GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin
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Jessica Gilmartin has nearly 20 years of go-to-market leadership experience, most recently serving as both the Chief Revenue Officer and Chief Marketing Officer at Calendly. Prior to that, she led marketing teams at an impressive array of companies, including Asana, Honor, Google, and Microsoft. As the cherry on top, Jessica also built and sold a successful frozen yogurt chain in San Francisco.
Discussed in this Episode:
Taking an entrepreneurial approach to ownership in an organization
The difficulty of selling to both midmarket and enterprise customers
Cultivating a culture of creativity and approachability
How to hire your first marketer
If you missed GTM 135, check it out here: How Marketing Creates Million-Dollar Exits: 6 SaaS Success Stories | Katrina Wong
Highlights:
06:29 How Asana moved from product-led growth to sales-led growth
18:00 Why refining your ICP is paramount for product-led growth
33:37 Fostering a culture of experimentation
40:23 Hiring your first marketer as a startup founder
Guest Speaker Links (Jessica Gilmartin):
Host Speaker Links (Scott Barker):
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Where to find GTMnow (GTMfund’s media brand):
Website: https://gtmnow.com/
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The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/
Sponsor: Pursuit
The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.
If you’re hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.
The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
GTM 136 – Jessica Gilmartin
Scott Barker: Hello and welcome back everyone to the GTM podcast as always. It’s your host, Scott Barker, and we really appreciate you lending us your eardrums for the [00:03:00] next 45 minutes or an hour or so, uh, we have a fantastic guest lined up, I am joined by Jessica Gilmartin, Jessica, welcome,
Jessica Gilmartin: Thank you very much. Happy to be here.
Scott Barker: excited to have you, and there’s a lot I want to get through, um, but really quickly, just for the listeners, uh, a quick bio. So Jessica has nearly 20 years of go to market leadership experience. Uh, most recently as the CRO and CMO, uh, simultaneously at, uh, Calendly, uh, we all probably use Calendly in our day to day lives.
Um, and then previous to that, she was the head of revenue marketing at Asana. So two incredible companies. And then the CMO of Honor as well, which is one of the largest privately owned home care companies in the U. S. And I thought this was cool. Prior to you getting into tech, you co founded a yogurt franchise.
Um, how did you get inspired to do that?
Jessica Gilmartin: As everyone does. It’s a very obvious thing [00:04:00] to start a yogurt business. So I moved out to the Bay area after a business school and a stint for a couple of years at Dell. And I reached out to a good friend of mine who had gone to Wharton with, and she said that she was planning to start a business. Asked me if I wanted to, I was really dumb and naive and said, sure.
And so we were brainstorming things that we loved, and we both love, um, healthy food. We’re both really passionate about it. And so we just kind of came up with this idea of a super healthy, super delicious frozen yogurt concept. And it was very, very successful. We were fortunate. And then we expanded it across the Bay Area.
And after a couple of years, I sold it. Uh, and then ended up kind of finding my way and some of my way into technology.
Scott Barker: Super cool. Super cool. Is there any, I’m sure there’s many, but what are some of the standout lessons that you took from the yogurt business into your career in technology?
Jessica Gilmartin: So many. And I think the biggest thing for me is I think of myself as an [00:05:00] entrepreneur. So no matter how big the business I am working in is, um, no matter what position I have, I really take that entrepreneurial mindset with me. And I expect everyone that works for me and that works with me to have that.
And when I mean an entrepreneurial mindset, I mean doing everything and anything to make. your business successful, having a true ownership mentality. And I think that’s actually one of the things that has made me as successful as I’ve been, um, is this idea that I don’t have a job. You know, my job is to make the company successful.
And so whenever I’m asked to take something on, whatever I see, That there’s a whole, when I see there’s a challenge, I just jump into it. I don’t wait to be told. I don’t say that that’s not my job. Um, I see so many people just being really passive, um, or saying like, Hey, that’s somebody else’s role. Like, that’s just not what I believe.
And that’s certainly not the culture that I build on my team. So it’s just that like true ownership mentality, I [00:06:00] think is so important to being successful regardless of the company size.
Scott Barker: Yeah, I love that. And it’s certainly a red thread we see with all our kind of like top performing guests is this idea of, you know, regardless of your role, you are there for one reason only to make the cust The company and your customers successful and you know, it takes wearing many different hats, um, on many different days.
Um, but, uh, I love that. So let’s get right into it. I think kind of 1 of the core things I wanted to chat with you about is, you know, you’ve been part of these 2 incredible unicorn companies in Asana and Calendly. Um, I think my understanding is there was a pretty strong PLG motion, um, out of the gate for both of those companies.
And then along the way. You kind of have to grow up a little bit and start using more, you know, sales led growth tactics, and maybe starting with your time at Asana. [00:07:00] Um, why make that shift? And when should companies start thinking about making that shift?
Jessica Gilmartin: So I’m a marketer, and so I will talk about the customer ad nauseum, so you’ll probably hear me talk about that in every single one of my responses because I really think it’s so important. And why it’s so important is that you can’t just decide to be a PLG business or an SLG business or an SMB business or an enterprise business.
Your go to market motion has to be driven by the product. It has to be driven by what the product can do and the value that the product drives for the customer. And so we saw the same things and same signals at at Asana and at Calendly, which is that we had very strong PLG motions. And the reason we had very strong PLG motions was that the, is that the product is incredibly intuitive and delightful.
It’s a delightful individual user experience. Someone can get value out of it from day [00:08:00] one, which, in my opinion, is one of the most important things. It’s the most important thing for PLG business. But then we saw that people wanted to share it and that there was exponential value and having more people within an organization use it.
And so once that happens, once you have a, an amazing PLG product that all of a sudden can be even better and provide even more value when 10 users have it, when 50 users have it, when 100 users have it, and when they’re reaching out to you, your customers, and saying, Hey, we would love all these additional features.
We would love to have a enterprise agreement. We would love to have a teams agreement. We need extra security features. We need, we need, we need. Then all of a sudden that becomes a great catalyst to say, okay, do we actually want to go up market? Do we want to have an SLG motion? Because that completely changes your company.
And so then you have to make that very conscious decision of okay Are we going to move up market? Are we [00:09:00] going to become a All SLG company or a hybrid or are we going to stick to our PLG route?
Scott Barker: Yeah. What I’m hearing is almost like. You don’t decide to make the shift your, your customers and your, where your product is at is going to naturally kind of pull you along in, in a direction. Was there any time, whether it was Asana or Calendly where, you know, you had some of this sort of like enterprise demand, they wanted teams, they wanted this functionality, but the PLG is still working so well that you’re like, Oh, maybe we don’t want to, um, divert too many resources.
Like, is there a tipping point, I guess?
Jessica Gilmartin: it’s really hard and there’s no right answer and we absolutely face that at both Calendly and Asana constantly. Most of the decisions that we had to make, most of the discussions we had were around resource allocation. I’d say that that’s absolutely the hardest part of having a hybrid motion is that everything becomes split.
I always say that it’s like having two companies. Because a [00:10:00] enterprise, if you work in marketing, you know that an enterprise marketing motion is wildly different than a PLG marketing motion. So you have to have two marketing teams who have very different skill sets, and you’re almost having to compete with each other for resources.
You also are competing with each other over your website space Because you know what is the thing that you were going to ask people to do? Are you going to ask them to sign up for a demo? You’re gonna ask them to talk to a salesperson You’re gonna ask them to sign up for free and so having to make those really hard decisions around with your very precious real estate What’s the call to action?
That’s just marketing. And then when you think about product and engineering, I mean, talk about scarce resources and prioritization. So, you know, building an enterprise product, building SSO and skim and data analytics and, and permissions. Those are wildly different than building a super usable, intuitive product with all the little features that an individual would want.
And so, We constantly had [00:11:00] to decide, like, what is the right allocation of resources? Is it 50 50? Is it 10? And there’s changed constantly. And then, of course, you’ve got a sales team that is, you know, wants to close six figure deals, and they’re often predicated on promising a feature set to specific customers.
And then you have to decide as a culture, you know, are you going to have engineering teams and product teams that are devoted? to bespoke requests for enterprise customers, which if you are an enterprise company is a no brainer. If you’re a PLG company that also does enterprise, then that further creates like more prioritization, more issues.
So it’s, it’s very difficult, much more difficult than one would think from the outside being like, well, it can’t be that hard. It’s just, it’s. But it is, there’s so many other issues like data warehousing, operations, legal, finance. There’s like just so many [00:12:00] cans of worms that get opened up as you start to think about this.
Scott Barker: Yeah. Yeah. I can imagine. You know, you, you said it’s almost like building two companies. So you’re going to go hire marketers, salespeople that have these two different skill sets. And you know, I imagine in its good form, there’s like healthy competition between those two companies internally. But I imagine it also leads to some, some friction and alignment issues.
Did you battle that at all?
Jessica Gilmartin: All the time, literally all the time. Uh, and I think, you know, I learned so much at Asana. I was able to take that to Calendly right away. So it took me probably two years at Asana to figure out how do we start to bridge the gap? And, um, as I said, I will go back to the customer. What I ultimately realized was that we had to think about the customer first and think about the customer journey.
Because there typically is no SLG without PLG. And I think that’s where people often get a [00:13:00] little bit lost and they don’t see the forest for the trees. So in almost, I’m not going to say everyone, but almost every hybrid company, people find out about the product through some kind of self serve experience.
And so people are interested in getting a thousand person license because they have had some experience with the individual product and you can’t shortcut that as much as we want to. You, you can’t. If, if you have an incredible, like the perfect title at the perfect company, what we often tried to do at first was to force them to talk to a salesperson, even if they wanted to sign up for the product.
You can’t do that. And so really what I brought to Calendly right away was this idea that you have to follow what the customer wants. And so if the customer, no matter how amazing that customer title is, no matter what your data enrichment tells you, if the customer wants to sign up for the product and not talk to a [00:14:00] salesperson, let them do that.
And so we really just focused on trying to make the buying and evaluation process as easy and customer driven as possible. And then look for all the opportunities to segment the customer afterwards and encourage them to upsell, encourage them, expand, encourage them to talk to a salesperson, but you can’t shortcut it to really just, um, validating and honoring what the customer wants just totally makes life so much easier.
Scott Barker: Yeah. Yeah. Yeah. Yeah. Talk me through a little bit about like the. The how and some of the, the tactical execution. So let’s say, you know. A great brand, Coca Cola, you know, you can see that they’ve come and they have 30 people across the organization who are, you know, using Calendly. What kind of data would you look for to then be like, okay, now it’s time.
To flip our [00:15:00] resources to the SLG motion and let’s get a, uh, strategic AE on this one. And like, let’s, let’s go and kind of do some, maybe even outbound into that account and the various, uh, stakeholders walk me through some of that.
Jessica Gilmartin: Yeah, there’s really, we tried so many things and people talk a lot about PQLs and they, most people do it very wrong. Um, and so I would say that there’s two things that we did that worked reasonably well. Um, so number one is looking at the, and PQLs is a reason to call product because they have to be driven by the product.
Everything has to be driven by the product. So one thing that we did quite well, accountably. is we looked at what product signals tended to indicate that somebody was ready to talk to sales. So we kind of did like a reverse, like a reverse engineering and looked and said, okay, when somebody contacted sales, what were typically the things that they did beforehands that led them to be interested?[00:16:00]
And so for example, at Calendly, what we saw was oftentimes when people did a certain type of integration. Okay. That was kind of a signal that they were interested in expansion. And so then we started to build in a true PQL process, which is whenever we saw someone with the right title at the right company who did one of a few different product integrations, we would then send them a personalized email.
It wouldn’t actually be from a salesperson, but it would seem very customized and very personalized from a salesperson and ask them if they would be interested in talking. To a salesperson because we could help them specifically with that integration and with other things related to it. So we gave them something valuable.
We didn’t just say, hey, talk to us, talk to us, want to talk to us now. Like we actually, we gave them a reason to want to talk to a salesperson because we would provide value. Um, and of course we’d have a calendar link right there so they could sign up, you know, to talk to a salesperson right away. That was very successful.
Um, the other thing that we did was we looked [00:17:00] at companies that had have a lot of individual users signing up, and that is by far the best source for large enterprise customers is when you have, you know, as you said, 30 50 100 small teams like licenses, individual users, whether they’re paid or not, but there’s some clear indication that that company has a real need.
And then we would, our sales team would have that information. You know, we would provide it in a, in a data poll. They would reach out to the it person, to a senior person and say, Hey, did you know that there’s 200 people at your company using Calendly, using Asana? This is how we can help you. We can reduce your costs.
We can increase your security. Would you be interested in a call? At the same time, from a marketing perspective, we would surround. Uh, the decision makers with marketing through a B. M. Um, to really kind of create a groundswell and that was quite successful as well.
Scott Barker:[00:18:00] How did you think about defining your ICP? So I think at like a sauna. You know, there’s a more defined like persona. I think Calendly, it’s one of those blessings and a curse where you can sell into all different parts of the organization, really, like everyone has meetings, everyone needs to schedule their, their day in their life.
Um, how did you refine your personas, your ICP when like you can kind of be everything to everyone, which again can be, can be hard when you think of marketing.
Jessica Gilmartin: Yes, that is such the the greatest part and the Achilles heel of a P. L. G. Business is your customers, everybody, and that is not helpful when you’re a marketer and a salesperson. And so, um, I think really the 2 ways that we looked at it, both at a sauna and a county was both. With industry, which is incredibly important, uh, in a PLGS LG hybrid business, like industry is very, very important in terms of how you can segment, uh, as well, usually as, um, company [00:19:00] size and, um, and type of work.
And so, uh, and function basically function. And so really what we looked at was not users, but we looked at customers that purchase that expanded and retained. And so we just did this very, very thorough analysis of who are the customers from a function perspective, a company size perspective, and an industry perspective that were, you know, the, the best long term customers had the highest LTV had the highest NRR.
Uh, and one of the things we also was actually quite interesting in County was we also saw that there was technology. That, um, that drove that too. So for example, certain, um, Microsoft users were much more likely to integrate Calendly with, with Microsoft for a variety of reasons. And so whenever we had, uh, a certain kind of Microsoft CRM, we knew that that was an incredible sale for us.
Uh, we also knew like [00:20:00] finance was an incredible sale for us, education. So we just. Saw historically, the sales that were easier to close had the highest acbs had the higher expansion retention. Uh, and so I think that that’s really what you have to do over time is ignore the users and really focus on the The money, the dollars.
Scott Barker: Yeah. Yeah. That makes sense. So. Less obsessed with the user or the title of that person and more like, okay, is this a, a style of company in the industry that we know we can drive incredible results for? It’s kind of like zooming out a little bit.
Jessica Gilmartin: Yeah. I’ve seen that a lot. I’ve seen, I’ve seen a lot of companies really focus on users for their ICP, but that’s not that helpful because especially in a PLG business, you typically have. a free trial or you have a free component and it’s great that people are using you. Hopefully they’re spreading it.
Hopefully that gives you some value, but if they’re not paying you, they are not your ICP. Uh, so you [00:21:00] really have to focus on those customers that are paying you. That’s your ICP. And if no one’s willing to pay you, then you have no ICP and you got to think of something else.
Scott Barker: Well said. Well said. I like it. Um, what would you do differently? Let’s say if I could fly you back to your first day at Calendly. Um, what are some of the lessons now looking back that you’re like, Hmm, I wish I could redo that. Or, uh, we would have sped up X, um, if we just knew these one or two things.
The importance of having good data and what it takes to get that data
Jessica Gilmartin: You know, I think I learned so many lessons at Asana. I actually feel like I did things pretty well at CalME. Um, where I, where it took me way too long at Asana was that merging of the PLG and SLG. When I, cause I had really come from enterprise marketing. And so I just kind of kept the enterprise marketing very separate from the PLG marketing and we had a whole growth team.
They were doing their own [00:22:00] thing. My team was doing our own thing. And it just took way too long for us to realize that it was not about an enterprise customer versus a PLG customer. It was about a customer, and it was about unifying that customer journey that just took way, way, way too long. Um, I will say, uh, actually, now that I think about it, it can’t be.
The one thing that I always wish we could do more of and faster is good data. And, um, it took us a really long time to clean up our data too. We had to overhaul our analytics team. We just didn’t have the right people. And so we were operating without data for a really, really long time. And when we finally got the right reporting in and the right data and it really transformed.
How we sold and how we marketed. And so I always encourage everybody day one have amazing operations, amazing analytics, because you can’t actually do anything without that.
Scott Barker:[00:23:00] Yeah. How, what did that look like in kind of the real world at Calendly? At Calendly, like what, I think a lot of people probably listening to this podcast are like, Ooh, I know our data isn’t where it’s supposed to be. Um, and it can feel like this overwhelming, daunting overhaul. Um, what are some like small steps, small wins that, uh.
People can do to try and get their data and operations and analytics, you know, back on the right track.
Jessica Gilmartin: Yeah, I mean, data is the most excruciating thing and it’s the least sexy thing, but it’s the most important thing. Um, and, and what happens in this, what happens, this happened to PLGSLG is that two completely different data streams pop up because you’ve got the PLG world and you’ve got, you know, usually an, an iterable, like, you know, some kind of marketing database.
You’ve got a charge beat, like you have like a bunch of. Databases where your P. L. G. Data lives. Um, and then you’ve got [00:24:00] sales force. You’ve got your, uh, all these other data sources where your S. L. G. Liz and they don’t talk to each other. And so that’s, uh, and then you what also happens is that you’ve got your Rev Ops folks.
That, uh, this is super in the weeds, but I spent like six months of my life talking about this at Calendly. You know, you, you have all of these like data labels and data tags that people are creating in a vacuum. And our problem for months and months and months was that we had a bunch of analysts that were just pulling completely wrong data.
Because they didn’t know what this data meant. Everybody was just creating these in a vacuum. Nobody was talking to each other. The data engineers and the analysts, the rev ops folks were all just building completely different databases and there was just no control. And so literally all the reports we were looking at was people just pulling bad data.
And it’s just finally when we brought in this incredible analytics leader, leader, she’s listening. Hello. Uh, and, um, she just like forced everybody to talk to each other. To build a [00:25:00] common source of data, and then we were finally pulling in the right reports. We were finally able to look at the data.
Scott Barker: Yeah, that making sure that you have a unified shared collective like source of truth is so, so, so critical. Um, would, as, as you were making these big kind of overhauls, um, did you have any, uh, kind of leadership meetings that would be focused on this? Like what were kind of. Some of the tactics involved in, in the data overall.
Jessica Gilmartin: One of the best things we did at Calendly was we created these ad hoc committees. And I think that that’s really important is ownership. You can’t just assume that you can get people from 10 different parts of the company to come together and to figure things out. So we created a, um, an operating committee and a governing committee.
And [00:26:00] so the operating committee would have. You know, one representative, like a, a typically a director or a VP level representative from every part of the company that needed to be there. And then we’d have 1 person in charge of the operating committee, and they would be the 1 that convenes them every week, make sure that they have, you know, the, uh, the agenda, make sure that things are moving.
And then our C suite would be the governing committee, and they would meet with us every 2 weeks. And it would be their job to report to us on the progress and we would unblock things and we would make decisions And we tend, we ended up doing that for four to five major issues that we had across the company.
And I’d say that that was a very successful process that I definitely plan to take to meet, take with me in the future. It just created a lot of accountability and visibility, um, and it kept things moving where oftentimes when you say, Oh, there’s, there’s issues go [00:27:00] solve it. There’s no clear leader.
There’s no accountability. There’s no urgency. We really wanted to create urgency.
Scott Barker: Yeah. I like that, that framework a lot. Um, and yeah, I think if you’ve been part of any organization who’s had data struggles, it’s always the thing that gets pushed if there’s no one actually owning it, you’re like, yes, we know we have to figure out all of this stuff, but at the end of the day, I have to hit my number.
I have to hit my lead opportunity goal, my revenue, my pipeline, and we’ll deal with that, that later. So I love this idea of these committees. If people want to steal that, it was You have this operating committee, you have a VP from all these different, you know, business units, um, and then they would basically kind of come up with solutions and then pitch that to the governing committee.
Is that how it Yes. Yeah, exactly. They, they would, I mean, they’re obviously much smarter about these things than I am. I mean, I could never create a solution for a data issue if my life depended on it. [00:28:00] Um, but you know, my, certainly my head of analytics could, and our head of data engineering could. And so their job was to come up with the solutions, but always, obviously there will always be trade offs.
Jessica Gilmartin: And so, you know, our job was to kind of say, okay, given. These constraints, uh, you know, these are two to three options. Which one is the most palatable? Which one do we want to go forward? So really, our job was to make the decision. Also, the reality is it’s not everybody, you know, is, uh, if there were blockers, if there were.
Priorities. That was the really big thing, right? So if we, if they knew that they needed to get two weeks of data engineering time in order to have a fix, but the data engineering team said, Hey, we have all these other priorities we have to work on. Um, our job was to say, well, that’s okay if you don’t work on those priorities or we would help them just figure out how to prioritize, how to unblock, how to get more resources when they just couldn’t make that decision.
They were not empowered. They weren’t able to.
Scott Barker:[00:29:00] Yeah, yeah. And was there any, uh, incentive structures for these operating committees or does it kind of go back to, hey. It’s entrepreneurial mindset. This is something that is going to help the business. You should, you know, devote time and energy to it. I
Jessica Gilmartin: We are all owners of this company. Their job is to make this company successful.
Scott Barker: it. I like it. Um, so we did a prep call before this. And one thing that you said has been rattling around my head since we had that prep call, cause I think it’s really interesting and I want to talk a little bit about it. And you mentioned this idea of creative destruction in marketing. And I would love for you to kind of explain the, the thinking and idea behind, um, Leveraging creative destruction to, to grow and make sure that you have fresh, new ideas, uh, constantly.
Cultivating a Culture of Approachability and Creativity
Jessica Gilmartin: Absolutely. So I think it goes back to me being an entrepreneur and wanting to cultivate that mindset. I just believe that there are so many changes and [00:30:00] there are so many new ideas and there’s so many things that we just don’t know, uh, and I have always wanted to encourage my team to be thinking differently, to be innovative, to create something new, to have absolutely no fear about trying new things, uh, because just, just because something works now or doesn’t work now, doesn’t mean that it will be the same a quarter from now or two quarters from now.
The world is changing so insanely fast and every, it doesn’t matter who you are, whether you’re a marketer, engineer, salesperson, you have to change with that. And so everything that I did with my team was encourage them to change almost everything that they did every quarter. So we would have very high level goals for the year.
Um, we’d have clear. Okay. Ours. We’d have, you know, very clear, a very clear path forward of what our strategy was and what we’re going after. But every quarter we would look at all of these sets of activities and tactics, campaigns, channels, um, that we were [00:31:00] doing and we’d have to change most of them, uh, and, uh, whether that was really major, like testing an entire new ad channel, whether that was minor, like, Instead of trying, instead of doing one hour webinar formats, try a five minute webinar format.
Um, it didn’t matter. I just wanted everybody to be looking at everything they were doing and be willing to throw most of it out and try something new.
Scott Barker: I love this idea. And, you know, particularly there’s a lot of driving forces behind it, but obviously with the AI revolution we’re in right now, like literally every week, there’s like a new big announcement that I’m like, Oh my God, this is going to fundamentally change everything. And so if you’ve built a plan that was pre whatever.
Um, would it be fair to say that, you know, your job as a leader was like, okay, we set the, okay. Ours, the, the strategy remains constant, but the tactics are always evolving. Like, [00:32:00] how we get there is going to change every, every quarter, every month,
Jessica Gilmartin: Yeah. There’s a really big difference. between cultivating experimentation and creating chaos. You know, so my, my job was to ensure that everybody felt extremely clear on our goals, our company goals, and how our marketing goals and sales goals ladder up to the company goals. So for example, you know, a year long company goal would be move up market very clear, you know, we, we need to hit.
Uh, 50, 000 enterprise financial services customers this year drive, you know, I’m just making this up drive a hundred million dollars in financial services pipeline. Extremely clear what people need to do. You know, you can’t every month be like, just kidding. We’re not going after enterprise customers. Now we’re going after us and be, you know, retail customers.
So that’s chaos. Can’t do that. You have to have a very clear idea of the customer that segment the [00:33:00] goals. But then all the stuff that people have to do to get there, that’s their job. That’s not my job. So I would never tell people, you know, I want you to try this set of emails, this set of tactics, go after, um, you know, go after the ad campaigns in this way.
Like that’s not my job. Uh, my job was to. Help them understand from a budget perspective. What is available to provide the resources that they need to help prioritize and allocate budget appropriately. And then their job is to figure out every single month, every quarter. What are the new things that they’re going to try?
And then how they’re going to report back to me about what worked and what didn’t work.
Scott Barker: How did you go about fostering the culture of experimentation? I think there’s a trap as companies scale, get bigger. Sometimes the, the type of talent that is maybe, uh, attracted to a larger organization as maybe a little. More risk [00:34:00] averse and, you know, it’s easier just like, Hey, let’s do the thing that we’ve always done.
Cause then I, you know, there’s, there’s no one to blame if it goes wrong, um, versus constantly having that startup mentality. It’s like, no, our job is to be scientists on the marketing team or the, you know, sales team to like always be running experiments and tests so we can optimize and, you know. Get better over time.
Jessica Gilmartin: Yeah, so I would say there’s 2 things that I did that extremely deliberately cultivated environment of kind of trust. and comfort. So number one is I tried very hard to be very, very approachable. I know that sounds silly, but I have very rarely worked for a marketing leader or any kind of leader that was actually very approachable.
And so I do a lot of very deliberate things. So I talk about my family all the time in meetings. I share [00:35:00] pictures of my family. I talk about my weekends, meetings. For me is always about baseball and soccer. Um, I, you know, and so, and I talk a lot about my own Uh, personal times when I have failed, I talk about my vulnerabilities.
So I, I just, I spend a lot of time building trust with my team so that they know me as a person, not just as this random person, three levels above them that they’re scared to talk to. Um, I do, I did, even though I had a very large team. I did skip levels with everybody, um, you know, in either individual settings or group settings.
I put, you know, I had a very open door policy on my calendar. Uh, you know, I just tried as much as I possibly could to be a human being and show them that, you know, they don’t have to be scared of me. Uh, so that’s number one. Um, and I can tell you having worked in many companies. That I was terrified when I had to go and [00:36:00] speak in front of somebody two to three levels above me.
And that is never how I wanted to, to create. That was not the culture I wanted to create. So that’s number one. The second is that, um, in public meetings, like in our all hands, uh, and even in our, my board deck, in other updates to my C level peers, I would talk constantly about the mistakes that we made. I would say, Hey, we tried this campaign.
It didn’t work. This is the reason why this is where we’re going to do differently. And I would share that with my team. Um, and it would be very clear that there was no blame. Uh, and it was just very factual, like not everything is going to work clearly. If everything works, it means you are absolutely not trying hard enough.
And so when people saw that I was very matter of fact about what worked and what didn’t work, it was, it just didn’t didn’t make it. worrisome anymore. They weren’t nervous about it anymore. And so people could come to me and say like, Hey, they tried this thing. It didn’t work. Um, and sometimes people [00:37:00] would really screw up, right?
Sometimes we would send an email out to a hundred thousand people with, uh, you know, dear XX, dear first name. And, um, that happens and it’s happened at every company I’ve been at. And you just, you just say, well, what did we learn from it? And let’s not do it again. What do you, I mean, what are you going to do?
You can’t, people try, people care. I know that they care. And if people make mistakes, they make mistakes. If people screw up, if people run a bad campaign, if people waste money, as long as they’re learning something, as long as they’re trying, I
Scott Barker: I think that’s a mark of a, a great, great leader is this open door policy, you know, talking openly about your, your mistakes. I think, uh, certainly worked for a lot of leaders to try and hide mistakes or skip over them. And then you’re just robbing your. Team of the lessons that are associated with those those mistakes, um, which is so
Jessica Gilmartin: will tell you one, one story that for me was so powerful. So when I was at Asana, it was when I just joined and you know, it was, I joined during COVID. [00:38:00] So I hadn’t really met anybody else in the team. Everybody else had been there before. I was the only one that had it. And my team had been working for months on this huge launch and, um, and it was the first launch that I and my team had done.
And it was, and it was the first time we were doing the launch and it was the first time I had met the rest of the marketing team in person. So it was all of my marketing peers and our CMO, Dave, who, you know, it’s my boss. And, um, everything that could go wrong in this launch. Went wrong and it was, it was with our CEO and our CRO.
I mean, it just could not have been worse and I’m sitting in this room and I’m so embarrassed because this is the first time that my work had been shown and we’re all sitting there watching the feed freeze and it was so bad and then every, all of my peers started talking about all of the terrible things that had happened to them, all the demos that went wrong, all of the launches that went wrong.
And it was [00:39:00] amazing. And I was like, Oh my gosh, like this is a group of people that care. And this is a group of people that are not going to hold us against me, that we tried something different and new and we screwed up and that just completely changed my whole relationship with all of them. And it made me really comfortable that I could try something and.
Make mistakes and I wasn’t going to get punished for it. So it just, it, it stuck so strongly in my head because it gave me that freedom, uh, to be able to experiment and know that they have my back.
Scott Barker: Yeah, for sure. It’s almost like, uh, some trauma bonding happens when things don’t go the right way. You know, you actually get closer as a team if you’re able to be open and discuss them, you know, freely without. Without fear and there’s, there’s trust built, built in. Um, well, I’m sorry, I’m sorry that happened, but thank you for sharing that, that publicly, uh, because it is
Jessica Gilmartin: Oh my God. To this day, I will never, it was the worst. It was the worst thing [00:40:00] that’s ever happened to me professionally.
Scott Barker: uh, the worst going back to one of the things you said with the high first name, I remember, uh, we did that at outreach and outreach was literally the sales engagement platform. That’s like never, that’s the problem we solve or one of them, you know? Um, so it, it happens to, to everyone. Um, I like it. Okay. I want to go quickly to a founder question.
Um, this one’s super interesting. We just did an episode on, uh, how to look for and identify what makes a great for sales hire. And this is kind of the same thing, except, uh, your first marketer. So this is an early stage founder who sent him this question. So if you’re a founder, let’s say you’re, you know, Pre seed seed stage.
And you’re like, all right, it’s time to invest in, in marketing. Uh, what do you look for in that first hire?
Jessica Gilmartin: Yeah. So I do a lot of advising and consulting, and this is [00:41:00] the number one question that I get. It’s a great question. Uh, so I would say, well, if you ask a hundred marketers who get a hundred answers, but this is, this is my answer. I’d say number one, I would suggest not hiring a marketer until you have product market fit because no matter what you do from a marketing perspective, you can’t market your way into product market fit.
You’re gonna be spending a huge amount of money until wasted money, until you figure out your ICP until you figure out the, the right product for the right person once. And that is a founder’s job. It’s not a marketer’s job. Uh, and so as a founder, when you figure that out, then you can scale it. Don’t try to scale it until you figure that out.
So that’s, in my opinion, I would wait. Uh, so once you have. product market fit. Once you’re thinking about a marketer, what’s really important to understand it’s marketing is totally different than all the other functions. So marketing is extremely [00:42:00] varied. There are five to six different functions in marketing.
They’re all completely different from each other. And there’s not a single marketer on the planet that is an expert in all of them. Um, also marketing at zero to one is very different than one to 10, very different than 10 to a hundred. So you, you’re not going to be able to find a marketer that can do all of those things.
It’s just totally different tactics. And it’s just, it’s, and that, so, um, when I often tell my clients that when you’re looking for a marketer, look for someone that’s going to be with you for two years. If you get someone for more than two years, consider that a bonus, but think about what you need for the next two years.
Don’t worry about scaling. Don’t worry about 50 worry about the next two years. Um, then when you have that, then think about what are your most pressing, pressing issues. Typically, you’re going to have one of two pressing issues. One is you feel like you’ve got a really good handle on your message and your narrative.
Uh, and really what you need to do is build pipeline. And that then [00:43:00] you’re going to look for someone that has expertise in demand gen. The other pressing issue you might have is actually your pipeline looks pretty good. Your user generation looks pretty good, but you don’t really have a good handle on your narrative and your differentiation.
So then you’re going to look for someone with product marketing experience. So that’s, that’s kind of how I would look at it, which is what’s your most pressing need? Find someone with that experience because you’re not going to be able to find somebody that has all the different experiences that you need.
Um, and just recognize what you are giving up to get that expertise and be okay with it.
Scott Barker: Yeah. Yeah. I like that. I think that’s a great way of looking at it. And I like this idea of. Just looking for someone for the next two years. I think it feels like such a monumental hire. Like, Ooh, the first sales hire, first marketing hire. And you’re like, Oh, I want this person to be our VP one day and they’re going to grow and they’re going to be with us for this whole time.
And in reality, you know, their jobs [00:44:00] required different skillsets as, as you scale, you know? Um, and so I think
Jessica Gilmartin: Yeah. And don’t consider it a failure. Yeah. Don’t consider it a failure if they only make it a year, a year and a half, if they provided value. Hopefully they will. It’s totally fine. And like, you’re just going to need somebody for that next step. And that next step, you know, getting from what you need at 5 million is definitely different than 25 million is definitely different.
50 at a hundred, 500. And that’s totally fine.
Scott Barker: Yeah. Yeah. Building on this question a little bit is. I would love to hear your take on when folks should start investing in brand. I think that’s become more and more important. Even some of the startups we see now out there, even quite early stage, you like you’ve heard of them and they have great, great brands.
Is it? Ever too early to invest in brand because it can be quite a expensive, uh, endeavor, but looking at Asana, Calendly, like those brands are [00:45:00] household names. Um, when do you think startups should start investing in brand?
Jessica Gilmartin: think there is a big misnomer that investing in your brand means. Billboards and TV campaigns, you know, Asana and Calendly had years and years and years and years before they spent a dime on marketing and Calendly was a household name before it spent any money on marketing, before it had a marketing team.
So I think your brand is really a reflection on all of the elements that make your company known and valuable to customers. And so investing in your brand could also mean just having an amazing product, having a super viral product, having great customer support, having great communities, having people that love you and talk about you having great reviews.
Like those are all things that you can do to build your brands without spending any money or very little money. And so I would say from day one, you should invest in your brand in those ways in building a [00:46:00] company that people love and want to support and want to share and talk about. And then typically what people think about more traditional brand spend, it’s often in relation to something else, some external force.
So maybe competitors have come in. Maybe you feel like you are on the precipice. Of something really big, like, okay, there’s a market shift and we think that we can really gain a lot of market share and we have to really go in heavily. Um, oftentimes it’s a repositioning of the company. It’s launching a big new product.
You have to reach new people. That’s how I would typically think about when it might make sense to do a big brand campaign is when you’re ready to accelerate or transform the way that people think about your company.
Scott Barker: Yeah. Yeah, that makes makes total sense. Almost like investing in brand is really just investing the right dollars into product and your customer and making them successful. And then they become, you know, your brand [00:47:00] advocates. It’s not all about just big flashy PR campaigns or, you know, investing in a Super Bowl commercial.
Uh, it’s kind of
Jessica Gilmartin: I can’t tell you the number of, yeah, I can’t tell you the number of times that I have seen an advertisement, seen an article, uh, about a company I’ve been intrigued. And then I go and I look at their reviews and they’re terrible and I don’t buy it. Right. So it, everything has to be about the product first before spending money on the marketing.
If your reviews are not good, people are not going to buy your product. If your word of mouth is not good, people are not going to buy it. So focus on that.
Scott Barker: Yeah, I think that’s great. Great advice. Um, well, this has been an awesome conversation. I have 2 final questions for you. Uh, and I appreciate you hanging out with me today. Uh, the 1st question, I call it the silver bullet question. Um, I say it almost every episode, but. Most of us know there are no silver bullets.
Unfortunately, I really wish there were, [00:48:00] um, people look for them anyway. Uh, what is one tactic or strategy that’s working for you or the companies that you’re serving, uh, like today?
Jessica Gilmartin: Yeah, I mean, we’re moving all of our budget from PR a lot from Google to social. It is astonishing over the past couple of years, how much, uh, value you can get out of both organic and paid social, particularly micro influencers. And so these are even for B2B companies, influencers on TikTok, on Instagram, YouTube, LinkedIn.
Uh, a ridiculous, uh, amount of value from Reddit, uh, and you can, there’s actually even Reddit SEO experts. Uh, so I would say that if you are just starting out, really focus on your social influencer strategy. It is, it’s going to really significantly pay [00:49:00] dividends.
Scott Barker: Yeah, it’s a great, a great call out. And I think we saw Clay run this playbook pretty, pretty well. Um, I know they were out there like engaging all these different social influencers within kind of the sales and, and GTM realm. Um, It’s funny you bring up Reddit. I keep hearing, I keep hearing about Reddit, um, from so many people, just like recently within, I think the last like two, three months, um, any learnings you can share from Reddit, the platform I’ve, I’ve never been a part of a marketing team or, um, or anyone that’s invested in that, that channel.
So I’m just kind of curious.
Jessica Gilmartin: Yeah, I mean, the reason, at least in my opinion, the reason that it’s become so much more valuable is that if you Google a company or if you Google a concept, Reddit appears among the top results. So it has just shot up in terms of the importance. So not only is Reddit itself a massive, has a massive [00:50:00] user base and tons of engagement, But when you’re searching for something on Google, instead of it showing, you know, a company’s results or other review sites, it’s showing Reddit.
So it’s almost becoming a de facto review site. And there’s just a lot of very Impassioned people on Reddit, uh, and they go, it.
yes, trying to be diplomatic. Um, but they also, they, they go into a lot of detail, so there’s a lot of depth around it. And so it’s almost like you’re getting a, like a review, um, and a series of reviews and there’s multiple different angles.
And so I think it’s just a place that people feel like they’re going to get an unbiased. review of, you know, an industry products. Um, but you can feed and you can source, uh, you, you can sort of, uh, infuse certain topics and certain subreddits by with [00:51:00] yourself. having other people asking your customers to chime in.
So there are just lots, it really is like SEO, but specifically for Reddit. So I would say that that, and also being really responsive when you see people with a negative review jumping in and really trying to be helpful. Well,
Scott Barker: I think I’m going to, you’ve inspired me to go deep on, on Reddit marketing. Um, so that’s going to be my, my, my homework, uh, for the next little while. Cause it’s so interesting. Right. It’s also like, yeah, the anonymous component to it is very interesting. Cause you can. Have almost like sub brands that might be kind of part of your brand that are like engaging the community and it doesn’t seem as, um, bias, I guess, if you were just to like, respond as Calendly or Asana, um, which I think is cool.
Um, all right. Final final question is, uh, what is one widely [00:52:00] held belief that CMOs, CROs, uh, Still believe to be true that you think is bullshit or no longer serving us
Jessica Gilmartin: So I am, I’m very surprised that I still interact with C level folks who think that there is a very clean, Customer journey and that it is like an assembly line where you start with marketing and marketing drives leads and then they kind of throw it over the fence to sales and sales close it and they throw it over the fence and customer support and then poor customer support is the one dealing with all of the existing customers and then their job is to do all the retention and it’s nobody else’s job at that point.
Um, I just can’t, that is not something that I have, I have actually seen over many, many years. be how customers think and how, and how we should all interact. Um, so in my opinion, like we are all as company, everybody is responsible for the customer. And it is a twisty, tangly, super interwoven, messy customer [00:53:00] journey.
That requires everybody to think about how do you act, how do you acquire customers? How do you sell to them and how do you retain them? Um, and to me worrying about attribution, worrying about credit. Uh, is very, very silly, and ultimately it’s about how does everybody collectively hit the number? And if that means that marketing stops driving leads because they need to focus on retention and upsell, then let’s do that.
If that means customer support has to be selling up front to customers, like let’s do that. Um, but again, going back to being an entrepreneur and that entrepreneurial spirit, it’s. Everybody’s role to think about the customer from beginning to end.
Scott Barker: great call out and I will tell you When I was an operator attribution was the bane of my existence I just always wanted to do the thing and not like look back too much and make who gets credit for the thing So much wasted [00:54:00] time and energy can be like sometimes it’s up to like 30 percent of people’s job It’s just proving what they’re doing is having an impact which I think it’s just incredible Waste of, of resources, but in, it’s always a balance, right?
How did you, cause you need attribution for knowing what’s working, what to double down on, what was that kind of balance for, for you of like, Hey, we all have shared goals. We’re driving towards them. We need at least enough data so we can make informed decisions, but we don’t want to slow people down with this attribution mess.
How did you think about it?
Jessica Gilmartin: Yeah. So what I would do is, is I would always, I think number one thing is building trust between marketing and sales and customer support. So if you all trust each other and value each other and recognize that you’re all doing the right thing, have shared goals. have shared like an understanding of what’s working or not, then attribution doesn’t really matter because you’ve all agreed that these are the things that you’re going to do.
Where I find other [00:55:00] problems is when marketing, which is like 99 percent of the time, creates all of their campaigns in a, in a silo and then just throws them over the fence in sales. And then complains and sales doesn’t, you know, follow up on leads or whatever. And then sales is complaining that marketing doesn’t listen to them.
Then of course, everything breaks down and there’s no trust. And then you start fighting about attribution. But if you all like believe the same things, and if you’ve all agreed on the plan together, then if something, if you don’t hit your numbers, it’s because all of you made the wrong call and it doesn’t matter whether, you know, marketing isn’t delivering or sales and the bottom of the leads, you all are in it together.
And so I think fundamentally that’s absolutely number one, which is you build a shared plan. The sales team has 100 percent input into all the campaigns that you’re going to run. All the things that you’re going to do, all of your goals, they see your numbers, it’s super transparent, you’ve all agreed on the assumptions, um, and then you just build the plan together and you operate the plan together.
Uh, and so that’s, and when I look at data, I am, as you [00:56:00] said, I’m not looking at attribution. I couldn’t care less whether marketing drives 50 percent and sales drives 50%. Who cares? Um, especially in this world where so much of it is about. Uh, a customer hitting, you know, hitting you up 10 times, 15 times.
They’re doing so much before they’re willing to contact sales. Also in this world where expansion is as important as the initial sale, like then marketing never gets credit for that and who cares? But if you’re doing all the right things and that’s what your data should show you, like are the campaigns that you’re running, are they influencing?
You know, are people engaging with them? Are they interacting with them? Are people coming to your webinars? Are people clicking on ads? Are the right people seeing them? You know, if you run an ad, an ABM campaign, are those customers eventually reaching out and upselling it? Those are the things that matter.
And you can look and say, yeah, like what we’re doing is valuable because we are touching customers in some way that’s eventually causing them to buy from us. [00:57:00] That that’s Yeah, only thing that matters.
Scott Barker: totally. I love that way of way of thinking. Do you think it was? easier for you to think that way since you, uh, had the CMO and CRO title, you could kind of see the whole picture. And I imagine that drove, uh, alignment from the very top down.
Jessica Gilmartin: Yeah, but even before, you know, even when we had our CRO before I took over. We had that mentality and I was very fortunate that she was someone that was interested in building that kind of relationship that understood that that was really important. Um, and I think that that’s, you know, and I think having that strong relationship with CRO, having the strong relationship with the CFO and the CEO, having that buy in across the organization, um, and a lot of that just took a lot of communication around our plan, getting a lot of buy in.
I just see so many CMOs who are very defensive and very closed off. And who take everything so personally, and who don’t want, um, any kind of input [00:58:00] and they like, they just want their goal. They just want like, I, I want to be able to drive 40 percent of leads and that’s it. And like, that’s my goal. That’s not going to make you successful.
And so just being really open and focused on what’s best for the company, uh, I think will serve you well. And building that bridge with the CRO is going to be really critical for you.
Scott Barker: I like it. I like it. Well, I think that is a great place to end. Uh, Jessica, thank you again for the conversation. Um, if listeners want to follow along with, with what you’re doing, um, are you an X person, LinkedIn person? What’s, uh, the best way to follow, I am definitely not an ex person. So LinkedIn. LinkedIn. LinkedIn.
Perfect. Um, well, again, thank you. And to all our listeners, appreciate you hanging out with us. I, I say it every week, but, uh, you know, listening is one thing, executing something totally different. Hopefully you take some of these ideas, strategies, and tactics and implement them in your own business. And we will see you all [00:59:00] next week.
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