
How Calendly drives SaaS growth by doubling down on core users and product-led strategy.
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Shane Murphy Reuter
I was like this. I found it. I found it. This is what I've been looking for, I can honestly say has genuinely changed the way I run my business. It's changed the results that I'm seeing. It's changed my engagement with clients. It's changed my engagement with the team. I couldn't be happier, honestly. It's the best investment I ever made.
John Jantz
What you just heard was a testimonial from a recent graduate of the Duct Tape Marketing certification intensive program for fractional CMOs, marketing agencies and consultants just like them. You could use our system to move from vendor to trusted advisor, attract only ideal clients and confidently present your strategies to build monthly recurring revenue. Visit DTM World Scale to book your free advisory call and learn more. It's time to transform your approach. Book your call today. DTM World slash scale.
Hello and welcome to another episode of the Duct Tape Marketing podcast. This is John Jantz. My guest today is Shane Murphy Reuter. He's the president and go to market. I guess you just call that GTM, don't you? @ Calendly, the platform helping individuals, teams and organizations create better meeting experiences by simplifying complex scheduling. He's focused on driving brand awareness and demand by ensuring alignment between sales, marketing and cx. So, Shane, welcome to the show.
Shane Murphy Reuter
It's great to be here. Yes, we shorten it to gtn, but call it whatever you want. Yeah, no, it's awesome. You're a big fan of the show. So great to talk.
John Jantz
Thank you. So I'm going to talk about, I'm going to ask this question in the context of Calendly, but I think that this applies really to a lot of businesses out there. I mean, Calendly started as a small idea, a technology for scheduling, just scheduling. And it's certainly grown to something much bigger. That's something that I think happens to a lot of companies. You want to talk a little bit about and I know you're. You haven't been there from the beginning, but you want to talk a little bit about the evolution of, of that thinking in Calendly.
Shane Murphy Reuter
Yeah, yeah, of course. Well, I've actually only been accountly now, I think four months. I like to write it down, you know, the expectations are lower and so yeah, I haven't seen the, the journey from inside, but actually I've known to for who's the CEO of Cali for about five or six years, you know, so I've been very much watching it from the sidelines. And I would say also if you look at my background the companies that I tend to join are at a very similar stage to Calumny where they've, you know, invented some new technology to solve some sort of pain point for a customer type and then have that exponential growth once they, they sort of like crack the market a little bit to get that product market fit. And then they start to think about, well, okay, we're, you know, maybe growth is starting to slow a little bit in that original market and where to go from here, you know, And I think Calendly has been on that journey. You know, originally we solved just that scheduling problem, that one problem around how do two people schedule meetings together? And it's been very, very successful. But now the question is, well, how do you extend from here? And I think a lot of companies get that wrong, frankly. Like I think there's broadly two pads, right? You either take the technology that you've built and apply it to different markets or you take a target market or customer segment that you have strength with with your original product and then extend the product offerings that they, that you provide to those customers. And certainly Calendly's strategy from here and hopefully very, very soon we'll be launching our first, our second major, major product is to really extend the products that we offer within a certain target market because we just believe there's massive opportunity there to solve other points in the relationship management life cycle for our customers. So it's been, yeah, I've been here four months, but I think that Calendly is on a pretty classic journey that I've seen a lot of companies go through.
John Jantz
Do you feel like you are on the journey to define a category or you have defined a category? You mentioned relationship management. I don't know that people would have applied what Calendly initially started doing to that term. I mean, do you feel like you're, you're categorizing, you know, a new way of working?
Shane Murphy Reuter
It's a great question, I think, scheduling our original product, we created the category, right? We are now basically the Kleenex for, you know, scheduling, which, which is amazing. I think the challenge though with it is different different categories of different tabs, right? Different total addressable markets. And I think for scheduling it is a relatively narrow use case, right? Like it's. While it's extremely important for our customers, it's narrow, but we have this incredible hook into the customer and so how can we add more? And to be fair, I think for a go forward strategy, we think about relationship management software more generally. No, I think the new areas that will go into are existing categories like I don't want to give up our product roadmap but you can imagine the types of other relationship management softwares that are out there like the CRMs, et cetera. I think where our unique advantage is is really in the, in the customer types that will go in service. And I think that we can, if we can build the software with hyper focus on kind of these SMBs and solopreneurs, I think that we can have great success relative to the incumbents that are in the market. So to answer the question more directly we've, I think we've done this category creation thing with scheduling and we'll continue to, to, to hopefully dominate that market from now. From here though, I think it's more about innovating within how we deliver in existing categories.
John Jantz
I'm sure you maybe talk about this in closed door meetings, maybe worry about it even sometimes but how does a company like Calendly, especially in the early days when you essentially created a product that had a certain set of features and the Microsoft's, the Googles of the world could easily squash that, you know, one day wake up and say we're going to do that. How do you kind of ward off that? Or do you worry about again I know you've, you've grown to the point where you know you probably have more market share in scheduling than some of the big people that you know that could have done that. But do you ever sit around and worry about hey, we have to create more features or get more hooks in so that we're not just this one trick pony that gets squashed?
Shane Murphy Reuter
Yeah, that's a great, it's a great question. And for sure, I think if you look at it from the outside you, you may imagine that something like scheduling is very, very easy to replicate. And I think this is where this hyper focus on urban customers is so important. If you talk to the majority of our customers, they are, their time is their money, right. A lot of them actually sell their time. If you're a coach, sure, you know your therapist etc and then others are in. If you're in sales like your, your time is how you get out there and therefore an incredible scheduling experience is really important. So for sure there are many competitors out there, lots of competitors but because they just don't have that hyper focus like we do around the true intricacies of the details of the problem set of our customers, they have not been able to compete. And for what it's worth, when we look at our data for sure, we're hearing a little bit more about other competitors popping up as you would expect, as any company scales. But in reality it's not impacted our business in the way that I think from the outside in you, you would expect. And so we actually think that we have a better opportunity to disrupt other incumbents than the other way around. Given just how critically important this is for our customers. They're not going to go and buy a slightly less good product. They're just not going to do it. They want the best.
John Jantz
You know, one of the things I've seen software companies do as they, as they grew is like, oh, let's take on this and this and let's do email and let's do, you know, the CRM part of it. And it makes a lot of sense, right? It's like, oh, I've got this end to end product. But then they make compromises in every single category because it's very hard to have the, the one thing that, that fits all. I mean, is there any danger, you think, in trying, you know, for somebody to actually start trying to take market share by adding, you know, more product that's already out there and actually diluting what they're good at?
Shane Murphy Reuter
It is an absolute risk and one that you need to be extremely careful of. And so every company I've worked out as we've gone on this multi product journey, there is a constant debate around how much resource should you put into continue to improve your core product versus how much did you put into new innovative areas. So it is a, is a debate and we will never stop innovating on our core of scheduling. I do think though, as you think about like the product areas that you move into, the question has to be, well how, what, what's your unique, unique advantage to win there? And I don't like, I've seen companies just sort of go, we're just going to go in there, we're going to build it and it's like, well, okay, well you really thought about the strategy and it can't just be like a price thing, right? That's not enough. And I think typically that unique advantage tends to come from, as I said before, one either is some sort of technology advantage that you have. I felt I'll give an example of webflow where I worked at last. Webflow's unique technology advantage was that built a way for you to manipulate code in a visual environment and very easy for them to take that technology and move it beyond just building websites into how you build other types of technology. They have a technology advantage they can apply to different markets. For Calendly, I think our like the reason Calendly has been so successful is are two things. One, I do think that we have a unique penetration within a type of customer that I mentioned before that we really understand and can as we go into these new areas make sure that we're addressing their unique needs for a new product. Because like, like cars right before used to be Model T, any color you want as long as it's black, which is fine when you've got a technology advantage like Henry Ford had, you had a technology advantage so you mass market it now that's crazy because that technology advantage no longer exists. You have every million type of car for different types of very specific segments of the market. And so as we think about our go forward product strategy, I think some of it, I wouldn't say we necessarily have a technology advantage but I think that we have a data advantage in being hooked so clearly into the customer's most important thing which is their time and the data around that. And then we have a unique advantage I think in making sure that when we build those new product areas they're beautifully connected and integrated with scheduling and that we build for that segment and we don't try and build the Model T, we try and build a very, very, very tailored experience for the customer set that we're, we know that we have the greatest right to win in. And for what it's worth, we also believe that the incumbents in duration management software market have left that, that market behind. And so I think there's a great opportunity for us to win. But back to your original question. Yes, of course we need to balance and make sure that we're not underinvesting in our, in our core. I, I use the phrase internally at companies that hey, if you kill the cash cow, nobody gets milk. And so yeah, you want to make sure that the, the, the core business which is for us scheduling continues to we continue innovating.
John Jantz
Let me ask you a few things. You feel like you know, what differentiates your business from every other business out there? Can you confidently charge a premium for what you offer? Are you working from a plan, a marketing roadmap that allows you to know precisely what to do next? Look, don't worry if you can't answer yes to any or all of these questions. You're not alone. See, marketers today get so focused on the tactic of the week staring them right in the face that they forget to look at the big picture. The overarching strategy needed to consistently grow their business. Over the years, I've worked with thousands of businesses helping them do just that. Create the perfect marketing strategy and plan that gives total clarity about what to do next, confidence to charge ahead and charge more, and complete control of the marketing tactics they choose. I would love to help you and your team do the same. Look to find out if our Strategy first program is right for you, visit dtm.world/grow and request a free consultation. That's dtm.world/grow.
One of the things that's really tempting as companies grow to the size that Gownley has now. I mean some of your original customers clicked on a button, signed up. It was just them in their, in their, in their house, you know, doing scheduling. And it worked for them. It was awesome. It was easy, no friction. And now you're starting to have enterprise con that, that security and adoption and you know, uptime and you know, all these kinds of things really have to be sold. How do you message? First off, let's, we can talk about operationally as well, but how do you message to such distinctly different sales channels?
Shane Murphy Reuter
Yeah, it's a, it's a great, great question. I think about this through two different lenses. The first one is obviously the who you're going after. And for what it's worth, typically in enterprise companies, if particularly for a company like Callendee, the user within that company tends to test it out first and the user is the person that has that problem. So a salesperson within an enterprise company will go, this is really painful scheduling preferred by calendar, go check it out and they'll come in through our PLG funnel or self serve funnel and there how you sell to them and the message for them is extremely similar as the message to a solopreneur in SMB because they are the user, they have this actual direct pain of the product solves. And so I think that when you know in a lot of ways that is consistent. Now of course if you've got that person in your funnel, right, who is the user within an enterprise, your job now is to use other channels to go and directly target the procurement team, the security team, the actual economic buyer with very targeted messaging. And this is typically through a sales team, but can also be using things like account based marketing to go do that so that you bring your enterprise value proposition to them. And this is like classic in SaaS. This is why if you go to most SaaS websites, unless they are purely focused on the enterprise market, the homepage will be very directed at the end user and they will have an enterprise section which tells their full enterprise value proposition in their pricing and packaging. Most of the packages are designed for the actual users and they've got an enterprise package designed for those other people that you're trying to sell to. And so I think it's about, and finding the balance of that is depends on your business and the degree to which it's like your opportunities in the enterprise versus in the SMB. So I think you need to do both. But I think my key point there is that even in the enterprises there are where you're going to get the adoption is getting a end user to love it because they end up becoming what we call in the, in sort of go to market the champion. They're going in, hey boss, we got to use this thing. Here's how much time it will save me if you don't get the champion, if you don't get that user to care. The procurement team, the security team, they don't give a shit. Oh, sorry, shouldn't have said it. They don't care. And so I think that's the key thing that I think oftentimes people miss.
John Jantz
So is part of what you've been brought to do is build a sales team or is there already a sales team that that's on the ground?
Shane Murphy Reuter
Yeah, we already had a sales team. So when I joined Alan Lee had already gone on the journey to build an enterprise product offering an enterprise sort of package and team. I think where I'm trying to do is blend the self serve and sales experience in a more natural way. So again, a lesson that I've had at pretty much every single company I've worked for in B2B has had a combination of self serve or product led growth and sales. Sales led growth. And typically speaking they tend to be pre siloed on an island. And so what happens is you either have this experience for the customer that's fully self serve, maybe a reactive support team, but pretty much self serve. And then if you're willing to buy the enterprise package now you go through this like really human intensive experience. The SDR goes to the ae, goes to the, you know, account management team with implementation. And it's like it makes actually no sense if you think about it from first principles, why it would be such a binary distinction between the two. And so I think a lot of companies are now realizing, you know, things like velocity sales or you know, much more softer touch sales to still support the customer but also get out of the way if they want to just like adopt and use. And so the team had already started to do some of that work. But it's a, it's a lot of what I think about Dan to Ed is how to, how to, how to blend the two in a, in a more natural way.
John Jantz
Just get rid of a few of the acronyms. That would help. Right. So, so have you, have you found, and this may, this may be a tough question for you to answer. You may not want to answer this, but have you found that, that the role that you've been brought into play is new and has that required a mindset shift because of the way the company's grown, because of the company culture? Again, I'm. You don't have to talk specifically about your experience as much as I'm sure other companies have, have experienced those kind of growing pains too.
Shane Murphy Reuter
Yeah, it's a, it's a great question. Like I think what a lot of companies are starting to realize is, and in my experience is that particularly technology companies are founded by technologists. And so a lot of the time they start self serve, right? They go, well we could, we can just set up a signup link and people can just buy it. And then at some point a board member, somebody said, hey, you've got, you know, larger customers here. You need to build an enterprise offering. They go and hire a head of sales from some enterprise company and that person brings a playbook and drops this like very classic sales experience on top of the self serve base, creating this sort of siloed nature and this kind of like. And so I think a lot of companies, and there's probably been about 10 years of evolution of that happening. A lot of companies are starting to really feel the pain of those things being so disconnected. And so it is becoming more common to bring in a person running all of go to market, particularly in companies where they have both experiences in their business. For all the reasons that I described because in the traditional model of having maybe a CMO who runs the self serve side and a CRO or you know, head of sales who runs a sales side in that traditional model actually beds in the fact that these two things are a silo. And so I do think that it's increasingly happening that whether it's they just use the term CRO to own all of it or a president of go to market like I am, a lot more companies are, are, are, are doing it now.
John Jantz
Yeah, I'm going to get you in trouble here probably. But do you think that the way that salespeople are incentivized really actually exacerbates that problem.
Shane Murphy Reuter
It's a really great question. I actually remember listening to Bill Macis on a, on a podcast who was the, he was head of a CMO at Slack. I think he was at Zendesk like kind of a goat in the industry. And he talked about, I think it was at Slack, bringing in for the sales team that part of their compensation was linked also to a customer satisfaction of the sales process. Anyway, I just thought I'd share that. But yes, I do think that there is a, there is a, I think in the more enterprise end of sales having incentivization to ensure that the sales team do a good job of maximizing the revenue potential is important. So if I'm not incentivized, what I'll do is I'll say oh yeah, okay, well maybe I'll maximize the discount that I give. Or I'll say I won't try and bother multi product sell. I'll just say just get them in on this one product. And so in certain instances you do want incentives for the sales team to push for the largest value cell as possible and incentivization around with commission structures, et cetera can be important there. And so for example at Calendly our enterprise sales team absolutely are commission based and I think that that's the right approach in a more velocity sales model that I mentioned before where it might be lighter touch. You're, you're semi helping a customer like support or you're answering questions. You're doing somewhat of a value sell but not the, the full thing. You, you. I do think that you want to be very careful not to have like a traditional model. And so for example Calendly we don't. Right. They're more salaried. And so I think you just need to apply the right incentive structure based on what, what are you trying to incentivize these people to do? And, and so I do think that there is a place for it as I mentioned, but maybe not across the board on a sales team.
John Jantz
All right, let's end today on, on a product question. I'm, I think this might be a record. I think we're 20 minutes in. Exactly. And then I'm the first mention of AI. So, so how is AI going to impact the product from what you know so far?
Shane Murphy Reuter
Yeah, that's a great question. So I mentioned that we believe this is an opportunity to innovate in the, the relationship management software space for SMBs and solopreneurs, you know, so the lower the, the, the smaller companies, one of the reasons that up until now it's been difficult to build this type of software for those customers is that typically those software types of software need like an army of operations people to set them up and manage them. Like if you talk to companies who have Salesforce or Marketo or any of these, there's like, there's like job boards of like, you know, kind of all these obstacles to manage these tools. And so if you're an SMB, that's really challenging. Right. The beautiful thing is that we're going to start entering the space just as AI is getting to the point point where they can start automating a bunch of the. What used to be take a lot of operational time and effort. And so you can imagine a world where like, you know, today a CRM even in most cases still looks like one of these sort of like databases. Right.
John Jantz
Line items of just a relational database. Right? Yeah, exactly.
Shane Murphy Reuter
Right. And why does that exist? Because it was a record keeper. It was just a database. Right. In the world of AI, that all happens automatically. Now a CRM or relational management software can be actually about surfacing the insights and actions of things that can truly lead to you creating better relationships. And so I think it's a beautiful time for any company that starts thinking about innovating into a new space, because you have a blank sheet of paper to define the way you interact with this product in an AI first way, which I think the incumbents are going to really struggle with. And that's why a lot of the incumbents are doing the copilot thing. Right. We've got this chunky, hard to use software. So how we use AI, we'll give you a clip to help you to figure out how to use a really hard software. Well, the other way you could do it is actually design it from first principles in a way that's really easy to use. And so anyway, we think that there's a huge opportunity there. And for sure our product roadmap from here is like AI first and we are trying to think about everything from that lens.
John Jantz
Well, Shane, I appreciate you taking a few moments to stop by the Duct Tape marketing podcast. Is there anywhere you'd want to invite people to connect with you? I know obviously calendly is where they can find out about the product, but anywhere you like to hang out, LinkedIn.
Shane Murphy Reuter
Is the best one. I used to be in other places, but I think we can safely point people to LinkedIn for now.
John Jantz
Yeah, awesome. Again, appreciate you stopping by and hopefully we'll run into you one of these days out there on the road.
Shane Murphy Reuter
Thanks so much, Sean. It was a pleasure.
John Jantz
Let me ask you a few things. You feel like you know what differentiates your business from every other business out there? Can you confidently charge a premium for what you offer? Are you working from a plan, a marketing roadmap that allows you to know precisely what to do next? Look, don't worry if you can't answer yes to any or all of these questions. You're not alone. See, marketers today get so focused on the tactic of the week staring them right in the face that they forget to look at the big picture, the overarching strategy needed to consistently grow their business. Over the years, I've worked with thousands of businesses helping them do just that. Create the perfect marketing strategy and plan that gives total clarity about what to do next, confidence to charge ahead and charge more, and complete control of the marketing tactics they choose. I would love to help you and your team do the same. Look to find out if our Strategy first program is right for you, visit DTM World Grow and request a free consultation. That's DTM World Growing.
Host: John Jantsch
Guest: Shane Murphy Reuter, President and Go-To-Market Leader at Calendly
Release Date: April 16, 2025
In this episode, John Jantsch welcomes Shane Murphy Reuter, the President and Go-To-Market (GTM) leader at Calendly, a platform designed to simplify scheduling for individuals, teams, and organizations. Shane brings extensive experience in driving brand awareness and demand by aligning sales, marketing, and customer experience (CX) strategies.
Shane discusses his perspective on Calendly's growth trajectory, emphasizing the company's transition from a simple scheduling tool to a more comprehensive relationship management platform.
Shane Murphy Reuter [02:11]: "Originally, we solved just the scheduling problem, but now the question is, how do we extend from here to solve other points in the relationship management lifecycle for our customers."
He highlights that Calendly has successfully achieved product-market fit with its scheduling solution and is now exploring opportunities to expand its product offerings to meet broader customer needs.
Shane asserts that Calendly effectively created its own category within scheduling tools, positioning itself as the "Kleenex for scheduling."
Shane Murphy Reuter [04:16]: "Scheduling our original product, we created the category. We are now basically the Kleenex for scheduling."
He elaborates on the challenges of expanding into new markets, noting that Calendly aims to innovate within existing categories rather than solely relying on its original technology advantage. This strategic focus ensures that the company addresses the specific needs of its target market—primarily small and medium-sized businesses (SMBs) and solopreneurs.
Addressing concerns about competition from industry giants like Microsoft and Google, Shane emphasizes Calendly's unique focus on customer needs.
Shane Murphy Reuter [06:21]: "Our hyper-focus on understanding the intricacies of our customers' problems has made it difficult for competitors to match our offering."
He explains that while many competitors can replicate scheduling features, Calendly's deep integration and understanding of its users' time management needs provide a competitive edge. This focus allows Calendly to maintain its market leadership despite the emergence of new entrants.
Shane discusses the delicate balance between enhancing core products and introducing new features. He warns against diluting the company's strengths by overextending into unrelated areas.
Shane Murphy Reuter [08:15]: "It's crucial to balance improving our core product with innovating new areas. We ensure that any new product leverages our unique advantages and addresses specific customer needs."
He shares insights from his experience at Webflow, where leveraging a unique technology advantage facilitated successful product diversification. Similarly, Calendly focuses on integrating new offerings seamlessly with its existing scheduling solution to provide tailored experiences for its users.
Shane highlights the importance of combining product-led growth (PLG) with sales-led growth to cater to both individual users and enterprise clients.
Shane Murphy Reuter [13:12]: "We aim to blend the self-serve and sales experience naturally, ensuring that enterprise customers receive targeted messaging while maintaining ease of use for individual users."
He explains that enterprise adoption often starts with individual users who become champions within their organizations, facilitating broader organizational buy-in. This dual approach ensures that Calendly can scale effectively while meeting diverse customer demands.
Shane addresses the challenges of aligning sales team incentives with company goals, particularly in balancing revenue maximization with customer satisfaction.
Shane Murphy Reuter [19:14]: "At Calendly, our enterprise sales team is commission-based, which aligns their incentives with maximizing revenue potential while ensuring customer satisfaction."
He underscores the need for carefully designed incentive structures that encourage sales teams to pursue value-driven sales rather than short-term gains, fostering long-term customer relationships.
Discussing the future, Shane envisions AI as a transformative force in relationship management software, particularly for SMBs and solopreneurs.
Shane Murphy Reuter [21:19]: "AI allows us to automate operational tasks, enabling us to design relationship management tools that surface actionable insights and foster better relationships."
He believes that AI will enable Calendly to create more intuitive and user-friendly products, moving beyond mere record-keeping to providing meaningful insights and actions that enhance customer relationships.
Shane Murphy Reuter's insights reveal Calendly's strategic focus on deepening its core offerings while thoughtfully expanding into new areas. By maintaining a user-centric approach and leveraging AI, Calendly aims to sustain its market leadership and drive continued growth.
Key takeaways from the episode include:
Shane’s discussion underscores the importance of strategic focus, customer-centric innovation, and balanced growth strategies in building a resilient and scalable business.
Connect with Shane Murphy Reuter:
Shane is active on LinkedIn and can be reached there for further insights and networking opportunities.
This summary is based on the transcript provided and captures the essential discussions and insights shared by Shane Murphy Reuter on the Duct Tape Marketing Podcast.