CRO Confidential: How to Sell in a Hyper-Competitive Space with Apollo CRO Leandra Fishman

Saster fans, welcome back to, uh, another episode of the CRO Confidential Podcast. I'm your host, Sam Blonde. Delighted to be here with an incredible guest, uh, and a topic that I am really excited to talk about. I, I'm, I've been thinking about this episode for weeks and it's finally here. First, uh, welcome Leandra Fishman to the pod. Leandra is just an incredible sales and revenue executive with over 30 years of experience. Leading large sales and revenue teams. If we just focus on the last decade, there are a few stints that you've had, Leandra, that are just exceptional. You were the SVP of sales and success at SendGrid. Leandra led that company through an IPO and then through a subsequent acquisition by Twilio. So spent some time at Twilio as well. Most recently, Leandra was CRO at Intercom for several years. And is currently the CRO at Apollo. So several names that folks listening to this pod are probably users of the products. And with that, Leandra, just delighted to have you. Thank you for joining us today.

Thanks so much for having me, Sam. Looking forward to chatting today.

Oh, awesome. Let's jump right in as I do with most guests. And to that end, Apollo is in what I would describe as a hypercompetitive space. That is the sales stack and is now in a way the market leader in this hypercompetitive environment. I want to talk about the go-to-market strategy that is allowing Apollo to beat the competition and probably have other sales leaders like myself share similar sentiment around like legacy systems that made a lot of sense in 2018 versus today, moving forward with Apollo and how you got there. So let's start there. At a high level, what do you attribute Apollo becoming a market leader in such a competitive space to?

Yeah, it's a great question. So consider what HubSpot did with inbound marketing in a very crowded space. HubSpot differentiated themselves by offering a better solution that crafted an in-house, not cobbled together product. And so what HubSpot did really successfully for the marketer, Apollo is doing for sales. And what's interesting about sales is we know that sales reps have a love-hate relationship with using tools. Across multiple dimensions that really matter to salespeople are things like ease of setup and ease of use.

And then moving on, if you were to list the things you're doing at Apollo that differentiates you from what your competitors are doing, specifically in sales and marketing, what are the things at the top of that list?

Yeah, a couple of things come to mind. What's different about Apollo is that our sales model is built around a PLG motion. And so what we see is that tech purchases and sales in the past forced users to go through a sales-led process. You don't get the tools in the hands of your sellers until you've gone through an exhaustive POC and implementation. And frankly, you're paying for the product and the sales process around it. And so Apollo stepped in with a PLG offering. We were the first to get there with millions of users at scale. And I think what the key is for us is that our end user needs to see value fast. They want to know how quickly they can book a meeting, how fast can they generate pipeline. That's their sole mission in life, right? So being accessible to end users, especially in SMB, has been a north star for us. And I really think it's paying off across our platform. Because we're seeing competitors now pop up and more established companies trying to play catch up. And the one awesome thing about our model is that our product gets better with scale. So we have a community with millions of free users that are unlocking that network effect, literally making our data the freshest in the industry because they're doing hundreds of millions of actions and activities on our platform. And in a way, the way we scale our go-to-market has created that virtuous cycle that helps us keep offering the best product, which keeps bringing in new people to buy. And I think when I really look back at Apollo differentiation, that I think that something unique about us is that when you have a really loved product, it's fostering that community around it. And that's the essence of the core of what salespeople are, right? They wanna talk to people, they wanna interact.

Makes sense. Okay. So couple takeaways, and then I'll talk a little bit about one thing that comes to mind from my experience at Brex, but couple takeaways. Um, you are selling in an environment where most competitors require businesses to talk to a salesperson before they get access to the product. Um, and one thing that differentiates you on the sales and marketing side is you actually want people to experience your product either alongside or before experiencing other products. And that's potentially a takeaway. If you believe that you have the best product in the market, you should be encouraging and incentivizing people to try it either alongside competitors or in a differentiated way where they actually can't even try their competitors. This does take me back to the days at EchoSign. We were in a hypercompetitive environment with EchoSign and DocuSign. EchoSign is what is now Adobe Sign. We were acquired by Adobe. And we both pitched and then actually encouraged and lived up to this concept that anytime a business trialed EchoSign alongside DocuSign, we would win 100% of the time. And we had 2 tech companies or whatever that we rattled off that did this side-by-side trial.

Yeah.

I think there were 2 things that happened there. One was the psychological impact. Of just suggesting to trial, pushing for the trial. There's so much confidence in our product that we want it to do the selling for us. And so many times people actually wouldn't even do the trial. They would just pick us because it's nothing about the product itself. And then we also were very thoughtful about when companies would trial us alongside our competitors. We would be very thoughtful about here are the things you should be paying attention to. You mentioned simplicity. You would oftentimes talk about the simplicity of sending and signing agreements and how important that was, especially to the signers who weren't the sort of paid users of the system. And so there's probably some analogy for you where it's, you have one system to set up versus 4 or 5 with competitors that you're looking at, API integrations, consulting support. I think just driving home two points that you made that were specific to Apollo, but I think are more universally applicable. One is just around using the product, encouraging using the product, but the psychological impact and then the actual impact, the simp— um, simplicity, making it easy to use your product. Those are a couple that, that really stand out. The last thing that I'm gonna mention and then we'll move on. One thing that Brex did that really differentiated us from our competition, we actually weren't the first corporate card that allowed for cash-based underwriting, where we took a percentage of a company's cash balance and then had no personal guarantee. That's really the sort of value prop that made Brex strong. But we were the first to brand ourselves as the first corporate card for startups. And I think the important part of that sentence is who we were for. We were extremely deliberate that we were going after this segment of the market that was technology startups. And when people, when we would market to people, when people would walk by our billboards, it, it just, they knew they belonged. And so when you go up against competition, it was, we're a corporate card for everyone. We were the first corporate card for startups. That gave us a real advantage in this sort of like innovator's dilemma approach, which is you pick a narrow segment of the market and you just go after it relentlessly and gain market share.

Yeah.

One other thing that sort of stands out on this specific to brand, how to differentiate yourself from competitors is something that worked really well for Brex. With that, let's move on. Continue along this path of selling and beating the competition. Do you target companies you know are on a specific product or products where you have high win rates? Um, how do you approach this? Do you call out the competitors in your initial outreach? Um, and this is like mapping back to the very top of the funnel, how we think about competition.

Yeah, I, I think we have similarities, uh, with your story, Ambrox, because we also are really known as kind of startups and founders. And so we don't target specific companies from a sales and marketing perspective as a core piece of our go-to-market strategy. As depending on where you're going and if you're going more upmarket, sometimes you're selling to a set of verticals or industries, or you've got a solution that's more niche. We are very broad. And so we are seeing win rates that are strong across lots of verticals, lots of industries, and actually lots of company sizes. Because again, we have a lot of end users that are coming to use Apollo to maybe augment their tools out of their own pocket, or that their teams are, are driving that end to end. And I've never typically been the type of seller or leader to aggressively call out the competition. I think that when you search for a problem to solve, and the value that you have to offer, that's how you really win. Of course, we have a point of view on how we compare and we advise our prospective customers on that, but we're really trying to just be trusted advisors, but more of a consultative sell mindset. And, and as mentioned, our foundation has been very focused on SMB all along. So we've been heads down building a world-class product for the audience, and the demand is creeping up market organically because it turns out a lot of businesses want sales tooling to be more accessible. And so many go-to-market solutions are focused on building and selling to the top echelon of mid-market or enterprise companies. But globally, there's an estimated, I think it's about 330 million small businesses driving the global economy. So it's a massively underserved market, and we estimate that TAM to be about $30 billion. And again, I think because there's no barrier to trying the product, we don't have to sell somebody in advance on the commitment. Of taking a meeting, see what it's about, and then trying to make comparisons. When you're trying to compare products competitively and you have a free offering, why wouldn't you try it?

That makes sense and it resonates at, at the sort of top of the funnel. Over time, you're probably measuring things like conversion rates by geo, by vertical, sub-vertical segment, meaning company size. And that's really driving a lot of your behavior in terms of who you're targeting. Over time, you may start to see some trends around, gosh, we're really switching a lot of people off of this legacy product, for lack of a better description. And then if that trend does exist and you can take advantage of it, perhaps you do. But specifically targeting users on a product may or may not make sense. And it sounds like, Leandra, in your case, not really the focus. It's more sort of firmographic information than it is which existing set of systems they are on. And then let's move down the funnel here. Top of the funnel, we're getting as many qualified opportunities in our pipeline as possible, regardless of which system or systems they're on. In, in a deal now where you're competing with another vendor or vendors, How do you balance highlighting what, how, why, or how your product is better with being perceived as selling too aggressively?

Yeah, I think aggressive and confidence are some things you have to be really careful about because I think that when you're clear on the value that per— you provide, you can be confident about that, but you have to make sure that you understand what is the problem that the customer is having. And are you the best solution to solve that problem? And I think when you can really nail the differentiated value on what you have to offer versus maybe what another company is using, that's where the magic can happen. Because it's easy to do a feature functionality comparison across competing products, but really to understand the value and the problem that you can solve differently and the impact that it's going to have for that company, I think really matters. And you know what's interesting? I think being a CRO, I am in the seat of actually being the persona to buy the product that I'm selling, which I think is a really cool perspective. And particularly sales leaders, we want to get to value fast. And also I think sales leaders can sense a song and dance when they hear one, because we're used to being on the other side of the fence. But in a PLG model especially, is if you're not getting what you came for, you can take your money elsewhere. We're not locking our customers into these massive long contracts or commitments where it's just, hey, we're hyper-focused on making sure they're getting to value fast. So getting them to have a meeting with an Apollo as soon as possible and then another and another. And that's like how that ball starts rolling. And then being really consultative about additional products, maybe in their use cases. For example, if we have a really terrific sales engagement solution, You might have reasons that you need to play nicely with another existing solution. So we teach our team how to navigate as advisors within the tech stack. And then we try and just be very transparent about, again, on our pricing and our functionality. So you don't have to ask to take a meeting with us to find out what things cost. It's just on our website. And so we think that it's better to be honest, be consultative, get to know our product, be confident. Someone should be able to have used it back and backwards and forward in a way that they think really adds value to their business. But we're not aggressively going against the competitors in a way that I think that our product just doesn't speak for itself.

Makes sense. One thing that we, or that I learned over time, the first is you do wanna know, and so we, you've referenced SMB several times, which I know is a core segment that Apollo sells into, but you also have some really large customers. And for some of the larger customers, especially those that might be migrating off of existing systems, they actually do want to talk to a salesperson because you need consulting around how this— they actually want to be sold to. And in those environments, and I go back to my days at EchoSign, one of the things that was really effective at a tactical level was just at the beginning of the call, to, to be, as you talked about, being perceived as a, a consultant that is helping them through this process. I would ask the question, I understand that you're either evaluating, uh, us in DocuSign or you're already on DocuSign. I'm going to show, I'd love to learn more about your environment and tailor our product demo to what you all are, are using today or doing today. Um, that said, there are some big differences between us and the other vendor that you're looking at. Um, if you— I can highlight those differences so that you can compare and contrast the products. Alternatively, I can just stick to, uh, our offering and just flag sort of the, the things that are exceptional about our product. And I would say 99 times out of 100 when I would position it as, what, what would you like as a buyer? Would you like to highlight some things that differentiate us in the space, or would you like me to not do? They, they would say, please highlight the differences between the products. Yeah. And it goes back to the framing of the question, which was something like, if you're competing, how do you balance highlighting why your product is better versus being perceived as selling too aggressively? If you ask how you want the conversation to go and the buyer asks you to highlight some differences, you're able to do so in a way where you're just doing what they have asked you to do. And then the second thing that comes to mind in this specific category is when we would highlight some of these differences, we would do so in a way that actually takes what the competitor thought were their advantages and puts them on the back foot that this is actually a disadvantage. I'll give one tactical example that I think helps highlight the point. When we were selling at Brex, we were competing with a company called Divi. In the early days, Divi was our, our primary competitor. And Divi had this really sophisticated budgeting product that was, was a feature that we were actually working on, hadn't yet released. And if it was like a feature bake-off, they would've checked this box. We wouldn't have had it. And the way that we positioned this was, look, you actually don't want this feature. One thing that we position ourselves and pride ourselves in is being simple. Anytime we actually maybe didn't even mention the competitor, but we would say something like, there are vendors in the space. That introduce complexity for complexity's sake.

Yes.

And they have things like budgeting, and here's why you don't want that. Cards are gonna get declined. You can give a bunch of examples as to why this is actually a bad thing. And then they would go get on the call and the competitor would like already be on the back foot. But again, I, I hope these things are coming off in ways that like, you know, when you say that, it doesn't sound like you're bashing the competition. It's much more to your point, like trying to be this trusted advisor and hopefully getting to a point where one, you're trying the product that we are offering. Our product is objectively better, but we're going to guide you into why our product is objectively better.

I think that's brilliant. And I think that you nailed something that's really important is to understand like when a feature is beneficial and when it can actually then drag down. And the, the, the use case that's really important. I always think, is it a table stake functionality that you actually need, or is it just feature glow? And people are trying to do the, the sparkly lights and, and excitement around something that's really not that important for some of them to, you know, execute on what their ideal use case is.

Awesome. Okay, let's continue down the funnel. We've talked about top of the funnel, selling, middle of the funnel against competition. Now let's get to, uh, closing. One thing that the, the first thing that comes to mind when I think about closing a deal when the deal is competitive is pricing. And oftentimes if you're in a hypercompetitive environment, it can, it can be a race to the bottom on pricing, or certainly like the buyer can position it as such. So how do you think about maybe that at a high level and then more specifically How do you all deal with price? Do you discount to match competitors? If you're replacing a competitor, do you buy them out of their contract? I'm just curious how you all have been so successful specifically as it pertains to pricing.

Yeah, it's interesting because we are really affordable at Apollo and what most companies are seeing with growth as it slows, they're really looking and trying to understand how they cut their costs. And how they take their tech stack and save money. And so they're with Apollo being able to replace like 5 to 7, maybe different tools with one solution that's more effective and less expensive. And so it's like cost is one thing, but when you look at your overall tech spend and your tech stack, that's another. And so we inherently can offer lower prices because of our product-led growth motion. And while many companies need to hire an SDR and AE and a CSM to grow their business, our word of mouth is our main driver, um, for Apollo. And so in PLG, we're really able to provide better services at less cost. And really when you have transparency as your mantra, as we talked about, and your go-to-market model is really hyper-efficient, you don't have to take the same stance as everyone else on pricing and competitive deals. What we find actually is legacy competitors are slashing their prices to match Apollo, and customers are telling us that our product is superior. So we don't have to get in this kind of, as you mentioned, race to the bottom or head-to-head competitive pricing situation, because I think it's really what's most important is going back to that value that you provide. And I would say it's less, less about us and more about companies thinking about like how they price go-to-market. And I would encourage people to get comfortable about me being more transparent in pricing, because I think today's customer has a very different expectation than they had a few years ago in resulting. Of PLG-type motions and self-serve and direct-to-consumer pricing. Remember sales back a few decades ago, you couldn't even find anybody's prices on their website. And so now because we're all consumers and we're having that Amazon experience and you can compare pricing and you can see pricing, I think actually when people don't show their pricing, there can be a little bit of a mistrust and not really clear on what drives the pricing levers. And so we really try to get back to value. Having them reach value fast, not racing to the bottom, as you mentioned, on price and really bringing it back to the essence of what we think that customers are, are gonna be able to experience on the platform.

Super interesting. A couple things that come to mind, and this episode isn't about pricing, it's about competition. And so I won't spend too much time, uh, on pricing specifically. That said, what, what I heard from you, Leandro, which really resonates is that in, in a product-led growth motion, you can undercut pricing if the competitors are using expensive sales and marketing resources to acquire customers. You also have the benefit of all-in-one. And so there's a number of things that I think are advantageous for your specific business as it pertains to pricing. The, the sort of counter to that comes to mind. I mean, to like period end of statement in the product-led growth or maybe even segment-based SMB customer acquisition environment, the thing that historically I have had a preference around when selling more into the enterprise is where we're like, we talked about this environment where somebody actually needs a sales rep. They, they want to talk to somebody. It's a much larger business. They want to have, have custom workflows built out or whatever. Their, their needs are more complex. I've actually benefited from being positioned as the higher priced vendor. And the logic, or, or what I attribute that to is the psychology behind proactively positioning as the premium provider in this space.

Yeah.

And like with that, you actually get more. We are the premium provider and I have to be explicit about that. But I think these things are almost conflicting with one another, depending on the motion that you use to acquire customers in the segment that you are going after. But a couple of things that come to mind as you were talking through, but I think the takeaway, at least in a product-led growth environment, is you, you can undercut competition if your customer acquisition resources are less complex as they are for your business.

And I think it also depends on your product. So are you a, if, are you leading in a disruptive market where there's nothing currently established, or are you a me too in an existing stack where you're having to then rip and replace and prove against? And so I, I love the premium aspect, but I think you really have to make sure the differentiation and the value hopefully is there to back that up. So somebody else that's just not trying to be a me too is saying, I can do the same thing at a lower cost.

Makes a lot of sense. Okay, let's move on to one of the last topics. We've gone through the funnel. Let's now talk about hiring. And I'm curious your perspective, and then I'll provide mine, but have you seen success in hiring salespeople from competitors?

I don't. And the interesting thing is because I think it more has to do with the motion than the product. And to me it's, it's always nice that they're coming from that same type of industry and you know that persona, but I'm really looking for somebody that understands more of the motion of the company, the size of the company, the stage of the company, because I think it's really a whole different beast to go work at a startup company or a hypergrowth company than it is to work at maybe a little bit larger company that's in a different stage of, of kind of their evolution. I really look for traits of people, not necessarily who they've sold to. And sometimes you could also bring over bad habits. You can get some good information out of it, obviously, but you can also bring over some bad habits. So I think sometimes just force a different type of conversation of the way that you're selling. To me, the traits are important, like curiosity and we know persistence and a proven track record, but there's a sales DNA that I think is really important because I don't think all sellers are equal. And so I think it's more important to understand the DNA of a seller. What's important for them to know? How they like to sell and where their strengths are. And are you like a hunter traditionally or a farmer? And again, like, who do you like to sell to in terms of your either company stage style or, or your persona? And trying to lean into somebody's strengths versus fitting everybody into the same mold. So it, to me, it's not necessarily a competitive advantage as it is, is just trying to find the right core persona.

Yeah. Philosophically aligned there with One, one thing that I heard Jason say the other— Jason from Zaster say the other day that really resonated with me. I think between us, we've been doing this for many years. The folks that I— and we made one hire from DocuSign at EchoSign, and then there was like Zenefits, Gusto, and then there was Brex and Ramp. And being on the, the receiving end of making a hire from one of those competitors, it hasn't worked out. And being on the end where one of the competitors hired directly from us, like the, the, um, direct competitors, DocuSign hired from EchoSign, Ramp hired from Brex. Yeah, they got the wrong person. Like the type of person that goes to a, a direct competitor where it was personal, there it says maybe something about that person that, that makes that jump. Jason's, and so that was like up until recently, that sort of would've been my perspective on this. Jason said something in a podcast recently that I listened to that really did resonate. And, and so maybe this is like an asterisk or a caveat, something like that, where if there's a vendor that is like pretty far down the list in terms of where they stack rank in this space, if they're like the 4th or 5th best vendor, in a competitive environment and they've figured out a way to be successful with an inferior product, an inferior brand. And I don't know what the exact example would be to, to highlight in Brex's case, but somebody, somebody that was able to figure it out with one hand tied behind their back, something like that. Yeah. Then I could totally see that person coming in and just being like free. Like they were able to make it work in an environment that was much harder. And maybe the takeaway from that is I would potentially try hiring a top rep at a competitor, but a competitor that was like far inferior to the product that we are selling for the reasons that I just mentioned.

I always had a, just an emotional attachment as a seller of the person I was selling against, and I could never go to the other team. So, I don't know, maybe it's the competitiveness in me that, uh, we could never allow that, that type of move.

It's totally true. Maybe there are like extenuating circumstances. They, they laid off the whole sales team.

Sure.

Or like the, the business went under. But I, I agree with you. But, uh, for the first time ever, I heard Jason say something and I was like, that actually is an interesting, uh, maybe counter. Let's end with one final question. Around, I know you consult and advise lots of other startups. Do you see any patterns around common mistakes or pitfalls that you've observed companies make when selling in a competitive market?

It goes back to some of the themes that we've talked about, which is really like feature selling versus value selling and understanding the differentiation. Especially if you're trying to sell up against something that's already there, you have to be really clear on that value benefit that you provide on kind of the know what and why that you're going to get someone to go through that process of changing. I think it's different if you're disrupting and you're, there's something out there that no one has before and you're really solving a problem. But then like, how do you make sure that you're really articulating the, the benefit and the kind of the ROI of solving that problem? And I think we can get a little bit into people not clearly understanding their persona, their ICP, making the product really hard to use or hard to buy. Again, I just think in the age now that we are in technology, in social selling and social business, and us all being consumers at heart and how fast that whole technology has evolved, I think we just have to think about how do we make it for customers easy to use, buy, try, understand, make it simple. Less is a little bit more. I'm sure it depends on the product that you're selling and who you're selling to, but I really think it all comes down to is how do you differentiate your product to be better than anything else out there in the market? I never wanna sell a me too. I'm always asking myself, is this a me too product? Because again, when you're selling me too, a lot of times you really just are selling on price.

Piggybacking off of those thoughts, one of the first things that comes to mind is something around, this is a strong word, but taking control of the conversation and really starting with, here is how we are different. And why that matters. I, I think that you, if you are behind on that, if you are talking with somebody who already believes from a competitor why they are different and why that matters, you're on like your back foot and you're playing, you're being defensive. And so I think you really want to be in that sort of lead position where you are controlling the conversation and you don't even have to bring up a competitor's name. I think you just really wanna focus on what differentiates you and why that matters and have that sort of be core to the evaluation process that your buyer is going through.

Yeah.

And then the second thing that comes to mind, and I've mentioned it a couple times on this podcast, but something that depending on the segment you're selling into can really differentiate you from a competitor is around a relationship. And I've used this statistic a few times, but we had something like 3x the conversion rates when we met a customer on site. So nothing to do with competition. It's just did we meet this person, this buyer in person? If we did, they were much more likely to close. A similar, I think, dynamic would exist where if you were selling against a competitor and you met them in person and your competitor did not. You will have an advantage. And I, I can't underemphasize the importance of like meeting customers, spending time with potential customers, hopefully doing this in person, building relationships, especially as we start to move upmarket in some of the larger, uh, deals.

It's such an important callout, Sam, even in this day and cycle where we're not necessarily always in person anymore because we're, we're doing these things now, like we are today, but relationships matter. And as they say, people buy from people that they like. So that's a lot of times the thing that pushes it over in the end.

Perfect. Leandra, positive note to end on. Thank you so much for being here. For folks that are listening, hope you enjoyed today's episode on competition, and we'll see you back soon. Thank you.

Thanks, Sam.