Scheduling Mastery: How Calendly is Transforming Business Relationships

Mark Smith: 0:14
Welcome to the Power Platform Show. Thanks for joining me today. I hope today's guest inspires and educates you on the possibilities of the Microsoft Power Platform. Now let's get on with the show. In this episode, we're going to focus on Calendly and the impact that it has added in the market and even the future of scheduling. Calendly is a tool that I've used now since about 2018, and I couldn't live without it when it comes to scheduling. Being that I live at the bottom of the world and multi-time zone, I work mainly for clients across the US and Europe. It has been an absolute lifesaver to me. My guest is from Portland, oregon in the US. He works at Calendly. He's the VP for the product marketing of Calendly, so a pleasure to have him on the show. He's received a 40 under 40 award for the Business Journal. He plays drums, he's a wrestling coach, he's a reader, a writer, and are you into cycling? Is that right?

Jeff Hardison : 1:23
Yes, I love to bike.

Mark Smith: 1:24
Awesome. You can find links, of course, to his bio and his socials in the show notes for this episode. Anything we discuss or we talk about links, etc. They'll be in the show notes. Welcome to the show, Jeff.

Jeff Hardison : 1:34
Thanks, mark, it's great to be here.

Mark Smith: 1:36
Good to have you on the show. I'm excited. I always, you know, when your team reached out and discussed coming on the podcast. You know I've been a massive fan of Calendly and I suppose, specifically I'm a massive fan because I work for multiple companies at any time and you know I'm at the bottom of the world, as I said in the intro, and I'm dealing with multiple time zones, but not just that nuance, I'm dealing with multiple schedules and in the past, let's say 10 plus years ago, before I came across Calendly, I used to work at doing automations between two schedules so I didn't get conflicts because people, in whatever company I was working for, would go, hey, I can see a gap in your schedule, but they couldn't see that gap wasn't in my other schedule, right.

Mark Smith: 2:18
And so to run this podcast, which has been running seven years now, calendly has been with me every step of the way. It's the way I use to run scheduling at scale and I couldn't live as in. Honestly, the time savings it saves for me is absolutely phenomenal and so I'm excited to have you on the show. And before we start, tell us a bit about food, family and fun. I always like my guests to kind of give some background outside of their day job.

Jeff Hardison : 2:48
Yeah, so let's see food. Well, I live in Portland, oregon, right, and we are kind of like a food epicenter for the United States. A lot of chefs have moved from around the world to Portland and so we're really lucky I can walk just three blocks away and be able to dine at some amazing places. So that's really great. And I'd say, probably our family's favorite food is kind of the newer kind of takes on Mexican food right now. We love we'd probably go do that once a week. You know, speaking of family, my daughters I spent a lot of time helping them with their sports. They both play soccer and wrestle and so you know, you mentioned earlier, you know, wrestling coach, and so I hadn't wrestled since high school and then I started volunteering and next thing, I know I'm assistant wrestling coach for my youngest daughter's wrestling team, which has been really fun to be involved in that. And yeah, so that's pretty much me. If I'm not working, I'm probably spending time with my family.

Mark Smith: 3:44
Nice, nice. I'm interested to hear the story of how Calendly got started. What was the origin story of Calendly?

Jeff Hardison : 3:53
Yeah, so I probably couldn't tell it as well as our founder Tope, but some parts of the story that I really love are that, you know, tope was a enterprise salesperson for technology companies, right, and he had gone to school for computer science.

Jeff Hardison : 4:09
So he has this amazing brain where he both has a product manager's brain as well as a salespersonperson's and customer facing team's brain, and he was working as a as a salesperson, uh, for large companies, and he noticed it was really difficult to find a time to meet with customers and prospects and then not only be able to meet with that customer prospect but also be able to bring in, like, say, let's say, a sales engineer, and be able to figure out, you know, is it two o'clock um eastern time or is it five o'clock, you know somewhere else, when this person is available, right, and then you have to be able to line that up with the customer and all the people on their end.

Jeff Hardison : 4:45
And so he ended up building Calendly as a solo founder with an engineering team. And here we are today, and so it's really moved beyond just being able to kind of find a time of what works to also be like team-based scheduling, like I mentioned earlier, being able to bring on that sales engineer, being able to bring a recruiter into a call with you as a hiring manager, being able to allow your customers to get email notifications before the meeting so that they don't forget about the meeting, or maybe after the meeting, sending them a case study, an ROI calculator, things like that. And then, of course, of course, we try to be this neutral Switzerland, if you will, between all the different platforms out there, and so we really believe in our integrations, and so that's, of course, integrating with Microsoft, like we're going to talk about today, integrating with those other guys out there, as well as integrating with CRM packages, not just Microsoft's but Salesforce and HubSpot, and really concentrating on that work of building this ecosystem.

Mark Smith: 5:41
Yeah, amazing. And I tell you what, as in I saw a post recently where somebody said and that would have been in the last 12 months that you know Google had come out something that was going to be a Calendly killer. You know, using AI and scheduling, and I had to laugh at that because I think it's something like 82% of the world's commercial email runs on M365 from Microsoft. And so I thought you know from your lens of living in Google land, awesome, but Google are not known for owning the enterprise when it comes to mail. You know, if you looked, I think, chopped off the Fortune 100, fortune 500 companies, you would find squarely 99 plus percent of those will all be running a Microsoft-based email system, being M365 and Outlook. And so I chuckled at that because, you know, no time soon will I be moving my commercial email to Google and, as I say, I think that 82% of the world's commercial email sits in M365. I think it's an amazing tool and, of course, people say to me why using Calendly and not using FindTime or something like that from Microsoft? The thing is, microsoft are good if you are just working for a single organization. They struggle the minute you're in a multi-tenanted environment.

Mark Smith: 6:58
And my world and what I'm seeing a lot more with you know, businesses is that individuals work for potentially multiple companies at a time. I work for over at least three companies at a time, simultaneous, any time about to take on a fourth, and so you know that means four email addresses, four calendars. You know that I'm running, and so for me I actually use multiple calendars, so multiple subscriptions with Calendly and, as I say, massive time saver for me in how I coordinate my life and make it easy across time zone. Just this week, a team of people in Canada wanted to book time with me in two weeks time. You know, and you don't want to be in that hockey game of backwards and forwards around as the morning of the state work for you, and then, where the times are different, you know I'm a day ahead of you right now from a date perspective, it gets very confusing, and so I just find it so easy to allocate my time, and you know, the other thing that I find as an a killer feature for me is that I have some people that want one-on-one coaching around the world, and so I can integrate Stripe Payment Gateway straight into there, make it super simple for them to ad hoc buy an hour here or there and be paid for it, without kind of raising invoices and doing all that kind of stuff on the side.

Mark Smith: 8:14
And I think the other feature that is really powerful that I use a lot is this ability to get notifications pre-meeting. I can send out four hours before a notification, like all that automation is just taken care of in the product. When you think about or if you look at your customer base, how big is it now?

Jeff Hardison : 8:33
We now have more than 20 million users Wow yeah all over the world and we're a product-led company, meaning people can just sign up for Calendly for free and the product will onboard them and will prompt them to upgrade to a paid plan with their credit card if they will, and if they need to reach out to a salesperson, they can. But that's really helped us grow quite a bit.

Mark Smith: 8:56
Are you seeing a massive adoption from the Microsoft ecosystem?

Jeff Hardison : 9:01
Yes, yeah, I would say that the Microsoft ecosystem is an extremely important ecosystem to us, because Microsoft has one of everything, right, as you know, but they don't always go deep on something, and so they have a product bookings, but they're not going to make it their main business, and we really care about what we offer, and so we can go much deeper than they might go in terms of, like, team-based scheduling, in terms of building out integrations with competing products to Microsoft that Microsoft might not want to do, and so, again, we try to be that neutral Switzerland between you know Google's ecosystem, microsoft Salesforce, et cetera so that you can use all those products together, because, as you know, people are not only working multiple jobs, or they might have Google Office products at one company and then maybe Microsoft at another company, but their customers have different platforms, and so you need to be able to integrate Calendly with Zoom as well as integrate it with Microsoft Teams, for your customer's sake as well.

Mark Smith: 9:58
That actually is another feature that I have been in the transition when you didn't have Teams integration and so Zoom, you know, back in I suppose 2019, 2020 timeframe and then seeing the Teams integration come in, just absolutely perfect right. So a custom Teams link being able to be embedded in to the appointment, I think is super important. Where do you see Calendly sitting in the market of tools out there in this category? So you know calendar management as such.

Jeff Hardison : 10:30
So I would say, you know, right now there's the calendar companies out there, right, there's like Microsoft Outlook and there's Google Calendar and so forth, and we haven't tried to replace that. What we're really more trying to do is help you book external meetings with people that can help further your business. So that could be booking a meeting with a salesperson who doesn't have access to your Outlook calendar. They can't find that time of when you're available and you don't want to be emailing back and forth to find a time or being able to book a meeting with that recruit. You know who's going to help build your business, or that investor, right? Or, like you mentioned earlier, a lot of people are kind of having side hustles. So at night they're taking their expertise from their job and they're booking meetings with somebody that they met on X or on LinkedIn and saying here's my county link and here's a Stripe or PayPal integration where you can pay me for this meeting and you can build a little bit of side revenue.

Jeff Hardison : 11:26
I would say that right now we are the Kleenex, if you will, of the scheduling link world, but to us that's not enough. I mean, our mission is to help companies and people build relationships with the people that matter in their lives, and so that could be those recruits, those customers, those investors right, and then you know, once they build relationships, we've done a lot around scheduling to help build those relationships, but increasingly what you're going to see from us is us offering other products and features out there that help you, you know, build your relationships even more I find interesting that you know the diversification I see.

Mark Smith: 12:32
You know companies create a killer product but then sometimes they diversify too far out, they go away. You know they move away from their core. And and one of the things I don't like you know and don't know how you factor this into your thinking is then you buy a product and it comes with 50 wingdings on the side and you don't want those 50 wingdings and they're being promoted is why it's so awesome. And listen, I wanted to be able to cleanly schedule. That's all I want to do. How do you make sure you don't create tons of do you want fries with that and the Coke and everything else, when really I just wanted the burger? I just want good, clean calendar scheduling without any fluff. How do you make sure your product team doesn't try to be all things to all people but really stay tight on the core?

Jeff Hardison : 13:19
Yeah, that's a good question.

Jeff Hardison : 13:21
So I've been at Cali almost four years and other companies I've worked with that are making as much revenue as we're making would have probably already come out with all kinds of features right and had a bloated UX and, like Calendly, didn't Calendly really thought about how do we really master scheduling? And I think one of the ways that Calendly did that was we have such a focus on design. And so, if you, when I look at customer research reports from my team, where we interview customers and so forth, why they chose us time and time again, one of the main reasons is that Cali is easy to use, and that ease of use really comes back to our engineering talent, our design talents, our product managers and everybody that's helping them make sure they're not building something that's too complex, too bolted together, and so our customers actually have been pulling us into these other areas outside of just scheduling, and we think, because we have such a design forward, user experience led culture, that we can build these things without it seeming too rickety and bolted on and so forth.

Mark Smith: 14:26
But we want our customers to keep us honest and let us know how we're doing you, you mentioned, you know, with with one of the things with microsoft and I've worked with microsoft for over 30 years now and with the last 21, just you know, being focused around their dynamic crm product and power platform and uh and now getting heavily into the AI side of things and one of the things you're right about Microsoft they do V1 of a lot of features not products, but features and really the calendar tool I'd call, like their forms tool is a feature and it definitely is not market leading by any stretch. It just fills a percentage of the audience that just wants something and that's why I think you're on the money around going deep in this one area and how you've I would assume you're the market leader in this category at the moment. Would that be right?

Jeff Hardison : 15:13
I like to think so.

Mark Smith: 15:14
Yeah, tell me about in the last two years two years ago, I think, last week, where ChatGPT became on everybody's radar right as in the adoption, and that end of the year two years ago blew through the adoption of television, social media, all these different types of things and what I've seen in the last two years is every company out there that have been in business for years and years have all of a sudden bolted the word AI into their name and their AI this and AI that and AI something else. I haven't noticed that from Calendly, but my question for you how do you see AI playing into the mix as, and particularly, perhaps, agents you know which are going to become a big deal in 2025? How do you see that playing into the mix with Calendly?

Jeff Hardison : 16:11
Well, I can't give too much information, but I do think that customers who are interested in AI will be heartened to hear that we will be releasing AI-powered products in the future.

Jeff Hardison : 16:24
What I want you to kind of imagine is all right, if Jeff is saying that this is about really helping you build those relationships. How can AI help you build those relationships? You know, there's not just scheduling a meeting which helps you build a relationship, but what about, you know, in the meeting itself? How could AI assist in the meeting so that you can really be present and and stare, you know, look in the eyes of the person that have, you know, maybe, like looking down at a piece of paper and scribbling out notes, you can be present. And then what if AI could maybe help you, you know, hypothetically, be able to follow up on that meeting, right, when you know better what happened? And then maybe what about in terms of, like, keeping track of all the people that you're meeting, and like how could AI, you know, really help with all of that? And so what I think you're going to see is, in the coming future, Cali will go from where you're not hearing as much about AI to you're hearing a lot about AI.

Mark Smith: 17:17
Interesting. I think there's a massive amount of scope, particularly on pre-research of folks coming in. As I say, I use it a lot for my podcast and for any kind of just-in-time type information that might've been published by that person or that guest that I'm having coming on being surfaced. I think would be pretty amazing. Tell me about from an integration perspective. Have you kind of reached the integration limits of the tools out there in the market? Like, do you have a situation where people are going, hey, I need an integration for this, and that you're weighing that up against all the other priorities? Do you see any kind of gaps? Because for mine I don't see them. But what are you seeing?

Jeff Hardison : 18:01
Yeah, and one other quick point I want to make about AI is we do this state of meetings report each year where we survey and interview all kinds of people other customers and non-customers and we ask about AI to kind of hear what they're comforted with. And I think it was like 54% that was up from the previous year. 54% of people said they were excited about what AI is going to bring, and so we look for signals like that to kind of give us a little bit of boost in terms of you know, are we on the right track In terms of integrations? So I would say that's one of the things that if you were to take us and have like a list of all the different competitors, there's dozens of scheduling companies out there and you know we might do this one thing better around, like bringing a coworker in a meeting better than this other company. Or we might do round robin better, where we like share meetings with salespeople, depending on when they're available, than another company, or they might do some you know little other thing better than us. But the one thing that we found that was consistently true across the board is that no one has more and better integrations than Calendly does out there and it's a lot of work.

Jeff Hardison : 19:10
Like, for those of you listening that have maybe worked for a technology company before, what is one of the main things in engineers that are co-workers that complain about it's having to build a integration with somebody else's api that they don't like oh, it's rest, or it's it's soap or whatever right, and so that's one of the main reasons that technology companies don't build more integrations. It's it's not like they don't know better, it's because it's a lot of work. And then you don't just have to build that integration but you've got to maintain it over time, like, hey, we're changing our API, you need to update it. Oh man, engineering team has to go back and make that update. Well, we as a company have really invested in all this engineering talent that helps maintain and build more CRM integrations, our calendar integrations, video integrations, those payment integrations you mentioned, market automation, so on and so forth.

Mark Smith: 20:00
Yeah, you mentioned your development team and when I did some research on you, is your development team still predominantly Ukraine-based.

Jeff Hardison : 20:09
No, our development team is primarily United States-based.

Mark Smith: 20:13
But in the early days, right, Ukraine companies pretty much built, yes, and your founder that was the other thing I wanted to highlight is from Nigeria, right? Yes, which I think is totally epic. As I was saying to you pre-call, the number or the size of the Nigerian community inside Microsoft has absolutely you know, since probably 2020, exploded all around the world. I'm seeing more and more Nigerians in the community.

Jeff Hardison : 20:41
So I, just when I saw that the founder was Nigerian, I just thought absolutely epic and such a good story with highlighting yes, and you know I didn't know as much about the Nigerian tech community until working at Calendly and I, you know I write this newsletter every month for our customers. It goes out to, like you know, millions of people and I have all kinds of replies come from folks from Nigeria or they'll go on to X and post on X, or you know about being so proud of Taupe, for you know, being part of the Nigerian tech community and, like I started to study up on all these people that are posting and there's so much engineering and like startup talent out there in Nigeria.

Mark Smith: 21:20
Yeah, absolutely Absolutely. And uh, you know it's, it's accessible across the med to a lot of European countries that are then, you know, setting up development centers and stuff. Uh, on the on the border of the med, there, um, your KPMGs and the likes I've seen quite a bit of, tell me what's the future of meetings when you think about where we'll be in five years from now. Will we be doing more remote meetings like this? Will we be doing more in person? What do you think is going to change in the next five, next five years? So, really, beyond what your product roadmap shows right now in the thinking of the space, what is it for you?

Jeff Hardison : 22:03
I mean, I think if you look back like maybe 10 years ago, well, 20 years ago, the way you got business done, whether you were recruiting people or you're trying to land a deal or whatever it was meetings right, it was either a meeting in person you know a golf course flying to, you know a customer's location Then it became easier to do, you know, remote meetings via video call, and so meetings have powered the business community for a long time. And then, about 10 years ago, some cynicism crept in, particularly around people who maybe were more introverted and they didn't like doing meetings and so forth, and so they started saying things like you know, this meeting could have been an email, right. You know what? I've read some long emails and I felt like it could have been a short, five minute meeting, right.

Jeff Hardison : 22:45
And so what has kind of emerged in that whole anti-meetings world is all kinds of amazing, asynchronous, or you know tools that you can use to communicate to somebody, whether it's via Microsoft Teams or it's via a Microsoft doc, where, hey, why don't you read what I have to say before coming to the meeting and then we can debate what was in my doc instead of me doing a readout to you for 30 minutes and you have five minutes to debate, and so that's one of the amazing things that's come out is all kinds of culture and tools around, maybe not meeting as much when you could have just read about it or watched a video about it, then met.

Jeff Hardison : 23:28
Well, there's kind of been a correction to that, where people are like man, I'm kind of tired of watching really long, you know hour long videos by somebody who's kind of rambling and they're not being concise, or they wrote this really long doc and they could have been much quicker with it, and so people are returning to meetings in many ways to try to be able to like connect on a human level and maybe be able to read your body language and so forth, to be like, oh, this is what this person is really trying to say. So I think that there will always be this world of, I hope, these asynchronous tools where you can write about things and you can record videos about the things or watch videos from meetings, as well as these in-person moments where you can kind of really get in touch with someone's humanity so that you can build a relationship for it.

Mark Smith: 24:12
Yeah, it's interesting because I see a movement away from those type of meetings being around, necessary a business discussion. You know the boards I'm involved with. I'm like, hey, let's make all board meetings online and let's do the business, and then let's go meet in person and have a drink or have a dinner or something like that and it's just social. We've covered the business stuff. Formally documented, you know, the tooling around AI and meetings now is just, you know, the note-taking ability etc. It's totally transformed things falling through the gaps in the meetings I'm in, like when there's an action on me, I can quite clearly see that Now I would hate to step back two years and not have that type of functionality in my meeting.

Mark Smith: 24:57
Now, do you see and I'm probably asking for a bias confirmation here I mentor a lot of folks around the world in a program I run, I don't know, for the last six years, seven years now, and one of the things that I think is becoming clearer is the need to be very good on video, as in that more and more meetings, the more and more, as we, I suppose, go into a more freelance world, even world even where there's been predictions by 2035 of 50% of the US workforce will be contractors, freelancers, that type of thing, and I'm already seeing it myself in that I work for multiple companies, even though I'm based in the bottom of the world.

Mark Smith: 25:42
I work for multiple companies and they all have a segment of my time because I have expertise across various areas and, as the world goes that way, I just see that there's a massive need to be really good at communicating via camera, as in you know, to be able to understand that you need to engage with the camera. You can't be looking off to the right and think that you're going to have a meaningful conversation. You're seeing NVIDIA creating software that capes your eyes looking at the camera even when you're not, which looks a bit uncanny. But I think that there is this need to get really good at communicating via video for business-based communications. Are you seeing anything in your research, your data, anything like that around meetings in this context?

Jeff Hardison : 26:25
I'd agree. I'd say that you know particularly in marketing we read this all the time that you need to get really great at video and this all the time that you need to get really great at video and be able to make not just make a high five video where you hire somebody who spent a lot of money, but you as an individual, have to be good at quickly speaking on camera, doing it in a very natural way, being able to edit on your own. You know, with various easy to use, like my, my oldest daughter is learning Adobe Premiere right, because that whole generation has to be is learning how to create videos right so that they can socialize with each other, and so I would say that it's extremely important to be able to be able to speak on camera, be able to do your own editing work, be able to publish it and so forth, and not fret about it too much in terms of like. This has to be perfectly polished.

Mark Smith: 27:11
Correct.

Jeff Hardison : 27:12
I think the other thing that we're seeing is that people are having all these meetings virtually and not everybody can attend the meeting. What if the person is in a different time zone? What if they were sick that day? You need to be able to record those meetings right and then be able to share those meetings. So there's a lot of companies out there that record all of their internal meetings, not just their customer meetings, but they record their internal meetings, the one-on-ones, the all-hands meetings and all that. And then people can go back and be like, what was that thing that our CEO said six months ago? And they can go watch that old recording and be like, oh, that's what they said. And so there's this whole culture emerging on just watching recordings and then sharing little snippets of the recordings, as well as learning more about your customers, your recruits, by recording them.

Mark Smith: 27:56
Yeah. Do you think there's still a fear, though, of you know, we always preface a meeting. Hey, is it all right if I record this? You know, I still see some people are like are you trying to catch me out, or is this you know, and am I going to say something on record that I'm going to regret? Trying to catch me out, or is this you know, and am I going to say something on record that I'm going to regret? Do you think that kind of feeling within three years, five years, won't be a thing, as in, it'll be standard that all meetings will be recorded because, as you say, there's going to be time offsets, not everyone's going to be attending, they need to watch the follow-up or whatever, and it's great content that could be repurposed as well, right? Sometimes that could be repurposed as well, right? Sometimes you get that soundbite that you're like, wow, let's use that somewhere else. We wouldn't have got that if it hadn't been recorded.

Jeff Hardison : 28:37
I think that there will be variety in terms of who's going to record internal meetings, like meeting with your boss, or you're meeting with the whole company. There's already variety around that and different rules. I think smaller companies do it by and large, but some of the bigger companies have rules against it. But I think what's going to be completely commonplace is you recording external meetings. So recording that meeting with the customer, recording that meeting with the recruit, because that's already happening and a lot of customers are accustomed to it, and so you're going to increasingly see more and more industries outside of tech recording all of their meetings with customer recruits.

Mark Smith: 29:09
Nice. To wrap up, anything else you'd like to add?

Jeff Hardison : 29:13
Well, I would just say, like you know those of you that use Microsoft you know, please check out some of our integrations. Some of the things that we allow you to do are you can integrate, you know, with Microsoft Outlook to make sure that your meetings you're checking to see if you have a meeting already, maybe internally at your company, before you let a customer book a meeting with you. We got integration with Microsoft Teams. Now we built this with the Microsoft Teams team where you can be able to get your Calendly meetings to show up in Microsoft Teams. It's really cool. We have an integration with Chrome which allows you to use the Microsoft Edge capabilities. And then we have the Microsoft Dynamics integration with the CRM so that you can be able to get all of your meetings data with, say, customers into Microsoft Dynamics. And, of course, you've got the Microsoft Power. Automate integration allows you to build all kinds of things with Microsoft and Calendly.

Mark Smith: 30:04
I like it. I like it. Those that want to learn more can visit the Calendly for Microsoft webinar and your Microsoft integration page on your website. We'll get the link to that. We'll put it in the show notes, Jeff. Thanks so much for coming on the show.

Jeff Hardison : 30:16
Mark, this has been awesome, Thank you, and thank you for being a customer.

Mark Smith: 30:19
Hey, thanks for listening. I'm your host business application MVP Mark Smith, otherwise known as the NZ365 guy. If there's a guest you'd like to see on the show, please message me on LinkedIn. If you want to be a supporter of the show, please check out buymeacoffeecom. Forward slash nz365guy. Stay safe out there and shoot for the stars.