Welcome to the Use Case Podcast, episode 284. Today we’ll be talking to Will from Calendly about the use case or business case for why his customers choose Calendly.

Calendly is your scheduling automation platform for eliminating the back-and-forth emails for finding the perfect time — and so much more.

Give the show a listen and please let me know what you think. Thanks, William.

Show length: 29 minutes

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Will Laufer
Head of Sales, Recruiting Calendly Follow

Announcer (00:02):

Welcome to Recruiting Daily’s Use Case podcast. A show dedicated to the storytelling that happens, or should happen, when practitioners purchase technology. Each episode is designed to inspire new ways and ideas to make your business better as we speak with the brightest minds in recruitment in HR tech. That’s what we do. Here’s your host, William Tincup.


William Tincup (00:24):

Ladies and gentlemen, this William Tincup, and you are listening to The Use Case podcast. Today we have Will on, from Calendly. And we’ll be talking about the business case, the use case, for why folks use Calendly in a professional environment. Will, would you do us a favor and introduce both yourself and Calendly?


Will Laufer (00:44):

Absolutely. Thanks for having me, William.


William Tincup (00:46):



Will Laufer (00:47):

It’s always good to chat and connect. I am also a William, I’m Will Laufer. I head up sales, recruiting solutions here at Calendly. Before joining this team relatively recently, which I’m happy to tell you about, I was the founder and CEO of Prelude, the leading recruiting operations and coordination solution. And just about a little over a month ago, Calendly acquired us. We’ve joined forces. Super excited to take all of what we’ve built at Prelude and working it into the Calendly ecosystem to benefit the many millions of folks that rely on Calendly today.


William Tincup (01:24):

Take us backwards real quick. Obviously you created the company for a reason. And we’ve seen this several times in recruiting, scheduling has always been not easy and very inefficient. I don’t know. You go back, and at points there was people, staffing coordinators, scheduling coordinators, and staffing firms, like that was their entire job, was to interface with the different people and schedule things. We’ve also seen bots that have come out over the past few years that do that ish. First, why’d you create the company to begin with?


Will Laufer (02:05):

Yeah, sure. Well, that’s spot on. The space of recruiting, scheduling, you talked to recruiting teams, and I don’t know, it’s called the Achilles heel, the bottleneck, yeah, just one of the biggest pain points that almost any person that works in the recruiting or HR space tends to talk about. And that’s because the recruiter’s job and the overall interview experience is complex. There are a lot of moving pieces, a lot of people involved, and it leads to this really just manual and administrative process for teams large and small.

To give you a little insight into how I got familiar with it, I worked at a startup in the education space. And we were growing pretty quickly. I had to build out the sales team there, so I was a hiring manager. It was my first time working closely with recruiting teams. But what I saw really shocked me. Recruiting was this, intuitively to me, it was this really crucial function. Our teams are just the group of people that we’re able to assemble. Recruiting is the most important step in getting those people to join you, join your vision and your mission. And yet, our recruiting team, who was incredible by the way, they spent the vast majority of their time on the most administrative, in many instances, lowest leverage work that I could possibly imagine.

You mentioned this before but, there even is a role called the recruiting coordinator, which we had. At the time, we had one recruiting coordinator named Nick. And she described her own day, seven or eight hours, five days a week, as playing calendar tetris. This drove me crazy. Nick was so incredible. There were a million things that really needed her help with to make sure that candidates had a wonderful experience and that we were able to show them the best of what we had to offer. But all of our time was being poured into just making sure the trains were running on time and scheduling and rescheduling and then rescheduling again. It was just so rough.

And of course, my thought was, “There has to be a better way. Software must be able to help us with this.” So I took a look at what’s out there. And to be totally honest, my first instinct was to say, “Why don’t we use Calendly? They’re the leading software for scheduling.” And it comes full circle, we’ll get there in a little bit. But at that time, Calendly was really focused on providing a really broad and extremely simple and easy to use solution that helped millions of people around the world. But what it didn’t do was support the complexity of what our recruiting coordinator, of what Nick was up against. We’re talking about panel interviews, multi-day interviews, campus recruiting events, these things where we’re not just matching one person and another person for 30 minutes of availability, it’s orders of magnitude more complex than that.

And when I realized there wasn’t an off-the-shelf solution to this problem, and we were just pouring so much of our time and energy and resources into this funnel, that’s when I said, “Hey, we’ve got to do something to…” Our first focus was just to help Nick. I got together with another hiring manager, who luckily was technical, he worked on the engineering side. And I said, “Hey Alex, what can we build that would help support this use case?” And that was the very first version of Prelude. We built something for our internal team. And of course, we came to realize, it wasn’t just our recruiting team that was struggling and facing this friction, but literally almost every recruiting team in the world. When we speak to them, still to this day, it’s like, “Oh my god, scheduling is just the worst.” So Prelude was built to supercharge recruiting coordinators, recruiting teams at large, and enable them to consistently deliver an amazing candidate experience by spending less time and energy on the manual scheduling challenges and more time and energy on the humans that are involved in the process. So, that’s how we got started.


William Tincup (06:08):

Okay, now that you got started, what year did you launch? And what was the go-market strategy at the time?


Will Laufer (06:10):

Sure. We launched in 2017. Hard to imagine, but basically five years ago. And at the time, the go-to market strategy was, “Do we have any friends that work in recruiting?” That’s literally how we got started and got introduced to folks. Nick, who I mentioned before, was somebody that we were close with. She loved what we were working on and how we were really focused on solving her problems. She and others at the company that we worked at were super supportive and introducing us to friends on at other companies and in other HR departments. And the other thing I learned pretty early on is that recruiters are friendly by trade. They have to have a strength of connecting and being open to new connections. So we just did our best to scrape together as many early conversations as we could, to understand, like I said before, was this just a problem that Nick and our team were facing or is this something that was broader?

Of course, we got a ton of early validation. I think I probably had a hundred conversations across, well, a hundred companies, a hundred different recruiting teams. And of them, the vast majority agreed and were motivated to work with us to help design early versions of the Prelude product. From there, go-to market, came a long, long way, but we’ve started. And still, to this day, really focused on organic and word-of-mouth as a super important channel because it validates that what we’re building on the product side is actually delivering value and leading our users to tell others and help spread the word. Of course, we’re a much bigger organization now and have lots of other channels that have helped us grow, but organic and word-of-mouth has really been, honestly, the biggest focus for us from day one.


William Tincup (07:53):

I’ve been a Calendly user for forever. I think I used another calendar tool, assistant.to or something like that for a while. I’ve used probably gillions through the years, but once I landed on Calendly, I can’t imagine a life without it quite frankly. People still send me time slots. I’m sure this happens to you as well, but some people would be like, “Hey, I’ve got these three time slots,” and they’ll give me time zones. And I’m like, “Yeah, there’s a tool for that. We don’t have to do the email thing again, ever.” I am a huge fan. I almost see it as one of those deals like, what’s the downside? Why wouldn’t you use this? I anted to, a, ask you, am I just one of those early adopters and I just get it? Or do you see, everyone’s making the same kind of realization? And then, the second part of that question is, the professional use, because you’re selling obviously into the recruiting world, of which you’re very familiar, how do they use Calendly, maybe even different than I would?


Will Laufer (09:11):

Yeah, absolutely. First, William, you probably at some point were an early adopter of Calendly, but today, for better or for worse, there are 10 million users of Calendly each and every day. I think the world is coming around to the fact that nobody wants to email back and forth 20 times just to get our meeting or our podcast episode on the books. So I think you’re in good company there. Calendly continues to grow at an incredible rate. And obviously has the advantage of, every time you receive the Calendly link, you just feel that ease of use and the three emails that you don’t have to send because the meeting is now booked. It’s been awesome to see as a fan of Calendly for many years, and now, to be part of such an amazing product and company.

But you also make another good point, which is Calendly’s use case historically has been really focused on that viral, very broad use, where one person sends out their link to someone else, they say, “Hey, this is cool.” They flip it on, that expands the three other users and so on and so forth. That’s been awesome and continues to power a ton of growth for Calendly. But there are also use cases that I think of as more vertical or departmental solutions, where the needs sometimes can be more complex. We talked about recruiting as a case that I know well because I really burrowed myself into that after seeing those problems that Nick and the recruiting team are facing at my last company. But there are also problems faced by sales teams and customer success teams and all sorts of departments across the organization that might have different integrations that they need to see or different, specific constraints or customizations on the type of scheduling that needs to happen.

And that’s what got me excited when Tope, Calendly CEO, reached out and said, “Hey, could there be a match here? We’re thinking about using this broad, powerful platform that we’ve built at Calendly to go deep in certain departmental areas and deliver the absolute best experience, especially to external stakeholders.” Recruiting teams want to make sure candidates have a great experience, sales teams want to make sure prospects have the best experience possible, success teams want to make sure that customers have a seamless time after they purchase a product and need to implement. And scheduling is such a core component and function of all of those processes. Calendly is that cornerstone that can ensure that process goes as smoothly and seamlessly as possible. So, I got really excited working with Tope, think, “Hey, how can we take what Prelude has built and use that to deliver both the broad and simple and elegant solution of Calendly, and the deep robust solution that Prelude provides to recruiting and HR teams?”


William Tincup (12:06):

What have you faced so far from the B2C model to the B2B model? When you first get on the phone with Global Head of Talent acquisition, if you have that person on the phone, they’re familiar with the brand, clearly, got it, check, how do you get them mentally over to the professional side of what Calendly does?


Will Laufer (12:29):

Yeah, great question. And the answer is, I ask them questions. I ask them, “What are your pain points today? What is your team getting stuck on?” And usually, it’s a mix of those two things. It’s, “Hey, our recruiters need to have an easier time scheduling in their own phone screens. Some of them are already using Calendly for that use case. But then we also have these really complex use cases where we’re having to hire folks or teams of folks to help support panel scheduling or big hiring events that we need to plan and schedule hundreds of candidates at the same time.” And that global head of TA is telling me, “Well, is there anything out there that can help across all of these use cases?” And again, that’s why I’m so excited about joining forces here, because now we can say yes. We’ve got solutions for the most complex, robust enterprise use cases that recruiting teams face, as well as those high volumes, simpler, more back and forth type use cases, and everything in between. And that’s really the vision of Calendly plus Prelude here that we’re just starting to see play out, which is really exciting.


William Tincup (13:37):

Do they ask tech stack questions? Like, does this need to be integrated? Or will this integrate easily into my whatever, if it’s a staffing CRM or if it’s an ATS, whatever tool that they’re using? Are they asking or are you getting into the integrations questions?


Will Laufer (13:57):

Yes. And usually William, that is minute number one, 60 seconds in, “Hey, if you don’t integrate with my ATS, let’s end this call now. I need the time back.” So, we get those questions all the time. And it’s not just ATSs, right? It’s, do you integrate with my ATS? Do you integrate with my calendar system? Maybe for a larger enterprise, we have a hybrid Outlook system that require some really specific setup to connect in. But it certainly doesn’t stop there. What do you use for video conferencing? What do you use for assessments, maybe coding challenges for your technical hiring team? The list goes on and on. As you know, we’ve seen a huge proliferation of software and technology popping up in the HR and recruiting space. And all of that is great as long as they can speak to each other. Scheduling is this, it’s a web that connects many of these point solutions together, and it’s a really important part of conversations that we’re having with teams today. Prelude, of course, does support just about anything you’re using. There’s always new stuff popping up where we’re working to keep up with what teams are using. But across all of those categories, we’re really proud of all the integrations we can support out of the box.


William Tincup (15:13):

Again, with Prelude and Calendly, are you migrating, or is the plan to migrate everything from Prelude over to Calendly, or do you want to keep the products separate in terms of one being more of an enterprisey product itself? How do you see that playing out?


Will Laufer (15:33):

It’s a great question. We’re working through those questions internally ourselves. So, lots of exciting stuff to come in 2023. But the high level is, we’re taking a customer centric view. What is going to enhance and add to the experience of customers on both sides? And we’re using that as our North Star. And we’ll be, like I said, announcing a lot of exciting overlap and opportunities in the coming months.


William Tincup (15:59):

I love that. We’re going to do some buy side stuff. The favorite part of the demo for you, for showing both people at Calendly, proper as it is, and also Prelude.


Will Laufer (16:13):

Sure. That’s a great question. I think it’s always those aha moments. So, for Calendly, just seeing the look in folks’ eyes of like, “Oh my God, this exists. For the past five years, I’ve been emailing back and forth 15 times for every phone screen I need to schedule, and you’re telling me, I can just set up a link, include it in my email templates, and everything’s just going to work? And I can have that be branded and create this really nice experience for the thousands of candidates that I’m dealing with every quarter.” That aha moment, I think, is really special.

And on the Prelude side, it’s the depth of the solution. We’ve really spent time with recruiting coordinators to understand, what are your bottlenecks? And a lot of times it’s the manual back and forth of scheduling, but a lot of times, it’s work around that. How do we manage the preferences and interview load balancing for the thousands of interviewers at my organization? How do we keep track of who is declining interviews at the last minute, which leads to a bad candidate experience? We’ve found coordinators take so much ownership over delivering a great candidate experience that they’re going to these unimaginable lengths with spreadsheets and sometimes post-it notes to keep track of all the different preferences and inputs and reports that are needed to wow every candidate.

So, when Prelude comes in and says, “Hey, first of all, you can now do that all in one system. And by the way, we can automate the tracking and reporting and interviewer management that you’re doing manually today.” I think that’s a real aha moment. Like “Wow, you guys thought of that. That just makes me kind of…” Yeah, I’m always proud when we do a decent job of listening and learning from our customers. I will say, I’m always still learning new things every day from them. There’s just so much complexity in the recruiting process. But I feel really proud when we can impress them with understanding where they’re coming from and empathizing with their challenges day to day.


William Tincup (18:27):

I know folks will ask or wonder with Prelude… Calendly’s pretty simple, right? It works both mobile, it’s desktop, it’s over the internet, it’s pretty simple. My mother can use it. I’m pretty sure most people can use it. I get that. Prelude deals with a little bit more complexity of different email and different systems. So, how do you demo differences between the two? And again, if it’s more of a complex situation where you got people in six different continents, more complexity hiring. And we’re just specifically talking about recruiting. You got candidates that are logging in on their phones. You got all kinds of different things going on here. All right? Fair enough? That’s not going to be a heavy lift. How do you take people through their own scheduling complexity? Because they probably don’t even think about it, not in the way that you think about it of course. They’re probably thinking of it like, “Yeah, it has to be done.” It’s, “Check. We all know it has to be done. You’re not going to hire somebody unless you’ve interviewed them, and you’re not going to interview unless you schedule an interview. So check, we got that.” But how do you break them down into the complexity and show them that, “Okay, here’s how you do it. Here’s how could do it more efficiently.”


Will Laufer (19:52):

Sure. To me, it always comes back to listening to the customer. What are you experiencing today? What is your interview process? In some cases, it might be pretty straightforward. “Hey, we just hire a few people a year. Just need to make sure we meet with them once or twice and do a background check and a couple of screens.” And in that case, let’s focus on some simple solutions that’ll make that process much better for you.

On the flip side, maybe I’m talking to a global head of TA who oversees a team of 80 TA folks, 10 coordinators, 65 recruiters, five sourcers. And across all of those channels, there’s international hiring going on, many time zones, many different systems being used, all sorts of integrations, some roles that require seven or eight steps in the hiring process, executive hiring, executive assistants being involved, the list of course goes on and on. And when that’s the reality on the ground, let’s talk about how we can best support that reality. And look, it’s not going to be, snap your fingers and tomorrow everybody is just sending out links and everything works. It’s going to be, let’s partner on a rollout plan. There’s going to be some change management. We’re going to help you think through that. We’re going to provide training and think about the best ways to support your talent team so that they can see the benefits and not just feel like a new product is being shoved on their plate. But instead they’re going to say, “Hey, after this six week rollout, we’re going to get 10 hours a week back. What are we going to do with that time? We’re going to spend more time interfacing with candidates directly and really being able to personalize every touchpoint in the experience.”

I think it really starts with, what does the reality on the ground look like? And let’s find the shortest path to getting you guys some support, some help. Whether that’s really complex or really simple, we just want to start with listening.


William Tincup (21:41):

I love it. Questions that buyers should ask of you and your team in the process? Maybe they’ve not bought this before, maybe it’s done through humans or maybe it’s just done really inefficiently by a lot of hiring managers and recruiters, et cetera. So, what’s the question set that you love to hear? If you were just trying to write out the questions’ form, what would those questions be?


Will Laufer (22:09):

Yeah, sure. The questions start with taking stock, like I said before, of current state. I love when folks come to the first conversation and say, “Well, let me walk you through my interview process. I think, no, I know there’s a lot of inefficiency here. I can highlight a few areas that my team is spending a ton of their time.” And where things get strategic and fun and creative is thinking about the best setups and solutions to solve those problems.

So sort of, “Hey, we’re going to have this bucket of my 15 recruiters who just are scheduling about 20, 25 screens each a week. That process, any one of those, not too painful. But as I zoomed out and started to add it up, I realized there’s just this huge amount of email back and forth that’s creating friction, both for my team and for the candidates they’re working with. How can we think through that together?”

On the flip side, maybe we’re looking at, “I’m taking stock of our tech stack. We use X, Y, and Z products. And like I said before, it should be non-negotiable that you guys integrate with those products. Because I’m putting in a solution for scheduling automation, but I need to go out and jump into HackerRank or CoderPad to copy and paste coding environments every single time we have an engineering candidate or a technical candidate coming through our process, that’s not going to be an acceptable. Just not going to speed us up, right? We need to make sure that these things work together seamlessly.”

So, it starts with the now, it starts with understanding what we’re doing today. And look, me, my team, we’re here to be a partner in thinking through that, but having a cogent understanding of what the current state is, rather than maybe like, “Hey, I just want to automate.” That’s a little bit more vague and harder to break down into how we can find the biggest levers for acceleration and leverage for the teams we support. So, really having those strategic conversations about what’s going on today and what are those areas of friction, whether it’s integrations, current manual work, or other steps in the process that are slowing the team now.


William Tincup (24:23):

It might be a little early in the process, but I’d love to talk about customer stories. Without brand names or customer names or any of that type stuff, but just stories where maybe, again, you just nailed it with the inefficiency. They were doing it this way, all of a sudden it’s like, okay, you unpack this new way of doing it, it’s like, oh. You got all their time back and all kinds of stuff like that. Do you have any so far? You might even have to go back to some Prelude stuff as well, but just any customer stories? And again, no brands or company names, stuff like that. I’m really interested in the storytelling aspect.


Will Laufer (25:00):

Yeah, absolutely. I think I mentioned this before, but there are I think 50,000 companies that use Calendly today and many hundreds of them are using Prelude currently. So, lots and lots of stories to choose from. And like you, William, I personally get excited about the stories that we help create and drive as a business founder. That is one of the most motivating things, is when we can hear from the folks that we serve and support every day that we’re impacting them in some meaningful way.

I think the stories boil down to the individuals, the people who are involved. A few things come to mind. In our pretty early days, we actually worked with some teams that… I talked about how coordinators are spending, sometimes their whole day, sitting there and really puzzling together the manual options for interviews. And we worked with a team early on that implemented our software. And as a result, the coordinators were able to create so much leverage and free up so much of their own time that two recruiting coordinators got promoted to full life cycle recruiters because they were able to spend less time on the manual scheduling pieces and so much more time on the broader value creation and life cycle. And that was so awesome to hear. We enabled this team to not just operate more efficiently but accomplish more at a strategic level because less resources were needed for that really manual scheduling work.

The other persona that I look at a lot is the impact we’re able to have on candidates. And I don’t know William, you probably haven’t personally gone through the interview process anytime recently, but it still is rough. Candidates do not enjoy the… I talk to them all the time. It’s stressful. There are so many touchpoints in the process, there’s so much back and forth. And a significant percentage of that is getting rescheduled on the day before your onsite interview or having to email with a recruiter eight times before you can get on the books with a hiring manager. That just takes away from what you really want to be doing, which is understanding the values and culture and team and potential of this place that you might be signing up to work at for years and years. That’s the important stuff. So to me, enabling those experiences.

And then of course, driving real measurable results. So, working with teams. I think we just did a webinar last week with Air Cable. They’ve been a customer and partner of ours as they’ve scaled to really amazing heights. And throughout that time, making sure that our resources are being used and dedicated efficiently so that we can support growing volumes and scale, drive better outcomes for candidates, and just building better teams ultimately, right? That’s the goal of recruiting. Having the right products and platforms in place, like Prelude and Calendly, allow fast growing, leading organizations to be able to accomplish that.


William Tincup (28:08):

Drops mic, walks off stage, done deal. Will, thank you so much. I love the acquisition. I just think it’s really smart on both sides. It’s going to be great for recruiting. And I just can’t wait to see how you expand and what you do with the solution. So, let’s keep in touch.


Will Laufer (28:27):

I appreciate that, William. Always a pleasure.


William Tincup (28:29):

And thanks for everyone listening to The Use Case podcast. Until next time.


Announcer (28:34):

You’ve been listening to Recruiting Daily’s Use Case podcast. Be sure to subscribe on your favorite platform, and hit us up at recruitingdaily.com.

The Use Case Podcast

William Tincup

William is the President & Editor-at-Large of RecruitingDaily. At the intersection of HR and technology, he’s a writer, speaker, advisor, consultant, investor, storyteller & teacher. He's been writing about HR and Recruiting related issues for longer than he cares to disclose. William serves on the Board of Advisors / Board of Directors for 20+ HR technology startups. William is a graduate of the University of Alabama at Birmingham with a BA in Art History. He also earned an MA in American Indian Studies from the University of Arizona and an MBA from Case Western Reserve University.


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