S02E33: Robert Wahbe, Highspot

Russ: [00:00:00] Thanks for downloading the 27th in our series of episodes of the csuite podcast that we’re recording in partnership with the European PR agency, Tyto and their own Without Borders podcast, where we are interviewing leaders of unicorn companies to find out about the key issues, pain points and challenges that start-ups face and how they can address them with a strategic approach to marketing and communications. My name is Russell Goldsmith and my co-host for this episode is Tyto’s Senior Partner Holly Justice. And today we are thrilled to be joined online from Seattle by Robert Wahbe, Co-founder and CEO of sales enablement platform Highspot. Founded in 2012, Highspot has raised a total of $648 million, with a valuation of $3.5bn. Welcome to the show, Robert. Can we start by you giving us a bit of background to your company?

Robert: [00:00:50] So Highspot is in the sales enablement space, as you said. We are a global software as a service platform, and we have data centers and customers in Asia-Pacific and Europe and North America and people partner with us and use Highspot to improve the performance of their sales teams. And so how does one do that? Well, how would one improve the performance of any team, let’s say a sports team? You need to equip those people with the right resources and the right place. You need to train and practice before you get on the pitch. You need to coach during and then watch the film afterwards, analyse what’s working and what’s not working, hopefully have hypotheses about how you might want to change. And then you would reequip, retrain and re coach. So, what our platform does is for customer facing teams such as sales, services and support, we help you equip, train and coach your people so they have more effective conversations. They can drive their business goals more effectively.

Russ: [00:01:45] Clearly, a time where you guys are rapidly growing but and listening back through what you were just saying there and describing how the business works, why is now the time for sales enablement?

Robert: [00:01:57] Well, you know, it’s a funny thing. It’s in some ways the oldest new category out there. We’ve been talking about how can you enable people? How can you enable sales for decades? But what’s happened in the last ten years or so is that we’ve had technology advance such that you can now approach the problem in a very different way with the advent of the cloud, with the advent of mobile technologies, with the advent of artificial intelligence being really democratized by the big players. You’re now able to apply a different set of features, a different set of capabilities to really make that happen. If you think about it, making your people most effective is one of the biggest strategic levers you have as a leader, as a CRO, a chief revenue officer, a chief marketing officer, a CEO, the board of directors. So, it’s always been a critical thing. It’s just that in the past, a lot of people have thought, well, I would love to help my people be more effective, but I don’t really have the ability to change what they’re doing. I don’t really have the technological ability to drive change in the ways that I want. So, what I’m going to do is I’m going to hire a lot of people, I’m going to see who sinks and swims. I’m going to have a lot of churn. Sales is in some ways infamous for the level of change they have in terms of people coming and going into the business. And therefore, that’s going to be my strategy because I don’t have another strategy. The fact that you can now decide that you have a set of strategic initiatives that you want to drive, let’s say you want to improve your win rate or you want to improve cross-sell or you want to land a new methodology, or you have a competitor that’s really surging and you want to do something about that, whatever that key thing you want to do to change your business rather than just throwing it out there, and that’s why most initiatives fail and then hoping that some people will get it and a lot of people won’t. And then you’ll have all this churn in your organization. Now you have a set of technological tools to actually implement that change on the front line so that people drive those initiatives, and you can do what you want to do in terms of the business. So really, it’s that technology can now be applied if you apply it in the right ways. And so, from our point of view and from the categories point of view, it’s two things. And this has been true for every major technological shift in marketing and sales technology. It was true for marketing automation ten years before this. It was true for CRM, the customer relationship management, ten years before that. It’s a lot about the technology and as a vendor, obviously we care deeply about our product and the features and all of those things, but it’s also about the best practices and methodology to use all that technology to help equip, train, coach these reps. And so, there’s a lot of additional things that one has to do on top of it. But that’s why the time is now for this category as it emerges into must have, because people have realized and many, many industries now have so many people that are using enablement that, oh my gosh, I can have a brilliant insight about how to change the business and I can get my 100, 1000, 10,000, 100,000 reps around the world implementing that change so I can drive the business. It changes everything about your engine, about your revenue engine. So, it is a really important must have in the coming years.

Holly: [00:05:03] One thing that will be great to hear from you is a little bit about your personal history as a company leader. Could you tell us a little bit about your entrepreneurial journey?

Robert: [00:05:15] Yeah, so I started a company way back in the late nineties. I was getting my PhD in computer science at Berkeley, and if you were getting your PhD at Berkeley or Stanford, which are two universities right close together with a rivalry on the West Coast in the United States, you clearly started a company. That’s what everybody did back then. And I, like everyone else, followed suit and started a company which got acquired by Microsoft very early in its journey. And the goal was to go to Microsoft for a couple of years. If you could go back to the late nineties. Microsoft was the gold standard of software companies at that time, and there weren’t the Googles and the Amazons and the Salesforce and all these other very, very large technology companies. So, the goal was to go there for a couple of years, learn the ropes from the very best, and then go back and do another start-up. I was there for 16 years, did a lot of different things. Most of my journey at Microsoft was in the product and building a lot of core technologies and Windows and other areas. But for the last three years, I actually was the CMO under Satya [Nadella], who’s now the CEO of Microsoft when he was the president of one of the major divisions, about a $20bn division back then, now a much bigger division. And it was in that role, cutting it fairly fresh from an engineering point of view, looking at marketing, looking at sales, looking at sales enablement, and realizing that so much of the stuff that we were doing at headquarters, and this was a big operation, hundreds of marketers, hundreds of millions of dollars of budget, tens of thousands of salespeople around the world. So, it’s a big, complicated operation, no doubt. But what became clear is that so many of the things that we were doing at headquarters, the new content, the new positioning, the new campaigns, the new programs, they simply weren’t being absorbed by the people on the front lines. I used to travel a lot in that role, hundreds of thousands of miles. And I would land in a subsidiary. I’d land in France, for example, and I would say, okay, what can I do to help from headquarters? And they would inevitably say, ‘oh, I need positioning A, I need content, B, I need program C’ and 99 times out of 100, I’d be like, we did that seven months ago, we did that five months ago, we did that four months ago, we did a webinar, we sent out email, we did all of these things. And yet it wasn’t landing effectively. And so, the question and why we started Highspot was could these broad macro technology trends, cloud, mobile, AI allow us to change that dynamic so that the things that people were doing from marketing, from enablement, from sales leadership, could those strategic things they were doing actually really effectively land with the front line, whether it was sales, services or support? And that’s why we started Highspot in 2012. And we’ve been we’ve been on that journey ever since.

Holly: [00:08:04] And as you’ve just alluded to, that you’ve now been leading Highspot for over a decade. What are you most proud of?

Robert: [00:08:12] Well, two things. One of the things that we talk a lot about is delivering breakthrough products, products that really push the edge, that transform the way millions of people work. So, we get very excited about can we have a broad impact? Can we build the company for scale? We have a thing we like to talk about, which is the airplane test. Can any of us anywhere in the world get on an airplane, sit next to somebody? And the odds are they are either a Highspot user, a Highspot customer, an executive that has sponsored Highspot, who have used it for their strategic initiative. They’ve used it to make their team better. We want to get to that level of scale, to have that impact. And we have been relatively successful so that we do somewhat pass the airplane test now. And we do get to talk to some of the best companies across the world in different industries. And I find that incredibly satisfying when an important company that I respect says, ‘hey, you are helping us achieve our goals’. That’s just a wonderful thing. That’s piece one. And then piece two is I love the people side of our business. We have a really supportive, collaborative culture. I love to see people that have started out as interns who then became early in career hires and who now are the leading enterprise rep or the leading services person in the organization or a really incredibly senior product person. I love that kind of success over our people. So that’s the other piece of it. So, one of it is on the customer side and one of it is on the people side internally. The thing that’s fun about our business and this is something we didn’t predict; it wasn’t like we planned it. But the really fun thing about our business is those two things are very deeply connected in the following sense. We consider ourselves a people first company. We think about three big engines the people engine, the product engine, the customer engine. And the idea is if you don’t have the right people, you can’t build the right product, you don’t have the right product, you can’t deliver the right customer experience. You need all three of those engines working and it’s people first. Well, it turns out that is the service, if you think about it, that we’re delivering as a vendor to our customers. It’s all about their people. It’s all about the rep, it’s all about the customer service agent, it’s all about the support person. It’s all about they’re putting their people first and making them more effective. So, the notion of people first is a steel thread through both our internal company, but also what we serve to our customers. And so, it’s a very inspiring thing for us to get to think about people and empowerment and tools and how we make them more effective in their jobs.

Holly: [00:10:49] And I can’t ask a question like that without also asking the flip side. So, I suppose what’s been the hardest moment over those last ten years for you?

Robert: [00:10:58] Well, you know, we, like everybody, have that wonderful existential moment early in the journey where, you have this hypothesis, you build product in our case, for a number of years because we really came out with a fairly complete enterprise scale solution, and you launch it to great fanfare. And then instead of having thousands of customers, you have three or whatever it is. And so, the question of those early days, which is really different from coming from a big company, is in a big company you’re mostly optimizing your go to market. And now at Highspot scale, we’re mostly optimizing. We’re asking the question; how can we do a little better? Whether it’s the product, whether it’s our go to market motion, whether it’s our post-sale support, whether it’s entering a new geography, those kinds of questions. But in the early days, everything is a variable. You’re not trying to optimize anything. You’re trying to get anything to work. And those early months, you’re like, okay, why isn’t it working? And then all the questions are on the table, which can either be fun with the right attitude or can be completely terrifying, which is okay, is it the product? Is it that I have the wrong go to market in terms of sales and marketing? Is it that I have the right product and the right go to market and yet people aren’t willing to take the time or the money to buy this service? So, it’s not enough of a problem. Is it, I’m in the wrong industry, the wrong sector, talking to the wrong persona? There are so many variables. And so, for those early months before you start to get traction, I think those were for me, the hardest times because it wasn’t clear what the next action was. It wasn’t clear what the get-well plan was. Now we started tweaking things as you would, the category, the messaging, the persona that we were targeting. And then we found that good product market fit with the right go to market. And then we’ve been on a wild ride ever since. But those first few months, right after the product is launched, is that for me at least, was the hardest.

Russ: [00:13:01] So we’ve talked about those ten years leading up till now. I mentioned in my introduction that your latest round of funding took you to a post-money valuation of $3.5bn. So, I’m keen to find out what’s next then. So, what’s the focus for, let’s say, the next 12 months or maybe beyond? Where’s that money going to be invested now?

Robert: [00:13:20] Yeah, so that money is going to be invested across the board. The journey that we are on is a dual journey. Part of our journey is to help the category. Just forget Highspot for a second. Forget our competitors for a second. The category to be understood as both a must have category and a strategic category. If you ask the average head of sales, head of marketing, CEO, board of directors about enablement, you’ll get a couple of answers. If you ask them a question such as, are your people important and should you enable them, they’ll roll their eyes and say, ‘of course’. Who would ever say, ‘No! I don’t think that’s important at all.’ Of course, it’s important. So, in their head, they do understand that their people are the key strategic lever, because at the end of the day, all the results of the business are delivered by that front line, especially in sales and services and support. But then if you ask in their heart, how are they acting on that belief? The answer is less clear because they’re not often investing as much as they probably should be in enabling and helping their people be productive. And so, they think about enablement as some very important, somewhat tactical things they have to do. For example, they have to manage all of their marketing and sales collateral. It’s a big, big, big job. Many of the larger companies have 50,000, 100,000 pieces of collateral that they have to organize and help their reps find. They think about training like onboarding and ongoing training, those kinds of things. They think about sales, kick-off events. They think about some very important, isolated things. But what they don’t yet understand is that if you take all those things and you bring them together and you equip train and coach with the right analytics, you actually now have this this strategic lever between I have a dream, I want to do more cross-sell, I want to implement a sales methodology. Whatever dream you have and the implementation of that dream by your front line. That becomes this incredible strategic lever. So, at one level, the journey over the next 12, 24, 36, 48 months is helping people understand the category and really what it can do. And we have big investments. We have the largest society of sales enablement professionals, what we call sales enablement pro, to really help not just elevate Highspot, but elevate the category. And this is both about what are the best practices and methodologies, but it’s also about making sure that function, which is a relatively new function both in Americas, in Europe and Asia-Pacific, it’s relatively new function, getting that function to have a seat at the table in the same way that if you go back 20 years getting sales operations with respect to CRM to have a seat at the table. So that’s piece one and then piece two is to make sure we win that category. So, we want to make sure the category is strategic and must have, and then we want to make sure we’re doing everything we need to be doing from a product point of view and just as importantly, from a partnership and best practices point of view to be the very best partner to be in that category. But really, we need to do both things. And this is true of any emerging category. Categories need to be nurtured until they become must have. And then one has a set of vendors that are going to compete within that category.

Russ: [00:16:38] Is there a particular size of business that, you’re talking about growing the category and having that seat at the table, at what point in a business’s growth lifecycle, should they be talking to a company like yours?

Robert: [00:16:50] It really depends on a little bit on the industry and how it’s being driven. But a rule of thumb is once you get to about 30, 35, let’s just do sales for a second, not support, not services. If we just focus on sales, once you get to about 30 people or so, you now have enough complexity that it’s probably hard just to walk either the physical or now the virtual halls, to understand, are they doing what they need to do? Are they fully enabled? Are they having the right conversations? Are they running the right plays? Are they using the content as we had hoped? It gets a little bit hard because at 30 reps, you probably have maybe hundreds, maybe even thousands, but at least hundreds of pieces of content. So now the problem is relatively complex. So that’s where for us we start. And then it goes all the way up to we have customers with hundreds of thousands of pieces of content, thousands of different sales plays, thousands of different training and courses, coaching, all of that, and literally tens of thousands of reps around the world. So, all the way up to the Fortune ten, basically in different industries.

Holly: [00:17:54] And just coming back to the topic of leadership, are there any individuals that have had a significant impact on your development as a leader? And if so, who has it been and why?

Robert: [00:18:05] Yeah, I would say a couple of things. One is I basically worked at one large company for many years, and I had the great fortune to have many great managers and bosses that I learned from. Satya Nadella, who’s now the CEO, was my manager for many years. Eric Rudder, who’s the chairman of an important start-up here in Seattle called Pulumi. Bob Muglia, who was the CEO of Snowflake, was my boss for many, many years. The list goes on. So, I clearly took a lot from all of those people and all of those configurations. And it’s not just from my managers or my managers’ managers, but really from a set of really interesting expertise across the company. But the other thing that I do is I get the luxury, if you will, of talking to a lot of leaders across our customer base, across our partners, across our competitors. And so, I talk to those folks all the time and I learn a lot from them. And I, I don’t know if I would call it reading, but I skim a lot of stuff. So, every book that comes out every post-mortem about a company’s journey. So, I do a lot of that trying to take away those nuggets that would might be helpful for Highspot or helpful for the for the business world. So really try to take a broad swatch. What I don’t do is adhere to one particular methodology, one particular way of doing things. There’s no easy answers here. And what’s interesting is there’s almost no right answers either. So, one of things I do and again, this is a wonderful thing for us. Let’s say we’re talking about how we should structure our own sales team. Well, I can talk to basically the leaders in the Fortune 100 of all of our customers, and they really are generous with their time. And I can say, think back to when you were our scale. What would you do differently? How would you structure the sales team on this one dimension? And I can talk to a lot of companies, and what has become really clear from those conversations is that they all have very strong opinions, very well-reasoned. They have deep reasons about why they did things in certain ways. And what worked and what didn’t work. And if I talk to 30 of them, there’s 35 answers. So, there is no like, ‘Oh, this is the way you do it and it always works’. It’s you have to weigh all the different factors that are going on. And the other thing that makes it so hard, which is also become clearer, is that things that work perfectly at a particular stage of the company or a particular macro environment like the economic downturn or what have you, are enough that you have to keep changing that. So, it’s not just about can I find the right formula for all of these different dimensions, but how do I evolve that quickly, which comes back to enablement. So, in a world where you basically inherently are going to be changing your approach to product, your approach to go to market, your approach to servicing your customers, all of that, if that is inherently going to be changing, then you better have better need some way to implement those changes. And this is what separates great from good companies is can they be resilient; can they ride with the tide and make those changes? And you need technology like Highspot and enablement to do that.

Holly: [00:21:14] And clearly in the last decade, you will have had lots of tides to ride. And as part of that, not only will of the technology have played a role, but so will leadership skills. And I guess I’d be interested to know from your point of view, what do you think is your greatest strength, but also for the wider Highspot management team, where do the strengths lie in the rest of the team you work closely with?

Robert: [00:21:40] One of the things that I try to do is understand the details, not to micromanage. This is something I have to say. This is something I definitely learned at Microsoft. And as I talked to other companies in the technology space, this is a somewhat common theme, but less common in other industries. In some sense, a notion, especially among senior leaders, that they are focused on strategy, and that is important. You have to be focused on strategy at some level. But you also have to understand, is that strategy, how is it playing out in the real world, whether it’s an internal strategy about your people or it’s a strategy that’s going to impact your customers or your partners? And one of the things that I like to do is get enough into the details to check if I understand and if the company understands how it really is landing in the real world. And so, I can remember so many stories where someone’s talking at a high level. Maybe they’re talking about their wonderful channel partners, and they have 100,000 channel partners, and it’s a fantastic program and it’s an amazing thing. And they talk about all the numbers and then somebody in the meeting goes, you know, and they just try in the meeting to become a channel partner and log in to the system and sign up for the system and find that it’s basically this tortuous process. And that’s the kind of detail that brings down like, are we really delivering what we are saying we’re delivering? And I think that’s a really important thing. So, to me, great leaders are able to fly at all altitudes as needed. If the business is doing great, maybe they fly at that strategic level. But if the business is not doing as well in a certain dimension, can they keep going down to more and more levels of detail to help support the business? I’m personally and I think the broad management team here at Highspot, it’s not about inspection to drive certain behaviours per se, it’s about inspection so, we have a common understanding of what’s working and what’s not working and then supporting the team, whether it’s setting clear goals, setting clear roles and responsibilities, setting a very clear get well plan, whatever the support is, but supporting that team to go do their jobs and do it really, really well. But I do think that you need to get into the level of details. So, one of the things that people often remark about is the level of detail that myself and the broad leadership team at Highspot gets involved in. Again, not for inspection, but to understand is it really effectively landing in the real world?

Russ: [00:24:13] Robert, a key focus of the discussions we’re having with all of our unicorn leaders on this series is on communications and culture. So firstly, I just wanted to ask whether or not the perception of the company changed when you became a unicorn.

Robert: [00:24:27] I don’t think so, per se. I mean, whether your evaluation is a billion or 5 billion or 10 billion, I think that it’s all a journey. There’s no magic switch. And so, I think what happens is as you get into these higher valuations, especially if you have relatively well-known investors, the inside baseball part of the community definitely takes notice. ‘Oh, that company must be doing pretty well if investor A was willing to invest at valuation B. Huh, they must be doing better than I expected. I haven’t really heard about them, but now I’m going to go find out about them’. That absolutely is going on. That’s kind of the inside track I think that the start-up community over indexes on all of that inside talk track. I think that customers don’t look at that as much. I don’t think analysts look at that as much. Yes, it’s a data point, but it’s only one of so many different data points. The one thing that is really great about the world today is that even the most conservative companies are willing to bet very important parts of their business on mature start-ups, maybe not on that early-stage start-up, but on mature start-ups. If you go back even ten years, but especially 15 or 20 and you had a start-up, even at our size, over 1000 people and all the success that we’ve had. And you went to the most conservative companies and said, hey, you’re going to bet a big part of your business on a company like that. They would say, no, it needs to be a public company. It needs to hopefully have been around for 30 years. We have to have a deep relationship with them. And so, the world has gotten more agile in that sense, and part of that is just the maturity of the marketplace. And part of that, I think is cloud computing because it’s just a different kind of relationship when you’re able to take advantage of a service that you don’t have to run and manage yourself. And so, it’s also amazing that the most conservative companies in the most regulated conservative industries, whether it’s pharma, whether it’s financial services, whether it’s medical devices, not only are they willing, they actually prefer, in many cases, to use cloud services as part of their core business. That’s an amazing thing. I can remember when I was at Microsoft, and I was talking to global CIOs, and I was talking about the fact that the cloud was the future, and it was inevitable.  My, point back then was it was inevitable because it was a ten X savings in terms of agility, in terms of cost. And ten X’s can never be ignored because if your competitor does it and it’s ten X, the world is going to change, and you can’t stop it. And it was one of these really interesting moments. I remember doing this in Paris actually for the global CIO Summit. So, these are literally the top 100 CIOs on the planet. And it was really interesting because I gave my talk, my standard pitch, and two things happened. One is the most highly rated talk of the entire summit, and it was the one that everyone disagreed with the most. Like, of course, this this is wrong. We’re not going to the cloud. It can never stand up to the security requirements that we have, the data privacy and localization, data sovereignty, and in the case of certain industries is clearly not going to happen. But it was obviously intriguing and now it has happened. So, if you think about just literally ten years ago, I don’t think most global CIOs would think that they would bet big parts of their business on cloud services.

Russ: [00:27:51] You just put this picture in my head of the two old guys from the Muppets in the audience going, that speech was awful, terrible, actually it wasn’t so bad, actually. Maybe what he had to say was quite good. You turned them all around to you, to your way of thinking.

Robert: [00:28:06] No, actually, the ten X turned them around over the next ten years.

Russ: [00:28:08] Well, yeah.

Robert: [00:28:11] I definitely intrigued them with the charts, graphs.

Russ: [00:28:13] Fantastic. And what about in terms of differentiating yourself? It can be difficult for any tech company to stand out in their market. And I think you’re aware we also spoke to another company in your space recently on this series. So, what’s your strategy for differentiating yourself in the market?

Robert: [00:28:33] Well, there’s different levels of it. So, one is how are we trying to stand out from a communications, from a marketing point of view? I can talk about that. And the other is, how are we trying to stand out from a product point of view and the service that we deliver? I can talk about that. From a market leadership and breaking through the noise, I think that one of the things that we’re really focused on is this notion of how should one approach enablement generally. So, we have this thing we call the strategic enablement framework. It’s really writing down what we think are the very best practices for the category, not just for Highspot, but for the category. How would you approach the fact that you want to drive a certain initiative? What does it mean to equip train coach at the next level of detail? How do you assess? Are you ready to drive this strategic initiative successfully? Do you have what you need the ability to equip? Do you have what you need in the ability to train and coach? So, we have a lot of methodology which gives us a really interesting way to have a conversation with our customers and our prospective customers and with the market in general. Because one of the things that’s really fun about our category is that one of the things that we can do, which is not true for most great software. There’s so much great software out there, so many great services out there. But one of the things that most of them can’t do is come to the most senior people in the company, CEO, the board of directors, the chief revenue officer, the chief marketing officer, and ask legitimately, so, what are the key things you’re trying to drive for your company? What is going to make a difference for you over the next couple of years? And you’ll hear things like, ‘Well, our strategy is that we’re going to do a number of M&A. And then part of doing that is I want to reduce costs. So far, we can’t help and I want to make sure that people understand that the two the three companies that I’ve just bought, those three products will be better together and they can reduce their own costs as a customer if they buy in my three products together. And so, the way I’m going to measure the success of my acquisitions is a reduction in cost. And I want to increase my cross-sell from product A to product B and product B to product C by five points’. And so, the only way to do that is to get all of your 10,000 reps, let’s say, around the world, to do something different tomorrow than they did today. That’s a pretty fun conversation to have with the CEO or the CRO because you’re truly asking them for real what is going to impact your business, and then we can help. And so that is a really wonderful thing about our category, is that it really does help at the highest level strategically. So that’s part of the conversation. And we have to help not just ourselves as a vendor, but we have to help our customers, the people that buy and use Highspot to have that conversation with their executives as well. And so that’s part of it. So, all of that is some of the things we do with sales enablement pro, with all of our best practices and all of the things that we’re talking about to the marketplace. That’s part one. Part two is the product itself. And what’s interesting about our space is that one of the difficult things about sales enablement is and this is going to sound obvious, but it’s really important, is that for sales enablement to work, the reps have to use your product. Turns out adoption is everything. If you don’t have a well adopted product, then I don’t care what analytics you have, what insights you have, what plays you develop, what training you develop. Nothing matters if they’re not adopting it. And it turns out adoption is tricky because these are people, whether it’s sales or services or support, people that are very busy and they vote with their feet. So, one of the things that we’ve made the decision uniquely in the space is that we are building an end-to-end unified platform, common experience for the user, common experience for the administrator. Absolutely integrated analytics, integrated partner, ecosystem and marketplace. So completely unified. All of our competitors, including the ones that have been on your show, have a completely different strategy. Their strategy is to buy companies and duct tape them together and have a suite. Absolutely, they have a suite, but it’s not a unified platform. So, a rep adopting Part A is not necessarily going to adopt part B or part C of their platform. So that is a pretty fundamental difference in the way we’re going to market with our technology. And I think you can gain some advantages in the short term by buying things, but you incur a lot of technical debt. And then to our earlier conversation, you incur a lot of cultural debt. You have five companies in there, seven companies in there. And getting those integrated is tricky. And it doesn’t set you up ultimately for building the right platform with the right culture, with the right way to partner with your customers. So that’s another way we’re quite different than the rest of the marketplace. We’re building end to end, which is one of the reasons we raised so much money. $650 million is a lot of money to raise. Part of it is that it gave us optionality. Part of it is because we are investing so much, not just in our thought leadership and all of that, but in R&D because we’re building all these things rather than buying them.

Russ: [00:33:37] You just touched on culture there. How would you describe your company culture and also how have you sought to nurture it?

Robert: [00:33:43] At the end of the day and I mentioned that we were people first, but at the end of the day, culture is everything. If you have the wrong culture, it’s pretty hard to be successful. So, you really, really have to think about culture from the very earliest stage because whatever culture you start with, you tend to have and it’s very hard to change it. We think about our culture at a number of different levels. I think at all levels we’re pretty intentional. The first is we’ve thought long and hard about why, why Highspot, what gets this company excited, and this is what I mentioned before: deliver breakthrough products that transform the way millions of people work. Those words mean something to us. The fact that breakthrough we really do try to push the technological envelope and the fact that it’s millions of people we really think about can we get this into the hands of essentially every company that has a customer facing teams, which is basically every company we want to impact the way go to markets work. We want to impact the way leaders think about their business and they think about their people as a core strategic lever. That’s a really important thing to us. And then we think about how do we go about that at the next level? And we have three things that we think about that we really focus on. One is to create products that customers love, what we call a spark beautifully designed software with the spark of magic. And that means that we really sweat the details of our software. And it’s okay if we might deliver features more slowly than just getting something over the wall that our competitors might do. Because in the end, it’s going to be a great experience. It’s going to be really easy to use. It’s going to tackle all of their different use cases, it’s going to tackle all of the corner cases. It’s really going to be a joy that is a really important thing to us and that drives a lot of our culture. That high level idea. Another high-level idea is that we want to provide the best customer experience at every single turn. And that results in not only cultural values, but also, we put our money where our mouth is in terms of our go to market structure. So, when you buy Highspot as a customer, you get a team with you, no matter whether you’re a small customer or a very large customer for the entire lifetime of that partnership. So, we have services, people, account managers, people that are there trying to help you be successful. And we have incredible net retention and gross retention, I think, because of that. And then the other thing we think a lot about is to inspire, empower people to do their best work. And that really has two aspects. One is heart, which is how do people feel? What is their experience in the workplace? What are the values? How are people respected? How is that interaction all done? But also, we think a lot about the head too, which is, it’s great that you feel good about working at a company if you’re working at Highspot. But are you truly empowered in the sense that are the easy things easy and the hard things hard? Or is there enough bureaucracy and enough confusion and roles and responsibilities and enough chaos in the tools that you use every day, that the easy things are basically excruciating and there’s it’s hard to get things done. So, to have a great culture, it has to be that you feel good 100% with the right values. That’s really critically important. But it also better be that it’s easy to get your job done. And we think about inspiring and empowering people to do their best work. So those are the why and the high level hows. And then we took a page out of, and this is what I said, we look around everywhere we can to take best practices. And one of the things that Amazon does, which is very interesting, is they have these 14 leadership principles and at first blush, 14 is a big number. And you think, how in the world does anybody have 14? What most companies do is they have three wonderfully inspiring sentences about their culture that no one could ever remember and not one employee can cite if you ask them. And when Amazon did it in Amazon way is they have these 14, but they’re very specific and they’re very detailed. And what I noticed early on is that the people that came from Amazon had them in their vocabulary. They were part of their language. So, we took that same idea and we have our 11 Highspot guiding principles and it’s things like all in, invent the future, details matter, most respectful interaction which we call MRI. The list goes on. They’re very specific things and they really do help us be intentional about our culture because you’ll see it in the language. People will say, ‘Hey, quick hashtag details matter, there’s a bug on slide four, etc., etc.’ or ‘Hey, that wasn’t MRI. Let’s talk about that. Let’s talk about why that meant most respectful interaction that wasn’t MRI.’ And MRI means basically making sure that not only are respectful on the surface, but that you assume that people’s best intent is there, that they thought about what they’re trying to do, that you give them the benefit of the doubt, and that if you are on the other side of that conversation there, you’re making sure you’re respectful of their time. So, it’s about respect on many, many different dimensions. And that’s what our MRI is. So, we’ve tried to get very specific taking a page out of Amazon’s book, and it really does work. So, it really is in our language and it’s part of our onboarding program and it’s part of one of the ways we reinforce these higher-level principles in the system.

Holly: [00:38:58] It’s really fascinating what you were saying about those principles, and I guess a big part of how you’ve gotten the wider Highspot team to embrace them and think about them and make them part of their language is through your internal communication. So, can you share any approaches to internal communications at Highspot that has worked really well for you and how have you managed to make that so ubiquitous across the company?

Robert: [00:39:23] Again, all of this stuff, I should say is not that we have the book written and we know how to do it. I think it’s all a journey. I’m just giving you where we are in our in our journey and how we hope to continue to improve as we go forward. So, we do a number of things. One thing is we try to be relatively transparent just philosophically. And so, as things come up, we definitely send emails out, we send Slack’s out, we use Slack as our internal communication mechanism. So, we’ll do that. But we do a couple of other things that might be a little bit more unique to Highspot. So again, taking a page out of various companies’ playbooks. One thing that was always very interesting to myself and the leadership team was Google. So, Google did an all hands for the first, I don’t know, 20 years, a companywide all hands every single week, week in, week out. Most companies do it annually or they do it semi-annually, or maybe they do a quarterly, but it’s a fairly infrequent thing. It’s a very big production. So, we decided to try Google’s and we’ve done it ever since day one. It used to be literally in a lunch conference room. Now it’s a little bit of a bigger production, as you can imagine, around the world. But nonetheless, it happens every single week. It’s 50 minutes. We stream it, we record it, we do all the obvious things, but we do that. And that’s a really important mechanism. And I would say about 67% of the company shows up every single week and we talk about it could be everything from a customer showcase to talking about the big trends going on in the marketplace to new innovation that we’re doing, to new ways we’re going to market. It can be any set of topics, it can be cultural things that we’re doing, all sorts of different things. But that is a really important rhythm that we have established. And then we have this other thing, this little tool called Highspot. And so, it turns out Highspot is really good at helping teams communicate. Now our focus is our communication to the frontline teams and their managers. So, sales, services, support, as I’ve talked about. But it turns out we use Highspot more broadly as you would expect. And so, when you log into Highspot, we have a completely nice and easy way to customize that home page to the set of things that are relevant to you. And so, you’ll see announcements, you’ll see different things that are coming up. You’ll see new content that might be relevant to you, all those different kinds of things that are going on. And so that’s another way that we can communicate to the entire company about what’s going on and what’s not. And often when you have an email, when you have a communication in Slack, often that points back to a fairly curated experience in Highspot. So, for example, we just did a little bit of our onboarding program. We’re pretty excited about it. The culmination of that is, ‘Hey, click on this link’ and it goes to a wonderfully curated experience in Highspot about what is that onboarding program, the why behind it, what are some of the new things that we’re doing? Who are the people that are involved? All that is very easy to curate inside the platform.

Russ: [00:42:14] And so that’s internal comms. Switching to external. What about your role as the company spokesperson representative of the business? How do you view that? And also, is there anything that you’ve learned and adapted as you’ve gone on that journey over the last ten years or so?

Robert: [00:42:30] Yeah. a number of people in the company are actually probably in some ways more visible than I am. Again, if you think about all the different ways that we engage our customers and our prospective customers, whether it’s user conference, whether it’s webinars, various events, lots of people on the executive team, lots of people throughout the company are doing that all of the time. You know, for me, conversations like this are just really fun and very natural because it’s something I think about, because we’re so much about people internally and helping people in the customers that we serve. Thinking about culture, thinking about communication, thinking about inspiring people is really what we do. And so, it’s a very natural conversation. So, these are the things that are very fun and easy for me. And then talking about the space of enablement is awesome that we think about every day. And one of the things that is interesting about a category like ours is that not only can you have these strategic conversations like I was talking about, but also, we’re big enough now that we’re a little bit of a microcosm of what our bigger customers see. So, we can practice things, try things out, try new ideas out, try new features out internally. So, we have a lot of that innovation going on internally as well, and that helps fuel the conversations that we’re having right now. So, when I talk about things, not only am I getting this from our customers, but I can get it from walking down the hall and really getting to that next level of detail. And so that helps fuel all of these kinds of conversations that we’re having.

Russ: [00:44:01] I’m pleased you’re finding this nice and easy and natural that’s good to know and that you’re enjoying it. And in terms of being a communicator, like you said, it’s a very free flowing conversation that we’re having. Have you always been a natural communicator or is it something that you’ve had to work on, formulate a plan over the years?

Robert: [00:44:18] I would definitely say I’m not a natural communicator in the sense that I have many people that I interact with that love the stage, are so natural at it, so very good, wonderful storytellers. I’ve seen what great looks like and that isn’t me. But I will say that it’s very easy to have a conversation like this. It’s a different skill to do a more curated experience where you get on a stage in front of ten or 15,000 people and you have a show to put on, and it’s more something that you’ve rehearsed and memorized. This is something that we’re just having a conversation basically, and those are always different and for me a little bit more natural. But of course, in my career I’ve had to get good at getting on that stage and putting on that show as needed and at our stage now just like, for example, a couple of weeks ago in EMEA, we had Saastr in Barcelona, we had the Soiree which is our sales enablement pro event again for sales enablement professionals, not necessarily Highspot customers. We had that in Paris, we had another Soiree again in London, and we had our EMEA user conference in London as well. And so, you can imagine many, many speaking engagements for those various audiences that we were doing across the company. So, a lot of these are we spend a lot of time on this kind of thing because it’s talking to the world about what we’re passionate about, which is, again, improving the performance of these customer facing teams. So, I think what you’ll find is that myself, but the leadership team generally in the company we’re a fairly passionate bunch about this topic. And so, what you’re passionate about, whether it’s sales enablement or airplanes, you tend to want to talk about it.

Holly: [00:46:06] And it sounds like you’ve had plenty of opportunities to refine and perfect your comms approach. But over the years, what would you say has been the biggest communications challenge you’ve faced personally? And how have you how have you overcome it?

Robert: [00:46:22] Well, something that we talk about a lot internally is trying to make sure we’re having the right conversations with the right people about in this case, about enablement, the category including Highspot, but really enablement the category. So, one of the communication challenges that we do have is making sure that we really land again, head and heart with these very senior executives, that there is a new strategic lever that they can use. And getting them to understand that and that’s tricky to do. They’re busy people. They have heard it all before for anything that’s being promised to them and really getting them to understand that this is a new macro trend in their business world that they need to take advantage of, like they took advantage of other big technological trends is a really interesting communication challenge. It is one that in some ways gets solved by time. It just becomes more and more part of the conversation, more and more part of the playbook, if you will, of building and running a big business. But we want to accelerate that. So how do you do that? How do you get to those people who are most senior and likely most sceptical about anything new and have a conversation with them where they not only nod their head and say, ‘Yeah, yeah, that all sounds good’, but like, ‘Oh no, that is something that is intriguing enough that I need to go think about my business differently’. That’s a really hard challenge. And so that’s something that we think about a lot, is how to have that conversation most effectively.

Russ: [00:47:54] Robert, we’ve been chatting for almost an hour. We’ve got one final question for you. I’ve been watching the clock behind you, which, by the way, for anyone watching the video, watching this podcast, not listening to it, it’s going to be a nightmare if we want to edit this video now, because from a content continuity point of view, we can’t chop and change the order of these questions now because that clock is going to obviously give everything away. So yeah, thanks for that. But we’ve got we got one final question for you. And as I said, we’ve asked this to all our unicorn leaders across this series. If you were to go back in time and speak to your old self, what guidance would you give yourself about communications?

Robert: [00:48:30] One is that you really do have to meet people where they are and take them on that journey to where you’re trying to help them understand. So, you need a vision. You need a North Star that you’re trying to communicate, that you’re trying to have that effective conversation. But then you have to ask yourself, where are they now? And what does that bridge look like? Just touting your vision at volume 11 all the time doesn’t mean that they’re going to go from where they are today to what you hope that they understand and internalize. That’s piece one and then piece two, and this is even the harder thing in some sense is where they are today, probably radically varies by persona. By where they sit in the organization, by geography and by industry. So, what you can’t do is have this wonderful, naive view that says, okay, I want to take the world to this vision and here’s where they are today. No. Who am I talking to? What’s the context of how I’m talking to them? Where are they today? What are their assumptions that may or may not be aligned with where our vision is? And then let’s take them and have that dialog and take them on that journey. So, what I would say is you really do have to think not only everyone talks about customer first, of course that’s important, but really you have to think about persona first. And that persona is going to vary by industry and it’s going to vary by, by geography. And it’s really going to vary about where they sit in the organization. If they’re an individual contributor early in career, that’s a completely unrelated conversation to the Chief Revenue Officer, which is probably, by the way, an unrelated conversation, even though it’s so close to the board of directors. And so, you need to really understand what conversation am I trying to have with that person to what that vision is. I think what a lot of unicorn companies and companies that are listening are clear on is their vision. The hard part is to figure out for each of the different people that I’m trying to talk to, how do I get them to understand that vision and then hopefully believe in it, but at least understand it?

Russ: [00:50:42] Robert Wahbe, thank you so much for taking the time to join us online today. Really appreciate it.

Robert: [00:50:47] Thanks for having me.

Russ: [00:50:50] Holly. Thoughts on what Robert had to say?

Holly: [00:50:52] Wow. So many insightful things that Robert shared. It was a great chat. But I think one thing that really struck me was one of those final points he just made, because I think it’s something that can be applied to any communicator, whether you’re communicating on behalf of a business or individually. But it’s a vital skill to have. It’s that point that he made where it’s really important to meet people where they are and then build the bridge back to whatever vision you have. I think so often spokespeople and people that are trying to communicate a message are just too blindsided by their own vision. They forget to put themselves in the shoes of whoever they’re trying to communicate with, and I thought that was just a great thing for everybody to take away from our chat.

Russ: [00:51:35] Excellent. Well, thank you for that, Holly. That is actually it for another episode that we’re doing in this special series with Tyto. So, if you want to find out more about Highspot, it’s very simple, their website is Highspot.com. We’d love to hear your comments on today’s chat. You can do that by sharing them on our Facebook, LinkedIn, Instagram, or Twitter feeds, or you can do it in the comments of the YouTube version of this podcast. Those are all linked from the top of our website at csuitepodcast.com, where you’ll also find all our previous shows and supporting show notes, plus links to where you can follow us for automatic downloads of each episode via the likes of Spotify and Apple. And if you like what you heard, please do give us a positive rating and review. We’re of course available on all podcast apps. Just search for the csuite podcast hit follow us or subscribe. You can, of course, subscribe to the Without Borders podcast as well from our partners at Tyto. All the details for that are on their website. Just head to tytopr.com and click on the podcast link in the top nav bar. You can also on that website download a copy of ‘Growing Without Borders, The Unicorn CEO Guide to Communication and Culture’. It’s a great overview of the first 15 of our unicorn interviews. Finally, if you are a unicorn leader yourself and you’d like to be part of this series, please do get in touch via the contact form on the website at csuitepodcast.com. Of course, anyone can get in touch with any feedback you may have. You can also reach me via Twitter using @Russgoldsmith or you can find me on LinkedIn. But for now, thanks for listening and goodbye.