Show 156 – Unicorn Interviews – Robert Wahbe, Highspot

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The 27th in our series of episodes 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 communications.

Russell Goldsmith and co-host, Tyto’s Senior Partner, Holly Justice were 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.

Company Background

Robert explained thatHighspot is in the sales enablement space. They are a service platform and have data centers and customers in Asia-Pacific, Europe and North America and companies use Highspot to improve the performance of their sales teams. They achieve this by equipping those people with the right resources and the right place. He compared it to sports, in that 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 his platform does is for customer facing teams such as sales, services and support, help them equip, train and coach people so they have more effective conversations and drive their business goals more effectively.

Robert said that sales enablement is, in some ways, the oldest new category out there. 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, mobile technologies and of artificial intelligence being really democratized by the big players. You’re now able to apply a different set of features and a different set of capabilities to really make that happen. He added that making your people most effective is one of the biggest strategic levers you have as a company leader. However, in the past, companies have not had the technological ability to drive change in the ways that they want. Instead, they just hired a lot of people and see who sinks and swims, with 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. However, now you have a set of technological tools to actually implement change on the front line so that people drive initiatives, and you can do what you want to do in terms of the business. So it’s a lot about the technology but also as a vendor, he said that obviously care deeply about their product and the features, but it’s also about the best practices and methodology to use all that technology to help equip, train, coach these reps. That’s why the time is now for this category as it emerges into must have, because people have realized and many industries now have so many people that are using enablement that you can have a brilliant insight about how to change the business and can get your 100, 1000, 10,000, 100,000 reps around the world implementing that change. It changes everything about your revenue engine.

Entrepreneurial journey

Robert started a company back in the late nineties when he was getting his PhD in computer science at Berkeley, which was acquired by Microsoft very early in its journey. His goal was to go to Microsoft for a couple of years, learn the ropes from the very best, and then go back and do another start-up, but he stayed for 16 years. Most of his journey at Microsoft was in the product and building core technologies and Windows and other areas. But for the last three years, he was CMO under Satya Nadella, now CEO of Microsoft, when he was the president of a $20bn division back then, now a much bigger division. It was in that role, looking at marketing, sales, sales enablement, that he realized that so much of what they were doing at headquarters – a big operation, hundreds of marketers, hundreds of millions of dollars of budget, tens of thousands of salespeople around the world, a big, complicated operation – the new content, positioning, campaigns, and programs, weren’t being absorbed by the people on the front lines.

Robert used to travel a lot in that role at Microsoft, hundreds of thousands of miles. He would land in a subsidiary in France, for example, and would say, “okay, what can I do to help from headquarters?”. They would inevitably say, “oh, I need I need positioning A, I content, B, program C” and 99 times out of 100, he would 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 he started Highspot in 2012 was ‘could these broad macro technology trends, cloud mobile A.I. allow us to change that dynamic so that the things that people were doing from marketing, enablement, and sales leadership, could those strategic things they were doing actually really effectively land with the front line, whether it was sales, services or support?’

Proudest achievement

Robert said that one of the things that they talk a lot about is delivering breakthrough products that really push the edge, that transform the way millions of people work. So, they get very excited about can they have a broad impact? Can they build the company for scale? They have what they call the airplane test. Can anyone in the team, anywhere in the world, get on an airplane, sit next to somebody, and the odds be that 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. Robert wants to get to that level of scale, to have that impact. And they have been relatively successful so that they do somewhat pass the airplane test now. They get to talk to some of the best companies across the world in different industries. And he finds that incredibly satisfying when an important company that he respects says, ‘hey, you are helping us achieve our goals’. Secondly, he loves the people side of his business. They have a really supportive, collaborative culture. He 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. They consider themselves a people first company. They think about three big engines:

  1. the people engine
  2. the product engine
  3. the customer engine.

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 its people first.


Robert explained that the money Highspot has raised will be invested across the board. Part of their journey is to help the category, which needs 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 to 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 Robert said that have big investments. They have the largest society of sales enablement professionals, what they 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, Europe and Asia-Pacific, 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. The second part is to make sure they win that category. They want to make sure they’re doing everything they 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.

Typical clients

As a rule of thumb, Robert said that once a company gets to about 30, 35 sales people, they have enough complexity that it’s probably hard just to walk either the physical or now the virtual halls. They 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 Highspot starts. And then it goes all the way up to customers with hundreds of thousands of pieces of content, thousands of different sales plays, thousands of different training and courses, coaching, and literally tens of thousands of reps around the world. So, all the way up to the Fortune ten, in different industries.

Inspiring Leaders

Robert named a couple of people who he has worked for. He referenced Satya Nadella again, now CEO of Microsoft, as well as Eric Rudder, Chairman of a start-up in Seattle called Pulumi. He also added Bob Muglia, former CEO of Snowflake, to his list, who was his boss for many years. He said he clearly took a lot from all of those people and all of those configurations. And it’s not just from his managers or his managers’ managers, but really from a set of really interesting expertise across the company. But the other thing that he does is get the luxury of talking to a lot of leaders across Highspot’s customer base, partners, and competitors. He also skim reads books that comes out every post-mortem about a company’s journey. What he doesn’t do is adhere to one particular methodology, one particular way of doing things. He can talk to basically the leaders in the Fortune 100 of all of his customers, and they really are generous with their time. And he can ask them to think back to when they were Highspot’s scale and ask what would they do differently? How would they structure the sales team on this one dimension? If he talks to 30 of them, there’s 35 answers! So, there is no ‘this is the way you do it and it always works’. 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, 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, to go to market, to servicing your customers, if that is inherently going to be changing, then you better have 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? Robert said that you need technology like Highspot and enablement to do that.

Leadership strengths

Robert said that he tries to understand the details, but not micromanage, which is s something he learned at Microsoft. As he has talked to other companies in the technology space, he found it 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 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? Robert likes to get enough into the details to check if he understands and if the company understands how it really is landing in the real world. To him, 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? He thinks the broad management team at Highspot are not about inspection to drive certain behaviours per se, it’s about inspection so that they 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 well.

Perception of the company on becoming a unicorn

Robert said that whether your evaluation is a $1bn, $5bn or $10bn, it’s all a journey. There’s no magic switch. And so, he thinks 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, 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. However, Robert said that customers don’t look at that as much, nor do analysts. Yes, it’s a data point, but it’s only one of so many different data points. He said 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. If you go back even ten years, but especially 15 or 20 and you had a start-up, even at Highspot’s size, over 1000 people and all the success they’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’. Robert said the world has gotten more agile in that sense, and part of that is just the maturity of the marketplace. And part of that, he thinks is cloud computing because it’s just a different 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, financial services, or medical devices, not only are they willing, they actually prefer in many cases, to use cloud services as part of their core business.


Robert said that there are different levels to differentiation. One is how are they are trying to stand out from a communications from a marketing point of view and the other is how they are trying to stand out from a product point of view and the service that they deliver.

From a market leadership and breaking through the noise, Robert thinks that one of the things that they are really focused on is the notion of how should one approach enablement generally? They have something they call the strategic enablement framework. It’s writing down what they think are the very best practices for the category, not just for Highspot.

  • 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?

Robert said they have a lot of methodology which gives them a really interesting way to have a conversation with their customers and prospective customers and with the market in general. They can go to the most senior people in the company, CEO, board of directors, chief revenue officer, chief marketing officer, and ask legitimately, ‘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?’.  Robert said you’ll hear things like, ‘Well, our strategy is that we’re going to do a number of M&As. And then part of doing that is I want to reduce costs. 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’. Robert said 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 their business, and then how Highspot can help.

Part two is the product itself. Robert said that for sales enablement to work, the reps have to use your product. Adoption is everything. If you don’t have a well adopted product, then he doesn’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, who are very busy, and they vote with their feet. So, one of the things that Highspot made the decision uniquely in the space is that they are building an end to end unified platform, common experience for the user and for the administrator. Integrated analytics, integrated partner, ecosystem and marketplace. So completely unified. Robert said that their competitors have a completely different strategy. Their strategy is to buy companies and duct tape them together and have a suite, but it’s not a unified platform. He can think you can gain some advantages in the short term by buying things, but you incur a lot of technical debt and 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.

Company culture

Robert said that 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. They think about our culture at a number of different levels. At all levels they are pretty intentional. The first is they have thought long and hard about why Highspot, what gets the company excited – delivering breakthrough products that transform the way millions of people work. Those words mean something to them. He said they really do try to push the technological envelope and the fact that it’s millions of people they really think about can they get this into the hands of essentially every company that has a customer facing teams, which is basically every company they want to impact the way go to markets work. They want to impact the way leaders think about their business and they think about their people as a core strategic lever.  And then they think about how do they go about that at the next level? They have three things that they think about that they really focus on.

  1. Create products that customers love, what they call a spark beautifully designed software with the spark of magic.So they really sweat the details of their software. And it’s okay if they might deliver features more slowly than just getting something over the wall that their 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 them and that drives a lot of their culture.
  2. Provide the best customer experience at every single turn. And that results in not only cultural values, but also, they put their money where their mouth is in terms of their 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. They have services people, account managers, people that are there trying to help you be successful. He thinks they have incredible net retention and gross retention, because of that.
  3. Inspire, empower people to do their best work. That has two aspects. One is heart.
    1. How do people feel?
    1. What is their experience in the workplace?
    1. What are the values?
    1. How are people respected?
    1.  How is that interaction all done?
    1. But also, they think a lot about the head too – are you truly empowered in the sense that are the easy things easy and the hard thing is 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.

Robert said that 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. They think about inspiring and empowering people to do their best work.

They also look around everywhere they can to take best practices. And one of the things that Amazon does is they have these 14 leadership principles that are very specific and they’re very detailed.Robert noticed early on is that the people that came from Amazon had them in their vocabulary. They were part of their language. So, they took that same idea and have 11 Highspot guiding principles, such as

  • all in
  • invent the future
  • details matter
  • most respectful interaction (MRI)

They’re very specific things and they really do help them be intentional about their 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 was an MRI. Let’s talk about that. Let’s talk about why that meant most respectful interaction that wasn’t MRI’.

Internal communications

Robert said they do a number of things. One thing is to be relatively transparent just philosophically. As things come up, they send emails out and use Slack as their internal communication mechanism. But they do a couple of other things that might be a little bit more unique to Highspot. Again, taking a page out of various companies’ playbooks, one thing that was always very interesting to Robert and the leadership team was Google and doing an all hands.  It used to be in a lunch conference room. Now it’s a little bit of a bigger production, with people around the world. But it happens every single week for 50 minutes. They stream and record it and it is a really important mechanism. About 67% of the company shows up every single week and they talk about everything from a customer showcase to the big trends going on in the marketplace to new innovation that they are doing, to new ways they are going to market. It can be any set of topics, it can be cultural things that they are doing. But that is a really important rhythm that they have established. And of course, they use their own tool in Highspot! When they log into Highspot, they have a completely nice and easy way to customize that home page to the set of things that are relevant. 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 things that are going on.

External communications and role as representative of the business

Robert said that a number of people in the company are actually probably in some ways more visible than he is. If you think about all the different ways that they engage their customers and prospective customers, whether it’s user conference, webinars, various events, lots of people on the executive team, lots of people throughout the company are doing that all of the time. Robert said that conversations like this podcast were really fun and very natural because it’s something he thinks about, because they are so much about people internally and helping people in the customers that they serve. Thinking about culture, thinking about communication, thinking about inspiring people is really what they do. And so, it’s a very natural conversation. So, these are the things that are very fun and easy for him. He said talking about the space of enablement is awesome that they think about every day, adding that one of the things that is interesting about a category like theirs is that not only can you have these strategic conversations, but also, they are big enough now that they are a little bit of a microcosm of what their bigger customers see. So, they can practice things, try things out, try new ideas out, try new features out internally. They have a lot of that innovation going on internally as well, and that helps fuel the conversations that they are having right now.

Robert doesn’t feel that he is a natural communicator in the sense that he has many people that he interacts with that love the stage, are so natural at it, so very good, wonderful storytellers. He said he has seen what great looks like and that isn’t him! But he finds it easy to have a conversation like we were on the podcast. 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 is just a conversation, and those are always different and for him a little bit more natural. But of course, in his career he has had to get good at getting on that stage and putting on that show. So, a lot of those are things that spend a lot of time on because it’s talking to the world about what they are passionate about, which is, again, improving the performance of these customer facing teams.

Advice to younger self

Robert said 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. 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. Robert thinks 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?