Arjun Pillai | Docket AI (00:13.044)

Hi everybody, welcome to the Rethink CRO podcast. Today we are super excited to welcome Jessica Gilmartin to the podcast. Most recently Jessica was the CMO and CRO at Callendly and you were responsible for all of the sales and marketing activities together. And before that you were at Asana, you were heading the revenue marketing for Asana and interestingly both the companies have a combination of PLG and SLG and an enterprise motion which is not that common and it makes, I guess, your job tougher than a typical CRO and we would love to hear about that. And you are currently a board member at TextExpander and you are also a limited partner at Stage 2 Capital.

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Jessica Gilmartin (00:58.031)

You got it. Thank you.

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Arjun Pillai | Docket AI (00:58.28)

Welcome to the show. Is there anything else that you want to add to that intro that makes more context getting added to the show?

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Jessica Gilmartin (01:07.867)

The only other big thing is that I'm an entrepreneur, which I think has led to a lot of the decisions that I've made and definitely has colored a lot of the ways that I've thought about marketing and sales. So I founded a chain of yogurt stores in the Bay Area and sold those before I entered into tech.

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Arjun Pillai | Docket AI (01:24.736)

Perfect. Yeah, I had seen that in your profile. is atypical to, know, typically people who are startup oriented when they go to big companies, they don't typically translate themselves into the corporate American executive, but you were able to do both, which is pretty interesting. And we would love to explore that aspect as well. What prompted you to start and things like that. But thank you for joining. We are excited to have you on the show. And my questions around

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CRO and how a CRO is thinking today would love to hear from that perspective as a CRO's hat mostly. As a CRO, if you were to drive a company today, let's take Callanly as an example or Asana as an example. What is that one thing that will keep you up at night?

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Jessica Gilmartin (02:13.179)

think what I have seen over the past 15 years that I've been doing sales and marketing is that pipeline generation has gotten dramatically harder. I think when I started, if you had good enough salespeople, good enough processes, systems, data management, you could create a pretty predictable pipeline. And I just am not seeing that these days. think prospects are not responding to emails or phone calls the way they used to and even

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fraction of the rate that they used to. And so a lot of the onus is now being put on marketing to generate leads. And that has a ton of other downstream effects in terms of the cost of acquisition, the noise of whatever is happening out in social and Google and now Chad and know, Chachi BT. And so I think it's just a lot harder to figure out how to get prospects to talk to you.

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Arjun Pillai | Docket AI (03:10.336)

And that directly translates to the cost of customer acquisition. If you look at the public companies, they are all taking their time to get back the investment that they are making. So as a CRO, how are you managing this today? If you were to put your teams back, whether you're CMO hat or CRO hat, how would you change your allocation of resources?

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Jessica Gilmartin (03:31.109)

So really it's about being as absolutely efficient as possible. and one thing that, that we saw at both Asana and Calendly, and one thing that I advise a lot of my customers to do is really start to look at, you know, how do you expand the concept of pipeline generation? How do you think differently about it? And so it's not just about cold outbound anymore. think that that, concept is very dated and I think a lot of people are moving away from that. think number one, it's.

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What are the smart tools? What are the systems and the tools and the processes that you can use to really try to reach out to people that are ready to speak to you? So I think that's fundamentally number one, which is not really thinking about pipeline generation is cold outbound anymore. I think number two is trying to mind your existing database as much as possible, not just thinking about your job as a CRO as getting that first deal, but it's about that first year, that expansion, that renewal. So really thinking.

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about a customer journey over a longer period of time and not just that first moment. And I think very closely working with marketing to figure out how do you create the right customer persona? How do you understand what the signals are that would allow you to understand what are customers that are ready to talk to sales?

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Arjun Pillai | Docket AI (04:50.896)

And if you look at the CRO title as such, the CRO title has been on the rise over the past couple of years. We have been hearing about sales and marketing alignment. And I would imagine CRO title is a way to kind of align your sales and marketing. And you had a role of CMO and CRO at Callanly. What's your perspective on CRO role and the responsibilities and how it's evolving in the world today?

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Jessica Gilmartin (05:16.985)

Definitely what I've seen the difference over the past few years is that the CRO title, I feel like, used to be almost siloed. Like you'd almost have a head of sales CRO that kind of was in their own world. They just focused on hitting the sales number and it was very much like they just kind of sat in a corner and they only came out once a week to talk about how the projections were, what their pipeline was, what their forecast was, and they didn't really get involved with the rest of the business.

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And now I'm seeing it very, very different. So I think a CRO has to be much more holistic in their thinking. They have to have a seat at the table when thinking about where the company is going, what the strategic direction is, what the product direction is. They need to be working really closely with the head of CS, with the head of marketing to really think about the customer journey and how do you make the most of every customer? You know, it's not just that first sale anymore. It's the first sale, it's the second sale, it's the fifth, it's the tenth sale, it's renewal.

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It's retention. Those are things that a CRO has to now be involved in in a way that I just don't think they had to before.

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Arjun Pillai | Docket AI (06:25.056)

It's interesting that you say that. I haven't seen enough and I hope it becomes more. I haven't seen enough leaders transitioning from marketing to CROs. Typically it is the VP of sales that becomes the CRO. We saw that Sixth Sense Latani moved from CMO to CRO and you are, you you had a marketing background. You went up to the CRO at a big company like Callendly. Why do you think there aren't more CMOs, CROs I guess?

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Jessica Gilmartin (06:52.955)

Well, I don't think a lot of marketing people want to do sales. Sales is pretty hard. But I think it is very different skill set. And I actually had taken over sales many years ago, or actually I started sales many years ago at a small startup. And so I understood what it was like to build a sales team from scratch, to build the sales process, operations. Very few marketers have done that. And I think it's also very hard for

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Arjun Pillai | Docket AI (06:56.714)

Bye bye.

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Jessica Gilmartin (07:21.923)

a CMO to take over a revenue team and understands what they're going through, understand the complexities of sales, have that empathy for a salesperson. And it's just, they're very different skill sets, even though marketing and sales are very inextricably linked, running marketing and running sales, totally different. Marketing is obviously a lot about the creativity and it's a lot about managing people.

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and managing the integration of activities among a group. Sales is very individual and sales is very much about creating processes and systems and operations and forecasting and hitting numbers consistently. It's just, it's very different. they, even though they are, they seem similar from the outside, they're actually quite different when you're running them. And I think, you know, there's just a lot of really great salespeople that come up through the ranks.

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that it's an obvious next step for them to be sales leaders. I just don't think it's as obvious for a lot of marketers to take that next step and understand how to build high performing sales teams.

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Arjun Pillai | Docket AI (08:27.712)

Makes sense, the KPIs that you look for when you're a CMO, because you're probably focused on the pipeline as the metric, and then you obviously look at the downstream numbers, but when you transition from like a marketing role to a CRO role, what were some of the other KPIs that became super high priority immediately for you?

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Jessica Gilmartin (08:46.395)

I think one of the differences with me is because I came from an entrepreneurial background, because I came from a sales background, I always focused on the revenue number. And I think that that's unusual for marketers. I think where a lot of the friction comes between marketing and sales is that marketing does tend to focus on some of those upstream numbers like MQLs, leads, pipeline, and are ultimately not focused on the number that is really the only thing that matters, which is revenue. And so I think that as a

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CMO and a CRO, both of you should be thinking about the revenue that the business drives. I also think one of the things that has really changed over the past couple of years versus previous years is customer acquisition costs. And that's very, very important. So that's something that I spent a lot of time thinking about and owning both sides. I can really think about the total CAC of, you know, the total efficiency, including all of sales, all of marketing, all the dollars we're spending.

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I think the other thing that changes a lot is moving from just thinking about acquiring a customer, but a CRO in my opinion should be thinking about retention too. Because it doesn't help the business to sign up a customer who doesn't use the product and who turns in a year. That is very expensive to the business to do that. so thinking about who are the customers that marketing should bring in.

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that not only turn into a first deal, but that turn into good long-term customers, I think is a really big change if you're moving to a CRO role.

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Arjun Pillai | Docket AI (10:22.73)

Yeah, if we can double click on the CAC point that you mentioned, which is a big difference between like a marketing alone looking versus looking at the load at CAC. So do you, there is the conventional saying that CAC to LTV should be one is to three, one is to two, one is to something. Do you follow that kind of a ratio? What does good look like when you look at CAC?

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Jessica Gilmartin (10:44.007)

So we looked at two different things. One is the lifetime cap. I think that, yeah, so LTV, which I think is probably the best way to look at things, especially in a PLG business where you would expect that a certain number of your deals turn into, have a significant upside over the next few years. You also have to look at retention. So if you're in a business where, you know, it seems good in the beginning and then all of a sudden, but your customers keep turning, then

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It's important to look at that lifetime value of a customer. The other thing we looked at was total new business that was coming in over the total dollars that we were spending on people and programs. And obviously you want that to be over one. So that's what we looked at on a year basis. And that gave us a good indication of not just our total amount, know, in a SaaS business, you can rely a lot on the amount of money that you brought in already, but you really want to make sure that the

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new money that you're bringing in is more than the amount of money that you're spending every year. And that's hard to do. That's hard to balance.

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Arjun Pillai | Docket AI (11:54.356)

And the new money is a sum of the new business, new logos and new money from the existing logos.

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Jessica Gilmartin (12:00.453)

Yes, exactly.

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Arjun Pillai | Docket AI (12:02.474)

Got it. That's a really good metric because it's almost like a unit economics. If you got that right, then you can scale because your unit economics is strong. Got it. That makes sense. And when you drive it like a PLG and SLG like an enterprise motion together, that is super complicated at that point, right? Because you're messaging your website. So difficult to manage. I've heard in the past, I don't know when, but there was a time when people...

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Jessica Gilmartin (12:09.241)

Exactly. Yeah, exactly.

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Arjun Pillai | Docket AI (12:29.312)

exclaimed that Calendly's website is reaching because, know, at the end of the day, it's a really good scheduling tool. But when you say that, hey, it'll help in, you know, higher conversion, conversion is probably right, but higher ACVs, you know, that's like a stretching thing for a scheduling tool to claim. But again, it's a PLG tool and an SLG tool. How do you manage it? When does a lead transfer from like a product led to like a sales led?

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Jessica Gilmartin (12:44.444)

Mm-hmm.

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Jessica Gilmartin (12:48.315)

Mm-hmm.

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Jessica Gilmartin (12:57.103)

Well, I could talk about that for days. So I'll try to do it not in days, but in minutes. And honestly, the reason that I have been attracted to Asana and Calendly for the past few years is that managing that hybrid business to me is the hardest thing to do in go to market. And so that's what's really fun for me is that there's no playbook. And when I came to Calendly, I thought it was going to be very similar to Asana and it was totally different, even though they were both PLG, SLG, enterprise businesses.

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they were fundamentally different in terms of how we attracted customers, how we expanded them. And so I love it. think it's the way that every company should go. And so I think it's kind of the modern way to sell in market. And I think the thing that I tell, and I advise a lot of companies now on their go-to-market motions, and the number one thing that I say and the number one thing I did when I got to Calendly is focus on the customer and what people

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always forget to do is think about the customer journey. And what they tend to think about is this is what I want a customer to do. So I want a customer like this to sign up and I want a customer like this to talk to a salesperson. But that's not necessarily what customers want to do. So that's really what I focused on with our website, account.ly, which is not, it was just getting a customer.

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to the right place as quickly and efficiently as cost-effectively as possible. And so if a VP at a Fortune 500 company wants to sign up for our product, we're not gonna force them to talk to a salesperson, which is what I've seen a lot of people do. We're going to allow them to sign up for our product, but we're going to have a lot of signals that allow us to understand whether that person is taking actions that would lead to us being able to reach out to have a conversation.

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And on the other side, if there's a solo entrepreneur who wants to buy one seat, but wants to talk to a salesperson, well, we're going to figure out how to get them to talk to a support person who's very inexpensive, but who can help them with their questions and help them close their business. And we can do that very cost efficiently. And so that's really how we think about it, which is creating

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Jessica Gilmartin (15:17.273)

as many pathways as we can to really enable people to self-serve, to talk to a salesperson in the way that they want.

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Arjun Pillai | Docket AI (15:26.378)

Got it. And was there specific metrics that you were looking at after this metric, then we would call it a BQL, like a product qualified lead.

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Jessica Gilmartin (15:35.793)

So the big thing that we did is we didn't focus on the demographic of the person, which is what a lot of people do. So they say, okay, a PQL is someone that the right title who, you know, logged in two times. By definition, that's not a PQL. PQL has the word product in it for a reason, because it's somebody that has taken action and has done something in the product.

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that indicates that they're ready to talk to sales. It's not just that they have the right title. And so what we looked at is we basically looked at all of the actions previously and we said, okay, when people upgraded or when people contacted us to talk to sales, what were the things that they tended to do before then that indicated that they were ready? And so we had a list of sort of three to four signals that indicated to us that this was most likely a person that was going to be

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ripe for a conversation. And so those would be the ones that would kind of float up. And we would then do a series of very targeted emails to them. So for example, one of the big indications for us of someone that was ready to upgrade is when they integrated their CRM. That was just a good indication that they were most likely going to want this for multiple salespeople.

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And so we would email them an automated email and say, Hey, we noticed that you just integrated your Salesforce. Did you know that you could do these other three things with Salesforce? You can do this on our enterprise plan, our teams plan. Would you like to talk to a salesperson? And if they said yes, then they could schedule a meeting with a salesperson right from that email using Calendly. And so a salesperson didn't even have to be involved in that. It was just all automated.

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felt very personal from the customer perspective. So those are the things that we started to look at and I think started to work very well.

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Arjun Pillai | Docket AI (17:31.264)

All right, and earlier you mentioned that the motions that you saw at Asana while you expected the same at Calendly, they were very, very different. Of course, Asana has like an in-company virality because I will bring in Asana and get my team together, versus Calendly has an external virality because I'm gonna bring in Calendly and send an invite to you. I can see that from the outside, but what else was different?

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Jessica Gilmartin (17:53.829)

Yeah. Yeah. You, you took the words right out of my mouth and that, that actually is very fundamentally different because at Asana you had to spend the, the, you had to spend a good amount of money on acquisition to get that first person to use it. And it was a very considered purchase because people are thinking about, do I want Asana versus multiple competitors? How am I actually going to use this? Am I ready to change my workflows? Cause Asana really

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is about changing, know, a project management tool is about fundamentally changing your workflows. And so the barrier to getting someone to use it for the first time is very high. But then, yes, as you said internally, so really our focus at Asana was getting that first person in and then really trying to work with them over time on that expansion at Calendly. And we had a harder time getting that sort of first big deal.

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because it was so much about land and expand. It's different now. I they're focused much more on enterprise. Accountly, it's, in my opinion, the most viable product on earth. I mean, there's literally zero cap. You don't spend anything about getting that first customer, but it doesn't have that internal morality. And so we had to spend a lot more time educating our existing users on, this is working great for you. You know, it's very easy to set up. You got it done. It takes almost no rejiggering of your workflows. It's just like genius and obvious.

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but okay, now you're using it for you, what's the value now of using it for five people, 10 people, 100 people within your organization? And so that just, a totally, it seems subtle, but it's actually a totally different way of thinking about the sales and the post sales process.

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Arjun Pillai | Docket AI (19:35.072)

Yeah, makes sense. did not foresee that considered purchase at the top. When I put myself as a buyer, if I have to buy like a tool, like an Asana, then I am thinking for my whole team, spending all the cycles upfront and then picking an Asana versus M1Day.com versus Callanly, I'll sign up like just like that. And then we'll figure out whether the team needs it or not. Makes total sense. I hadn't considered that.

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Moving on, let's talk a little bit about AI because you cannot not talk about AI these days. right, exactly. Certainly growing in adoption. How do you see AI impacting the CRO role, the go-to-market motion in B2B companies in the, let's say near future and also a little bit far-fetched as you see?

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Jessica Gilmartin (20:06.332)

Legally required.

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Jessica Gilmartin (20:21.831)

Yeah, so I would say right now the hype is definitely bigger than the impact, but I see that changing pretty quickly. And I was a big AI skeptic about a year ago, but I'm coming around. So I think what I'm seeing is pretty interesting. So I think number one, we're seeing a lot of bad AI outreach happening.

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I think that's just worsening the pipeline issue and the pipeline generation issue because it's just going to be noisier and noisier with the number of AI tools that are be out there. I think eventually it's going to be better. Right now it's not. But I think what's going to happen then is you're going to have to rethink, you may not need SDRs. It's going to be totally different in terms of pipeline generation. The second is around forecasting.

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So I'm already seeing that and obviously every CRO knows how much time they spend on pipeline management, on forecasting. And I think that that's gonna pretty dramatically change. I think you're gonna have a lot of AI intelligence that's really going to allow you to understand what is real, what's not, creating forecasts for you, creating a real pipeline for you, which I think is actually pretty amazing, just given how difficult it is to really accurately forecast. So I'm probably most excited about that.

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I think the other thing that I'm seeing are AI agents and I'm seeing like AI agents that are coming out that totally automate the sales process. And I think a lot of the work that people spend right now on repeatable sort of manual tasks, my guess is a lot of that's going to go away, which I think is pretty exciting. And I think the final thing that I think I'm most excited about, which I'm not seeing yet, but I believe it's going to come.

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is we talked about PQLs. I think there's gonna be a lot of ways that you're gonna be able to understand the signals that allow you to figure out whether a customer is ready to talk to or not. I think to me, that's one of the hardest things is if you have a available universe of say, five million sales operations leaders, who are the ones that you should actually talk to? Who are the ones that have indicated interest or are looking at this

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Jessica Gilmartin (22:38.259)

problem are using your product, but are ready for expansion. And right now it's so manual. And I think there's going to be a world where all of that's automated.

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Arjun Pillai | Docket AI (22:49.632)

As you were speaking about individual things, I was thinking about companies that are operating in this space, including Docket, for example, when you mentioned about manual processes and automation of like, know, RFP processes or, you know, sales engineering processes, things like that. But I think I'm aligned 100 % about AISDRs and then forecasting and all of it. By the way, I run an AI company, I'm obviously bullish, but I also agree with you that the impact versus the hype

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is hype is way more than the impact that it's delivering today. If you could automate one part of your process with AI today, what would that be?

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Jessica Gilmartin (23:31.591)

Annual planning is not my favorite thing.

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Arjun Pillai | Docket AI (23:35.552)

So when you say planning, it capacity planning, it allocation, is it territory management, which part of the plan?

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Jessica Gilmartin (23:42.867)

the planning, the figuring out the number, the ultimate goal and how you're to get there and the people that you need and the monthly, the waterfall of what leads you need and pipeline you need. If you program dollars, it's just, it's a lot of work. It's months and months of work and I like to do stuff. like to be active and just to be selling and marketing and taking three months every year to do planning is pretty painful. Important, I do it, but painful.

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Arjun Pillai | Docket AI (24:08.896)

So for the founders who are listening, looking for the right problem statement to go after, there you go. That's a very, very interesting problem statement. And to be honest, I haven't seen enough AI agents directly focused there yet. So it's actually a pretty good opportunity, at least I do think.

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Jessica Gilmartin (24:17.112)

Ha ha ha!

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Jessica Gilmartin (24:26.611)

I'd be pretty great to press a button and then have the whole thing just done for you. Yeah.

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Arjun Pillai | Docket AI (24:30.58)

Yeah, at least a few options right here are the two options and then you say, this is not right. You know, we want to move it to this one. And in a conversation, you kind of get the plan to 80 % and then you take that and then work on it. It's pretty cool. In your world, obviously CRO, CMO, both worlds, it's moving so fast today, right? And you have to upskill yourself. You have to learn yourself. How do you do that? Is it books? Is it podcast? What do you do?

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Jessica Gilmartin (24:57.701)

number one thing for me is I just like to talk to other smart people. So I'm in a ton of networking groups. I'm always trying to go to as many dinners and events. I'm on a ton of Slack groups with other CMOs and CROs and I just listen to what they're saying. I like to attend a lot of webinars. So for me, it's very much face to face. I'm not a big podcast person. I just don't have the time. And not about like a big book person. I do love newsletters.

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So I love blogs and newsletters, anything, because I think for me, I like the frequency of information. So I like, know, every week I know that I'm just going to get like really intelligent information on the latest stuff. So Kyle Puyar, I don't know if you know Kyle from OpenView, he has a great newsletter called Growth Unhinged. And I love that one. It got, and he's really going all in on AI now too. So it's really interesting. He's got a lot of the, he's got a pulse on, you know, what are the latest.

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latest and greatest in terms of pricing models and go to market models. So I think that's really interesting.

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Arjun Pillai | Docket AI (26:04.294)

is amazing. I had a recent interaction on LinkedIn with him about the exact same topic that you mentioned which is pricing models the post that he put up. Other than growth unhinged which is awesome are there other newsletters that you would recommend to the listeners?

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Jessica Gilmartin (26:08.956)

Yes.

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Jessica Gilmartin (26:18.983)

So the biggest one that I love, it's not as relevant, it's more of a marketing one, but it's called Gobbledy. And it's very much about messaging, which I love. It's very much about understanding the customer and making sure that your messaging is relevant to your customer. And it's very funny. So I look forward to his newsletter that comes out every week.

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Arjun Pillai | Docket AI (26:42.368)

Awesome. And are there any communities that you recommend to the revenue leaders?

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Jessica Gilmartin (26:47.795)

The ones that I'm in are all closed. So I'm trying to think of ones that are not. So probably, yeah, probably not as helpful. Sorry.

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Arjun Pillai | Docket AI (26:59.744)

No worries, I am also part of a bunch of communities and yeah, I also get to learn quite a bit. I think you would be thinking like a pavilion. So I do like, I'm on pavilion, it's awesome. And then there is a RevGenius. Then I'm also part of a few enablement communities because docket is about account executive enablement. So I'm part of sales enablement collective, enablement squad. Then yeah, there's something called

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Jessica Gilmartin (27:06.223)

What are the ones that you like?

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Arjun Pillai | Docket AI (27:29.044)

pre-sales something. So a few of these are all Slack communities. And obviously there's a ton of interaction happening there. I do like every four days or three days I go look at everything that's happening. Another hack that I do is in Slack you can put up notifications for your own keywords. So in every community I'll go and put like five keywords that I care about like RFP and know, like enablements. So when people are mentioning that I get a notification I'll quickly go look at that.

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Jessica Gilmartin (27:31.442)

Mm-hmm.

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Jessica Gilmartin (27:53.969)

Mm, yep.

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Arjun Pillai | Docket AI (27:58.72)

Otherwise the noise is so much that you cannot really go through the whole thing. So that's my hack to kind of getting information from communities.

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Jessica Gilmartin (28:05.735)

Yeah, I always like search for Calendly and Asada just to make sure. it is actually great, especially if you are selling to this group. It's, awesome. You should be a part of all of them because you see all of the chatter. And that's like another really interesting, that's such an interesting thing that's happened now over the past few years in terms of selling is, know, people used to do a very surface amount of, of, of sort of research before deciding to reach out to a company. And then they would.

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Arjun Pillai | Docket AI (28:08.734)

I'm sorry.

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Jessica Gilmartin (28:35.219)

get their information from the different salespeople and then make a decision. That's just not the case anymore. People are 95 % decided on the tool that they're using by the time they reach out to you. And so much of it, I see it as, you hey, how about this versus this, this versus this? you ever used an RFP tool? you used this? And it's all happening in social. It's all happening on these channels. And so you've got to be there. You have to know what people are saying. You have to be involved.

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because by the time someone's contacted you, they've basically already figured it out. It's totally different.

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Arjun Pillai | Docket AI (29:10.336)

And as a last question if there is an upcoming revenue leader whether it is marketing side or sales side What's your advice if they are eyeing to become a CRO in the future? What should they do now?

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Jessica Gilmartin (29:24.167)

Think as expansively as possible. Know as much as you can learn about the other go-to-market functions and all the functions that will impact you. So finance is a great example. You have to have a really strong relationship with your finance team. You have to understand finance really well. You have to understand the numbers really well. You have to have a great relationship with your product team. Understand that, understand the development, understand marketing, how they make decisions.

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understand the post-sale process. When you move into a C-level title, your role and the expectations of your role change completely. You're now an executive that's responsible for the entire business, not just your part of it. And so if you can speak intelligently about all of the parts of the business, how they all impact sales and how you will be a great steward and leader of the company, that's what people are looking for. They're looking for someone that

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is not just thinking about their world and their number, but someone that's thinking about the best thing for the company.

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Arjun Pillai | Docket AI (30:28.18)

Perfect. There you go, everybody. Thanks a lot, for joining today and dropping the wisdom here. I appreciate your time and to all those listeners joining us. We'll see you on the next episode of Rethink CRO Podcast. Thank you.

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