Build Trust by Saying What Others Won’t

John Jantsch ( 00: 00. 93.)

Hello and welcome to another episode of the Duct Tape Marketing Podcast. John Jantsch is who I am. My guest today is Shane Murphy-Reuter. 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 aims to promote brand awareness and increase demand by ensuring sales-to-consumer alignment.

marketing and CX. So Shane, welcome to the show.

Shane Murphy-Reuter ( 00: 32.607 )

Great to be here. Yes, we shorten it to GTM, but you can call it whatever you want. Yeah, no, it’s awesome to be your big fan of the show. So great to talk.

John Jantsch ( 00: 41.07 )

Thank you. I’m going to discuss this in detail in relation to Calendly, but I believe it really applies to many different businesses. I Calendly started as a small idea of a technology for scheduling, just 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 since the beginning, but you want to talk briefly about how that thought evolved in Calendly.

Shane Murphy-Reuter ( 01: 13.087 )

Yeah, of course. I’ve only been at Calendly for four months, I suppose. I like to write it down, know, the expectations are lower. And so, yes, I haven’t personally witnessed the journey, but Tope, who is the CEO of Calendly, has been around for a good while. You know, 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 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 believe Calendly has traveled that far. 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 incredibly successful. But now the question is, well, how do you extend from here? And I think a lot of companies get that wrong, frankly. I suppose 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 as we all know, Canley’s strategy from here, and hopefully very soon, will be launching our second major, major product, is to really extend the products we offer within a certain target market because we just think there’s a lot of opportunity there.

solve other points in the relationship management lifecycle for our customers. yes, I’ve been here for four months, but I believe the account is on a pretty, classic journey that I’ve seen a lot of businesses 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. Do you feel as though you are categorizing a novel way of working, as you may be.

Shane Murphy-Reuter ( 03: 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 believe the difficulty is that there are many different categories of towns, right? Different total addressable markets. 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 )

Yes. Right.

Shane Murphy-Reuter ( 03: 54.753 )

How can we increase it? And to be fair, I think for a go-forward strategy, we think about relationship management software more generally. No, I don’t think the new categories that we’ll enter are existing ones, like,” I don’t want to give up our product roadmap,” but you can see the different types of relationship management softwares that exist, such as CRMs, et cetera. I think where our unique advantage is really in the customer types that we’ll go in service. And I think that we can

I believe that we can have a lot of success in comparison to the market’s incumbents if we can create software with a hyper focus on some of these SMBs and solopreneurs. 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. However, I believe it’s more about innovating within how we deliver in the already-existing categories from here.

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, you’ll say,” We’re going to do that,” when you wake up. How do you kind of ward off that? again, I know you’ve advanced to the point where, again, worry you.

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 ( 5: 36.421 )

Yes, that is a fantastic question. And for sure, I believe that something as simple as scheduling can be replicated if you look at it from the outside. And I think this is where this hyper focus on your most fervent customers is so important. 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 to do it if you’re in sales. And therefore an incredible scheduling experience is really important. There are undoubtedly many competitors out there, many of whom, but they have not been able to compete because they lack the genuine attention we do to the specifics of the problems facing our customers. 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 think. 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 won’t go out and purchase something a little less expensive.

John Jantsch ( 06: 53.304 )

Yeah.

Shane Murphy-Reuter ( 07: 01.419 )

excellent product, but they won’t do it because they want the best.

John Jantsch ( 07: 04.962 )

Let’s take on this and this, let’s do email, and let’s do the CRM part of it, is one of the things I’ve seen software companies do as they’ve grown. And it makes a lot of sense, right? 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 an absolute risk and one that you need to be extremely careful of. 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, it is a debate, and we will never stop creating new ideas for our main point of scheduling. I do think though, as you think about like,

What is your unique advantage to succeed in the product areas you move into? 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 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 give an example of Webflow where I worked last. 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. Consider, for Calendly, that there are two things that account for Calendly’s success. 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 in any color, 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 million car for various kinds of very specific 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, in my opinion, we have a unique advantage in making sure that when we build those new product areas, they are 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 know that we have the greatest right to win in. 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. However, to return to the original question: yes, of course we need to maintain a balance and ensure that our core is not being underinvested. I use the phrase internally at companies that if you kill the cash cow, nobody gets 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. They were just working on the scheduling in their home, and it turned out well. It was awesome. 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 someone first? Let’s let we can talk about operationally as well, but how do you message to such distinctly different sales channels?

Shane Murphy-Reuter ( 11: 38.185 )

Yes, that’s a great question. I think about this through two different lenses. The first one is undoubtedly who you want to pursue. And for what it’s worth, typically in enterprise companies, particularly for a company like Calendly, the user within that company tends to test 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 )

I’ve heard by Cano, you’ll go check it out and they’ll come in through our PLG funnel, our self-serve funnel. 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 is consistent in many ways. Now, of course, if you’ve got that person in your funnel, right, who is the user within an enterprise,

Your current task is to use other means of communication to directly target the economic buyer, security team, and procurement team. This is typically through a sales team. 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 end user will be very targeted on the homepage, and there will be an enterprise section that explains the full enterprise value proposition. And the price in the 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. 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 believe you should have done both, but I believe my main point is that even in enterprises, the adoption process is about fostering a end user’s love for it because they end up becoming what we refer to as the champion in a sort of go-to-market. They’re going in, Hey boss, we’ve got to use this thing. Here’s how much time it will save me. The champion is not the thing to do if you don’t get the user to care, and the champion is not the person.

John Jantsch ( 13: 50.894 )

Sure.

Shane Murphy-Reuter ( 13: 59.883 )

Procurement team, the security team, they don’t give a shit. 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 part of what you’ve been brought to do is build a sales team or is there already a sales team that’s on the ground?

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 that what I’m trying to achieve is a more natural blending of the self-serve and sales experience. 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 led growth.

And typically speaking, they tend to be pretty siloed on islands. So what occurs is either you have this completely self-serve experience for the customer or you have a reactive support team that is 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 account management team receives the SDR after the implementation, and the AE receives the SDR. 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 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 of the acronyms, that would help, right? 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…

Shane Murphy-Reuter ( 15: 45.353 )

yeah.

John Jantsch ( 16: 10.142 )

I’m sure other companies have experienced those kind of growing pains too.

Shane Murphy-Reuter ( 16: 14.465 )

Yes, that’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 they do frequently self-serve themselves, right? They go, well, 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 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 think that it’s increasingly happening that whether it’s they just use the term CRO, it’s your tone, all of it, or a president of GoToMarket like I am, a lot more companies are doing it now.

John Jantsch ( 17: 50.982 )

I’m likely going to make 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 great 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. I just thought I’d share that anyway. 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, you know, the sales team do a good job of maximizing the revenue potential is important. So, for example, if I’m not incentivized, I’ll say,” Oh, okay, well, maybe I’ll maximize the discount that I offer,” or” I won’t try to bother some multi-product sell,” I’ll just say, just get them in and on this one product. And so, in some situations, you do want sales team incentives.

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 instance, our enterprise sales team at Calendly are utterly commission-based, which is the right approach. In a more velocity sales model that I mentioned before where it might be lighter touch, you’re semi-helping the customer like a support, 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. So I believe you simply need to put in place the appropriate incentive structure based on what, what are you trying to encourage these people to do? And, 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 Jantsch ( 19: 58.75 )

Okay. Let’s end today on a product question. This might be a record, in my opinion. think we’re 20 minutes in exactly. And I’m the first mention of AI. How will AI affect the product, based on what we currently know?

Shane Murphy-Reuter ( 20: 16.935 )

Yes, that is a fantastic question. I mentioned that we believe this is an opportunity to innovate in the relationship management software space for SMBs and solopreneurs, know, 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

There are job boards of like, you know, kind of, all these operations 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 wonderful thing is that we’re going to start entering the space just as AI is advancing to the point where it’s possible to start automating a number of the, previously, 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? items of the people’s liners. Exactly. Right. And why is that possible? Because it was a record keeper. It was merely a database, was it not? In the world of AI, that all happens automatically. 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 )

Yes, that’s just a relational database, isn’t it?

John Jantsch ( 21: 25.422 )

the

Shane Murphy-Reuter ( 21: 41.601 )

I believe it’s a wonderful time for any business to start thinking about innovating into a new industry because you have a blank sheet of paper to define how you interact with this product in an artificial intelligence first way, which the incumbents are going to really struggle with. And that’s why a lot of the incumbents are doing the co-pilot thing, right? This difficult-to-use, chunky software is available. 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 show you how to use a really challenging program. 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, 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.

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 am aware that Calendly is where they can learn more about the product, but where else do you like to hang out?

Shane Murphy-Reuter ( 22: 45.117 )

The best one is Linked In. I used to be in other places, but I think we can safely point people to LinkedIn for now.

John Jantsch ( 22: 51.692 )

Awesome, yes. 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 )

Thanks so much, John. It was a pleasure.