North Star Leaders Podcast

Lindsay Pedersen

The world needs what only your business can bring. And as a leader, it's your job to deliver. But where do you focus?

Where do you direct your time, your team, your budget, and your emotional energy? We're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that they make to create audacious economic value while also realizing their distinctive purpose.

I'm Lindsay Peterson, brand strategist, author of Forging an Ironclad Brand, and host of the North Star Leaders Podcast. Let's get to it. Today, I am so happy to be joined by Robert Wahbe, CEO of HighSpot, the sales enablement solution.

Robert, welcome to the show.

Robert Wahbe

Thank you for having me.

Lindsay Pedersen

To start us off, Robert, what is your favorite thing about what you do?

Robert Wahbe

It's really a couple of things. One is customer. We have the opportunity to talk to our customers and get relatively close to our customers.

And so we know why they're using the solution, what they're trying to accomplish, what their strategic business goals are. And so being able to engage with them and see that we really are delivering value and helping them, both the company achieve their goals, but we have many, many cases where the teams that bought and use us have been promoted, have had broader scopes. That's one part, which is wonderful and fun.

And the other is the team here at HighSpot. You know, getting to see people grow, getting to see people do really brilliant work. That's the other side of the fun.

And it's really great.

Lindsay Pedersen

What is the culture like at HighSpot? And how conscious have you built it versus serendipitously?

Robert Wahbe

We attempt to be very intentional about the culture. There's many aspects to it. One is in this environment, especially given all of the transformation with AI, we really need the company to have a sense of urgency and a sense of velocity.

So that's been a theme for the last couple of years. I think that for many companies, HighSpot included, COVID kind of threw a wrench into things and we had to relearn how to work because now we were hybrid. We're still hybrid today, but we really need to make sure that we are innovating as fast as we can and with a sense of urgency and breaking down barriers and breaking through bureaucratic things.

So that's one big piece of the puzzle, maybe the overlay, if you will. And then we have a lot of principles around making sure that we can inspire and we can stretch people to their full potential. And so we have a lot of guiding principles around earning the next challenge and most respectful interaction and all of these different things that add up to be, we want it to be a good place to work, a challenging place to work, where you can really grow your career and grow your skill set and ultimately have some fun too.

So one of our guiding principles is enjoy the ride.

Lindsay Pedersen

Ooh, I love that. I have heard you talk about your guiding principles that there are 11 and that I was intrigued by something counterintuitive you said, which is that more principles is better than fewer. I'd love to hear more about that. Like why is 11 good?

Robert Wahbe

So this wasn't really my insight. This was more Amazon's insight. I learned about it from Amazon.

So when you look at most companies, they have three, maybe four principles and they're very high level and they're so high level as that they're very hard to put into practice every day. What Amazon did is I think they have 14, maybe they have even more now, maybe they have 16, but back in the day they had 14 and they're concrete enough that they actually get into the language of the company. They become part of the vernacular and Amazon people still use them even when they leave Amazon.

So we have something around details matter as one of ours, for example. And what you can say though is, hey, this is not quite right. It's worth fixing.

Details matter. And you'll see emails with hashtag details matter. And so I think that by having them very concrete, you could actually influence the day-to-day operation of the company.

Whereas they're high level, that's wonderful, but they're great for a poster. They're not going to influence what you do day-to-day because they're simply too high level in most cases.

Lindsay Pedersen

Yeah. Well, and it's also like an anodyne, like integrity or authenticity, something that's kind of like a table stakes sort of thing, like who's going to not be for integrity. I feel like it breeds a little bit of cynicism in some ways because it's like, yeah, it's a poster on the wall.

Robert Wahbe

I think the problem is when they're high level and you only get three, then it's not going to be integrity. It's going to be integrity, authenticity, value. It's going to be some very long, hard to remember, high-level thing.

The guiding principle at the top level, and there's only three, was it's all about authenticity. That could be actionable. That could be something that really permeates the culture, but it's never like that because there's only three of them.

Whereas if you have 11 or 14 or whatever the number is, you can decide what are those top things that you really care about and name them. The one thing that we talk about is open and real. Some companies have radical candor.

It doesn't really matter what the exact words are, but you'll see people saying, hey, we need to have an open and real conversation, i.e. a candid conversation that might be a hard conversation. It still needs to be respectful, which is most respectful interaction is one of the other guiding principles, what we call MRI, but we're going to have an open and real conversation. Or we might say that wasn't open and real or that team is not being open and real.

Again, it's concrete enough to actually permeate the culture and shape the culture.

Lindsay Pedersen

Well, and I heard a couple of things there. One is because there are enough of them, they can kind of provide dimension to one another because there's both open and real and there's the deep respect that that's always coupled with. And so they foil each other in kind of a way that feels like real life.

And then the other thing that you said, I think is telling is you said this a couple of times, it influences day to day behavior, which and if it's day to day, you can get a lot of reps of conversations where you're utilizing these and therefore it's like kind of it's not just a cognitive abstract idea. It's like actually behavioral.

Robert Wahbe

Yes, absolutely. Exactly.

Lindsay Pedersen

And then you see it and then it actually breeds more trust and hopefully it's acting as a filter for people who are coming to join and people you're considering joining.

Robert Wahbe

Absolutely. And it's a difficult exercise because you have to take all the things you could say. I think the exercise is go to your top favorite 50 companies and now you'd go to your favorite AI and say, give me some guiding principles.

But then you, the company, the leadership and the rest of the company need to decide, OK, what is it that we actually care about? It's a difficult exercise, but you ask the question, you know, is the culture intentional? Well, it starts with deciding what is it that you care about?

Lindsay Pedersen

Yeah. What is the right moment in the journey to get really codified like that? As a leader, is it good to do that from day one?

Is it good to wait until there's some product market fit evidence?

Robert Wahbe

I think you want to do it early. We did it actually a little bit later. We were probably, I don't know, 20, 30, 40 people and we had an offsite and one of the deliverables of that offsite were these guiding principles.

And at that point with 30 and 40, in some sense, we were asking ourselves, what is our culture? And we were trying to pull that apart. But given that I had been in the industry and my co-founders have been in the industry, I think we were being intentional.

We hadn't written them down per se. There's no downside to writing them down early and often. And then the one thing I would say is you want to write them down, but I will say that in some ways they're emotionally charged because they're conflicting.

So for example, invent the, I'll just give you some of ours, invent the future, make it happen and details matter. Those are conflicting in some sense, make it happen, do whatever it takes, have urgency and velocity to make it happen. By the way, details matter.

They're tricky. And so once you get to a certain scale, it is tricky to change them because now there's all of this context and there's all of these different personas in the company and they'll read into whatever they need to read into those guiding principles. And they'll put a lot of meaning in every single change in every single word.

If they're just there, that's one kind of dynamic in the company. Changing them is tricky. So I will say you want to write them down, but you want to be careful that you kind of get them mostly right.

Lindsay Pedersen

Along those lines, do you ever as a leader yearn for the days when you didn't have those written down so that you could like, is there like a, oh gosh, now that I've held my feet to the fire by writing these down, is there ever a moment where you kind of like, wish that you didn't have to do that because it would be easier as a leader to not have to abide by something that you'd said that you wanted to abide by?

Robert Wahbe

The short answer is no, because you are going to have a culture, whether you get two people together and you now have a conversation about what is our culture. And if you get a thousand people together or 10,000 people, you have an important conversation about what is our lived values, what culture is. And since you're going to have one, you want to be intentional about it and you want it to be the culture that you think best suits the organization, best suits the mission.

So I think it's one of those things where you're going to have one, you might as well have the one that company collectively thinks is the right one.

Lindsay Pedersen

I love that in the world of brand, we talk a lot about position or be positioned. You could allow the market to decide for you what your brand position will be, or you could decide on your own and you improve the probability of it being a favorable position by being the one to consciously choose it. It's similar to culture in that way.

Robert Wahbe

Yeah. And when we, we actually, this is a hundred years ago, but when we started, we actually started at a little bit of a higher level. We tried to answer the question that Simon Sinek poses, which is the why of the company and the how of the company, which is a little bit higher level.

And then the principles in some sense was the double-click on that how and the double-click on the culture.

Lindsay Pedersen

So you actually did start with the higher order. Why are we here as an organization? And then the values, can you share like, what is the statement that you came up with?

Robert Wahbe

Yeah. And what's interesting is these statements really haven't changed and they mostly still capture why we're all here. So our why is deliver breakthrough products that transform the way millions of people work.

And the subtext on that is life is short and we want to spend time creating something that matters. We want to believe in a mission that impacts people. And at some level, this is very high level, but there's lots of really important businesses, large at scale businesses that aren't about breakthrough products per se, and, or they're not about impacting millions of people or tens of millions of people.

There's very successful businesses that target a very specific persona. That's probably millions, but it's not tens and hundreds of millions, which is what our market is. And they're wildly successful.

But we wanted, you know, when I think about this, I think of the airplane test. You know, I travel quite a bit and when I travel alone and I'm sitting next to somebody, I want to have an impact. The company wants to have an impact such that when I sit down next to that person, they're hopefully either using the product or their company is using their product or their cousin is using the product.

My son got married recently and his daughter-in-law's aunt uses the product every day. And so I want that kind of impact. Or another way I think about it is my day.

So I wake up in the morning and I get a delivery from Amazon, you know, and that's a customer and I get a package through FedEx and that's a customer. And I might check various social media. And those are almost all customers of ours on and on throughout the day.

The hope is that we're having enough of an impact that we're touching all these lives. And so that's the millions of people side. And then breakthrough is because we want to do something interesting.

Lindsay Pedersen

With the millions of people part when there literally are hundreds of millions of people who make up the How do you distill the insight, like a unifying idea for what's the problem you're solving, like when it is so broad and I imagine diverse?

Robert Wahbe

Yeah, well, so that's the why. And then you decide how you're going to apply the why. And in our case, we applied the why to transforming the way go-to-market team.

So sales services, support, marketing operations, all of those teams work. And how do they go about driving business outcomes? And so our platform helps drive those business outcomes by bringing all those different roles together and managing all of the aspects of what it means to be a go-to-market.

So all your content, all your sales plays, all of the digital rooms that you share with customers, all of your training and certifications, all the role plays, all of the coaching that you have to do, all the things that it takes to get a team, especially the field, the sales field, to do something different tomorrow than they did today. So they can be better at what the company is trying to accomplish. And to do that, you need all those roles to work together in various ways.

And that's what our platform does.

Lindsay Pedersen

Is there like an insight around like what keeps your customer up at night? Like what's the primal pain that they're in that HighSpot is solving?

Robert Wahbe

Yeah, I would say, first of all, it really depends on the role. What keeps a marketer up at night versus an operations person versus an enablement person versus a sales leader versus a service leader versus that person on the front line trying to close deals or keep customers happy, they're going to have pretty different things that keep them up at night. But from a leadership point of view, the challenge is they have a set of what they would think of as growth or strategic initiatives that they want to implement to drive some business outcome.

So the most common initiative is a product launch. I'm going to launch a new product and I want to go sell it to all the right customers. And so how do I get my salespeople in this case to understand the product, be able to sell the product in all the appropriate ways and make sure that we're winning against the competition?

That's a whole bunch of change management. And so how do you go from, I have a vision, I have a dream to 25,000 salespeople around the world are selling that product and in the most effective way possible. That dream to execution is this big, complicated change management problem because our companies tend to be very large companies that not always, we serve SMB all the way up, but let's do the large companies, 25,000 reps, let's say around the world, multiple theaters, multiple languages, probably different kinds of products in different regions.

And yet you have this global product launch and you need all those people to do something different tomorrow than they do today and be smart about it and say the right things and know the right things and do the right things. That's the challenge. And that's why if you ask the average leader across marketing, sales support, all these things, how did the last launch go?

They will all say not as well as I had hoped. How did it go? Well, how effective are we at selling?

In many cases, it's more of a struggle than they would have liked.

Lindsay Pedersen

So that gap between the hope and the reality is what you're solving. And it's going to depend what that gap looks like will vary from persona to persona, but there's a gap for everybody.

Robert Wahbe

Exactly. And you need a platform that allows you to understand in all the things you're trying to do around that product launch, what's working and what's not working. So you have to have some level of insight.

If you think about it, the questions become quite basic, but very hard to answer for most companies without a platform like HighSpot. Do people understand the new product? Are people talking about the new product to customers?

Are people sharing the right content as they're talking to them as they get objections or potential objections from the customer? All of those kinds of things. Eventually it ends up in a revenue number, but there's all these leading indicators that take months and months and months.

And you want to know, how is it going? The new messaging that we put as part of the product launch, what are customers thinking about it? What are customers saying about it?

All those questions need to be answered. And then some will come back in a really positive way and some will come back in a negative way. A really common one is you have a big sales team.

They sell hundreds of products. You introduced a new product and no one's talking about it because it's one more thing to do and no one's really kind of gotten ready to do it. So if it's the case that you could ask the question, are my salespeople that are supposed to talk about the new product?

Are they talking about the new product? And if the answer is no, then our platform gives you lots of ways to help them start to talk about the product, as an example. Or maybe they're talking about the product, but the customer has a whole bunch of objections and the answers that the people are able to give aren't the best.

So now we have potentially a training problem, potentially a role-play problem. But whatever the problem is, you have to identify it and then mitigate it by taking action. And so if you think about what we do for a living, AI in the core, it's have insights, what's working and what's not.

And then based on what's working, amplify it. That's the best practice. And things that are not working, mitigate it by taking an action, which is the actions usually equip people differently, train people differently, or coach people differently.

They do something differently.

Lindsay Pedersen

I mean, it starts with visibility to what it is that needs to be amplified or mitigated.

Robert Wahbe

Exactly. Otherwise it's random acts of stuff.

Lindsay Pedersen

Yeah, yeah. With being a purpose-driven company and also having an audacious economic valuation and also ambition, is there ever conflicts between those two things? Does the purpose that you just described, the why, always serve the economic interest or do they sometimes check one another?

Robert Wahbe

In our case, they're relatively aligned. In the abstract, I think people imagine that more money, more resources, larger organizations are going to be able to more effectively deliver against breakthrough products that transform the way millions of people work. But we also know in reality, scarce resources often drive real innovation.

Big complicated teams are big and complicated. When you have a thousand engineers or 5,000 engineers and you're working on very complicated things, there's just a lot of inertia in those organizations. The iPhone was built with 100 people, famously.

Now, of course, now the organization I'm sure is thousands and thousands and thousands. But a lot of the breakthrough kinds of things that you have to do are done by a small number of people that have outrageously sized impact on the team.

Lindsay Pedersen

I love this. I don't know that I've ever thought of it like this, that in the creative world, creative directors will say, you know, give me a really, really tight brief because those constraints unlock brilliance. You know, constraints actually are the thing that kind of allows for unlocks to happen.

And so you can think of purpose as one of those constraints. It's a constraint that unlocks innovation.

Robert Wahbe

Yeah. I would have written you a shorter letter if I had more time.

Lindsay Pedersen

That's actually a really beautiful way that that comes to life with idea conveyance.

Robert Wahbe

And it's the same thing in life too. I mean, anybody who has built a house, there's always this painful part of quote unquote value engineering. But in my experience, as you're trying to save money, what it does basically is push on the ideas again, the original ideas, the original assumptions, and maybe they hold, but often they morph, they evolve.

And if you've thought about the problem really hard, they typically evolve to make the thing that you're trying to do, the creative thing that you're trying to do better. And it could be your house gets better because you had less money, but you realize these two rooms could be merged in this really cool way. And all of a sudden you have a better design because you pushed on the core assumptions.

I think that happens in many walks of life.

Lindsay Pedersen

I love that. And there's something initially it's kind of counterintuitive. You'd think, yeah, the more money that you have to throw at it, the better the house is going to be.

But that's only true if you want a 50,000 square foot house or you want, like, and actually even then it's still not true.

Robert Wahbe

Money and resources does not buy taste.

Lindsay Pedersen

Oh, that's like a mic drop. That's like such a mic drop. That actually is taste.

Maybe the word taste even is sort of what happens at the other side of the crucible of these constraints.

Robert Wahbe

It's a Jobsian quote.

Lindsay Pedersen

Oh, okay. Well, I'm going to credit it to you.

Robert Wahbe

Okay, great.

Lindsay Pedersen

Awesome. This has been so much fun. I've got, as we close, five rapid fire questions to ask you one word-ish answers.

Are you ready?

Robert Wahbe

I'm ready.

Lindsay Pedersen

Okay. Do you prefer a beach vacation or a city vacation?

Robert Wahbe

Oh, I love both. I guess beach if I had to choose.

Lindsay Pedersen

Okay. What language do you wish you could speak? French.

Robert Wahbe

French.

Lindsay Pedersen

What's your favorite meal?

Robert Wahbe

My favorite restaurant is the French Laundry, which is in Yonville. And my favorite food, I love food generally. And so I have lots of favorite foods.

I have French, I have Japanese, I have Mexican. I have lots of favorite foods. But if I had to pick one restaurant to eat at, it'd be the French Laundry.

Lindsay Pedersen

Okay. I think you're in good company.

Robert Wahbe

Having just come back from Paris and eating at Many Three Stars and Two Stars and One Stars, I stick with French Laundry right now.

Lindsay Pedersen

French. I love it. Okay.

Are you a morning person or a night owl?

Robert Wahbe

I grew up as a night owl, but after years and years of conditioning, I am now a morning person.

Lindsay Pedersen

Culture has beat that out of you.

Robert Wahbe

Yeah, exactly. When I was a student, I stayed up late, late, late, but now it's been beaten out of me. Exactly.

Lindsay Pedersen

Okay. And last but not least, what is a memorable splurge purchase?

Robert Wahbe

A splurge purchase. I would say my... Well, I'll just give you my latest splurge purchase, which is an absurd, absurd purchase, but it is what it is.

I just bought beautiful hangers from Japan.

Lindsay Pedersen

Oh my gosh. I've never heard that answer before.

Robert Wahbe

They're not elaborate. They're just wood, but they just have that wonderful attention to detail. The arc of every type of hanger, whether it's a coat hanger or a suit hanger or a pan hanger, they're all exactly perfect.

It's just unbelievable attention to detail, which somehow tickled my fancy and I had them literally shipped from Japan, which is ridiculous in every possible way. Let me just say that at the forefront, but that is my latest honest splurge.

Lindsay Pedersen

I love it. And it matches back to the idea of taste and how constraints breed beauty that is sort of ineffable. Oh, I love that.

Thank you so much for this, Robert. As people listen to this, if they want to learn more about you or Highspot, where should we send them?

Robert Wahbe

Just go to highspot.com and hopefully it's all there and we can always have a conversation.

Lindsay Pedersen

Awesome. Thank you so much. Thanks for listening to this episode of North Star Leaders.

Make sure you don't miss an episode by subscribing on your favorite podcast app. If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com. Also on that website are show notes, transcripts, and a way to sign up for our monthly newsletter.

I hope you join us again for another episode of North Star Leaders.