Experiment and learn from failures, rather than seeing everything as either a total win or a total loss.

In this episode, Jessica Gilmartin, CRO of Calendly, shares her perspective on defining go-to-market and the importance of coordinating customer-facing teams like marketing, sales, and customer support. Join us to explore the challenges of serving diverse audiences and keeping employees focused on the customer through initiatives like a brand manifesto.

Listen to the podcast here:

Being Customer Obsessed: Insights from Jessica Gilmartin, Calendly’s CRO 

Let’s just get right in, which is how do you view and define go to market? 

So I really think of it as the coordination of the strategy and execution between all the customer-facing teams. So when I think of customer-facing teams, I typically think of customer support, sales, and marketing.

Understood, and where does the product come into play over there?

So obviously, the product is really important and plays a very different role, whether you’re a PLG company or an SLG company, I’ve worked in both. But really, I see the role of marketing as the liaison and a link between our customer-facing teams, our customers, and our product team. So very important, square rectangle, triangle, however, you think about it, but the product really is the definer of where we’re going. And sales and marketing are the ones who bring it to life for our customers.

Yeah, for sure. And in fact, I love this. This is the exact reason why I started this podcast because there are so many perspectives on how people view and define think of go to market, there has been one variation. And this I think, really captures the essence of the go-to-market for me, which is it always starts with “who are you solving for”? And “what is the problem that you’re solving”, and “how are the product and the solutions”? And then you have all the go-to-market aspects, which is exactly what he talked about, which is you got the marketing, you got the sales, you got the customer success support. And then of course product, and bringing all of these teams and functions together again, going back to the problem and for who you’re solving.


Yeah, and I would say that the function that is most left out is typically customer support. What I have found so interesting in my career is how much people think about, you know, the initial signing customers up and getting their revenue, and how little we think about supporting our customers once they are customers. And I think that that’s such a big mistake. And it’s something that I really spent a lot of time thinking about. So now when I think about go to market, I think that the relationship between sales, marketing, and support is incredibly important. And something that I just think a lot of people are alike.

Yeah, absolutely. You’re spot on on that. Right? I wish more people thought about customer support and leaned on customer support, even in turn in terms of thinking about the cold market. So as an example, if I like a product market or building content and campaigns in marketing, I would absolutely lean on the customer support team or even the customer success team in identifying and sourcing, like how are the customers? How are the customers changing because of a product? Better is it bad? Why not write and tell the stories to bring and build that brand about your company?

Yeah, nobody knows your customer is better than your support team and your customer support managers like nobody. And so if you’re not taking advantage of that, then I think you’re missing out on a lot of that richness.

Yeah, fantastic. So you did mention, actually, even before I get into the details of that, so why don’t you share with us your career journey and story and what you do at Calendly today?

Yes, so I have a super weird journey. If you’ve ever seen my LinkedIn, it does not look like most other CMOs or CROs pass. So I started my career in investment banking, I did that for quite a few years and then realized that I wanted a career change. I just didn’t know what it was. So I went to business school, which was a great opportunity for me to reset and took my first marketing class and fell in love with marketing there and ended up getting a job at Dell as a brand manager. And my husband, I always kind of talked about moving out west. And we moved out here and said to start my own business and started the chain of yogurt stores, which turned out to be very, very successful and sold those and somehow ended up stumbling my way into tech marketing. So that could be a whole other podcast about that whole process. But a lot that was that was the short version. 

No, for sure. I don’t know why I didn’t. By the way. I noticed that you did your undergrad at Cornell University. And I got my MBA from the Johnson School. Oh, nice. So we have a common connection there. 


Yeah. Very cool. Yeah. So yeah, let’s dive into several of those aspects that you didn’t mention you started off your career in investment banking and back to business called Wharton. And then more and more into the brand and the marketing side of the world. So what really attracted you, and what aspects of marketing and border market did you gravitate towards?

So when I first took my first marketing class, what I realized was how important both the creative side and the data side were. And, and I knew I already obviously had all the data, you know, my background in banking, I had a lot of financial background, a lot of financial knowledge and interests. But it was when I started taking marketing classes that and realized how much of it was an art, as well as a science. And I realized, gosh, this is such a great way for me to bring together both parts of my brain, and really think about the beauty of marketing and storytelling and customer engagement, but also grounded in data. And so I think that that’s something that I’ve always taken with me through my whole career is really focusing on the art of storytelling, the data creative, but also the data. And I think that really, any successful CMO kind of has to have both and be interested in both. 




Yeah, yeah, I see that your first role after your MBA was being a brand manager at Dell. So that’s the creator and the storytelling side. And somehow something got into you and your husband so you decide to start a yogurt store chain. So what is why I mean, why didn’t go down that path?

To be very clear, my husband did not start with me. It was emotional support. But that was about it. So when I moved to the Bay Area, I reached out to a good friend of mine from business school, and she was interested in starting in business, she had been looking at business ideas and asked if I would be interested in starting a business with her. And so we thought, Gosh, this sounds really cool. I was young in my 20s. I thought, why not? And then we just started batting around a bunch of different ideas. And I think, for me, what was the most important was finding something that I was really passionate about. And then again, going back to the creative and the data, which is, what do we love to do? 

But then also, where do we think that there’s a big market opportunity? And one thing that we kept thinking about was that there are, you know, a lot of unhealthy choices for food, you know, so if you want to give yourself a treat, get ice cream, and cookies and cupcakes, but very few healthy options. And we thought there’s got to be a market for health-conscious women who want to bring their kids who want to bring their friends who want to treat after a hard workout. And that just didn’t exist. And so we kind of kept batting ideas around and we ended up coming up with the city of yogurt. And then the more that we thought about it, the more that we felt like we had a really unique opportunity to build something that was something that we personally believed in, but also felt like it was a big opportunity.



Yeah, I mean, sure, and just share a personal story and experience from my own thing, which is having been at business school, yes. I’m thankful for all the courses the professors and the guest lectures and the speakers who share their experiences. And I so wish I could apply a lot of those things. So as an employee, myself at different companies, I got to think about and be responsible for applying maybe half or even less, yes, marketing, sure sales, kind of, sort of, though, because I need to interact with them. And there is a financial aspect. But it was truly only when I decided to go down my own path. That’s when it really kicked in, in terms of the sales. I mean, there are different aspects of sales even before that there’s a psychological aspect, which is, why does a human being any person care about it? Why should they care about you in the first place, even if it means giving you one second of their airtime? 


And for me, when I got in, when I started going down that path, that’s when it really hit me all those fundamentals of a little part of what we learned at the school, but a lot more from life lessons outside. 

Yeah, I have a lot of conversations with people who are interested in going to business school, and they asked me if it’s worth it. And my my perspective, you know, obviously just mine is that I think it’s incredibly valuable. If you don’t know what you want to do if you’re switching careers. And it’s an incredible opportunity to meet a lot of super smart people understand their career paths, and get exposed to, you know, amazing guest speakers and professors and, and, you know, different subjects and sort of learn what you love to do. If you know, if you’re like a tech marketer and you want to stay in tech marketing, you’re probably not gonna learn very much, you’re better off just staying in your job and sort of advancing that way. 




Yeah. Imagine not just the time that you spend like one to two years, but even the opportunity cost and the tuition. Even those one to two years if you decide to go down the path of starting something on your own. That’s an invaluable experience and lessons learned from that itself, if done.

It’s not cheap. 

It’s not cheap. Yes. Yes. Fantastic. So yeah, we got stuck at the yogurt shop and yogurt business. So going forward. So after that, you joined Google

So some Yeah, so So basically, I was at a startup. So I joined us as the first marketer at a wonderful social media startup. And we just hit the definitely right place at the right time. And we ended up getting bought by Google. So I was there for a few years. And that was a really amazing experience, I learned a ton, and I think, what I learned a lot was that I really am very passionate about building businesses. And so as much as Google has a great culture and a great company, I’m fundamentally an entrepreneur at heart. And so that kind of really solidified to me how much I enjoy working at smaller companies, and just having an impact, you know, sort of a broader impact on on a company. And so that was very helpful for me. And so I’ve kind of been at various stages of startups ever since that opportunity.

Fantastic. And then you grow. Then you shifted more into this C-Suite and senior roles after that, which are Chief Operating Officer, Chief Marketing Officer, GM, CMO, and then CMO now CRO at Calendly. Yes. Very cool. Yeah. So tell us about what you do at Calendly, who do you serve at Calendly? And the role of AI in all things?





Yes. So if you’re not familiar with count, I think most people are but it’s it’s basically the world’s largest scheduling automation platform. So we really help people create better meetings and more effective meetings. And it’s, it’s incredibly rewarding to be accountable. Because everybody loves it, everybody uses it, it’s so fun. No matter where I am, I could be literally under this totally happened, I was in a with a guy who was coming down the mountain after skiing. And I said I was, you know, CMO account leader, oh, my God, let me tell you all about how I use Calendly and how critical it is in my workflows. And so it feels really good to be to be selling something that people use to, to feed their families. And it’s really important for me to be able to have a job that I believe contributes in a really meaningful and important way. 

So I run, I run all our go-to-market functions on our sales and marketing teams. And we sell to anyone from solopreneurs up through the largest enterprises in the world. And really, the common factor is, you know, anybody that relies on external meetings for their success. So we typically sell to recruiters, entrepreneurs, small business owners, salespeople, marketers, customer support, and financial advisors a really big market for us. And then when we look at industries, it’s typically you know, sort of technology, financial services, professional services. So that’s kind of how we think about and generally, sort of individuals to small teams within those organizations. And, you know, of course, AI is something that we think about a lot, the one thing that we take very seriously is the fact that we have millions and millions of users. And we want to be extremely careful with how we deploy it and make sure that it is valuable. And they show that it really enhances our existing customer’s workflows. You know, I think we all talk a lot about AI. It’s kind of like a requirement these days. And I think what’s interesting, we can only do a status scheduling report. And one thing that we learned was that you know, 94% of our respondents said they were really interested in using AI, and only about a third of them are actually using it. So I think that that delta to me is kind of that hype, that, you know, we’re I think we’re at the mass of the hype cycle. And so anything that we do and anything that we’re working on, we want to make sure that it is really valuable.

Fantastic. So something unique about Calendly is, as you mentioned, right different personas, different segments. It’s a b2c, it’s a b2b. And I don’t know maybe there’s also a partner angle where it’s sort of a reseller angle. So how are you thinking in terms of how you position Calendly, even today versus going forward? And who is the primary message targeted towards? 

So I think, you know, because we have the plg angle, we have the SOG angle, which I’m used to from Asana, you know, it’s something I’m very comfortable with. And I think a lot of companies are going this way, you do have to be really tailored and targeting in your messaging, it’s hard to have one message for everybody. And so you know, if you go to our website, we very explicitly focused on sort of small teams, we focus on that recruiter, salesperson, marketer, customer support persona, but we make it really easy for you, if you’re an enterprise customer, if you’re a financial services customer, we make it really, really easy for you to try to get to that information as quickly as possible. 

So I think the important thing is just trying not to boil the ocean with trying to have every message on your homepage, but getting people as quickly as possible to pages that speak very deeply to them. So if you’re a financial services company, you’re one click away on our website from getting a huge amount of extremely tailored information like case studies, and you know, and talk about your security and integrations with financial services platforms. So I think that that’s a really important part is to be incredibly thoughtful about understanding the customer journey and making sure that you’re just getting people to the right place. So you can have a very specific message for them. You know, obviously, also in our advertising, we try to be really sophisticated and how we segment our customers and make sure that when we are serving ads to them, we’re doing it in a way that feels really relevant, really meaningful to them. But it’s hard. It’s really hard. 

It is. Yes, yeah, absolutely. Maybe, yeah, I was not thinking about this. But then just based on what you shared. Jessica, it is what really attracted to what attracted you towards Calendly, what are the big challenges that you’re thinking about in terms of pushing your team towards?

So the reason I came to Calendly was, it’s always about the people. And I’ve learned after all these years that, you know, the places that I love to work the most are the ones that I enjoy the executive team, I have a good relationship with the CEO. And I feel and I feel like marketing is respected, and has a seat at the table. And that was very clear that that was the case here. So that’s number one. Number two was just I love the product, I’ve always loved the product. And so you know, it’s hard for me to imagine selling a product that I didn’t love and believe in. And so that is really valuable and meaningful for me and I love the product so much. And I know everybody else loves the product. 

And the third thing is just that it’s so interesting for me to be at a company that is in this sort of scaling phase, where we have strong product market fit, we have millions of users, but I feel like there’s so much opportunity and there’s so much more to do. So I love you know, coming into organizations that are still having to solve really hard problems, and we’ve got lots of problems to solve. And because that is really fun for me. And so, you know, some of the problems that we think a lot about are, you know, how do we tell this message? How do we focus? How do we sell to everybody at the same time, but also being really specific? How do we get people to understand how sophisticated Calendly actually is when a lot of people think of us as a scheduling link? And so it’s a really interesting problem to solve where it’s we have incredible brand recognition, but not everybody actually knows all of the things that we do and all the very sophisticated and complicated use cases that we solve for. And so that’s for me, like really fun is thinking about, like, what’s our brand message? And how do we get that out of the market?

Very cool. Yeah, and I’ve heard this, you haven’t heard this, say, or you mentioned this quite a few times and your own conversation, which is being customer obsessed. And maybe if I had to deduce there’s also the data angle, you didn’t mention going back to your earliest job. There’s a data angle. So how do you tie or combine both? And do that at Calendly?

Yeah, so I probably have a broken record around being customer-obsessed, because I just don’t know how you can do great marketing, do great sales do great products without really deeply understanding your customers. And I’ll give you an example of sort of how we did this recently that I’m really proud of. So we recently codified our differentiators from our competition, super important, right? Understanding, how are you different? How do your customers see you I know like a lot of companies would just hire an outside firm and do this whole big research project and come back, and you know, with a lot of like, very big words, and it sounds very sophisticated, but ultimately not necessarily grounded in what our customers are actually saying. 

So we took a very different approach. And we started by interviewing our customers, we interviewed our support teams, we do your salespeople, we have this great service that looks at all, a lot of our closed, lost and closed one opportunity and actually interview live those, those sales, those prospects, and those customers to understand why we won and lost those deals. So we took sort of all of that information, both at our community, we looked at our support tickets. And we looked at online reviews. 

Then we basically organized all that data to come up with the four pillars that really differentiated us from our competition. And then we like ran that by our salespeople, we actually, you know, my team actually got on calls with customers, and, you know, did the pitch to them, they got feedback and whether it resonated or not. And then after all of that, they felt comfortable rolling it out. And I think that that process of using customer language and using what our customers actually say and did, really helped make it really powerful and really specific and meaningful and very effective.

Very cool. You did mention a couple of data sources you didn’t mention about the support tickets, you didn’t mention about the close loss and close one. So how did you tease out the way I’m reading this, Jessica it’s almost like going back to the drawing board figuring out and doing like a positioning and messaging exercise in terms of who is currently and what are the alternatives are out there. Why should anyone care about that? 


And the brand pillars the value pillars? 

Yes. Yeah. Brand pillars should come from why your customers are buying from you and to me it is so rewarding when we look you know, I still look all the time obviously about why we win deals, why we lose deals, and you see that language being parroted by our customers is so meaningful to me because it means that we’ve got it right. You know, when our customers say, hey, you know, I bought, can we because you had the best security? Or because you had these integrations with Salesforce. And you know, our competitors didn’t. That makes it very clear to me that we have a right. 

Yeah. And so how are you making? Sure, because you did mention you serve different personas, you had got the individual people, the buyers from a big portion, they can be like solopreneurs or freelancers. And then you have the agencies, and then the different personas within an enterprise. So how are you making sure that you’re actually servicing and targeting most of these personas?

Yeah, and I think you obviously can’t get it 100%. Right. I mean, there’s no way. And I think the just making sure that when you’re looking at the breadth of customers when you’re looking at review sites, we’re looking at all this, that you’re really taking a representative sample. So I think, you know, what I have definitely seen mistakes happen is people will only look at enterprises, or they’ll only look at small businesses, I think it’s really important for you to look across the organization, look at all those personas and figure out the commonalities, you’re not going to get it 100%, right. But you should get it to about 80 to 90%. And then of course, if you have certain use cases, or personas or industries that are very different, then that’s totally fine. I mean, it’s fine to have a set of differentiators that are specific to one industry if they are very different than another one. And obviously, even within countries that can be very different. So what you know, what Germans care about is very different than what you know, people in the UK care about is different than what the US cares about. So it’s important to also take that lens and be willing to adjust. But it should be, you know, a 20 to 30% adjustment versus something completely new for every single customer that you serve. Is that if that’s the case, then it means that you’re not you’re not getting it right.

Yeah, I mean, I’m going through a similar exercise myself, I’m working on one and I’m working with a Chief Product Officer of a 100 million plus company that’s launching a brand new product in the auto industry. And then on the other side, I’m working with a co-founder at a pre-seed and angel-funded startup who is looking to come out of stealth. And I’m doing similar exercises just who is reserving Why should anyone care about us? What are the alternatives that are out there without our product or service? And the core pillars, the differentiator’s exercises that came out? And I’d love to get your thoughts on this Jessica is a manifesto. It’s actually a brand manifesto, or it can be a product manifesto. But typically, it’s a brand level. It’s all about what we stand for. Why should someone care? And to even give their time or dollars for that matter? And what can they be confident about our promise to them? Yes, to spend time with us? Right? So so curious to get your thoughts. Do you have? Or do you currently have a manifesto initiative or a project or maybe that’s in the pipeline? 

I wouldn’t say we have a manifesto. But I think we have a lot of different things. So you know, we do brand surveys, I think that, again, it always comes back to what our customers are saying about us. And so in our brand survey every year, we asked, you know, what are words that you would use to describe Calendly. And that’s incredibly helpful for us, because we take that, and that’s the language the customer stories we use. But I love the idea of a brand promise, I think that completely makes sense. And I think the important thing is for everybody within the organization to agree on that and to live that every single day. Because if you know, every person that’s interacting with a customer should understand that and should live that. And, you know, and and express that. 

And I think like, for example, I think of the Four Seasons, that’s gonna be the classic example of a company that has a brand promise, and every single solitary employee lives and breathes that. And that’s always something that I think a lot about, which is how do you make sure that no matter what the situation, everybody comes back to what are your core values, which to me is kind of similar to the brand promise, the core values are internal, the brand promise how you express it externally. 

Yeah, yeah, totally. And that’s exactly I mean, that’s one of the primary reasons why I pushed for working with these folks in terms of why you really need to have a manifesto, because every, it’s very common and very often you have new employees coming and joining onboard and and even the existing employees, they lose sight in their day to day work as to what they’re doing and why they should put in and the customer obsession or customer focus, right, it’s almost reminder because very often again, it’s not intentional, we are so in the weeds in our day to day on a week to week basis. And then it’s it’s really good to step back and just do like a 10-15 minute read of the manifesto that reminds you as to this is what I’m trying to do. This is why I should invest in this initiative, even though there are a lot of challenges of friction. 

Yeah, and the way we do that is just bringing customers in all the time. Yeah. So we are constantly bringing and we’re bringing customers into all hands. And it’s to me, it’s incredibly rewarding. I think it’s rewarding for everybody to understand the tie between their work and then real customer value. And so when an engineer launches the future, and then a customer talks about how important that was to them, that is that to me that that like a manifesto, that’s the moment that people recognize how important their work is. And so it’s constantly reminding them that we are building for real people, and we’re solving real problems. 

So yeah, we touched upon a lot of points over there in terms of customer obsession in terms of talking about the different teams that make up the go-to-market. But curious, I mean, are you in as a CRO at Calendly? How do you actually manage a line? I think that’s the biggest challenge when it comes to go to market. Typically, what I’ve seen from my own experience and others, Jessica is, there’s like a one to two-day workshop we do every quarter, we talk about alignment, we talked about the big goals, but then between the workshops, and between the quarterly, something happens, things don’t fall in place for what really happens. How are you making sure it doesn’t happen currently? 

Yeah, I mean, you just can’t be once a quarter. So we and obviously, I have to say I think every marketer should run sales. Because it has been really game-changing for us, I thought we were really aligned, I thought that we were very sales-centric. But it was only when we were actually ingrained in each other’s day-to-day that we saw so many opportunities for more alignment. So I think it’s just really been game-changing for us. So I’d say the number one thing is just you have to have the teams feel like they’re part of the same team. So you know, the sales operations team, the marketing operations team needs to be meeting constantly, they need to be sharing feedback with each other they need to be I think one of the big things too, is there need to be looking at shared data. Because I think what I’ve seen one of the biggest issues is when sales has a bunch of reports that they’re looking at marketing has reports they’re looking at, and they don’t, they’re not looking at the same data. And oftentimes the data is even more complex. 

And so I think having a shared set of dashboards and a shared set of goals. And then we meet every single week as leadership, team, sales and marketing. And we talked about those shared goals. We talked about the pipeline, we talked about the work that marketing is doing to drive the pipeline, we get feedback right away on, you know, hey, this campaign was great, this campaign didn’t, didn’t work great, you know, you’re sending us a bunch of leads, these are really good leads, these aren’t. And so I think that that’s really important is just the constant alignment and feedback and marketers being open to that feedback and sales, giving feedback in a constructive way. I think just everyone being part of the same leadership channels, the same strategy discussions, so that we can understand that when things move really quickly, everyone is aware of them. And then they can share their opinion right away versus like a month later, when we realize, oh, we made these changes in sales. Do you really understand the ramifications of that?

Yeah. So something that comes to my mind and this is something that I’ve seen as a marketing leader and a growth leader previously in my previous roles, is, to your earlier point, whenever I’m tasked with leading marketing teams, I make sure that the folks in the marketing team are playing or playing the role of a salesperson, either one day a month or once a quarter just sitting there, as calls listening to the calls. So that’s really crucial. That’s one that’s one way to build empathy. The other. And the other piece is a mix of PLG. I mean, you did mention the go-to-market motion. The cycle currently is a mix of PLG and SLG. And in between, maybe it also includes partners. So when you have that weekly meeting, the alignment between marketing and sales, I would presume that it’s mostly around the sales lead aspect or sales assist aspect. But what about the product lead aspect?

Yeah, so we have totally different committees and motions for that. So that is really our growth marketing team and our demand gen team working really closely with our product team. So we have actually our support team. So we have an operating committee and a steering committee really just focused on the first 30 days of a customer’s lifecycle. And so we’ve got really tight alignment between, you know, how do we get those customers to the site to sign up? What do the lifecycle marketing efforts look like? What do the in-app notifications look like? What’s the first sort of product experience? And then when, what does that trial experience look like? And then that post-trial experience, and so I’d say we have tighter alignment than I’ve ever seen here, either here or at another company, because we identified, you know, a couple of leaders within each group, and they meet very, very frequently. And then the executive team, we’ve formed a steering committee. So then this team will come to us with their recommendations, their ideas or blockers. And our job is really to help them move quicker.

Yeah, I think a couple of things, especially when you’re looking at a plg motion. One thing to keep in mind is the time. I mean, there are so many flavors and so many aspects. One is what are the different channels in which you’re on the radar of your target users and how are they signing up? That’s one aspect of it, and once someone has signed up, are they seeing value within the first day or two for them to actually use the product? I think that’s the biggest step right within the first day or two after signing up, if they’re not using your product, it’s as good as you lost them. 

Yes, has to be you have to hit them from all sides. So it can’t just be email, it can’t just be in products. It can’t just be in-app notifications, it’s got to be a combination of all of them. And you also have to have really great support, you have to have opportunities for people to, you know, ask questions at the moment so that they can understand those blockers. And so having that consolidated view between support and marketing and product is incredibly important.

Right. And that’s that exactly goes back to my earlier point, which we started in our conversation, which is the role of product in go to market. Yes, for sure. Yeah. Something else that I want to get your thoughts on is? How do you see the difference in terms of roles, responsibilities, and outcomes between growth and dimension?

So I think it depends on every company, you know, Asana definitely was very different than Calendly. So my perspective is that the demand gen job is to get people to the point of action. So whether that is to sign up, or a lead, and then growth marketing, his job is to take them from action through to revenue. So we’ve got, you know, demand gen team is really focused on all of our top of the funnel advertising, you know, basically everything that we can do to drive awareness to drive people to our site to sign up. And then growth marketing is responsible for our website, conversion, activation, and then all of the emails, the nurture, emails, peak URLs, anything that really supports someone understanding why they should move from signup through to a conversion page conversion, or a paid lead that goes to sales. 

Yeah, and you’re totally spot on, right? I mean, growth and demand take different shapes and perspectives, depending on the leader as well as the organization. So I’ve seen one definition of growth, which goes beyond just the signup and the initial revenue, there’s also okay, how do you think about expansion? How do you convey this to customer success? That, hey, by the way, this account is a quote, unquote, it’s a dirty word, but it’s right for expansion. Yeah. And that is growth. It’s not just from the initial awareness to sign up to initial conversion, but even the adoption and expansion piece.

The adoption experience piece is incredibly important. I think that that’s the one that is often missed by growth marketing teams. But nobody knows how to market to customers better than marketing does. And so when you think about, especially in a plg motion, just because a customer signed up, as you said, doesn’t mean they’re going to use the product. And so marketing can play an incredibly, incredibly important role in creating really strong content, and really thinking about the customer journey after a signup, to enable a customer to understand why they should use this product that they signed up for. And then, you know, what are the features that they’re missing if they didn’t continue to pay? And then also, as you said, over time, great, you love it. So how do we then encourage you to think about the value that you might have if you now have three members of your team 10 members of your Team or 100 members of your team on Calendly? Right? 

And then there’s also product marketing. I’m assuming there is a product marketing function at Calendly. What is their charter and the biggest challenges, if you will?

I think it’s just the same challenges that we all have, which is they are really doing two separate jobs split between the PLG motion and the SLG motion and supporting both, they are totally different. And they support me, it’s basically two different jobs. And so really figuring out how to prioritize that is, is challenging. So you know, they, they really have two fundamental fundamental jobs. The first is that, is helping us launch products, not surprisingly, right? So they do a fantastic job of that. And the year they launched it both within our sales channel, but also within our field G channel. The second is they are really helpful in helping us to understand our customers well enough so that we can build really high-quality materials for them, for onboarding. So one thing that we’ve actually done over the past few months is we’ve looked at all of our onboarding materials and tried to make them much more specific. And so when a customer joins, we try to ask them, you know, but when someone signs up, we try to ask them, Hey, are you a salesperson or we try to, or infer that if they, for example, do a Salesforce connection, we kind of guessed that they’re a salesperson. And then we try to take them on a very bespoke path for salespeople. And so you know, they can now view an on-demand webinar about what it’s like to you was counted as a salesperson versus just an M, it’s different if you’re a recruiter, and it’s different if you’re a financial advisor. And so I think that creating that very customized path is really important. And like growth marketers, that’s not their strength in creating content. They’re extremely good and understand the customer and think about experimentation. But you have to partner with people who deeply understand our customers and our product to be able to create really high-quality onboarding content.

Yeah, that’s a key, right? It’s super hard for someone to be really good at in terms of like growth experiments and hypotheses and how you test it out versus at the same time, can you also create the content. It’s extremely hard for some.

Yeah, I think it’s, it would be unfair to ask the same person to do both. It’s just not the same thing with demand gen, you know, the people that really deeply understand our channels, and deeply understand how to experiment and how to think about reducing cost per sign up, they’re not creative. They’re not, they’re not like amazing at, you know, building beautiful designs and thinking about our ad copy and how to do 50 variations or a copy, you just, it’s just not fair to ask them to do it. And so you really have to have that specialization, and you have to have dedicated resources to really helping the demand gen team, think about let’s create a 100 variations of ads and see what works. 

Yeah. Very cool. So I’m sure in your many, many roles as a hands-on executable player, and as a C-suite leader, you must have seen a lot of go-to-market success stories and go-to-market failure stories. So if you can share one of each, I’ll let you choose which one you want to start with first. 

Sure, maybe I’ll start with the failure story. I don’t actually believe that anything is a failure just because we’re all experimenting so much. I mean, I really encouraged my team and challenged my team to experiment nonstop. And like, of course, not everything that would be successful. So I’d say like, I don’t really think about campaigns that are not successful as failures, I think more about the process, that could be a failure. So one example recently was we launched a really huge campaign, it was everything, I think it touched every single person in marketing. And I think we were like, exercising a lot of muscles that we hadn’t exercised before. And it was during the retrospective that one person got really upset because they felt like they hadn’t been heard. And they felt like the process was really chaotic. And to me, I felt like there were like quite a few failures in that, which is, you know, maybe we didn’t have a culture where people felt comfortable speaking up, and sharing in the moment that they were frustrated. And so I was upset that you know, if somebody is upset, they should be able to speak up, and we should be able to fix it, that should be our culture. The second is that we just hadn’t thought through the process well enough to be able to understand how to get those touch points at the moment. And so like I took from that, that we really have to train our team on how to give feedback, how to give feedback in the moment how to beat the learning culture. So I’d say for me, the failure is never in the outcome, the failures of the process. So does that make sense? 

Yeah, in fact, I can pay any sense that you’re a good leader and a good people person, just based on that story. 

I try. I mean, my job is all about people. My only job is to attract and retain great people and keep them motivated and excited to do great work. That’s what I tell people. So that is my job. And then, oh, go ahead. 

No, I’m just going back to your point. There’s no failure, it’s more of a learning. And how do you take that learning and apply going forward totally aligned on that as well? 

Yeah. And if you don’t give people the room to not succeed, then nobody will ever try anything. I mean, that. And the reason I do marketing is because I love to try new things. And I love to experiment, I love to learn. And I love how marketing is so dynamic. And I’m, I’m hoping that everybody that works on my team feels the same way. And so if you’re not creating an environment where people can feel safe to make mistakes, then you’re never going to be able to progress, which I think would be a big shame. 

Yeah, for sure. And then go to the market success story. Let’s!

So I am actually really, really proud of this one. So, one of our big challenges which which is a great challenge to have is that we have an enormous amount of leads that come into our website, just an unbelievable amount. Because our product is so viral, and everybody knows it. And we have a kind of a very typical lead flow, which is somebody would sign up on their website, we would do some data enrichment, we would eventually get it routed to the right sales team, they would reach out and that will be you know, then maybe a small percentage of those who responded actually booked the meeting. 

And I thought gosh, you know, we’re scheduling company we got to this a little better. And so we worked really really, really, really closely with the sales team. And we’ve iterated probably 30 or 40 times on this. But we really have an amazing process now where we use calumnies on products. So I’m also super. And whenever a, someone comes to the website, and they want to support, or they want to talk to us about, you know, a small team deployment or a large enterprise deployment, we get them immediately to the right person. So they basically come to our website, we do all sorts of data enrichment, but also people’s, you know, sort of fill out forms and right on the website, and plus, they would self select. And either if they want support, or if they’re a very small business, they can chat right away with a support agent and get exactly what they need. If they want a small team deployment, they can set up a meeting right from our website and get to one of our Velocity Sales Team reps. 

And if they’re a large enterprise, they can schedule a meeting right at that moment, and talk to an enterprise rep. And that has been game-changing for us, you know, we’ve seen just absolutely skyrocketing in terms of our lead to opportunity rate. Our salespeople love it, we don’t have you know, lead purgatory where leads just accidentally get routed to the wrong places, though, it sounds very nuts and bolts, but you know, when you think about these precious leads that come to your site, and we’re now able to capitalize on them, and most importantly, we provide a much better customer experience, because customers don’t have to like wait anymore, they can get exactly what they want in the moment. I’m incredibly excited about it. I’ve just been really, you know, really energized by the feedback that we’ve gotten. And I just think it’s just a great a better experience for everybody. 

Yeah, and I can sense why this is really critical, right? I mean, for me, if I’m on the other side, I love but I’m a big user of Calendly in my day to day, it just makes my life so easy and so comfortable. And if I sense that I need to speak with someone in support, or get someone, let’s say, get someone on the other side who’s in sales. And if I don’t hear back, it’s going to be frustrating. So I’m excited that yes, the product is exciting. But there’s also the other elements, the people the processes that have to be really tight, not just a product alone.

Well, also the way that people buy is totally different than it was a few years ago. I mean, people are only buying after they’ve made a ton of decisions on their own. So people have done all of their own research, they’ve usually narrowed it down to a couple of vendors, and then they’re reaching out and they don’t want to wait a week, they want to wait even a couple of days, like they want to talk to someone right at that moment. So if you’re not responsive to them, and you’re not getting back to them, they’re just gonna go with somebody else. And so the way I think about is like every one of those leads is real dollars to calumny its real value. And because usually, those leads have done their research, they’ve educated customers, and I want to take advantage of that as much as I possibly can. 

Yeah, very cool. So in our conversation, I mean, he’s been speaking for about 40-45 minutes or so there’s so many aspects that came that popped out for me about you, I mean, the person Jessica, right? And so I’m curious, like when others reach out to you, or when they are struggling with a challenge in terms of go to market? What are those one or two things that they say, Hey, you know what, this is something that I need to speak with Jessica about?

So I’d say for sure. It’s around just orchestration of very complex workflows, and like, so basically, how do you take? How do you take very, very, very complicated systems and people and data? And how do you sort of make sense of it? I think that that’s something that is very underrated when people talk about being a CMO like everybody thinks about being a CMO, as you sit around and have a bunch of just, it’s like the ad was a madman where you sit around and talk about branding, I don’t get to do that very much. I’ve got lots of people that do that. And I’m very jealous that they get to have really interesting conversations about brands. That’s not what I do, though, you know, so much of what I’m doing is, really, is, is providing the strategic direction for my team. 

So, you know, obviously, I have access to information that my team doesn’t have because I’m talking to the board, I spent a lot of time with the other executives. And so you know, really understanding what’s our product direction, you know, who are we selling? To? What, what, what’s the path forward? What are we what does success look like in a year or two? And so I’ve got to then take all of that information and work backward and say, How can I share that with my team in a way that they can understand and digest it, and then turn those big strategic priorities into ways that they can execute and to very clear goals. And so that’s a really big part of what I do, which is just, you know, create that strategic direction, give them the information that they need to be successful. And the other thing that I think a lot about is talking to my peers, and really thinking about where is the direction going. Where’s marketing going? So how do you know, it changes so much? And so I think that that’s really important is, you know, and when I share with other folks that asked me, you know, how do I think about what a modern marketer does? And how do I think about that blend between the traditional marketing tactics of email and you know sort of Google search and billboards and all kinds of home, and product marketing and messaging with all this stuff that we’re seeing new, which is social influencers? And all the dark, social, all the things that are incredibly important, but then how do you balance those things? 

Yeah, no, I’m glad you touched upon product marketing, right? I mean, for me, I do have a bias because that’s my expertise. And that’s a service I do provide, but at the same time, to be fair, and when I look at it from a good market perspective, unfortunately, product marketers are almost, quote-unquote, abused, and not seen in the right way, because they’re seen as reactive order takers, and hey, by the way, sales need this content or a pitch deck. I saw hated to the core versus product marketing done, right are like your growth engines?

Yes. Yeah, I always joke, I say I have a no martyr rule, which is like my product marketer job is not to just be a ticket taker for sales and product, they need to be at the need to be, you know, at the table, making decisions, and our product marketers understand our customers better than anybody else within the team. And so they’re the ones that are really driving those insights. So they are, and our product marketers are excellent, I have a fantastic team. And so they are partners, true partners, with the product team to figure out what is our how are we bringing products to life. You know, how are we bringing them to market? What’s the customer value? What’s the story there? So they are definitely not order takers, and I would never, ever have a team that was order takers. And the same thing on the sales side, you know, it’s like, Hey, you’re, you’re a partner to them. And your job is to figure out what they need, and to suggest things to them and to work together with them to come up with the priorities, and to come up with a roadmap, but you’re not just you know, they’re not just giving you tasks that you complete. That’s not what a good product marketer is.

Fantastic. And clearly, again, going back to your career and growth journey, I’m sure a couple of people must have played a big role in your inflection, at your inflection point is shaping you. 


Who are those people who come to your mind in terms of mentors? 

Yeah, so I definitely have so many I mean, I’ve been doing this for a while. I’d say the first one was this woman, Darcy, who I reported to at Dell. And she was the first person that gave me really hard, but really good feedback. And it really changed my perspective on how I showed up at work. And from what I learned from her was that you could be really direct, but also really kind. And so that’s something that I take with me all the time is that the kindest thing that you could do is give people feedback, so they can be better. So that’s like, for sure. I really respect her and really appreciate everything she did for me. The second one is, that when I was at Google, it all came back to feedback. Because it’s how it’s hard. But that’s how I get better. So when I was at Google, I was incredibly lucky to be accepted into this leadership program. And it literally changed my life, it changed the entire trajectory of my career. And there was a VP of ads, her name was Lisa developer, and she concepted and executed, and built this whole program on our own. And it was extraordinary. And I absolutely would not be here without that program, because I got some incredibly difficult feedback during that process. And I changed my whole perspective on life and my career because of that. And so I’m super, super grateful. And then probably the final person that has been really meaningful for me was Dave King, who was the CMO of Asana. And I reported directly to him. And he just has a way of building relationships and caring about you. And I just learned so much from him in terms of how I want to show up as a leader every day, you know, he, when he left Asana, he put together kind of a little dossier on me to give to my new boss. And it literally, I was like, God, you know me better than myself. And that was like, that is the kind of leader that I want to be as somebody that people say, you know, they know me, and they care about me, I could trust him with anything. And I would always want people to have that kind of faith in me. 

Yeah, I think you’ve touched upon two points. And thanks for calling that out. It eventually depends on the impact that really happens during the performance review and feedback time. And feedback plus being kind. I think that’s a real combination if you really care about that person.

Yes. I mean, the worst thing that you could do is care about a person and not give them the tools to be better. Right?

For sure. All right. So the first I mean, I don’t know why I say first, but it’s the last question. I so wish this was the first I just know that speaking with you, Jessica. Yeah. The last question is what advice would you give to your younger self if you wanted to go back in time on day one of your go-to-market journey?

Say don’t worry about any of the external trappings of success. Don’t worry about money, don’t worry about the title. The only thing you should worry about is finding a culture where you really enjoy the people that you work with, that you feel like you can make an impact, and that you love what you do every day. Fantastic.