
Tech Bound Podcast · 2023-06-19 · 35 min
Key moments - from our scoring
Substance score
55 / 100
Five dimensions, 20 points each
Calendly has achieved remarkable growth - 50% YoY in 2021 to $85M ARR with 53% US market share - but faces saturation in the horizontal scheduling market and competition from larger players like Google Workspace. The appointment scheduling market itself is growing at 13-19% CAGR toward $500-700M by 2027, but Calendly must evolve beyond self-serve to sustain momentum. Kieran Flanagan articulates a three-phase PLG framework: (1) self-serve horizontally, (2) product-led sales via product-qualified accounts (PQAs) to move upmarket, and (3) platform development to build defensible, sticky products around the calendar as the core asset. He proposes adjacent use cases - shared notes, video context, contact data capture - that integrate within the scheduling workflow rather than forcing context switches. For verticals like medical, he highlights opportunities around referral networks and specialist coordination, while acknowledging that different verticals (medical vs. sales vs. HR) require different growth mechanics based on their buyer dynamics. The discussion positions Calendly's Prelude acquisition as a move toward vertical depth, mirroring HubSpot's hub strategy (Marketing Hub, Sales Hub, Service Hub, Ops Hub) but built around calendar rather than the contact record. Integration opportunities with tools like Gong, Outreach, and Chorus are identified as differentiation levers.
The three phases are: (1) self-serve horizontal growth across broad user bases, (2) product-led sales overlaying sales teams to convert product-qualified accounts (PQAs) within domains, and (3) platform development building vertical-specific products around a core sticky asset (in Calendly's case, the calendar) to increase defensibility and lock-in.
By aggregating product usage at the domain level - tracking new signup velocity, number of active users per company email domain, and feature adoption patterns - to flag accounts meeting PQA thresholds, then routing them to vertical sales teams rather than relying on individual user adoption.
Shared notes for pre/post-meeting collaboration, video context submission during scheduling setup, and contact data capture from meetings - all integrated into the scheduling workflow rather than as separate products, allowing distribution through the core use case.
Prelude is an enterprise interview scheduling tool for recruiting with hundreds of customers; the acquisition signals Calendly's shift toward vertical depth and platform strategy, similar to HubSpot building separate hubs (Sales Hub, Marketing Hub, Service Hub) around the contact record.
Medical has weaker gate-keeping than HR (doctors accept direct bookings while sales requires pre-vetting), strong website embedding opportunities, and unique backend needs around referral networks and specialist coordination - requiring different feature sets and go-to-market approaches.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains genuinely useful frameworks - PQL vs. PQA distinction, the three-phase PLG growth journey, and the calendar-as-contact-record analogy - but these are interspersed with well-worn PLG truisms that experienced operators already know. The brainstorming format produces several interesting but shallow ideas without enough depth to be immediately actionable.
how do I move from a PQL model, which is like, how does the user identify themselves through usage within the product to a PQA? which is product qualified account, which is how do I aggregate all of the information that I have within that domain to actually flag that and rotate it to a sales team
the mistake people make is when you're trying to build adjacent use cases if it's a totally new use case and doesn't actually interact with the core use case at all it's really hard you're kind of just building a separate product
A few genuinely non-obvious angles appear - using ZoomInfo's freemium scraping model as a Calendly data play, and the calendar-as-contact-record reframe - but the bulk of the strategic discussion (PLG maturity stages, hub-and-spoke platform model, land-and-expand) recycles frameworks widely circulated in SaaS operator circles.
if you sign up for the freemium version of the product which is called their community product it allows them to scrape your contact list
I think Calendly is like, how do I build around the calendar, right? The calendar is my version of the contact record
Kieran Flanagan is a legitimate senior operator - former SVP of Marketing at HubSpot where PLG was core strategy, now CMO at Zapier - and draws on real experience rather than theory alone. His credibility is genuine, though he hedges noticeably on specifics (e.g., unable to name a best-in-class product-led sales company) and the conversation stays conceptual rather than drawing on deep war stories.
Yeah, I don't know because it's actually harder to know what company is doing really well with product-led sales. It's not as easy in terms of just knowing what company is doing really well with PLG because it's the inner workings of the company
I think it's always better to build. I think it was an interesting decision they made to actually buy that
The host supplies solid market context in the intro (Calendly $85M ARR, 50% YoY growth, $3B valuation, market CAGR of 13-19%), and a few concrete data points surface mid-episode (Linktree's 45M monthly social visits, Fellow's $30M raised). However, the strategic ideas are debated almost entirely at the conceptual level with no data backing up the prioritization or sizing of the opportunities.
They grew 50% incrementally year over year in 2021 to about $85 million in ARR
they get around 45 million visits a month just from social like not from not from everything else they get like hundreds of millions a month
The episode is structured as a mutual riff rather than a traditional interview, which keeps both parties contributing ideas, but it also means neither pushes back on the other's claims. The host asks reasonable follow-up questions (recession M&A timing, best-in-class product-led sales) but accepts every answer without probing weak logic or challenging the half-baked ideas on their own terms.
Is there a company that in your mind is best in class when it comes to product-led sales or does it just outstandingly well?
Do you think that the recession could be a good opportunity to lean stronger into merchant acquisition?
Computed from the transcript - who did the talking, and the words that came up most.
Today, I’m unpacking a fascinating conversation with Kieran Flanagan, CMO at Zapier and former SVP of Marketing at HubSpot. This discussion centers on Calendly, a scheduling app used by millions, and its strategic acquisition of Prelude. We talk about the critical role of platforms in product-led growth (PLG) businesses. AI tools, for instance, are seen not as standalone products but platform features. Canva's freemium text image generator exemplifies a platform disrupting the market. Grammarly and Jasper also come up in the context of branding and market disruption. Distribution is vital for platforms. Calendly's acquisition of Prelude, an HR enterprise tool, is a case in point. Flanagan compares Calendly's potential growth strategy to HubSpot's approach of building individual hubs around the contact record, each catering to different roles like marketing, sales, customer success, and operations. We also explore the idea of Calendly morphing into a platform and integrating with other established products to multiply its value, for example, Gong, Outreach, Chorus, Jira, Monday, Asana, Dovetail, and Qualtrics.
Transcribed and scored by The B2B Podcast Index.
Hello and welcome at another episode of the TechMond podcast. My guest today is none other than Mr. Kieran Flanagan, the new CMO at Zapier, former SVP of Marketing at HubSpot, angel investor, startup advisor, and co-host of the Marketing Against the Grain show. Today, we're talking about Calendly and why it acquired Prelude.
A key component of Calendly's future growth strategy is expansion into specific verticals. And that's exactly what Kieran and I talk about. We each brought three different ideas to the table and riff on Calendly's growth. I hope you learn a lot from that.
And if you like it, please rate it five stars wherever you listen to podcasts. Please enjoy my conversation with Kieran Flanagan today about Calendly. Three, two, one. Kieran Flanagan, welcome to the show and thanks for being on.
Yeah, thanks for having me, Kevin. I'm excited to be on. Oh, and I'm excited too. Today we're talking about Calendly, a product that I've been using for many years.
And as always, our first one is set the stage about the company market product challenges and so on so i'm sure most of our listeners here uh heard about calendly before it's a scheduling app that's used by over 10 million people from tech workers to yoga instructors and everything in between their vision is to be the go-to platform for work and leisure life planning the basic functionality for those who for those five people who don't know calendly yet uh it's as simple as if you want to schedule time with someone you can just define or pre-define slots on your calendar send them a link and then they can pick a time that works for them so it makes scheduling super simple they also added some functionality for charging for time and making scheduling even easier but we're going to come to that in just a second the company itself was founded in 2013 by topi awetona it's profitable today and valued at three billion dollars that's the status quo as of 2020.
And it reached a valuation by raising $350 million from investors and Autona's life savings, which I found pretty impressive. Calendly saw massive growth, especially during the pandemic. They grew 50% incrementally year over year in 2021 to about $85 million in ARR, which is pretty impressive, which means that they're growing faster than companies like zapier or docusign and have reached about 53 percent of market share in the us so pretty explosive growth um the appointment scheduling market in general has been valued at about uh 300 million in 2021 uh of market volume it's growing at a 13 to 19 percent compound annual growth rate uh so so fairly well and it's predicted to reach 500 to 700 million in 2027 so there's There's a lot of movement there.
The market is growing. And remote work and the pandemic have accelerated their growth. There are direct competitors to Calendly, like Calendar.com, SetMore, and TimeTrade.
And then indirect competitors like Google's new business suite, scheduling features, HubSpot, and Drift. A couple of the bigger trends, as you might already tell, bigger players are moving into the market. I already mentioned remote work and the pandemic being acceleration of market growth. there is just more vertical growth as well like doctors using scheduling software to schedule appointments for example real quick about the challenges uh as i already mentioned google's workspace um product is a direct competitor and offers customers to schedule directly to google calendar for eight dollars a month actually google calendar is the second largest calendar app after outlook which i wouldn't have guessed uh outlook is used by over 500 million people who knew uh and fun fact on the side, if Google Calendar was a social network, it would be bigger than Twitter or Snapchat.
So yeah, a lot of volume there. So what that means for Calendar is that they need to win the enterprise market segment and they need to go deeper into verticals like sales, HR, or productivity. The context of this episode is that Calendar, sorry, Calendly acquired Prelude, which is an enterprise interview scheduling app for recruiting. Prelude raised $2.
4 million and has hundreds of customers. And they make it easier to schedule a series of interviews, which they call Journey, with several stakeholders without the typical back and forth. So it's more than just scheduling. It provides information to applicants, to the company that's hiring, makes interview preparation really easy, and provides companies with hiring analytics.
That kind of sets the stage for today's episode. And as the guest here, and I want to pass it over to you for the first growth idea. So we step back a little bit and talk about Calendly being a product-led growth business and talk about fundamentals in terms of how you grow a product-led business. You really have to grow self-serve, which is what Calendly did through a horizontal and user-based model.
So it means users can actually use product by product. You kind of then layer on product-led sales, right? You look at your self-serve base and you try to figure out How do I find accounts in there that can actually buy my higher tier packages? And then I actually layer on true enterprise, which is IPAN and targeting companies.
And so the kind of magic trick that all PLG companies have to kind of pull off is, how do I continue to have breadth across my self-serve? So how do I continue to get mass amount of users to use this thing? And how do I actually go for depth of features and target a specific cohort or group of people who will buy a more in-depth version of my product. And Calendly have obviously gone into HR and likely sales and these other kind of verticals that they can go into.
So I think the first one I started with was really like, how do you continue to grow self-serve? I think it's really hard when you're a kind of mature PLG business, that balance of self-serve and going up market. It's actually really complicated. I've talked to a lot of companies who are trying to pull that off.
To grow self-serve, you really need new users for your primary use case, which in Calendly's case is scheduling. Is there more juice left in the scheduling market? I don't really think there is. Or how can I have new use cases that I can use my primary use case to accelerate?
So how do I create new things that users can buy in a horizontal fashion? And I can use my core use case of scheduling to actually accelerate the growth of those. And so I think Calendly are likely at the point where they need to build more products, horizontal products to keep growing. I don't think there's a lot of people who don't know about Calendly probably are not using Calendly for scheduling or have not chose a competitor tool.
And I think when you think about that, right? Okay, well, how would Calendly potentially build new use cases for users? Well, the calendar is really, we think less about the scheduling and more about the calendar. Like the calendar is at the heart of how work gets done, right?
And scheduling is one form of how Calendly interact with the calendar. and the mistake people make is when you're trying to build adjacent use cases if it's a totally new use case and doesn't actually interact with the core use case at all it's really hard you're kind of just building a separate product and you have to try to convince users to use that product so what i kind of went through is what are some things that can only can build that you would actually interact with in the same kind of user journey as setting up the scheduling for the calendar right so you're not having that kind of context switch into a whole new thing and so a couple for Calendly that I think are kind of interesting when I'm setting up my scheduling I can request someone to include or I can actually hit a toggle and include shared notes which I think is a pretty self-explanatory one where like me and you could you could book time with me I would have an option where it would send you our notes our shared notes and we could kind of collaborate in that pre and post meeting and it would capture all of those notes for each of ours so again i'm not actually having to get outside of my setup my scheduling it's actually within that scheduling and i can use the scheduling for distribution another one that i think would be really cool is i can request people to include a short video as part of setting up that video to provide context like there is just so many meetings that i have no context for and i don't think written word does a great job of that in that context so again i can toggle on add video and again i'm using scheduling to accelerate use of this new kind of adjacent feature and i can actually have people kind of opt in to buy those at a later stage and then the other one that i think is super interesting probably like outside of what calendly would want to do if you actually look at how zoom info has grown their data base or like grown the amount of data they have access to now it's not just this but they have a freemium version of their product and if you sign up for the freemium version of the product which is called their community product it allows them to scrape your contact list Now you can argue whether that is good or bad for the world but that is just one of the ways that they capture data Calendly probably have a better way of capturing that data Like on the freemium platform you can use it for free but only if you allowed to capture the contact record that actually scheduling with you and script the LinkedIn data and have a database You'd have to really squint your eyes for Calendly to go after Zoom info.
But it is one way they could think about continuing to grow the self-serve. But I think coming back to like, what is the learning for listeners here? I think at some point you can, you know, you have this use case that is horizontal, which is scheduling. It's applicable to users across industries.
And at some point that starts to plateau and you have to think about, do I want to continue to grow myself for a business or can I just sustain my growth by going up market? I think in this case, if you have to grow Calendly need to continue growing the self-serve business, they're going to have to build adjacent products. and those adjacent products should have accelerated growth because they're tied into the core use case, which is scheduling. What I love about this idea, about the points you make, is that different verticals come with different growth opportunities.
And that's why I totally agree you might want to tie some growth strategies to specific verticals. What I'm thinking about explicitly is the medical or doctor market, right? So obviously there's a strong fit between scheduling and doctors because they make appointments all the time. However, doctors often already have a website and there might be a strong fit between providing some sort of like an embedding between Calendly and the doctor's website, or maybe even at some point allow doctors and other players and customers create their own little Calendly website if they don't have one themselves.
That could be like a little growth mechanism because there's such a strong desire for doctors to just say, hey, look, you can just book a time, right? And then we'll figure out what you have as opposed to verticals like sales or HR, where you don't maybe want to allow anybody to just book an interview or a conversation. You want to pre-vet them first, right? So there are differences in these verticals of what growth mechanisms you can already leverage based on how these verticals set up and what the dynamics in them are.
Yeah, if I was going into medical for Calendly, actually the thing that is really archaic in that industry, because I spent time with a company I was potentially going to do a seed round in and didn't end up doing it. But what I learned was there's this whole ecosystem in the backend around referrals. And so doctors refer you to like specialists and all these different people that they, and then they actually get a fee for actually referring you to those people. So there's this like, they all have their own little networks and it's all done through like really rudimentary ways, like email and spreadsheets and all terrible ways.
And so if Camely could actually help not just book in with your primary care physician, but actually having ways that they could then refer you to a list of people within their network and book time with them. I think that would be really useful for people in that industry. Yeah, love that. And shared notes, right?
Like as you mentioned, there might even be a way to transfer information. Could be implications about privacy. I know that this is a very sensitive part of the market. My father is a doctor.
I know from experience that scheduling, transferring information, coordination, referrals, that is all a huge mess. And I would say the standard is probably even more paper and phone instead of email. Email is already pretty advanced. So there's probably tons of opportunity to reduce friction in these markets as a doorway for growth and getting customers on board.
So I love the very vertical, specific growth strategy. One that I brought to the table is a land and expense strategy to fuel enterprise growth. Totally support and agree with your points about going vertical specific. I think one way to increase the size of the pie for Calendly could also be to go up market, which you already said, and that is enterprise growth.
They need to build out an enterprise sales team. But the growth tip that I want to bring to the table is that they can, first of all, probably identify users that belong to an organization, either based on their email address, which is probably the easiest way, or if maybe users sign up with a personal email, Calendly could use a tool like Phantom Buster to scrape LinkedIn profiles and see if similar users or groups of users actually belong to the same organization and then have the sales team reach out to that organization and make them a good deal, right?
Maybe it could be 10% off if you buy an enterprise account or extra features like two-factor authentication, like security is often something that enterprise companies care about and it's often part of an enterprise offering. Then from there, within the sales land and expand strategy, once Calendly has a foot in the door with maybe a small team or an organization, then the question is how can they expand from there to other teams or organizations? One way could just be to identify internal ambassadors or champions, but another one is just to simply highlight the perks of people using Calendly across the whole company so one of them could be to just you know make scheduling much much easier between teams organizations and people but then there's also a big advantage in understanding where time gets wasted or lost with an organization actually meetings can can be huge productivity killers as you know somebody who has worked at Shopify I can you know we had this or still have this thing which is called the chaos monkey and the chaos monkey is a program deployed by and developed by toby lutke the founder and ceo that will just delete every meeting on the calendar with more than two people um and so there could be a morning where you wake up and you see that you know you feel like you're on vacation because your calendar is empty but in fact the chaos monkey has been employed and it's it's a it's an attempt to remind people how much time can get wasted and lost in meetings i think calmy has a huge advantage by providing analytics and maybe even suggestions for reducing the time waste for meetings.
It might even help people optimize their day. One thing that I have gotten a bigger fan of over time is to optimize for energy rather than time, which means I did an exercise where I look at when do I have the most and least energy and what activities increase or decrease my energy. And Calendly can make that super simple. And if you multiply that across a large organization, that can be a huge productivity booster.
Yeah. Yeah. So I think, um, again, if we come back to the kind of three ways that you grow a product led business self-serve, I think what you have to continue to go horizontal in some ways, what you're talking really about is like product led sales. Like how do I overlay sales on top of my self-serve business and start to use that data to sell into accounts?
And they are, they are for sure doing that. Uh, they actually have vertical sales teams. I think one of the ways to think about Calendly as they move up market is just as like CRM platforms, like a HubSpot or a Salesforce or these kinds of companies, the lifeblood of those platforms is to own the contact record and to build products around the contact record because a contact record is the thing that's sticky. I think Calendly is like, how do I build around the calendar, right?
The calendar is my version of the contact record and I can build things around the calendar because that's going to make it much more sticky. And so as they go up market, I think the key for any kind of company as they layer on that product at sales is really how do you move from a PQL model, which is like, how does the user identify themselves through usage within the product to a PQA? which is product qualified account, which is how do I aggregate all of the information that I have within that domain to actually flag that and rotate it to a sales team.
And so things that could actually be, you know, signals for product qualified accounts as you lay around product that sells and move up market are the velocity of new signups. So if you see an influx of new signups come in through a domain, that could be a signal when you see, you aggregate the usage from that domain. Like you have 10 people who sign up and they all have some form of usage and you aggregate that to qualify an account and it kind of goes through the threshold.
The hard thing actually around, really around product-led sales and going upmarket, I think you kind of mentioned it in terms of, it's really hard to identify the buyer sometimes, right? And so the PQL is like someone who self-identifies themselves as the buyer because they raised their hand. And in a PQA environment, product-qualified account, you sometimes can actually have a lot of users using the product, but actually not have the buyer using the product. like a really good example of that is when you have to sell your enterprise package to it like most of the things that you mentioned to uh two-factor authentication and these kind of security things are all things that it would want within the product when they upgrade to an enterprise package and so it may not actually be users of your product but you still have to kind of sell into um it every plg business at some point they'll see the self-serve business self-serve business start to slow down and they need to layer on product that sales and use that kind of self business to qualify domains and qualify domains and have sales kind of call out to those domains Is there a company that in your mind is best in class when it comes to product-led sales or does it just outstandingly well?
Yeah, I don't know because it's actually harder to know what company is doing really well with product-led sales. It's not as easy in terms of just knowing what company is doing really well with PLG because it's the inner workings of the company. You kind of have to be in the company I do know Miro. I'm a big fan of Miro and everyone kind of knows Elena.
And I think that most things that Elena touched are really good. And Miro, I think, are an incredible company. But it's really hard to know the companies that are doing really well with product-led sales other than PLG companies that have moved up market. And Miro actually has straddle one of the few PLG companies that truly straddle both sides of the market.
They have some of the Fortune... A lot of the Fortune 500 use that company. And then actually they have a ton of like individual users and SMBs. And so for me, where you can see product-led sales work really well is when you've seen a PLG business successfully move up into the kind of upmarket enterprise space.
Sure. Sure. Not up. Cool.
Kieran, idea number two, what do you got? Yeah. So I think I'm kind of going through really the journey of building a PLG business. I went self-serve.
You kind of took the product-led sales, which I think is a natural next part of building that PLG business. And the third part of really, we're probably at like a hundred million in AR, right? Like self-serve probably gets us at 50 million. We probably have to layer on sales around 50 million.
Now we're up at around a hundred million. We're like, oh, okay. Like we really need to figure out how to continue to grow this business. And I think what PLG businesses need to do at this point is how do I be a platform, right?
If you're every feature needs to be a platform or it will get bought by a platform or disrupted by a platform. A really good example of this is, for the most part, I think the AI tools you're seeing today are cool and get a lot of publicity and people are using them. But they're really features of a platform. And you saw Canva come out with a freemium version of the text image generator and could just kill the entire market because it has a disruption.
Grammarly is another good example of a company that I think could have killed the writing space if they had been a little bit quicker. I don't know if they can do that now because companies like Jasper have a really great, done a really good job of branding themselves, but it's really hard for features to not get disrupted by platforms when platforms have distribution. That's why you saw Calendly buy Prelude. And I think Prelude is an interesting, like it's an enterprise tool in the, it's an enterprise tool in HR space.
Definitely hard to acquire. I think it's always better to build. I think it was an interesting decision they made to actually buy that. But I suspect Calendly could look a lot like HubSpot, actually.
Coming back to the way I think about Calendly, what HubSpot really did was build hubs, like individual hubs, which are different products or verticals around the contact record, right? Marketing hub, which is basically a set of marketing features that interact with the contact record, but specifically for marketers. Sales hub, same for sales. Customer success hub, the same for customer success.
And ops hub, the same for ops individuals. calendly is really the calendar right so you can actually have a version of their tool that's built for marketers where the calendar is at the heart of that but it's a set of features built for marketers around the calendar the same for sales and hr that's what i where calendly would need to go post product-led sales is how do they be a true platform how do they make sure that the product is much stickier and harder to rip out because scheduling is really easy to rip out and commoditize and uh so less of idea and more kind of like the third act on building a kind of billion dollar plg business that was my very similar to my to my second idea as well uh i think it's all about the platform and my fear is a little bit that calendly right now is a bit of a one of all is a bit of a jack of all trades which are disgusting to go into verticals um you know already said but the second thing is that they're becoming a or that they're a little bit of a commodity calendar scheduling you know it's it's not a it's not a very defensible type of product that can be developed relatively quickly we already talked about google and other players as you said one of the ways to make your to differentiate your product better are the integrations i could see for example that in the sales vertical calendar integrates with products like gong outreach or chorus to provide sales transcript and tie these conversations back to the calendar basically make the calendar the true source of progress over time, right?
They could even play with something like color coding or so to make it blatantly obvious which deals are coming to a close or which deals need more vetting, etc., etc. And if you can make that public, then whole teams could circle around the calendar to move deals forward. On the engineering side, I think it would be critical to integrate with Jira, Monday, or Asana to tie meetings to projects.
One common challenges are in product development or product management are roadmaps, keeping roadmaps up to date and aligning teams. And I think calendars are the most atomic unit that teams can circle around and that teams can use to measure progress on a product roadmap. And then lastly, with marketing, I think it would be interesting to integrate with products like Dovetail or Qualtrics to tie market research to meetings. So if you have, for example, interviews with research participants or focus groups, that could all be mapped and organized with a calendar.
And then you have that same sense of progress as you would have on the engineering side, for example, or on the sales side. So I truly agree that the platform is kind of the next big step. And then the question is, how can you allow developers to build on top of that platform? And how can you tie already established products to your platform to multiply the value?
yes agreed sweet um do you have a third idea yeah so so this is why i'm going to uh incorporate this into a segment of half-baked marketing ideas so i have a podcast marketing against the green we do half-baked marketing ideas which are half thought out marketing ideas uh just to get creative i'm going to give you two that i think are kind of cool for calendly and again half-baked so uh feel free to poke holes in them the first one is kind of super interesting which is uh again if you we We went self-serve business, product-led sales platform, right?
That's how you kind of build a billion-dollar PLG business. So we're coming right back to self-serve, right? I want to actually continue to grow the self-serve business. I don't want to just make my money from going up marketing enterprise.
I want to keep growing the number of users who use my product. One of the interesting ways that Calendly could think about this is they could acquire a company like Linktree, right? And let me tell you why that's somewhat interesting is because Linktree have amazing distribution, terrible monetization right they have amazing distribution terrible monetization and so they get around 45 million visits a month just from social like not from not from everything else they get like hundreds of millions a month but just from social because you have all of the people using Calendly or not Calendly Linktree within their bio and what Linktree is for your listeners is a way to show basically just your primary links like you can find me here here here and here and I think they're going to integrate probably e-com but one of the things that naturally fits in there is okay you can find me here and you can also schedule time with me right have an open calendar to allow people to schedule time with me and so it's like an interesting way that calendly could get distribution in a product that already has massive amount of distribution but is struggling to monetize now it could be too horizontal for them like very horizontal where it's applicable to like everyone uh for the most part but anyone who has anything to promote or any links to show off.
But again, I think if you want to grow self-serve, that's somewhat interesting. The other part of the hard-picked marketing idea, which is just a fun idea, is one of the things that really happened over COVID is that network can be more accessible. So pre the remote being the primary, a lot of the ways that we've interacted with each other, you had to be in San Francisco or Boston or all of these core cities to build your network. Whereas now I think we've got used to people, meeting people online on Zoom and building our network that way.
Calendly could run this kind of cool campaign where they do this like global mixer. And the global mixer is basically anyone can put their Calendly link into the global mixer and they should actually purposely get people in different sectors who are really hard to get access to people. Like you would never expect to have a meeting with this person. And then they should do random mixers, right?
And so they should be the way that you actually connect with people within work to meet more people to network with more people to share ideas So you could put in your account link you could put in the sector that you want to meet people and you could put in some of the topics that you want to discuss And then they actually do this global mixer where they'll kind of match you up with other people. And so what you're trying to do is market the core use case and really help to brand Calendly as being this global way that you connect to other humans and interest in humans.
I think they're actually pretty good. And what I love about it is that, especially something like Linktree, it opens the door to the creator economy which i think calendly should play some role in the reason i'm saying that is because a lot of creators have mixed income streams and some of these income streams are often some form of coaching or consulting or advisory and that's i think that's where calendly just has to dominate and be the number one solution uh so i think the the idea of acquiring link tree is actually a really good one county already started uh to use M&A as a vehicle for growth.
I think they should continue down that path. And again, I think creator economy makes a ton of sense. The third one that I brought is built on the same lines. And I think they should acquire the product or company called Fellow.
Fellow is a tool that makes meetings more productive by providing agendas, notes, and templates, some of which you can share with the meeting receiver, right? So you have several people in a meeting. And the problem that the fellow solves is that not everybody's looking at the same document. So this allows you to set an agenda beforehand.
They have already raised $30 million. So the question is, is that the right striking time now before they become even bigger? As far as I heard, they grow pretty well. And again, I love the product.
And I think they need to get a strong foothold just in a productivity space in general. So it's similar to how DocuSign backed into the e-signature space and then integrated with document management and document analytics and document generation, all that kind of stuff. Calendly needs to figure out what can they back into as a natural step. And I think productivity is the next logical one.
I also think that there's something to be said about task management that Calendly should participate in. um i personally started to map all my tasks on my calendar because i'm a i'm a chronic over committer and that helps holds me accountable do you do the same thing you're nodding are you doing the same yeah yeah yeah i all everything is in my calendar yep yep same here so i think i think that's a huge opportunity for for calendar as well uh and m&a is probably one way to not having to reinvent the wheel but you know acquire a company that's growing but early on and uh and get a strong foothold in productivity yeah i think their biggest challenge is like you can see it even on some of our notes is they could do a bunch of things, right?
Because they're a horizontal product, but you have to figure out where your sweet spot is. And I think on the acquisition, you have to have a real clear philosophy on when you buy and when you build. Acquisitions are super tricky. They're building a different tech stack.
The integration is really hard. All that stuff is really hard. And so I think there has to be a real good reason to buy over build. The thing for Calendly is where are the verticals that are going to be best verticals to build that upmarket motion because they could go in so many directions.
Do you think that the recession could be a good opportunity to lean stronger into merchant acquisition? We know that Calendly is profitable and they have decent funding and that during recessions, I mean, right now, companies are dropping in multiples left and right. Do you think that could be an opportunity to lean even harder into M&A or do you think Calendly should rather extend its runway and see what they can do with, you know like the the sales driven motion from spending a bunch of time on these kind on mna type things i think it's way trickier to buy than people likely think even i had used to likely think like it's um for the most part it's always a good idea to try to build and then you have a philosophy when you buy like it could be something where it's tangential to the core use like you don't build your any anything that buys that overlaps with your core product we don't we build that anything that's tangential that can get us into a foothold into a new sector which is really the prelude like gets us a foothold into hr we would buy that so i think on the fellow that seems like something they should build because it's like fundamental part of it touches the calendar right anything that touches the calendar you build anything then you can kind of get a foothold in market to like use that use case on you can maybe buy do i think there will be more m&a I suspect there would be, but it does take, it depends how many of those companies have runway to get through the recession because they would have to take a sizable markdown.
And most of these companies are VC backed and VCs are not going to take a large markdown. And so I think there may be less M&A than we think. Going back to the last, like was it the financial crisis where LinkedIn got bought by Microsoft? Like we saw some real traction in the M&A market.
So I suspect there will be some interesting deals that do get done. Maybe his last question, if you were head of growth at Calendly, how would you prioritize these ideas or which idea would you prioritize at the top and why? So that's a great question. I think it's where will I get the most stickiness from my use case?
Some of the things they could do, like productivity and project management. It's like, how do I get things that are truly integrated with my core use case, which is the calendar? Again, if I think of the calendar as a contact record, like how can I build around that contact record and make sure that I'm building for a specific vertical that will be much, much stickier because they use that in a much deeper way where it's not just like surface level. So I think sales is a really good example of where that automation of scheduling is like fundamental part of the business, like the calendar, all of that is a fundamental part of the business.
And I think you can make that use case very, very sticky. So I think it's something like a combination of like, how much money can I make? And how sticky do I think that use case is? And then how competitive is that market?
Like how much can I actually, do I think I can get traction in there? But it's a good question. I don't know if I have a good mental model in terms of how to pick the verticals, but I think it's a combination of those things. Love it.
Yeah, I agree. I think one often underrated point or argument that you made in expanding into verticals, which is how fast can you get traction? Because every minute and every day and every month is costly, especially in a recession where, you know, probably Calendly might be somewhat affected by that as well. It's often more helpful to prioritize traction rather than size sometimes when the water level is dropping across the board, simply because you're more agile, more flexible, you keep cash flow running and you don't spend too much time in the cave to come up with a product or an acquisition that takes a long time.
And then, you know, who knows what happens to deals or teams eventually that then get cut. So I think prioritizing speed over accuracy during those sessions is one principle that I've seen work really well. And I think there's an application here to Calendly as well. Kieran, as we're coming to an end, do you think there's anything left unsaid here that we should really voice, discuss, any question that we should send to Calendly or any angle that we haven't looked at yet?
No, I think we've covered like the, we really covered the journey of self-serve, product-led sales, platform, had some really good half-baked marketing ideas. And then I think, how do you use a recession in a smart way to come out of that much better? And I think for all SaaS businesses, that's managing your churn. Calendly's big thing is, if you really want to be a large business, you have to be multi-product.
And so you have to be able to cross-sell and upgrade because it's the only way to actually get positive churn. They're moving to prelude. Prelude is probably a start of that, but they're definitely going to have to be cautious about the build versus buy, because buying your way there, even though companies have done that, and there's a good examples of companies who have done a good job of that. It is like, it's not, it is not, it is hard, it is complex.
Totally agree to that, plus one. Kieran, thanks for coming on and riffing and presenting your ideas. I had a lot of fun with this. I think there's some really good ones.
I hope Toby and team hear this and it is useful to them, but I want to thank you very much for your time. Before I let you go, Kieran, where can people find and follow you? Yeah, I think if you're in the mood for another podcast, you can check out Marketing Against the Grain. It's on the HubSpot Podcast Network and then at Search Brad on Twitter.
Perfect. Yep. Check out Marketing Against the Grain. And of course, this interview or this conversation was scheduled with Countly.
So thanks for a great product. And I want to thank you all for tuning in and I'll hear you next time. Thank you.
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