Read more at Duct Tape Marketing’s article, How Small Businesses Can Use AI ( Without the Hype or Overwhelm ) by John Jantsch.
Cut the Noise: A Practical AI Guide for Small Business Owners AI is everywhere, and if you’re a small business owner, you’re probably wondering:” How do I actually make this work for my business without adding complexity or draining my budget”? Here’s a quick check. You’re not only. Many small businesses are stuck between the]… ]
Jarret Redding‘s book Win by Focusing on Your Main People can be found at Duct Tape Marketing.
The Duct Tape Marketing Podcast with Shane Murphy-Reuter
I spoke with Shane Murphy-Reuter, President of Go-To-Market at Calendly in this season of the Duct Tape Marketing Podcast. Calendly, best known for revolutionizing planning technology, is now redefining its area by expanding deeper into relation management and SMB tools without losing sight of its core value: improving time.
During our chat, Shane shared the behind-the-scenes approach behind Calendly’s evolution—from a basic time management tool to an intelligent, AI-powered company automation system. As the business expands, its unwavering commitment to providing solopreneurs, SMBs, and customer-centric tasks like sales and coaching has made it stand out in a crowded SaaS business. Shane emphasized the importance of matching sales, marketing, and customer experience—a essential piece of Calendly’s GTM plan that supports green SaaS development.
Important Remarks
- Customer Obsession Wins: Calendly’s success is rooted in its deep knowledge of time-sensitive experts like coaches, therapists, and salespeople—its most sincere people.
- Develop Without Diluting: More than chasing every pattern, Calendly avoids becoming a “one-trick mare” by carefully expanding within its strongest client base.
- Business Can Still Be Personal: Calendly maintains the convenience and freedom that made it popular with people even as it transitions into business planning.
- Smart Product Expansion: By anchoring innovative products in its timing base and enhancing them with AI, Calendly innovates while staying true to its goal.
- Blending Sales Models: Shane discussed combining a customized sales approach and product-led growth, ensuring that customers receive value whether they choose to buy now or speak with a sales representative.
- Category Creation + Innovation: Calendly isn’t just a tool, it’s shaping how modern professionals manage relationships and time—key pillars of any successful business.
Chapters:
- ]00: 09 ] Introducing Shane Murphy-Reuter
- [00:51] Extending Your Core Business
- ]04: 47] How Hyperfocus Protects Your Business
- Find your Unique Advantage at [06: 51]
- ]10: 28 ] Messaging for Clients with Different Needs
- ]15: 05 ] Shifting Mindset to Deal with Growth
- [17 :00] Encouragement Sales Teams
- ]19: 00] How Will AI Effect Scheduling Software
More About Shane Murphy-Reuter
- Check out Shane Murphy-Reuter’, s Website
- Connect with Shane Murphy-Reuter on LinkedIn
John Jantsch ( 00: 00. 93.)
Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. Shane Murphy-Reuter is my guest today. He’s the president and go-to-market. You probably just call that GTM, don’t you? At 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.
CX and marketing. So Shane, welcome to the show.
Shane Murphy-Reuter ( 00: 32.607 )
Great to be here. Yes, we shorten it to GTM, but call it whatever you want. Yes, no, being a huge fan of the show is awesome. So great to talk.
John Jantsch ( 00: 41.07 )
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 Calendly began with a meager notion of a scheduling technology, or simply scheduling. And it’s certainly grown to something much bigger. That’s something I believe many businesses do when you want to talk a little bit about. I know you’re
You haven’t been there from the beginning, but you want to talk a little bit about the evolution of that thinking in Calendly?
Shane Murphy-Reuter ( 01: 13.087 )
Yeah, of course. I’ve actually only been at Calendly for four months, I believe. I like to write it down, know, the expectations are lower. And so, yeah, I haven’t seen the journey from inside, but actually I’ve known Tope for, who’s the CEO of Calendly for about five or six years. I’ve been closely watching it from the sidelines, you know. 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 Calendly where
They’ve developed some new technology to address a customer type’s pain point, and then they experience exponential growth when they sort of like market-catch a little to get that product market fit. And then they start to think about, where maybe growth is starting to slow a little bit in that original market and where to go from here. And I think Calendly has been on that journey. Originally,
John Jantsch ( 01: 51.778 )
Mm-hmm.
Shane Murphy-Reuter ( 02: 03.561 )
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 the question is now, well, how do you leave this place? And I think a lot of companies get that wrong, frankly. Like, you believe there are generally two paths, right? You either take the technology that you’ve built and apply it to different markets.
John Jantsch ( 02: 28.077 )
Yes.
Shane Murphy-Reuter ( 02: 28.409 )
Or you take a target market or a customer segment that you have strength with with your original product and then extend the product offerings that you provide to those customers. And in all likelihood, Canley’s plan from this, and hopefully very soon, will be to release our second major, major product because we think there is a lot of potential there.
solve other points in the relationship management lifecycle for our customers. it’s been, yeah, I’ve been here four months, but I think that the account is on like a pretty, classic journey that I’ve seen a lot of companies go through.
John Jantsch ( 03:07.394 )
Do you, do you feel like you are on the journey to define a category or you have defined a category? You made mention of relationship management. I don’t know that people would have applied what, what Cowan Lee initially started doing to that term. mean, do feel like you’re, you’re categorizing, you know, a new way of working.
Shane Murphy-Reuter ( 3: 24. 641 )
It’s a great question. Think scheduling, our first product, we created the category, right? We are now basically the Kleenex for scheduling, which is amazing. I think the challenge though with it is different categories of different towns, right? various total markets that can be addressed. And I think for scheduling, it is a relatively narrow use case, right? Although it’s very important for our customers, it’s narrow, like it’s, but we have this incredible hook into the customer.
John Jantsch ( 03: 28.034 )
Yeah. Right.
Shane Murphy-Reuter ( 03: 54.753 )
How can more be added? 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 we’ll 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 believe that the key to our success lies in the types of customers we’ll serve. And I think that we can
If we can create software with a particular focus on these SMBs and solopreneurs, I believe we can achieve great success in comparison to the market’s current leaders. So to answer the question more directly, I think we’ve done this category creation thing with scheduling and we’ll continue to hopefully dominate that market. From here though, I think it’s more about innovating within how we deliver in existing categories.
John Jantsch ( 04: 52. 974 )
I’m sure you maybe talk about this in closed door meetings, maybe worry about it even sometimes, but how does a company like Calendar, especially in the early days when you essentially created a product that had a certain set of features and the Microsofts, the Googles of the world could easily squash that. You know, when you wake up, you say,” We’re going to do that.” How do you kind of ward off that? do you worry about, again, I know you’ve grown to the point where,
You are likely to have more market share in scheduling than some of the big people who, you are aware, might have been able to do 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 ( 5: 36.421 )
Yeah, that’s a great question. And for sure, I think if you look at it from the outside, you may imagine that something like scheduling is very, very easy to replicate. And I believe that this hyperattention to your most devoted customers is crucial. If you talk to the majority of our customers, their time is their money. Many of them actually sell their time. If you’re a coach,
John Jantsch ( 06: 03.032 )
Sure.
Shane Murphy-Reuter ( 06: 03.263 )
you know, your therapist, et cetera. And then there are people who think your time is how you get paid if you’re in sales. 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. However, in reality, it hasn’t had the same impact on our business as I would have hoped. 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
John Jantsch ( 06: 53. 304 )
Yeah.
Shane Murphy-Reuter ( 07: 01.419 )
good product, but they won’t do it because they want the best.
John Jantsch ( 07: 04.962 )
One of the things I’ve seen software companies do as they they grew is like, let’s take on this and this and let’s do email and let’s do the CRM part of it. And it makes a lot of sense, don’t you think? It’s like, 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 one thing that fits all. Essentially, do you believe there is a chance that someone will actually try to take market share by adding more?
you know, more product that’s already out there and actually diluting what they’re good at.
Shane Murphy-Reuter ( 07: 37.345 )
is a risk that you must be very cautious of and is an absolute risk. So every company I’ve worked at as we’ve gone on this multi-product journey, there is a constant debate around how much resource should you put into continuing to improve your core product versus how much should you put into new innovative areas. Therefore, there is a debate, and we will never stop creating new ideas for our scheduling fundamental. I do think though, as you think about like,
the product areas that you move into, the question has to be, what’s your unique advantage to win there? And I don’t like it because I’ve seen businesses kind of go,” We’re just going to go in there, we’re going to build in,” and say,” 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 as I said before, I believe that the most distinctive advantage typically comes from having some sort of technological advantage that you have.
John Jantsch ( 08: 12.792 )
Yeah.
Shane Murphy-Reuter ( 08: 33.375 )
I’ll provide an example of Webflow from the last time I worked. Webflow’s unique technology advantage was that built a way for you to manipulate code in a visual environment. Very simple for them to incorporate that technology into how you build other types of technology beyond just building websites. They have a technology advantage they can apply to different markets. For Calendly, think the reason Calendly has been so successful 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. like cars, right, before it was a Model T, you can get any color you want as long as it’s black, which is fine if you have a technology advantage like Henry Ford did. He had a technology advantage, so you mass market it.
John Jantsch ( 09: 24.27 )
you
Shane Murphy-Reuter ( 09: 30.205 )
Now that’s crazy because that technology advantage no longer exists. You have every single car made for a number of distinct market segments. And so as we think about our go for product strategy, 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 so 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 to build the Model T; instead, we try to create a very, very specific experience for the customer base that we believe has the greatest right to enjoy. And for what it’s worth, we also believe that the incumbents in the relationship management software market have left that market behind. And so I believe there is a…
great opportunity for us to win. But back to the original question, yes, of course we need to balance and make sure that we’re not under-investing in our core. I say to employees at companies that if you kill the cash cow, nobody will get milk. And so, yeah, you want to make sure that the core business, which is for us scheduling, continues to, we continue innovating.
John Jantsch ( 10: 55. 394 )
One of the things that’s really tempting as companies grow to the size that Connolly has now, I mean, some of your original customers clicked on a button, signed up. It was just them in their house doing scheduling and it worked for them. It was fantastic. It was easy, no friction. And you’re starting to have business con now. That security and adoption and uptime and all these kinds of things really have to be sold.
How do you message first off? Let’s say we can discuss operational issues as well, but how do you communicate to such distinctly distinct sales channels?
Shane Murphy-Reuter ( 11: 38.185 )
Yes, that’s a really good 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, especially for a company like Calendly, the user within that company typically tests it out first. And the user is the person that has that problem. This is very painful scheduling because a salesperson will leave an enterprise company.
John Jantsch ( 12: 00.429 )
Mm.
Shane Murphy-Reuter ( 12: 06.625 )
You’ll go check it out, and they’ll enter via our PLG and self-serve funnel, as I’ve heard from Cano. And there, how you sell to them and the message for them is extremely similar as the message to a solopreneur and SMB because they are the user, they have this actual direct pain of the product solves. And so I believe that when, in many ways, 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. A sales team typically handles this. We 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 SaaS classic is. 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 the full enterprise value proposition. And the cost of the packaging: the majority of the packages are made for the real users, and there is an enterprise package made specifically for those customers you’re trying to sell to. I think it’s about, and finding the balance of that depends on your business and the degree to which it’s like your opportunities in the enterprise versus in the SMB.
John Jantsch ( 13: 08.675 )
Mm-hmm.
Shane Murphy-Reuter ( 13: 33.409 )
So I think you needed to do both, but I think my key point there is that even in the enterprises, are where you’re 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 are entering, and we need to use this, boss. Here’s how much time it will save me. The champion is the only thing that you can do if you don’t get that user to care.
John Jantsch ( 13: 50.894 )
Sure.
Shane Murphy-Reuter ( 13: 59.883 )
The security team, the procurement team, they don’t give a damn. Oops, sorry, shouldn’t have said it. They are uninterested. And so I think that’s the key thing that I think oftentimes people miss.
John Jantsch ( 14: 09.402 )
So, is one of the things you’ve been given to do is create a sales team, or is there already a sales team that is operational?
Shane Murphy-Reuter ( 14: 17.457 )
Yes, we already had a sales team. when I joined, Cal and Lee had already gone on the journey to build an enterprise product offering an enterprise sort of package and team. think what I’m trying to do is blend the self-serve and sales experience in a more natural way. Again, a lesson I’ve learned from almost every B2B company I’ve worked for was a combination of self-serve or product-led growth and sales-led growth.
And typically speaking, they tend to be pretty siloed on islands. So what happens is that you either have a completely self-serve experience for the customer or have a reactive support team that is essentially 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 account management team with implementation. And it’s like, if you think about it from the beginning, it actually makes no sense. Why would it be such a big deal?
binary distinction between the two. And so, I believe that many businesses are now realizing things like velocity sales or, you know, much more soft touch sales to support the customer while also getting out of the way if they want to just adopt and use. And so the team had already started to do some of that work, but it’s a lot of what I think about day in day out is how to blend the two in a more natural way.
John Jantsch ( 15: 37.496 )
Yeah.
Just get rid of a few acronyms, right? That would be helpful. So have you found, and this may be a tough question for you to answer, you may not want to answer this, but have you found 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, you don’t need to discuss your experience in particular as much as you do…
Shane Murphy-Reuter ( 15: 45.353 )
yeah.
John Jantsch ( 16: 10.242 )
Other businesses have certainly experienced those kinds of growing pains.
Shane Murphy-Reuter ( 16: 14.465 )
Yes, that’s a really good 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 can just create a signup link so that customers can simply purchase it. And then at some point a board member, somebody said, hey, you’ve got a bunch of larger customers here. An enterprise offering is necessary. They go and hire a head of sales from some enterprise company.
John Jantsch ( 16: 25.612 )
Yeah.
Shane Murphy-Reuter ( 16: 42. 591 )
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 in this kind of like a, and so I think a lot of companies, there’s probably been about 10 years of evolution of that happening. Many businesses are beginning to understand the pain caused by that disconnect. And so it is becoming more common.
John Jantsch ( 16: 54.082 )
Mm-hmm.
Shane Murphy-Reuter ( 17: 10.305 )
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 head of sales who runs the sales side, that traditional model actually beds in the fact that these two things are on a silo. And so…
John Jantsch ( 17: 35.054 )
Sure.
Shane Murphy-Reuter ( 17: 37.205 )
I do believe that it’s becoming more common for businesses to use the term CRO, whether it’s their tone or a GoToMarket president like I am.
John Jantsch ( 17: 50.982 )
I’m likely going to get you in trouble here. But do you think that the way that salespeople are incentivized really actually exacerbates that problem?
Shane Murphy-Reuter ( 18: 02.387 )
It’s a really excellent question. actually remember listening to Bill Macias on a podcast who was the, he was head of CMO at Slack. I believe he was working at Zendesk, which he describes as a goat in the sector. 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. And so anyway, I just thought I’d share that. However, I do believe there is a and that there is a.
I think in the more enterprise end of sales, having incentivization to ensure that, you know, the sales team do a good job of maximizing the revenue potential is important. So, for example, if I’m not incentivized, what I’ll do is say, yeah, okay, well, maybe I’ll maximize the discount that I offer, or I’ll say, I won’t try to bother some multi-product sales. I’ll just say, just get them in and on this one product. And so in certain instances, you do want incentives for the sales team to
John Jantsch ( 18: 50. 968 )
Yeah, yeah.
( 1976 ) Shane Murphy-Reuter
push for the largest value sell 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’s the right approach. You’re semi-helping the customer like a support in the earlier, more clocked sales model, where it might be lighter touch, right? You’re answering questions, you’re doing somewhat of a value sell but not the full thing.
You, you, do you believe you should be very cautious in order to avoid acting like a typical model. And so for example, I currently, we don’t write their more salaries. 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 so, I do believe there is a place for it on a sales team, though perhaps not across the board.
John Jantsch ( 19: 58.75 )
Okay. Let’s end today on a product question. I think this might be a record. Think exactly 20 minutes in. And I’m the first mention of AI. So, based on what you know so far, how will AI affect the product?
Shane Murphy-Reuter ( 20: 16.935 )
Yeah, that’s a great question. I mentioned that we think SMBs and solopreneurs, as well as smaller businesses, have a chance to innovate in the relationship management software market. 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
There are like, there are like job boards of like, you know, kind of, all these ops to manage these tools if you talk to companies that have Salesforce or Marketo or any of these. And so if you’re at 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 where they can start automating a bunch of the, used to be, take a lot of operational, time and effort. And so.
John Jantsch ( 20: 45.314 )
Yeah.
Shane Murphy-Reuter ( 21: 12.033 )
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? Line items of people or whatever. Absolutely. Right. And why is that possible? Because it was a record keeper. It was just a database, right? That all happens automatically in the world of AI. Now a CRM or relation 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 believe it.
John Jantsch ( 21: 18.722 )
Yeah, it’s just a relational database, right?
John Jantsch ( 21: 25.422 )
the
Shane Murphy-Reuter ( 21: 41.601 )
You have a blank sheet of paper to define how you interact with this product in an artificial intelligence first way, which I believe the incumbents will struggle with, so I think it’s a great time for any company to start thinking about innovating into a new space. And that’s why a lot of the incumbents are doing the co-pilot thing, right? We’ve got this chunky, hard to use software. So how we use AI will give you a clip.
John Jantsch ( 22: 00.589 )
Yeah.
John Jantsch ( 22: 04. 162 )
Right.
button.
Shane Murphy-Reuter ( 22: 10.517 )
to help you to figure out how to use a really hard software. The other way to do it would be to actually design it from the ground up in a way that’s really simple to use. And so anyway, we think that there’s a huge opportunity there. And for sure, AI comes first on our product roadmap from here. And we are trying to think about everything from that lens.
John Jantsch ( 22: 28.142 )
Yeah.
I appreciate you stopping by the Duct Tape Marketing Podcast for a moment, Shane. Is there anywhere you’d want to invite people to connect with you? Where do you like to hang out, besides Calendly, where can you find out about the product?
Shane Murphy-Reuter ( 22: 45.117 )
LinkedIn is the best one. Although I used to work elsewhere, I believe we can still safely point people to LinkedIn for the time being.
John Jantsch ( 22: 51.692 )
Yes, that’s 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 ( 22: 56.893 )
Thank you so much, John. It was a pleasure.
Sign up to receive email updates
Enter your name and email address below and I’ll send you periodic updates about the podcast.
