SaaS Marketing Makeover for Calendly with Kortney Osborne

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This is a podcast episode titled, SaaS Marketing Makeover for Calendly with Kortney Osborne. The summary for this episode is: <p>It's makeover time. </p><p>In this live show, CEO and Co-founder of Directive Garrett Mehrguth and a SaaS marketing leader work together to build a strategy for a recognizable SaaS brand - as quickly as possible.</p><p>The company will be randomly selected by spinning a wheel at the beginning of the show, and together, the two will craft a strategy for SaaS marketing leaders everywhere.</p><p><br></p><p>Today, our guest is Kortney Osborne, who landed on Calendly for her marketing makeover. Tune in as Kortney and Garrett share tips and insights to help you step up your product marketing strategy. </p>
A first look at Calendly
02:19 MIN
Potential threats to consider
02:13 MIN
Why Calendly over their competitors?
02:40 MIN
How Calendly incentivizes, and what can be improved
03:09 MIN
A dive into Calendly's enterprise page
03:37 MIN
Final thoughts on walking through Calendly's website
02:32 MIN

Garrett Mehrguth: Well, hello everybody and welcome to another episode of the SaaS Marketing Makeover. I am very excited today to be joined by Kortney Osborne. She's been a marketing leader at named brands like Qualtrics, Weave, and is now out on her own fighting the good fight. Welcome to the show, Courtney.

Kortney Osborne: Hello, thanks so much for having me. I'm excited to be here.

Garrett Mehrguth: No, I'm very excited to have you. It's cool just to see someone who's had your kind of career trajectory and growth, and now you're trying to take my business. So, that's great.

Kortney Osborne: Oh, no. We're frienemies, we'll be frienemies. How about that?

Garrett Mehrguth: I love that. Well, I'm glad to have you here and excited to hear kind your perspective and viewpoint as we get to look at this wheel. Now, before we pull up the wheel, who do you want to be on this thing? Who are you hoping we get today?

Kortney Osborne: And before we pull up the wheel, I just have to introduce Freddy Mercury. He might come in and out. He's like a little leach, so if you ever see him just hopping in say," Hey everybody."

Garrett Mehrguth: Hey, what's up Freddy. Don't be afraid to use your voice. Okay, crosstalk.

Kortney Osborne: I know. I don't have a desire for who's on the wheel. I'm kind of hoping it might not be somebody I know, just so I can completely just take it from the outside in. Just no perspective, right.

Garrett Mehrguth: I love it.

Kortney Osborne: I'll see, or maybe it's going to be somebody I love.

Garrett Mehrguth: No, and as always, right, it's a critique, but it's also, let's find those positives and then I think those areas of opportunity so that the best marketers in the world can grow from it.

Kortney Osborne: Yeah, exactly.

Garrett Mehrguth: Very excited. With that being said, let's pull up the wheel. Let's do it, Sean.

Kortney Osborne: I know. Oh, my gosh. Okay. I've heard there's only one of these on here I haven't heard of. Okay.

Garrett Mehrguth: I'm guessing it wasn't that one?

Kortney Osborne: It was not that one. I do know this one, not as well as... There was a two on there that I know really well, but...

Garrett Mehrguth: All right.

Kortney Osborne: Okay.

Garrett Mehrguth: Let's do it.

Kortney Osborne: Well, let's do this.

Garrett Mehrguth: Calendly, free online appointment scheduling software. Okay. I just have to say it. That is the funniest logo read inaudible.

Kortney Osborne: I know, I know.

Garrett Mehrguth: I don't know if you've heard, I'm on Twitter maybe too much, kind of in this marketing community, but they had some jokes around what this might look like and I guess it's memorable and I think that's an important part.

Kortney Osborne: I don't want to guess.

Garrett Mehrguth: inaudible But I do like inaudible. I like the way it translated to everything else. I love this. This is pretty cool, the way they show the product.

Kortney Osborne: Yeah, I think it's great. I think it's clean. I think that they do a good job of right ahead easy scheduling ahead. I think so many people try to be so fluffy. It shows what is the problem and it creates the solution in three words. I think that's great.

Garrett Mehrguth: Yeah. I have a question for you.

Kortney Osborne: Yeah.

Garrett Mehrguth: And I know this, maybe this is just me being a kind of copywriter to a certain extent, but I'd like to get your...

Kortney Osborne: Oh, it's so small. I should have brought my glasses.

Garrett Mehrguth: What if I did this? Okay, I'll rewrite it. So it goes into their style.

Kortney Osborne: Okay.

Garrett Mehrguth: I'm just, out of curiosity-

Kortney Osborne: Action, create an action from it. inaudible.

Garrett Mehrguth: Yeah, we make scheduling easier. The only reason I'm wondering that is because sometimes I feel like... If I could spell whatever-

Kortney Osborne: I can get that, I can get behind that. I think the whole point is having conflict in resolution. You have conflict, you create a resolution. I like both of those.

Garrett Mehrguth: So, let's say-

Kortney Osborne: We're frenemies. I don't want to tell you it's better, but it might be better.

Garrett Mehrguth: No. Well, it's like when you say easy scheduling ahead, this word is what throws me because it's like they're aspirationally alluding to something without perfect clarity. So I'm not sure everyone who scans it gets it, but that's just like a no and I would test it if I were them. I think when we look at Calendly, I'm actually a user and so I'd like to maybe present a use case for what I believe the hardest part of Calendly is. I think the hardest part of Calendly is you have a bunch of individuals, have a bunch of clients and you're not able to get their team account. In other words, there are a bottom- up product that to really get the AOV they want to advertise and get aggressive with growth, needs a larger deal size, and needs to be more of a team buy, but is often.... When I had this, I found out that I had four different Calendly products in my company and had no idea because all these different people had signed up for it, for example. So for me-

Kortney Osborne: So I'm not a user of Calendly. I mean, our sales team at one of my organizations was, I wasn't. So I'm on the opposite where it's very easy to use, but I don't see that problem. My problem was always like," Great, I can see your schedule. I can't see mine, I'm in two different things trying to organize something." So kind of similar, but from a different angle.

Garrett Mehrguth: Well, I love that and then the other thing in the market is HubSpot is including scheduling for free now. A lot of the software companies that are housing the marketing are now offering scheduling. Drift offer scheduling, HubSpot offers scheduling, and it's becoming a very commoditized offering that people are almost giving to you for free for the sake of their platform. So I think that's also probably a threat that we want to think about as we're reviewing inaudible.

Kortney Osborne: Yes. Can it be at standalone and continue adding value?

Garrett Mehrguth: Yeah, exactly. And by the way, I had to get rid of Calendly for my sales team because what they were unable to do was massive calendar control at scale. So I couldn't cap each rep with X amount of meetings while having a different overall meeting on the link. So let's say I'm running a LinkedIn campaign and I've got a link, and I have a capacity of 20 meetings across two SDRs a day. I couldn't cap each SDR at 10. So one SDR would have 14 and one would have seven and then they would ruin their life because they were just drowning in meetings. It was an ironic problem but you couldn't balance someone's calendar at that time. So they didn't have some of those bigger functionalities, if that makes sense with lead routing. So I had to move over to Chili Piper, for example.

Kortney Osborne: Oh, which has its own issues. Well, first thing I will say though, if we're going to do an audit is if you're going to have a tagline, you better own it. I just googled easy scheduling ahead. They're the fourth add down.

Garrett Mehrguth: Okay.

Kortney Osborne: In the organic... Let's see one, two, three, four. They might not even be on the first page.

Garrett Mehrguth: And then when you click on the top online appointment scheduling software, they're below the fold.

Kortney Osborne: Yep. What's the easiest way to schedule a meeting, they are number one. That's good.

Garrett Mehrguth: Okay.

Kortney Osborne: I don't know. That's just one thing. If you're going to have a tagline and it's going to be the top thing that you have on your website, you've got to freaking own it.

Garrett Mehrguth: I agree with that and I think that's a really interesting point. Now, when we're looking at this, a simplified scheduling for more than 10 million users worldwide, I have a question and I know I'm just a huge positioning guy. If I would imagine their goal is to increase average order value in revenue, especially since they have a free product and they only make money when it grows, would you use the word users when you thought about or companies? That's out of curiosity because I think that this, I know it sounds simple, but I think this is critically important on how you position yourself for what action you want out of your business.

Kortney Osborne: I agree with you. I think that people get caught up in trying to throw out a huge number, but what's the intention of that number. And I think if you're trying to drive growth, users are going to come and that's how crosstalk in. But I like what you're saying companies, because I'm sure even if you took two zeros off of that, you're still at a million companies. That's still a big number.

Garrett Mehrguth: Yes.

Kortney Osborne: So I completely agree. Even if it was 500,000 companies, I mean that's a big number and you got to have an intention when you use that kind of data storytelling.

Garrett Mehrguth: I love where your head's at and once again, let's say this real quick. I want to just, two second though.

Kortney Osborne: I will say that they even have a video. It was great, but...

Garrett Mehrguth: Oh I agree, but why isn't it right here? I bet you, if you did GA, so what they could do just as a note to the Calendly team, you could put this in Google Analytics and then you could run a segment of users who watch the video and then you could see how much more likely is someone to take the action you want and click get started if they watch at least X amount of the video. And I don't argue, it's a pretty large amount versus those who don't.

Kortney Osborne: Yep.

Garrett Mehrguth: I would put this up here, get it right here, baby. I want to see that video because this is cool. But I would argue this is cooler and it tells a better story and it connects emotionally.

Kortney Osborne: They may run an inaudible test on that too, but I'm also not seeing a lot of CTAs. I mean right off the bat, give you my email. There's not a lot of CTAs going on.

Garrett Mehrguth: No, there's not. I think it's like sign up, but yeah, it's create your free account, no credit card required. I would maybe, instead of sign up once again, it's all silly, but this is literally the stuff you do as a performance marker. It's create free account and you go like this. It's this little stuff that actually matters, if that makes sense.

Kortney Osborne: Yep.

Garrett Mehrguth: And then get started is vague. I think they want to tie this to the actual outcome, create account today, crosstalk.

Kortney Osborne: I like the animated gifs.

Garrett Mehrguth: This is dope, yeah.

Kortney Osborne: Yeah. It's a little busy with the graphics behind it. Some readability issue, but I do like the animated gifts.

Garrett Mehrguth: I think their brand's clean like that, yeah. I do think they've done a good job on it and then Calendly coordinates it all. Meetings are scheduled without calendar conflicts, reminders go on automatically and scheduling is a breeze. I would really harp on these. You remember how we talked about earlier, how do you uncommoditize yourself in a world where everyone's offering scheduling for free?

Kortney Osborne: Mm- hmm( affirmative).

Garrett Mehrguth: I think you got to double down on why your product's more valuable. I don't see how else you stay relevant other than right here because this looks really sweet. I wonder if they explain it more? Oh, here it is. Cool. So automate reminders and follow ups.

Kortney Osborne: I like that they're owning who they are. I think so many people are trying to go so wide lately. I love that they're just owning it.

Garrett Mehrguth: Oh, yeah. No, that was literally my... What did I do last? I did Airtable last time and it was the opposite of this. Instead of staying focused Airtable was everything thing, right, instead of saying their one thing.

Kortney Osborne: Yeah.

Garrett Mehrguth: On demand scheduling is cool. Is this live scheduling? Because that would be dope. I don't know if it is live scheduling. You could essentially have an SDR-

Kortney Osborne: inaudible like a hot handoff. Yeah.

Garrett Mehrguth: Yeah, like a hotline, so an SDR, right. They partner with Drift and SDR could immediately hop on or something.

Kortney Osborne: Yeah.

Garrett Mehrguth: And then delight invites with modern scheduling. Oh, this is cool. So I think some of this stuff is really good. I have a question for you though. Let's assume you're one of every other marker in the universe on Marketo, HubSpot or inaudible?

Kortney Osborne: Mm-hmm(affirmative).

Garrett Mehrguth: Is it good enough that you want Calendly instead of HubSpot? I think that's a real question we have to ask right now as we go deeper. Are you seeing enough here that it's worth paying for when you have a free option that says they do the same thing? Because I think you're like,"I think this is superhuman. I think I'm selling an email service when Gmail's free."

Kortney Osborne: Yeah.

Garrett Mehrguth: I really do. I think we're pretty close to that point with this-

Kortney Osborne: I think people that are searching for that are searching for something different. I think that's an opportunity for a content download, a white paper, talking about the comparisons. Why you should do this from... I wouldn't start that off right off the top on your homepage and try to sell that perspective because I think it's a use case that probably only a third of the market cares about. So I would say yes to your answer. Is it enough? No, but I don't think I would expect it right off the top.

Garrett Mehrguth: Yeah, I'm still trying to see what's that hook where I say," Oh, I'm going to be an investor of Calendly for the next five years," right. I want to see that hook where they get me. So where do you want to go next. Teams, enterprise product or pricing?

Kortney Osborne: Let's go resources.

Garrett Mehrguth: Okay.

Kortney Osborne: I'm kind of curious on resources. Seems kind of light to me, especially in that context of why should I use you instead of somebody else, especially when you were fourth on the ad list for your own tagline.

Garrett Mehrguth: I'm with you. So 50, 000 companies-

Kortney Osborne: Let's still inaudible number. Yeah.

Garrett Mehrguth: inaudible.

Kortney Osborne: You know what? Honestly, go up.

Garrett Mehrguth: Yeah.

Kortney Osborne: That should be on their homepage.

Garrett Mehrguth: I think this is a better homepage. I'm on the same page as inaudible.

Kortney Osborne: This is a better homepage and then you had all those numbers, 50,000 companies, partner integrations, then you start thinking," Oh, maybe they already integrate with something that I do." I love the other tagline so I'm not going to mess with that because that's what they do.

Garrett Mehrguth: But this is more aspirational for being real. I think-

Kortney Osborne: inaudible and that globe underneath, I feel like this is being wasted.

Garrett Mehrguth: I agree. The reason I'm saying all this about Calendly by the way, I actually freaking love their product. I use it every day and it's amazing product so I want to be crystal clear. What I don't think they have though, is a moat. I don't think they have a reason that they competitively exist because I use it. Everyone else's scheduling stuff and they all frankly kind of work the same and so I think if I was Calendly, I would lean more into the brand side of being a lover of the Calendly brand. So it's more than just the product. Does that make sense?

Kortney Osborne: Yeah, I can see that.

Garrett Mehrguth: Yeah. See, I would push into the kind of more on the DEI side.

Kortney Osborne: This is interesting to me. This was the resources hand page and they went into their leadership right away. That seems like a missed opportunity.

Garrett Mehrguth: Well, we're not on resources. I clicked resources and it took me to about, so I think they might want to inaudible.

Kortney Osborne: Oh. Yeah, maybe inaudible that up. Okay.

Garrett Mehrguth: Because I was trying to go to resources, but they don't have a traditional resource center. They just have a blog from what I can see. Our traditional, inaudible resource center is some type of data study. By the way, that would be dope as hell. What if they benchmarked everything to say like," Your attendance rate is 3% lower than other people in your industry. Why don't you set up some more reminders?" You see what I'm saying? That kind of stuff I think brings this thing to life.

Kortney Osborne: Yeah.

Garrett Mehrguth: I just want more creativity crosstalk.

Kortney Osborne: crosstalk to get people to show up. Three ways to, just those tips, tricks, how- to's. Because you're setting up a meeting for a reason. You're setting up a meeting to get something done. How do you help them use your platform to get what you need done? And you could easily create a lot of content around that.

Garrett Mehrguth: No, 1, 000%.

Kortney Osborne: I love this productivity. That's awesome.

Garrett Mehrguth: Yeah. So they're showing it and I think they have some customer stories. It's pretty clean. I would-

Kortney Osborne: inaudible use of video though.

Garrett Mehrguth: No, and I think what I would do if I were them, because for the content I've seen perform the best, especially for going up market, is I would anonymize all of my data and I would have benchmarks on SDR attendance rates, recruiting attendance rates. So I would just take my category, sales recruiting productivity and I would be like average time saved booking meetings by CEOs," right? Average attendance rate from recruiters, no show rates from SDRs. Whatever that is and I would essentially do a ton of benchmarking and those data studies get the most links, the most coverage, the most shares and only Calendly can say that because it's based only on Calendly's data. So you get a moat, once again, around your brand with your content, because anyone can write an article around 11 pro tips for this. Any other competitors can write the same article. What they can't write is an article based on data that only Calendly has.

Kortney Osborne: Yeah. It'd be interesting too, to take that and then create a matrix by industry.

Garrett Mehrguth: Yes.

Kortney Osborne: And you have the business type, sales, recruiting, which is awesome. The search volume isn't as high, but you take that industry perspective and then it's like," This feels specific to me." crosstalk.

Garrett Mehrguth: crosstalk spice up your TAM, you give that asset to the SDRs and then you start breaking into the accounts better. You start leveraging it as maybe a direct mail. You turn it into a magazine, you ship that to the C- level execs and the VP level to see if you can't grow enterprise in teams. But that's where my mind goes, if that makes sense.

Kortney Osborne: Yeah. Yeah, I think that it's awesome. I think they're doing great. But sometimes people just want to copy. People don't really want to create. So if you can be like," This is for sales within this market," and boom like," Okay, cool. Go do this. Now, here's a template. Anonymize that data. Say this is what you can do with it." I think that matrix is really beneficial.

Garrett Mehrguth: What I want to see right here is how do they from the pricing moment show you that it's better to have more people. In other words, how do they incentivize, increasing their average order value? I want to see what they do. Okay. So they're starting off with annual billing. See how they still are first individually. They're still staying on this individual path. I find that so interesting from a strategy standpoint because they're still trying to sell crosstalk.

Kortney Osborne: Three out of the four options, right, there are all individual

Garrett Mehrguth: You see how they do and small teams? But fam, let's be real for a second. This is expensive as hell for a scheduling inaudible per month tool when HubSpot's free.

Kortney Osborne: Yeah. And then for teams and companies that want to collaborate more efficiently. More efficiently, is that really what they want? It feels fluffy. To spend that much money just for us to collaborate better? Auw, cute.

Garrett Mehrguth: Well, it's not just crosstalk.

Kortney Osborne: crosstalk how is this impacting your bottom line?

Garrett Mehrguth: Teams that use Calendly save 30... You actually did this really, really well and one of the best I've seen in a while. Where the hell is it? I like this page? Where is the benefits of your product page? I'm trying to remember inaudible.

Kortney Osborne: Oh, it's kind of weaved throughout.

Garrett Mehrguth: There's a section though where I can click through. I don't know why I can't find it right now.

Kortney Osborne: Maybe go to industries and then go to dental. A lot of it's industry specific.

Garrett Mehrguth: Yeah, maybe is there. Yeah, right here. See this to me is hitting on those value props and it lets me really consume it. I don't know. When I'm looking over here, I want... Teams that use Calendly save 30% of their hours on administrative tasks, okay?

Kortney Osborne: Yes, yes.

Garrett Mehrguth: Hell yes. Hit me with it. Let's go.

Kortney Osborne: Because that's instantly like," Ah, yeah,$ 16 a month for that. That makes sense."

Garrett Mehrguth: Because what I'm trying to do is crosstalk instead of what I think they've done so freaking well, which is get someone to sign up for free, I want to show who's going to put their neck out on the line and essentially sponsor Calendly. What are we empowering this champion with? What are we giving them so they can go above themself and say," We need Calendly?" I don't know if I would-

Kortney Osborne: That's why I would love right here underneath where you have that. I love how straightforward they're being, but why is there not social proof under each of these? Why is there not an example of somebody that's gleaning value from this? Or just at least one example, that's getting them to the 16. Show that video, show that social proof of where you ultimately want people to land. I feel like this is really straightforward and I like it, but I think that's a missed opportunity.

Garrett Mehrguth: They could replace this with a quote from each of the personas for each crosstalk.

Kortney Osborne: Yeah, with a picture and a quote and I think, yes.

Garrett Mehrguth: That would be dope. And then I do actually love this scroll. See how you can scroll while holding the prices? I think it's one of the better pricing pages I've seen actually on the show.

Kortney Osborne: I like how inaudible they are too.

Garrett Mehrguth: It's really strong. So this is awesome work, Calendly. I think the... See how teams is an afterthought again, though?

Kortney Osborne: You're right.

Garrett Mehrguth: If I was chief revenue officer, everything I would do would be focused on increasing my average order value so I could grow ad spend. Everything. crosstalk

Kortney Osborne: inaudible you got to increase ad spend. I don't think most CROs would add that end of the sentence to what you just said.

Garrett Mehrguth: But I could control growth organically and I wouldn't be codependent on acquisition and integration. So it's like...

Kortney Osborne: Most CROs just wouldn't do it to increase ad spend. They wouldn't free just give you that money. But we can dream as marketers, right?

Garrett Mehrguth: I'm dreaming, I'm dreaming.

Kortney Osborne: We can dream, we can dream.

Garrett Mehrguth: So you can remove Calendly branding on a free account? Oh, no, you can't. Okay, okay. We can't.

Kortney Osborne: I think they did a really great job. I love the interface. I think there's just some opportunities to story tell. I think people want data. They say they want data, but really they want a story and so I think if they could connect that back to an actual use case, you think that they're going to get a lot more action here. Or at least if they say try for free, let's click on one of their try for free buttons or start professional, whatever it is.

Garrett Mehrguth: That's pretty clean.

Kortney Osborne: Yeah. Clean even maybe an opportunity there. You don't want to mess up conversions, but maybe some opportunity there to make it look like the person that's actually clicking the buttons.

Garrett Mehrguth: Yeah.

Kortney Osborne: I do like this, just email address. Some people over complicate that.

Garrett Mehrguth: I agree, but I think you need to highlight credit card if it's required or not and how many more steps until you can schedule your first meeting. So you're 45 seconds away from scheduling your first meeting and then I would have something like no credit-

Kortney Osborne: Interesting you started with professional and it went straight to their free as well.

Garrett Mehrguth: I know. I can't really... That's what I'm trying to explain. It's because the pro is a more feature rich individual plan. So let's see what happens when I go to teams. See how it's still for individuals? Let's see what happens on teams. See that's interesting because-

Kortney Osborne: Somebody's clicking for the team and you're still focused on the individual.

Garrett Mehrguth: For free.

Kortney Osborne: For free.

Garrett Mehrguth: I know. That's what I'm trying to explain, I just don't think they've... This is what happens to everybody though, right? You get big and Calendly sense and you have product- like growth and then you get the money people come along and say," Hey, how do we go up market? How do we get higher average order value? How do we get better inaudible," and they say, " Well, we're going to offer enterprise." So let's see what happens when we click enterprise. See, this is probably what you want on the teams one, to be completely honest. I think this is a healthier sales environment. I don't know how effective it is to say teams, but not sell the champion.

Kortney Osborne: Good point.

Garrett Mehrguth: And by the way, enterprise is not 100 employees. This is teams. Directive has almost 150 people. I'm not enterprise. crosstalk.

Kortney Osborne: It's interesting, just that word enterprise. It's not, but I do think that that pushes people off. I don't know, even when necessarily I'm going with this, but they're trying to be enterprise, but are the people that are coming here considering themselves enterprise and are they really looking for that? And the person that is a true enterprise account, probably isn't looking on this website. So I don't think their verbiage is quite right to maybe the audience that's searching.

Garrett Mehrguth: Well, yes. Just so you know, in this space I used to do everything for... Damn, why did I just lose their name? God damn. They are the enterprise one and I can't believe I just lost their name. Oh, let's see. It was Time Trade. I did everything for Time Trade and that's definitely an enterprise version of this. I would just say see how there's submitting your inquiry for your team or enterprise?

Kortney Osborne: Yeah.

Garrett Mehrguth: But they didn't send teams crosstalk.

Kortney Osborne: And I haven't seen a video. I haven't seen contact our sales team. Most people aren't going to put themselves into somebody's funnel just willingly without a little bit more.

Garrett Mehrguth: Let's see what they do though on the enterprise page. Let's take it out. Way more than a scheduling link. Okay, that's cool. I like that. Okay. Now you're selling. Okay, cool. What standardized-

Kortney Osborne: Let me know why you're there. Let's push it up.

Garrett Mehrguth: Okay. So trusted by more than 50, 000. So now this is when they're using organizations, not users, which I like. Meetings are the lifeblood of high performing teams.

Speaker 3: We know that making a good impression is more than just an old saying. It converts candidates to new hires. Pushes big deals-

Garrett Mehrguth: This video style doesn't hit the same as it used to. crosstalk talk about?

Kortney Osborne: crosstalk we talked earlier about you meet for a reason. They just right away, why are you actually meeting with people? I think that was good.

Garrett Mehrguth: Yeah.

Automated voice: inaudible a good customer interaction into a great one. But as important as a good impression is, a messy scheduling process can leave a bad impression. Emails are sent back and forth, rescheduling at the last minute and does anyone know what this meeting's about? All this time consuming work happens every day across your entire team and important connections slip through the cracks. But what if we could uncomplicate scheduling? Introducing Calendly for enterprise. Calendly is a modern scheduling platform for high performing teams. It unites your team, your invitees and your data into one streamline process. Get to meetings faster, scheduled right from your email, phone or website.

Kortney Osborne: I need data proofs.

Garrett Mehrguth: Yeah.

Kortney Osborne: I haven't seen any, but I liked it.

Garrett Mehrguth: This is it. There we go. There we go, fam. This is what we wanted.

Kortney Osborne: Boom. Put that in your video. Boom.

Garrett Mehrguth: And right up here. You can put this on a weird left scroll thing. It would be kind of sexy. It would look good. You could take this. Where is this? inaudible go. You could take this thing vertically and you could put it right here on scroll. There's ways to do that. I like... Oh no, let me click in, baby. Because enterprise buyers are selfish. They want to know what it does for them and their use case. So how does it help me as head of people op with my repeating team? How does it help me as the sales VP inaudible? Yeah. Immediate adoption. This part's true. I would focus on this a lot. I think it's a highly adopted platform. Okay. They're talking about their sock. This is the sexiest part of marketing, but you got to do it on enterprise. Cool. This is good. At least they have it crosstalk.

Kortney Osborne: Your CSO's going to get on the call. You got to have something on there.

Garrett Mehrguth: Yep. And then easy to use. Easy to integrate. I like that. HubSpot Salesforce, Slack, Zoom, Greenhouse. I mean, those are kind of the biggest players in each vertical. Workflows. I can't click in again though. I just think we need a little bit more product marketing here. A little bit more product marketing. Because you're telling me I got team pages. Okay, don't believe you show it to me. Oh, I can do groups. crosstalk I can't even imagine. Where the hell is a group for scheduling? What does this look like? Change my perception. Make me need you. I think this is a great moment that we're just intelligent routing. Well, this looks like a inaudible chart or whatever. Like a org chart. Show me what-

Kortney Osborne: Well, inaudible it'd be pretty easy too. I was just saying their product section, they probably have something somewhere just linked to something that has it already.

Garrett Mehrguth: And now we're back to why Calendly, which doesn't exist in my menu. Do you see what I'm trying to explain? This is the little stuff where I'm like," Come on." Imagine if you got rid of individuals, which everyone thinks you're already for and then just did this.

Kortney Osborne: Yeah. Yep.

Garrett Mehrguth: Right? Now you're obviously still for users, you have product- like growth, free onboarding, but it's why Calendly teams and enterprise and we're trying to educate as we go at market?

Kortney Osborne: Yeah. We once trained changed from solutions or something to why the company I'd worked for and our conversion went up 50%. People just-

Garrett Mehrguth: When you do that well on Weave, you're using jobs to be done in outcome based messaging instead of input based messaging, if that makes sense.

Kortney Osborne: Yep. We have a great team over there. They're incredible. So I can't take... Weaves' awesome.

Garrett Mehrguth: No, 1, 000% and I'm just thinking about this, but once again, do you see how they said learn more about the products?

Kortney Osborne: Yeah.

Garrett Mehrguth: I didn't learn anything about their products here. No, I'm being dead serious.

Kortney Osborne: I didn't learn anything about your products.

Garrett Mehrguth: Well, no, because they crosstalk I want to be clear on how I got there. I clicked on see all product features. So I thought I was going to see information on these features that they just... This is the story they just told me. So when I clicked here...

Kortney Osborne: It took you back up.

Garrett Mehrguth: Well, no, they do that. It's a weird UX thing. I'm not actually on that page. So change that. I'm on four enterprise, but the way they do UX, I'm going... It's a new page, but they have me scroll up. So I feel like it's the same. It's actually not. Isn't that wild?

Kortney Osborne: That is wild. Just tell me about your product. I'm asking about your product. I'm trying to click on product.

Garrett Mehrguth: Well, you got me excited about your product. That's why I want to know... I wonder if that exists it. I think it... See all features. Let's see. No, they don't talk to me about those damn things. Do you see what I'm saying?

Kortney Osborne: This is an easy one where it makes you look like you have all that stuff on that other page, you put it on this other page and you just link back and forth. So you don't have to create multiple pages.

Garrett Mehrguth: Yes.

Kortney Osborne: Yeah, I don't...

Garrett Mehrguth: Because this is dope. You understand? I'm actually excited when you tell me about intelligent routing, team pages, groups. inaudible I get, I don't know what these three things are. crosstalk. Yeah, and then CRM plus sales tools. Do you auto record my meetings? Do you document it as a task in Salesforce? Because that's pretty dope. With ATS, do you go into my lever instance and record the meeting? This is actually really cool stuff. I just don't get to learn more yet.

Kortney Osborne: Yeah.

Garrett Mehrguth: Interesting.

Kortney Osborne: I feel like I'm ripping apart Calendly, but I really do like your product.

Garrett Mehrguth: Well, no, it's a phenomenal product. I think that's why we're so excited.

Kortney Osborne: Most of our stuff was like, I was pleasantly surprised going through that, what they were doing well, but I think there was some low hanging fruit that would be easy for them to accomplish.

Garrett Mehrguth: Well, I think the beautiful part about Calendly is their product is so good and it's so adoptive, it's so usable. I literally tried it four years ago and I've never thought about trying anything else.

Kortney Osborne: Yeah.

Garrett Mehrguth: My sales team needed something different for a different use case. But me personally, I didn't adopt that new product. I kept my Calendly. I love my Calendly. I think the issue is, is when it's not about me loving my Calendly, but instead the effectiveness or efficiency Calendly drives for my organization you need to change your narrative, your story and you got to develop that product marketing, the resources to support why I'm paying$ 16 a freaking user. Because that ain't cheap and I can't just roll it out to this person and that person. I think if we roll out Calendly, we roll it out to the broader organization. We all schedule calls with each other on Calendly. So I got to know why the hell do I need that instead of just slacking someone or clicking on their Google GCal which I can see in my own calendar since we're all in the same organization. I want to know that narrative. I don't know if I've got that today, if that makes sense.

Kortney Osborne: Yeah. And I think, now we've very well could have made some wrong guesses, but I do think that there's a simple question that a lot of people can't answer and it's what are you optimizing for? And I think you made the point. They're optimizing for the individual, but we don't think that they should be nor do we think they are. I don't think that's their intention, but they're optimizing for the individual hoping they'll, then that's probably worked for a long time, but why not go for the thing you actually want a little bit more and you can still balance with... What got you there isn't what's going to get you there. Is it that saying?

Garrett Mehrguth: crosstalk everybody has that right now. Everyone in inaudible, right, starts product led. They're eventually," Oh, crap. We got to go enterprise and get groups and teams." And then you have to shed your entire identity and that's really hard, 10 times harder than the inaudible.

Kortney Osborne: You don't need to shed it. Hide it. Hide it a little bit. People can still get there. They can still go through the workflow that's worked for you for along, but take all the goodness from that and optimize for what you actually want.

Garrett Mehrguth: 1, 000%. Courtney-

Kortney Osborne: 1,000%.

Garrett Mehrguth: It's been phenomenal. Thank you so much for being on the show. If someone want-

Kortney Osborne: It's so nice to kind of get to look and say," Hey, this is crosstalk".

Garrett Mehrguth: crosstalk have a free opinion, right? It's kind fun to be able to kind of say what you think. So welcome to the consulting world. It's been great having you on the show. If anyone wants to learn more and kind of follow along with your journey, what's the best way for them to do that?

Kortney Osborne: On LinkedIn, you're welcome to follow me, connect and sadly it's probably on Instagram. If you want to contact me, I'll probably contact faster on Instagram than anything else, but you're going to get a lot of the real Courtney on that inaudible.

Garrett Mehrguth: Yeah, inaudible the real Courtney. I love that.

Kortney Osborne: There's a lot and I am a lot, but I'm fun too.

Garrett Mehrguth: inaudible. Nobody wants a little. So thank you so much for being on the show. This has been phenomenal and that's another episode of SaaS Marketing Makeover. Bye everybody.


It's makeover time.

In this live show, CEO and Co-founder of Directive Garrett Mehrguth and a SaaS marketing leader work together to build a strategy for a recognizable SaaS brand - as quickly as possible.

The company will be randomly selected by spinning a wheel at the beginning of the show, and together, the two will craft a strategy for SaaS marketing leaders everywhere.

Today, our guest is Kortney Osborne, who landed on Calendly for her marketing makeover. Tune in as Kortney and Garrett share tips and insights to help you step up your product marketing strategy.

Today's Host

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Garrett Mehrguth

|CEO & Co-Founder at Directive

Today's Guests

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Kortney Osborne

|Unicorn Maker