Ep # 181: What Revenue Leaders See in the Data That Others Miss ft. Sara Archer (CRO, ChartMogul)

Sara Archer 00:06 I've asked Megan to think about how we can do hyper-personalization within our account management strategy and what might that look like? So building more specific segments of customers and treating them a bit differently. Intro 00:24 Welcome to Across the Funnel, where we dig into concrete Go-To-Market moves across sales, customer success, and account management so you can build revenue that lasts. Brought to you by Hyperengage and Dextego. Adil Saleh 00:40 Hey greetings everybody, this is Adil on the Across the Funnel podcast. I know that there's some conversations going around for the last quarter, even from the whole year, since this AI evolution has come up, building has been easier than ever. Now it's everybody building products. But why we are bringing on these conversations is to educate people how they can articulate the revenue impact while they're building with their customers across different customer verticals. We are talking about the top-level SaaS metrics that everybody cares about, from every investor to revenue leaders. Today we have Sarah from ChartMogul. She's a Chief Revenue Officer and she's responsible for all the SaaS metrics for more than 130 million SaaS applications cracking their SaaS metrics using ChartMogul. So thank you very much, Sarah, for taking the time. Sara Archer 01:37 Yeah, it's a pleasure to be here. Looking forward to today's conversation. Adil Saleh 01:40 I love that. So now, building Go-To-Market analytics for revenue ops, I know that analytics have been a bigger part of how to drive AI because AI needs data and all these resources to be smarter over time with this AI. How do you see this has changed, if you just talk about the revenue operations at ChartMogul? Sara Archer 02:03 How AI has changed our revenue operations function? Adil Saleh 02:06 Yes. Sara Archer 02:07 Yes. Fair question. So I oversee sales, revenue operations, marketing, and account management here at ChartMogul. Although my background is largely defined by sales and sales operations, RevOps is really one of my favorite areas to play. I would say that our strategy has shifted from running early 2020s traditional marketing playbooks to forcing both our RevOps and our demand gen function to operate more like the old days of growth hacking. And so designing and deploying quick technical experiments to validate ideas and then turn on and off things very quickly. So for example, a year ago we were sort of running $12,000 to $15,000 worth of Google Ads because we thought that's what we were supposed to be doing and we didn't want our competitors to be outfitting us. But when we looked at the data a bit closer, we said, you know what? We could do something else with this money. And so instantaneously we turned off all of our Google Ads and we ran some quick experiments where my head of RevOps and I got on a call like this and we vibe coded some new ads because we wanted to try some experimentation on LinkedIn and Reddit. So that's just a short example of how AI has transformed our revenue operations function, where we're a bit scrappier, more technical and faster, which is a delicate balance. Adil Saleh 03:52 Yeah, that's what it takes. I was just listening to this team at Anthropic, and they were like, it's not just like long ago, like eight months, it seems like a pretty long time with this AI and all this going pretty fast. They were preaching towards building vertical agents across organizations for internal uses. So how do you see this in-tech big shift that has come in the past six months for your sales, marketing, revenue, all of that? I know Claude has a bigger contribution in it, but how are you trying to do it internally for your team at scale, to operationalize, to automate, and all of that? Sara Archer 04:40 Yeah, I think it's pushing everyone to challenge themselves as it relates to AI. So the sentiment is like if you tried LLMs six months ago or eight months ago and you were largely unsatisfied with the results, I think a lot of folks have been like, yeah, it's not all that, it can't do it. Right? And so a lot of the use cases were rather simplistic, like a slightly souped-up version of what you would build with a workflow engine like Zapier or n8n. And so we've just been forcing our team to say, actually, if you haven't touched this stuff in a year, you are gonna be blown away. And what you should do is you should just give it the hardest things that are on your to-do list and see how it performs. And I promise you'll be surprised. I think the impact of this for us internally is that it's making folks more capable generalists. I know how websites are built and hosted, but it's been a long time since I've touched HTML. Two weeks ago I built a microsite for an event series we're running using Cowork. And then the next thing I know I was editing HTML in Cursor. That's cool, right? Because it makes us more capable. And I like the idea of high agency, no pun intended, generalists where we can have really ambitious senior operators impacting all areas of the Go-To-Market strategy. Adil Saleh 06:25 Interesting. And then also, I know the SaaS metrics, being from marketing to post-sales, to revenue expansion and all, and of course advocacy. If you only talk about the revenue retention side of things, this is the biggest challenge, because acquiring customers has been the hardest now. Distribution is failing, outbound is going dead, and SDRs and BDRs are doing like 150 to 300 calls a day compared to six months ago when they were just doing 50 or 60 because the connectivity and deliverability is not that big as everybody's doing it. So now it becomes even more important to retain your customers and installed base and find ways and build systems around it to increase the lifetime value. And find out the hidden opportunities, whether it's going multi-product, whether it's building internal agents like Gong did, a lot of agents at once. So what is your playbook towards the revenue expansion and retention side of things? If you talk about the Go-To-Market. Sara Archer 07:31 Sure. Yeah. I have a call later today with our head of account management. She's been tasked with an interesting challenge. In BDR/SDR world, the idea of hyper-personalization at scale has been around for a long time. But traditional account management or high touch customer success has largely leveraged a one-to-many approach versus a one-to-one approach, with the exception of QBRs or renewals, right? Like, obviously those are specific to an account. In my experience, most SaaS businesses at scale are running marketing campaigns on their installed base to say, okay, if this signal then that expansion opportunity, I send you an email, I tell you to upgrade. I've asked Megan to think about how we can do hyper-personalization within our account management strategy and what might that look like? So building more specific segments of customers and treating them a bit differently. For example, ChartMogul the product has many integrations. When I launch a new update to our Stripe integration, the traditional product marketing playbook would just be to email everybody and say, hey, look at this new feature. We've updated our Stripe integration, but for all of your Recurly users or your Chargebee users, that product marketing update is largely irrelevant. So what would it look like if you could say, actually, I know what Sara at ChartMogul cares about and I'm going to deliver only the feature updates to her that are relevant for her role and how she engages with our product. And that could be a more meaningful experience for your customers, and make them feel thought of afterward. So that expansion or retention decision is a little bit easier. So that's an ongoing project. I wouldn't say we've totally gotten all the way there, but we're making strides. Adil Saleh 09:44 Yeah, it's always good, boost segment by segment because the customer behaviors are always going to be exceptional across segments, and it is so hard to articulate what metrics matter to them and how they perceive value out of your product. Starting from maybe onboarding, we've done a survey with more than 170 GTM leaders and most of them agree that more than 25% of the customers actually churn between the stage of onboarding to adoption. So it is so hard, especially in these legal and healthcare industries, to track the customer education part. And with this AI, it's even harder because the noise has increased so much. So what kind of industry verticals is ChartMogul, I know that SaaS, it’s is all about SaaS, but now SaaS is expanding more than ever. Even legal, healthcare, real estate, and ed tech are expanding at a rapid pace. So what kind of new industry verticals are you trying, or maybe some new customer segments that you’re exploring, or some customer stories that you have to share in these less AI-enabled verticals that I’m talking about? Sara Archer 11:00 Yeah, sure. So I'd say our business has been around for 11, 12 years and our ICP focus is probably as hyperfocused as it's ever been. We've really been serving the B2B SaaS industry for the past few years, which makes deciding what to build from a product development perspective quite easy, right? The more you expand your footprint into different verticals, the harder it is to decide what to build. But it is true that with the focus and attention on AI and agentic, the conversation feels less central to B2B SaaS. And I don't know how long that's going to last, so maybe it's six months, maybe it's a year. One thing that's been encouraging me to look at is that anyone with recurring revenue can be a ChartMogul customer. I don't know if you know this coffee shop Pret, you can go to Pret, you can get a cup of coffee, a croissant or breakfast, whatever, and you can also sign up for a Pret membership. And so this recurring revenue business could be a prospective ChartMogul customer. So as investors and founders are excited about AI and agentic versus B2B SaaS, it's forcing me to say, hey, maybe there are some other verticals: streaming, media, publishing. They end up in our pipeline all the time. But we don't do anything necessarily to market or find those folks because we are so focused on serving B2B SaaS. So it's a question I'm exploring: should we be going after some larger enterprise digital verticals, e-learning, for example? So we’ll see, we'll do some experimentation later this year for sure. Adil Saleh 12:49 Yeah, absolutely. Okay, so now let's talk about your process. It's almost a decade now and you've got pretty stable industry verticals, pretty deep run into this customer base in North America and overall as well. Thinking about how you're tracking success from the point of onboarding to delivering value faster, and then all the way to expansion opportunities, how does this all work, ofcourse revenue operations also come along in that lifecycle, so how does this all work at ChartMogul? How are you measuring success for your customers? I know that you have account management customer success, CRM, you have revenue operations, sales, marketing, all of that. But is there any system of record that you have that triggers or makes these teams proactive, whether it's an enterprise customer or an SMB in a pretty low touch? Sara Archer 13:42 Yeah, so our business model is largely inbound. We drive all of our demand to a 14-day free trial, and we're lucky in that we get hundreds of free trials every single month. Then I have a small sales team that sits on those free trials. Now they only touch probably 30% of the inbounds because the rest are funneled through a self-serve motion. Their job is to get those customers to activate and engage in an evaluation of ChartMogul, the product. And we do that with calls and Loom videos and onboarding sessions. And we try to be aligned with how our buyers want to buy. Do they prefer to go at their own pace and try, or do they need a little bit more handholding? And once those folks hopefully convert to paying customers, they stick around for a decade and we just continue to service them both with the product and then the support and engagement experience. We use n8n to drive a lot of workflows and alert folks in Slack to take actions based on things that happened in the product. And of course, ChartMogul itself is our operating system, because ChartMogul knows who your prospective customers are, your trial list, your churn customers. And it really offers basically all the information about who your subscribers are, or could be, and then the revenue data itself. And so the focus is on converting trial users to high LTV subscribers, and then keeping those folks happy for a decade. And that's a cool thing to say, we do have customers that have been with us for 10 or 11 years, from the very beginning of our journey, which I think is a testament to the ultimate goal, right? Which is to build a product and a business that delivers on its promise. And so that's what we're accountable for, for pushing the standard on. Adil Saleh 15:56 Yeah, of course. I know that revenue operations have changed over time. And of course, you now must be seeing a lot of different customers thinking about having technology or a platform like ChartMogul for their subscription management and all these SaaS metrics that they care about more than ever. So now, talking about these SaaS companies that are more towards the health or expansion side of things, how do you articulate it for your own post-sales, or you mentioned customer success, which is more like a hybrid touch? Is there any kind of tech stack or any kind of triggers, any nudges that you have to measure the health alongside the journey? Because it might change over time because a lot of these customers have so many options. A lot of these mid-size companies are building their internal tooling. So how big of a trend is that and how is it hitting churn, or what system do you have to forecast it ahead of time? Sara Archer 16:56 Sure. A couple of questions there. So how do we track, so we previously used a customer success platform, like the Gainsights, the Totangos, the Custify Underworld. A few years ago, I challenged the team on that because to me, a customer success health platform and a CRM are ostensibly the same thing. They're databases with data points about the same customers and workflow tools. So we actually turned off our customer success platform, migrated everything to ChartMogul, making ChartMogul really central. And then we built some rudimentary health scoring using some automation tooling and our BI tool, which is Superset. I'm a little bit of a contrarian around lead scores and health scores. Like, I don't know what the difference between a 57 and a 64 is. And I'd rather you just go out and form relationships with your customers. So you can definitely over-automate things there. But you know, one of the things that ChartMogul competes with is an in-house build. And so ChartMogul is this opinionated analytics platform that gives you all of the SaaS metrics you need: monthly recurring revenue, churn, lifetime value. If you're a business with growth and retention in mind, then ChartMogul is a great option for you. But lots of teams opt to DIY. They say, hey, we have Thomas on our data team and he can export the data from Stripe and put it into Tableau or Looker, which is where all this other data lives. So I'm not seeing a major change from my point of view about AI and vibe coding replacements. It's just a different version of the same thing. You could build a ChartMogul alternative on Tableau five years ago or seven years ago. And the competitive tooling has changed slightly, but it's still a question of: do you want to build and maintain this and allocate resources on a continued basis to it? And so the narrative is slightly different, but at the end of the day, it's kind of the same thing from my point of view. Adil Saleh 19:23 Yeah, absolutely. And of course, a lot of these platforms like ChartMogul, they're so sticky. Like once you have all your data, it's so hard to do the change management, especially for mid-market to early enterprise companies. And it is hard to make sure to migrate all of that, just like a CRM. So if you have ChartMogul as your system of record, it's so hard to migrate and have your team train on another platform. Sara Archer 19:48 Yeah. Adil Saleh 19:49 On top of everything that it does. Sara Archer 19:51 Maybe. We also try to be complementary to the data stack, right? So we don't want you to be beholden to ChartMogul necessarily, but say you do have your data warehouse and some BI tooling, and you want to do more analysis than ChartMogul offers. And so the conversation internally is like, hey, I think we've outgrown ChartMogul, right? Like, that's the thing we're trying to combat. We actually have capabilities to push ChartMogul data to data warehouses and BI tools. So you have the flexibility to use those things in concert, versus, we don't want to force you, we want to enable you. But yeah, it is true. It's interesting, the things that are very sort of unsexy about ChartMogul are some of the most sticky things. So we have basically the ability to ingest all these different kinds of data and then normalize them. And then we have this suite of data cleaning and editing tools. So when you make a mistake, you can just fix it very simply. Adil Saleh 21:06 Oh, you don't need to be a data ops manager or engineer to do the configuration or all the changes. Sara Archer 21:12 Yeah, it's pretty hard to break ChartMogul. Like I'm sure you could do it if you go and delete a bunch of stuff with the wrong permissions. But you know, it's simple things. So for example, imagine you have a customer on a monthly plan, and then they say, oh, I saw the promotion you're running and I want to upgrade to annual to take advantage of those savings. I'm very happy. I want to commit, I want to give you more money. In ChartMogul, in many systems, you'll have to cancel their monthly subscription and then create a new annual subscription. And what that looks like is false churn and reactivation, when really it's just one contiguous movement. And so these little data cleaning tools, you just click two buttons in ChartMogul, or you can set it up to run programmatically. We're very good at handling the complexities of subscription data, I guess that's what I'm trying to say. And do you want your team to figure out when to recognize churn or how to handle proration or currency fluctuation? That would be our argument as to why you ought not use a DIY approach or a vibe coded approach to SaaS metrics. Adil Saleh 22:33 Right. So now, as somebody, of course yourself, you are being a sales agent long, almost more than decade now, how do you see this notion growing with this AI, like going multi-product or building internal agents for sales, and of course, consolidating everything. I know that you have pretty deep, workflow integrations like CRMs and all those integrations, but every platform is thinking of doing everything adjacent. Like sales analytics is now sales enablement and they're also doing post-sales as well, customer success, they're jumping into a lot of these CS platforms. You mentioned they're now more into the support side of things as well. Like they're overlapping a lot of these analog functions, just like sales and revenue and sales and success are, they're trying to go adjacent product-wise. So I know you're not a product leader, but you are a leader yourself. A lot of this decision making goes through you. So how do you think of planning all of this? How does this all align with your product vision? Sara Archer 23:43 It's hard, right? Because you're building at such a rate that your product marketing or your customers can't keep up with your feature development. So if tomorrow you released all this adjacent functionality, you run the risk of overwhelming or confusing your customers. I'm actually thinking of, we bought a product a couple of years ago for call recording and sales coaching, and then I opened up their product roadmap and they were like, no, we just launched scheduling. And I was like, no, no. I have Calendly for that. I don't need you to, I want you to be the best at call coaching. And the fact that you're investing product and engineering resources in scheduling, that's not the problem I want you focused on. So I think you have to instill your customers with confidence that whatever is your mission or the reason customers are trusting you, that you are displaying continued focus and expertise. And what happens when you get too far adjacent from that mission or that core value driver? You run the risk of no longer being a credible domain expert... Adil Saleh 25:04 in the category, yes Sara Archer 25:05 Yes. I mean, that happened to us, right? We had inbound demand for revenue recognition capabilities, and so we were like, great, let's build a revenue recognition product. We'll sell it to all of our customers. Expansion, voila. And then years later we deprecated the product and we did a postmortem on it and we were like, oh, we should have never built that. Different ICP, but moreover, to me it's a different domain expertise. Our team's not back-office finance experts. We can consult you on growth and retention and what best practices are around scaling a SaaS business, but back-office compliance is a very nuanced, different kind of thing. And so I think being mindful of your ICP or your domain expertise and just being mindful about saying yes to the right things. That's tricky, right? Because the design and development cycle for launching things has collapsed. You're hearing people say like the end of prototyping, you don't even need to design that spec. You can just build it. And then someone can review your PR, but it is worthy for some things to go through the design process, to redesign, and say, should we build this? And so having the decision criteria to put things in the right buckets, I guess, is what we're trying to do. Adil Saleh 26:54 I love that because on the flip side, as you mentioned, so many platforms that are going, just trying to do everything, they're falling apart. Of course you need to make sure that you are serving your category at the end of the day. And 12 years down, it becomes, you get a little more informed. Now thinking about you as a leader, I am a co-founder, we think a lot. Most recently, we think, hey, we are going to be commoditized. Whatever we build, Claude can have their own CSPs next day and everybody can do all these copilots inside Claude. And a lot of this tooling is going to be commoditized and there's not going to be as many consumers because AI and agents are going to be the next wave. So how do you think as a leader, how secure do you feel? Sara Archer 27:38 I mean, hypothesizing too far in the future is a fool's game, right? We do know is to double down on your moat, and your moat beyond product too, which is your relationships with people. We do a lot of data-backed industry content with the idea of trying to create things that are not product, but are still useful for relevant consumers. And so yeah, investing in these things, for me, interpersonal relationships, networking is one of my superpowers. And so I can control the controllable. And we can be communicative and proactive within our executive team to say, here's my understanding of the risks. And here's what I think we should do, just given the landscape. And so yeah, no good answer to that question. But I guess it goes beyond the product, and the business of product. Adil Saleh 28:49 Yeah, absolutely. So my response is more like: you can go and build a tool next day like what I built, but the people that love me, they're gonna buy what I build next. So it's just about people, as you mentioned, relationships. Sara Archer 29:04 You see that in the early days of SaaS and you see that with AI-native companies now, where when people make a purchase decision about something, should I give you my money, right? And part of that is, okay, for this price point, am I going to get the intended value or ROI from this product experience? But if you think about the last 10 purchases you made, maybe professionally, but also personally. The tricky thing about people is they don't always make rational decisions, right? They make emotional ones. And so sometimes you actually vote for a business with your dollars because you love seeing that founder build in public, or you think that mission is interesting. And so when you see some of these businesses that are growing very quickly, some people just want, you know, it's a fear of missing out. It's like, I want to be on the hype train. I'm buying my monthly or annual Claude Cowork because I have to learn Claude Cowork to stay relevant. Do I want to give them $200 a month? Do I want to spend my Sunday morning building apps in my guest room, maybe not a little bit, somewhere in the middle. But that's where it gets tricky. And so yeah, I think that's the fun part, a little bit. I mean, that's why I like sales, honestly. Adil Saleh 30:32 Yeah, absolutely. It's all about, you gotta decide that you are going to be the beneficiary of your choices. So you gotta know why you're doing it, how it's gonna impact and whatever you want to make an impact. And that's about it. So now a little bit about your culture. I know that you've been almost more than seven years now. ChartMogul and team, they must love you. That's why they kept you for long enough. So how is the culture, not just in your team, but what kind of onboarding principle are you cultivating across teams? I know that most of your teams have been consistent. You're one of the SaaS companies that have consistent people working for them. So that gives a good testament of a very consistent culture. So could you walk us through, for our audience, what is it like working at ChartMogul, working with you? Any openings you guys have? Sara Archer 31:24 Yeah, absolutely. So ChartMogul is 60 people, represented by many nationalities and cultures, which is quite fun. I always have the idea of doing a ChartMogul cookbook, which is silly and I don't know if I'll ever do it, but we've got an office in Seoul, Korea. We've got our presence here in Germany, where we're headquartered. And then we also have a legal entity and office in Toronto. But the 60 of us are scattered globally, with folks in Manila and Bangkok and Athens, Amsterdam, like all over. So I quite like that. I would characterize us as European. I'm one of the oddball Americans, originally from Baltimore, Washington DC, but I've been in Germany for a decade now, which is crazy to say. And you know, we're a bit nerdy, right? I think we all quite like SaaS. We've had a lot of fun building software for the last decade together and we're sharing memes, video game recommendations, music, gardening and recipes. So at least compared to previous employers and cultures I've been a part of, we're a bit academic and kind of fun. And I would characterize us as more of a high-performance team. A lot of senior operators, high agency, want to get things done and help our customers. And so we're not hiring at the moment, but you can always check out our careers page if that changes. And we're going to do a road show, so we're going to be in a lot of cities: Paris, Amsterdam, London, Bangkok, Melbourne. And so maybe, Adil Saleh 33:31 Oh, Australia. Sara Archer 33:34 Yeah, maybe our paths collide. Adil Saleh 33:35 When is that happening? Sara Archer 33:39 It is starting next month. We kick off in Paris and then we do San Francisco in May and Adil Saleh 33:47 Oh, I've been in San Francisco in May too. And we have a SaaStr as well. Another event we are doing alongside. Sara Archer 33:56 Cool. Adil Saleh 33:58 Okay. I'll be in Europe in July. Is there anything happening in July? I'll definitely check out Berlin, of course. Sara Archer 34:04 Yeah. TBD, some things are still in the works, but we'll publish everything shortly and Adil Saleh 34:12 we'll, coordinate Sara Archer 34:13 hope to meet some folks beyond the Zoom. Adil Saleh 34:17 Absolutely. And as you are one of the leaders, what is that one thing that you advise to female sales leaders? Because just a day before, it was International Women's Day, and we had some of the women that made a huge impact in terms of their leadership and all. So what is that one advice that you share with women aspiring to be sales leaders? Sara Archer 34:45 Yeah, I think I would maybe give this advice to all sales leaders, but maybe particularly female sales leaders: don't shy away from the technical stuff. I always tell sales candidates in general, I say, ChartMogul is a great place to learn APIs, integrations, rate limits. And if you take a job at ChartMogul, I can't promise that the onboarding and the learning curve is gonna be easy. It's not a Google Chrome plugin. You're gonna have to model data and calculate churn, but you'll make more money in a technical sales role than you will selling a simple widget or traditional sales roles. So I would say, especially now, you force yourself to do the hard things, like edit the HTML or get some advice about how to take your Cowork project and put it in Cursor, and don't be afraid to fool around in GitHub within reason, because I think it adds to your credibility and helps quite a bit. Adil Saleh 35:59 Yeah, a lot of these sales leaders, including myself, when time changed and it changed so quickly, it's so hard to get outside of your comfort zone because sales leaders are always known to be talking on calls, meeting people in person. They're not so much into tech. The maximum they've done is Google Meet and Zoom, and before that it was phone calls. And it is so hard for them to evolve with the way sales have changed now. I would say five years from now, every sale is gonna be a technical sale, especially in SaaS. So you pretty much hit the point that it's all about getting technical and embracing this change and making sure you go outside your comfort zone. And the best part about salespeople is they're so adaptable because they Sara Archer 36:44 Right. Adil Saleh 36:45 They don't know, but once they start liking something or start enjoying, they'll just get in deep. Sara Archer 36:54 Yeah. And so long as you don't lose the voice of the customer, which is part of your job. It's funny, I say don't be afraid to get into the weeds, but at the same time, two of my sales teammates are gonna be on extended leave later this year. And I know what I'll be doing for those two weeks. I'll be making all their cold calls. Adil Saleh 37:17 Mm. Sara Archer 37:18 So, Adil Saleh 37:20 That's the biggest thing about leadership. They go first. Sara Archer 37:23 Gotta brush up, right? Adil Saleh 37:26 Yeah. Sara Archer 37:27 So it should be fun. Adil Saleh 37:28 Yeah. Perfect. Sarah, it was really nice meeting you. Your energy was infectious. Insightful conversation, getting to know ChartMogul and the operation, how you guys are making a massive impact. Best wishes for all that you guys are planning later this year, and I'll definitely follow your journey. Sara Archer 37:45 All right, well, thanks for having me and see you later this year. Outro 37:48 Thank you very much for listening to Across the Funnel. If you got one useful GTM idea out of this show today, please share this with a teammate and hit follow. Explore Hyperengage at hyperengage.io and Dextego at dextego.com.