer site. That eventually had that conversation with my [00:43:30] wife and had a kind of an open conversation with

Rob Balena: Sheila Stafford, CEO of TeamSense and said, Hey, I'm thinking about turning off my business and going to be a head of sales somewhere. Because I [00:43:40] have this desire. I have this feeling that I want to go do. And she said, would you consider TeamSense? And so one thing led to another. And here I am.

Andrew Kazlow: Amazing. Well, you talked about storytelling earlier. You've certainly got that [00:43:50] down. Talk about what you have been surprised by as you've double clicked over the last couple of years in this role leading a whole [00:44:00] team. kind of this I think you've got six people under you, seven. 

Rob Balena: The whole go-to market team today is, 5-6. There's a whole story here. So sales [00:44:10] leadership is hard. It's really hard. And like I, Having done this role for 18 months, it was like, Oh, I suddenly have so much [00:44:20] more respect and empathy for those sales leaders that were trying to get me to fill out my forecast or nailing me because I didn't have the CRM updated.

Rob Balena: And I was like, now I get it now. [00:44:30] Now, I'm not just the free and loose sales guy that does whatever he wants. It was also challenging too, because. I I was never a just a frontline [00:44:40] manager, most folks they're a seller. And then if they want to go the management path they're going to be, like a regional director or something.

Rob Balena: And I went straight to the top sales job at a startup. I don't [00:44:50] think that I appreciated the amount of time and focus that it would require of me for things like, building out process and building out a [00:45:00] CRM and understanding the operations. I did that with mixed success for sure.

Rob Balena: And actually it eventually led me to late spring, [00:45:10] early summer where I've got a fantastic relationship with my CEO, Sheila, and just sat her down. I was like, Sheila, I miss selling. I miss being in front of customers. And I [00:45:20] thought when I took this role, it was like, Oh, I'm going to spend all my time coaching my team and being with customers.

Rob Balena: I spend way less time doing that than I thought. And there's this whole other side [00:45:30] of the job that TeamSense requires that I, I don't enjoy. And I don't really think I'm particularly good at. I've worked for other sales leaders that I know are excellent at instrumenting [00:45:40] a business and creating process and enforcing process.

Rob Balena: And she's such a fantastic leader in that she like really understands a [00:45:50] person's strengths and weaknesses and gives people space to figure that out. She was willing to let me decide to take a role being a strategic seller at TeamSense. And so I [00:46:00] moved into that role in the fall and have been doing that since then.

Rob Balena: And got to be part of the team that found my replacement. And he started just a couple of months ago, James. I am, [00:46:10] honestly, love in life a little bit because I get to do the thing that I'm really passionate about, which is go be with customers. I do miss coaching my team and Adam [00:46:20] and Ramil and they're still on the team and we're peers now.

Rob Balena: I miss spending time with them. I spend far less time with them now than I did since we're peers, but I do not miss the spreadsheets and the [00:46:30] process and everything else. I do find that I'm so passionate about being with customers and walking alongside them. The role was exactly what I hoped it would be.

Rob Balena: It was a chance to [00:46:40] try something new and build new muscle and experience something firsthand. We've got great investors who, Brett Queener one of our first investors from Bonfire Ventures. And he [00:46:50] spent regular time with me, coaching me and mentoring me and giving me space to mess things up.

Rob Balena: And very grateful for that relationship. If nothing else, it got us 18 [00:47:00] months further down the road at TeamSense with a bit of success to hang our hats on and really helped me hone in on what I'm passionate about and what I love to do. So grateful to be able to do it here.

Andrew Kazlow: Well, Rob, I'm certainly [00:47:10] grateful for your time today, sharing some of these insights. This has been fantastic. We will wrap things up there. But I very much look forward to staying in [00:47:20] touch and our next conversation.

Rob Balena: Likewise. Thanks so much. 

Andrew Kazlow: Thanks for listening to this episode of the diligent observer. I'm your host, Andrew Taslow. And if you're [00:47:30] looking to make better bets as an angel investor, subscribe for more at the diligent observer dot sub stack. Dot com.