Ep # 187: 97% Trial-to-Paid, 21-Day Sales Cycles, and the New SaaS ROI Bar ft. Sara Wyman (CEO, Stackpack)

Sara Wyman 00:05 For us, honestly, it's pretty clear. It really is like usage and engagement, right? And so there's a few signals we have. So if we have a good portion of your contracts on file as a percentage of your vendors under management, you're likely a pretty happy customer. Because you're getting alerted on renewals and savings opportunities and spend increases. Intro 00:31 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 00:46 Hey, greetings everyone. This is Across the Funnel. I'm your host. I've kind of grown with this podcast, and my now nine months old daughter. When I started back like four years back, things were different, technologically wise as well as otherwise in life. So thank you very much for listening to all of this. And I try my level best to do a decent amount of service to bring unique stories, unique products. Today we're gonna be exploring what we have at Stackpack and how they're helping with vendor intelligence. This is the biggest thing for a lot of companies going upmarket. Mid-market startups never want to stay as a startup for more than three years. Whether they get their next round of funding or not, they want to grow. A lot of these technology companies that are AI first, they're trying to consolidate a lot of use cases, so that is a big cut down on the tooling side of things. Even bigger companies, they're trying to do more with less. Offsetting the cost of technology, like tooling and all of that. In GTM tooling, there are a ton of tools. So that's why we have the CEO and founder of Stackpack today to discuss how is this going, what's going on with companies thinking of investing in and managing those skills or the tech stack that they consistently get. There's so much noise, so how Stackpack is helping, I think there is no better person than Sarah herself. Thank you very much for taking the time. Sara Wyman 02:19 Yeah. Thanks for having me. Adil Saleh 02:22 I love it. So now I know that you've been there for almost like two and a half years now. You guys started back in 2024. Even at that time there were some tooling that were targeted more towards enterprise companies, a thousand, 1500, 2000, 5000 employees. There was no such platform because we came across some founders as well here that are thinking, hey, we are only gonna be working on RFPs and big contracts. This is more of an enterprise problem. Now, two, three years down, it is more like an SMB and mid-market problem too. So how do you see it as a leader? What's your viewpoint with all that AI impacted so far, with the good and bad and ugly? So you go ahead. Sara Wyman 03:01 Yeah, I think to your point, there really wasn't a solution out there for kind of mid-market companies. So the way I came to building Stackpack was really just feeling the problem being kind of embedded at Etsy and Affirm. Those were the two companies that I was at before. And I kept seeing this problem that vendor management was broken. And essentially what that means is that these massive companies, and even small companies, were really just using a spreadsheet as their system of record. And as you know, spreadsheets become outdated very, very quickly. So we saw a very nice opportunity to go in and to really change that and to build a system that's constantly monitoring and acting for you. And so the way I think about it, it's very similar to what the world looked like for CRMs before Salesforce was there, or what cap tables looked like before Carta was there. And so that's how we think about our world. And then you mentioned, with the emergence of AI, how is this whole world gonna change? And I think what I'll tell you is it's changed so much even in the two years that we've been doing this. So I think the big pieces to call out are that, for better or for worse, corporate spend is shifting away from humans to some extent. I think that will change, and it's moving in favor of AI and vendors. And so the actual OpEx is changing. And so the chaos that comes with vendors is increasing, right? And so that can be contracts everywhere and invoices. And now we have AI spend, you have tokens and credits that you need to manage. And so it's just a lot of chaos. And so we see this interesting time in the market for us to kind of go in and help support these changing businesses that need new infrastructure, essentially. Adil Saleh 04:55 Absolutely, and also to your point, a lot of this is revolving around two or three players. These are majorly companies like Anthropic and OpenAI, and they have connectors and they are workflow integrators that every company, even as a product, like as myself as a founder, we also think of doing first thing like MCP server, MCP connector to connect with Claude or OpenAI, so it gets everything workflow integrated and all. So how do you see that component in your vertical? Mostly these companies are kind of reluctant at this point of working with vendors or platforms such as those that have MCP connectors or integrators, or what's going on with the decision making and everything. Sara Wyman 05:40 Yeah, so we work with a hundred companies today, all over the place, right? Some of them are 20 person companies, some of them are 3000 person companies, and they're across the United States, across verticals. Almost all of them are using some form of AI now, which has changed a lot over the last two years. Most of them are kind of picking a lane with OpenAI and Anthropic kind of as their base. And then we are seeing a lot of them getting very interested in these vertical solutions. Right. You mentioned that there's so many Go-To-Market tools. We see them all. There's now finance tools in our space. Lots of them, and then obviously lots and lots in the engineering space with the cursors and the augments and all of that. So we're seeing a lot of interest. I mean, the market is forecasting a huge influx of agents or individual skills. I think it will be interesting to see how those are distributed, right? Are they distributed through big organizations? Are there resellers? Are there just lots of individuals, small entrepreneurs selling these skills and agents? It'll be really interesting to see. Right now there's a lot of consolidation in those big LLMs. We do expect to see that change a bit as these vertical platforms get more and more niche and provide a lot more value. We think it will get messier before it gets cleaner, we'll put it that way. Adil Saleh 07:05 Absolutely. So it will get to its peak and then everybody would realize, hey, we need authentic content. We were fed up with AI generated videos or product demos and we want more authentic things, like podcast conversations and really concrete knowledge that AI couldn't replace. And then the feel of it, like how a human makes you feel human, that is something I will take, it'll take years or maybe a lifetime for AI to replace, and people will get caught up because if you enable anybody, or at a large scale enable someone, to create content, the content will not be of good quality. Let's say if somebody in Nigeria is thinking of creating content or a demonstration of any product or any service, they can use AI. I was just following the Oscars, like the Academy Awards, as long as I was pretty young. And this time they had one movie that was 70% of the time, 80%, it was shot in natural light. Sara Wyman 08:04 Mm-hmm. Adil Saleh 08:04 And that went big on Oscars and nominees and everything because it was genuine. Versus a lot of these producers, big names, directors, they're using AI to cut up their cost. But of course, in a bigger picture, people don't like it as much and this is gonna happen more and more. Perfect. So now Stackpack, one thing before we move to your post-sales GTM. I know a lot of these companies above 50, before 50, they're more concerned about growth and serving their customers, getting the product market fit. Plus two and a half, three years, if they're funded, they're more kind of allergic to a lot of tooling and everything because of pressure and everything. But as soon as this surpasses 50, like first three years, they try to now think of cutting out the cost. Let's say if you talk about the CRM and all these tooling, like for success, for product analytics, for customer intelligence, sales intelligence. A lot of these big players, you talk about HubSpot, Salesforce, Gong, they have their own agents. A lot of this is consolidating and then they think about cutting up the cost of the tooling. And how is that impacting Stackpack? Your platform is intelligent, I know that you have this AI component into it, like there's an AI system. Yeah. Does that analyze, hey, you are using HubSpot, you're using, for example, Gainsight. I'm not paid for any service, so we always been unfiltered, so I don't mind taking the names. Let's say integration with Gainsight and HubSpot. Does your tool, Stackpack, notify the procurement team or a revenue team or the decision maker on this, hey, you don't need Gainsight. HubSpot does have this feature, and you can leverage this for all of your customer lifecycle management or customer journey mapping or segmentation. Same goes for product analytics. Majorly, there are like five different spectrums a company of a mid-size spends into tooling or tech stack. How does Stackpack help with these customers? Sara Wyman 10:15 Yeah. So the first thing we do, we typically work with finance leaders first to get them kind of set up. We pull in all their spend, we pull in all their contracts, and that's kind of when the first aha moment happens, right? They see, oh my God, our renewal is coming up in seven days, like thank God I have this. And so, yeah, to your point, there are these moments when not only finance, but also department leads, IT, security, legal, et cetera, get to come to the table and say, hey, does this platform make sense for us to renew? Right? And so we do help them through that process. So we have a renewal calendar that we manage, and then every renewal, we really dig into, right? We extract all the terms from the contract. We provide price benchmarking. We show them what their seat utilization or logins have been so that we can really assess, is this a tool that's business critical, or is it something that, hey, it doesn't make sense. Maybe we need to move away from it. And then you mentioned being able to line up alternatives. And so we are in the process of building out a very large vendor catalog. We have 35,000 vendors that we have today. And we're deeply building out those profiles so that, again, when one is coming up, you can say, hey, listen, maybe you do want to look at Gainsight, for example. But yes, HubSpot does offer some solution, but maybe it's not gonna be as fully baked as the Gainsight one, and show you that difference. So the good news is we have AI on our side now. It's pretty easy to train AI on this, and so that you can have a very natural dialogue and potentially very easily set up an RFP or a comparison. So that's how we do it. Adil Saleh 11:56 Yeah. I love the way that you are doing the comparison part because previously, like two years from then when you started, a lot of these companies were thinking, hey, this is a huge change management. When it comes to tooling that are more customer facing, like GTM tooling, they think, hey, to migrate from HubSpot or CRM or from a product analytics, it's such huge change management. Now with AI, with all these LLMs that are superpowers, you can build capabilities inside those LLMs that can do a lot of the change management easy. So I think this is now a bigger use case for Stackpack to present. Hey, why don't you just look at some options. It's gonna take like one week of onboarding. This is what it takes to onboard like 50 of your team members in one week, and you're good to go. Saving 70% or 60% every year out of this tech stack. I love the way that, and do let us know when you're ready for that because you're already looking at the vendor. Sara Wyman 12:54 Yeah. And we have just great signal, right? Like we know, hey, this is a really good fit for an enterprise, or this is a really good fit for a PE backed company that really cares about value creation or whatever it may be. We have a lot of signals so we can start telling you where your best fit is, I think, and also breaking through the noise. That's the biggest problem we're seeing, especially in Go-To-Market tools right now, is there's so many new AI tools, but do you actually know the ROI on those? Do we have proven data that we can show you, hey, this works and it's sticky? We know that they're renewing in the next year. That tells us there's value there and that's a good path to potentially take. So lots of cool data that we get to play with. Adil Saleh 13:34 Yeah. And also a lot of categories are getting a big hit, you know? Yes. Especially these CRMs and product analytics are just recently clobbered. Claude design just came up last week and they ripped off the Figma and Canva and everything. I asked my team, hey, why don't we just change the website just for an experiment? So just use Claude design and change the website. Give me a draft of it. I won't publish it, and it was like a thousand times better. It was better than what we did in Figma in like 1, 1 and a half month, with of course a couple of resources and all also. Great. Love that. So now thinking about AI in tech is gonna, of course, stay constant, and how you leverage and augment that the way you are doing it for these vendor onboarding vendors and have sort of a marketplace for people to compare and have your own quality checks to make sure your customers get the value fast and they're able to get the best price points for best tech. Second, so when you talk about the first value, you already mentioned that. I kept seeing some of your posts as well, so first value path, how you guys define it in a more strategic, systematic way for one segment. Could you also brief us a little bit about your segment? You already mentioned that it's more like revenue teams. What kind of segments are kind of a sweet spot for you guys in Europe and elsewhere, meaning that they have pretty much defined their customer journey, the entire journey from onboarding to your expansion, and what systems you have around it. I know it's a long question, so you have all the time in the world. Explain that. Sara Wyman 15:02 Yeah. So we really focus on like our wedge is really finance getting into a company. So finance and accounting, they're the ones that feel this pain the most. So we start with them, and then we try to create kind of a magical moment in the product so that it expands beyond just finance. And so typically it is there's a renewal coming up or maybe there's a new vendor that they're looking at. They need to bring in all these different team members. So that's where kind of expansion within the platform happens. I think you were asking about how to find these folks. Is that right? Adil Saleh 15:42 Yes. Like how, let's say if you talk about finance, like if you talk about this persona, what is the typical journey starting onboarding and where, at what point, you guys indicate ahead, these are like successful onboarding, because a lot of these, like more than 25% of the customers actually quit, whether they tell you or not, and for quarterly contract or monthly, but they quit more than 25% between onboarding to adoption. So what kind of success metrics you guys have to ensure that? And that comes like the first value as you mentioned. So at what point for these finance team that your team gets triggered or gets sort of a proactive notification that, hey, we need to deliver this first value to make sure that we have to lead this impact so they're successfully adapted to the platform and they start the journey. Okay. Sara Wyman 16:29 Yeah. Let me talk a little bit about the funnel. So as we acquire them, and then I can talk a little bit about post-acquisition. I think that would be a good way to approach. Adil Saleh 16:38 Yeah, that's a good way to explain. Sara Wyman 16:40 Cool. So yeah, on the Go-To-Market side, I think there's a few things that we obsess over. So the first one is, I guess I'll call it velocity. So it's really like lead to close velocity. And so for us that's close rate and days to close. And so right now we're at a 33% close rate, 21 days. And that's been pretty stable the last year. So if that starts changing, we're going to be looking at that very closely. And so 33% close rate, 21 day sales cycle, that's very, very different than doing 33% over 90 days, right? And so we're really trying to figure out like, hey, is this channel, are they ready to buy leads there, or is there noise? So that's kind of the first thing we look at. The second thing you mentioned is our trial to paid conversion. We're obsessed with this because this tells us, is the product delivering on its promise and is the lead quality high? So today we're at 97%. If that starts trickling down again, that's telling me this channel is a problem. It's probably not a sales issue. And the last thing, we're just starting to get more savvy on this, but is like CAC, cost of acquisition by channel. I think we're finding that referrals have very different unit economics than paid, for example. Trust is very, very important. So now that we're understanding that, it makes capital allocation a lot more obvious. So that's how we think about the kind of acquisition side. Adil Saleh 18:18 Yeah. I have a quick question on this. I was just looking at your packaging and everything. I know that there's a monthly plan as well, and there's an annual plan. So when it comes to monthly plans, how long does it take for you to actually get the ROI from the customer, keeping the capital for acquisition and everything? Is it two months, three months, four months? How much is that? Like how long is the period? Sara Wyman 18:40 Yeah, it's a great question. We try to get ROI in 30 days. It takes one day to set, it takes five minutes to integrate us. We ask for 24 hours just to make sure the whole platform is set up, that our AI did its job, and that all the information's coming in correctly from the accounting platforms. So then we're able to start adding value immediately. Within 24 hours. And so the kind of first moment there is really a sigh of relief. It's visibility and it's control. Like that's the immediate thing that you get day one. And then as we go through the month, then we're looking at cost savings. So we're immediately telling you, hey, here's the places to reduce spend. Here's where there's duplicates, here's where there's overlap. Hey, there's this renewal coming up. Here's the way to negotiate it down. And then over time, I think the third piece is time savings. Right? Because all of a sudden now your contracts are all in the same place. All of your spend is in the same place. All your reporting is where it needs to be. So over time, you will save quite a lot of money and time. But the time piece does come in in that first month. Adil Saleh 19:46 Absolutely. So for the second month, you start making money and that's where it's also mission critical for customer success as well. You gotta make sure that they see enough value that's true for them to be able to pay for the second month, for you to make money as a business, so that becomes critical. So what kind of success metrics you have, in terms of data that you guys are tracking for the second month, when you're trying to digitize or hybrid kind of a touch or low touch, if that is a small customer. That is completely obvious with all of this AI and everything. So what is the process and workflow post second month that is driving success across the journey of the customer and, in best cases, they've already adopted? In most cases, it's going to be something like they need to integrate or they need to do some actions or anything, any activation that they need to do in the second month for you to get a signal, hey, I can sleep on this customer now for your CS team. Yeah. Hey, is it good to go for the following at least three months. So what is that process? Sara Wyman 20:40 Yeah. For us, honestly, it's pretty clear. It really is like usage and engagement, right? And so there's a few signals we have. So if we have a good portion of your contracts on file as a percentage of your vendors under management, you're likely a pretty happy customer. Because you're getting alerted on renewals and savings opportunities and spend increases, and you're showing a lot of engagement. So that's one thing. The obvious one is if your team is logging in every day and doing procurement workflows or maybe speaking to our AI assistant, or looking at our spend numbers, then again, that's telling us that you're getting value there. So those are the two major things. I mean, they're pretty obvious, but it's kind of like data under management. How much are we now a part of your workflow? And then the second piece is usage. And so that kind of tells us how things are going. Adil Saleh 21:36 All those data points are basically available and being well articulated from the success standpoint to the customer facing teams. Meaning like account management, customer success? Yes. So they have some sort of dashboard or triggers inside Slack or email? Sara Wyman 21:50 Well, all the above. I think the important thing is, when we get to that QBR or that annual renewal, we don't wanna have that be the first time that you've seen our value. We're constantly kind of in your face about it. So yeah, it's on the dashboard. We're telling you how many vendors are under management, or how many renewals we're working on, or how many new requests are in the flow. So we're telling you that. We are emailing you with opportunities to save, we're emailing you with alerts, and obviously in Slack too, and other channels. And so the whole goal was that Adil Saleh 22:20 click on them. Sara Wyman 22:21 Yeah. Adil Saleh 22:22 I'm sorry, go ahead. I'm sorry. Sara Wyman 22:23 I was saying the goal is that the value is so obvious that when we come up to a renewal, it's a pretty natural conversation, right? It's less of a conversation around features and more about like, oh yeah, of course. I need this, I'm gonna keep using. Adil Saleh 22:39 Yeah. It's just like my six, seven months old daughter. If I showed her the Coke the first time, sorry, because I became a first time parent and now I knew it, like Coke is such a big brand. I just showed her once while I was eating Diet Coke on a dining table, and she just started screaming like, I want Coke. So it's just like that, you don't want Coke or you want Coke to a kid. I mean it's sticky, that I realized as well because I was just looking at the feature set and everything. Now thinking about the product, one last question that we can move forward on this. Thinking of the power, let's say we have on our platform, we have signals, we have copilot setting up skills inside those. There are some features that are okay for them to use and there are some features that are kind of having a direct business impact on them. So the tracking, because a lot of times when your CSM is managing 50 or 60 books of accounts, now at that time, and like 15 of them are hitting renewal in like 10, 15 days, one to two weeks, they're gonna burn out. So at that point then you're gonna track some of these power modules, whatever you call them. Do you have any of those segmented or do you have any smart views set for whatever system you guys use or any platform for your CSM team to stay on top of those features first, until the customer doesn't engage with those features and keep nudging them, keep giving them feedback or maybe doing some cadences and anything. So do you have any system to maybe power features among them? Sara Wyman 24:10 We use kind of a mix, I'd say, of HubSpot, Amplitude, and Pylon, is what we use for our stack. And so we do segment our customers into various buckets. And when we were just getting started, it was kind of like high touch, low touch. Now we actually have cost buckets, right? We have pricing buckets, either that are basic or standard or enterprise plan. That makes segmentation very, very easy, and we can match the service levels required for each of those. So we do that primarily in HubSpot. And then that does get managed actually in Pylon, which is a great kind of new CRM. Adil Saleh 24:49 Yeah. They've got such big bucks to spray. Their pockets are always hot. I was in London two, three years back and I attended their marketing play in the heart of London, and they spent huge amount of money on the marketing. At that time they were kind of smaller, might be smaller than now, but yeah, I'm pretty sure they have a really good platform because everybody was talking about them. But yeah, I'm pretty sure Amplitude is also building another kind of a success or revenue management platform, because they hired one of our partners, he was building a product management tool, which Amplitude was at the beginning, and now they're thinking of moving more. Like a lot of these companies are consolidating revenue management and all of that too, and that's how our category is kind of getting noisy and that's why we are. Sara Wyman 25:40 I think we would be interested in that because when it comes to renewals, we think about them in cohorts kind of by quarter. Adil Saleh 25:46 Yeah, they'll take some time. Yeah. That's why we have it. Sara Wyman 25:48 So it's pretty manual. Adil Saleh 25:50 Yeah. That's why we have it because it's not easy to build on that layer. But from an engineering standpoint, when it comes to building something like Amplitude and a really, really good product for product managers, the engineering is different in the backend, although they have sources and everything that is different. But it was not for a customer facing role. It never was because these were more for product managers, how to make the decision making across the features. Maybe the feature related feedback they could compensate into that. It's similar to Mixpanel in a lot of these. Now that they realize that, hey, the revenue management off of this usage is super important, so having a direct ROI impact, they're also gonna integrate. I'm telling you right here, they're also gonna integrate the qualitative data sources too. Right now you're more concerned about thinking about, hey, these are the things that they are, maybe some of the features and modules people are using, and that gets us triggered like this is the health of the customer. This is how we're gonna go about the QBR and customer outreach cadences going forward. It's gonna be more about stakeholder tracking and thinking about what kind of mentions they have on the email, external data sources like their layoffs, their new vendors that they are hiring from LinkedIn and public sources too. And this is what we are doing. So that's why we are one of the AI first or AI native new age GTM tool for customer lifecycle management. When we call it customer lifecycle, it comes with anything when your customer becomes your customer and beyond. So it's just like that makes sense. So perfect on thinking about a lot of this, net dollar retention, net revenue retention is some of the biggest talk in the town. What kind of operations do you think that you suggest that you are foreseeing going forward in 2026? It's a big thing internally as a chief executive. I've taken some initiatives to make sure that we have our revenue and have a complete foresight and forecasting around the health, around the revenue or expansion, and increasing the lifetime value of the customer. Because when you talk about a monthly, and we talked about the ROI calculation from the capital or acquisition to you getting to the second month, if we talk about account value more than 10,000 a year, as in your standard plan, how do you see the ROI part managed? What's the process to increase the lifetime value over time for the next year? Any process, any operation, any initiatives you guys are thinking about? Sara Wyman 28:14 Yeah. Yes, very obsessed with that dollar retention. We're pretty lucky. Ours is 250% right now. We're lucky in a sense that, yeah, it's quite high. But part of that is because we priced way too low when we first went to market. And so we have, probably for the next 12 months, a lovely kind of tailwind there. We have these pretty natural upsells. So there's that piece. I think another piece that we're seeing great results with this, and I think others are looking at it, is usage based or outcome-based pricing, if you can. So we did move recently from a flat subscription fee to a usage based fee. Adil Saleh 28:52 Usage based. How is that going along, ROI wise? Sara Wyman 28:55 Wonderful. Adil Saleh 28:56 For customers, annual customers, they're paying like 10,000 or above a year, like in your standard plan, is that economically, it's like Sara Wyman 29:05 it helps us out quite a bit, right? Because from a cost of goods sold perspective, these AI costs are getting quite high, right? Adil Saleh 29:13 Token consumption. Yes. Sara Wyman 29:15 As customers are using our platform more and more, adding in all their contracts, it sometimes can be like 3000 contracts, for a company. It's pretty expensive. Adil Saleh 29:25 Document generation, image generation, video, that costs a lot of tokens. Sara Wyman 29:28 It's a lot. Adil Saleh 29:29 And Optum, right? Sara Wyman 29:30 Yeah. So we literally had to charge by usage basis. And I think it may even need to move to contracts at some point because they're so expensive to process. And so I think you're already seeing it, but I think there will be a big move to that model. What's nice about it too is it allows us to go work with that 20 person company and it allows me to work with the 5000 person company and give them a similar type of product if they wanna start with that base. And then you asked about how do we expand these customers. I think it comes with a lot of feature expansion, obviously, as well. We're in a space of feature expansion. Lots for us to build, and so our roadmap has really looked like, year one was building that system of record, visibility, control. Year two was all about the intelligence, benchmarking, utilization, building a true procurement product. This year we're so lucky, we're in this place now where we get to just build agents on top of it that actually can do all the work for you. And so with that, when you're taking work out of the hands of humans, naturally, there's a willingness to pay for that. Adil Saleh 30:36 Yeah, absolutely. And especially when it is about economic events, all of them like buying tooling, optimizing the cost of the tooling, optimizing issues. To be very honest, it's not millions. It's billions of dollars being spent between the valuation period. We, a very small company, a team of 10 or 15, we are barely at 5000 monthly MRR, we took like two months to evaluate three or four different tooling to get to a tool that can help us do the editing and everything. So now we are building our own agent. That's another thing. But three months we paid like, what, $150? Think of big companies. So if you just help enable companies to evaluate really, really fast by bringing all these insights that you're talking about, the comparisons and all those valuation components, this could be a big market. And I see this category moving really, really fast because every company is thinking about optimizing cost. Sara Wyman 31:33 That's right. So, yeah. Very natural ways I think you had good levers for folks to think about is pricing structure, which is changing so fast, and human labor into feature sets. High willingness to pay. So lots to do there on the expansion. Adil Saleh 31:52 Absolutely perfect. So now I know that you guys have most of your team members out on the West Coast and the culture has been there two years. And the kind of person that I see, the energy, the infectious and everything, you are as a chief executive, what kind of culture are you trying to cultivate across this small team and what is that one thing that people would recall or put you guys down as, this is Stackpack's team is like this. They're witty and they're so marketing heavy and they're so vocal about all the things and they're so into the culture, like trips, events, these kind of things. What is it you guys are recognized for? Sara Wyman 32:31 Yeah, that's a good question. We actually screen for this a lot in our interviews, but the number one thing we look for is curiosity. And so people that are very comfortable and excited to question the status quo and kind of everything happening around them, you need that right now with the emergence of AI. And so we've really built in the culture to have a deep curiosity. Adil Saleh 32:55 How do you measure curiosity during the interview while onboarding people? Sara Wyman 33:00 Yeah. You can do it with kind of throwing surprises at them and seeing how they handle it or pushback. Are they comfortable debating, you know, testing them out? Are they comfortable thinking through new concepts, right? How quick are they on their feet with that? And again, you don't necessarily need speed. Maybe it takes you a bit to think about it, but just that there's comfort around that. And excitement that comes with the new, right? Adil Saleh 33:27 Absolutely. Absolutely. And a lot of these, do you think that this is more like a team, because of course you're chief executive, you're responsible for all these people, like a family. The head of family, I prefer it more like that for a small team because we are a small team. Everybody knows everybody, everything about everybody. Like their pain, their struggles, everything. So now thinking of in this AI age, whether you are struggling with it or not, because a lot of these team members, they are over reliant on AI. So that is taking the power of thinking away from them. I know that AI and everything is so intelligent and gets them outcomes as they want, but that takes them away from their natural thinking model. So what is going on? This is asking for myself and my team just to learn. Sara Wyman 34:19 Yeah. We talk about this as a team quite a bit. I think there's a natural, this is a good thing, I think there's a little bit of skepticism on our side, which helps, right? So using AI as a guide, but maybe getting it 80% of the way and then taking it the final 20%. This is exactly that 80/20 split, is how we're coding right now. It's how we're designing right now. It's how we're doing Go-To-Market outreach, right? It's putting the human piece back in. And I think we've all been talking about how over time, that demand for that human experience and that human touch is just gonna go up. And so again, that human touch, human judgment, human relationships are just really important. So yeah, I think it's a split. And so just upleveling the team, it's been interesting already to watch folks that are ICs now be able to say, actually I can give parts of my job to others that maybe are not on my team, necessarily, they're in other parts of the organization. And now I'm just going to advise them. So like, an example is a design team. Before they used to design every single little piece of the product and every piece of marketing. Well, now your marketer can do some of that. Maybe your product manager can do some of that. Because that uplevels my designer actually, because they're just giving feedback and making sure to uphold the brand and the product design values. And so it's changing the roles for sure. Adil Saleh 35:49 Absolutely. And for this, a quick question on this too before I set you free, I'm sorry, taking a little over in time. Because these are some of the problems that we are undergoing as well, and I'm asking like five or six founders some of the problems every single month that we are facing. So we get to learn, is the expansion of the roles. Of course, product marketing two years back, a year back, was only doing a lot of things and now they've gotta do a lot of this, maybe some content, video growth, component automation, building agents, managing agents, all of that. So how are you getting people on the same board. But number one, of course, they cannot do it if they're not passionate about it. Like this new team, how you're trying to instill this whole vision into it. Hey, previously we had like three people doing it. Now you gotta be doing this and leading all of this decision making, doing all of it using AI and all of that. So what's the backlash that you're, not in a negative way. A lot of people say like, hey, I was never good at content. There was this one guy who was really good at technology integration and all, really smart guy, and we still have him and we're gonna keep him for the longest time. But that guy told me a year back when he started after probation that I'm not good enough with the content. I said, that's fine, we can have someone else do it. And we hired another team member that does it now. The same person, I'm just laying off that other person, and the same person's gonna do the content, but now with AI and everything, so yes. But he has it in the back of the mind. A lot of these people are so opinionated sometimes, for good or bad, that they think that they cannot do it with AI. They can now. So how to instill that thought or vision in a way that it doesn't hit, it doesn't demotivate them. It doesn't take away their passion and everything. So how you do it? Sara Wyman 37:30 Oh, it's a good question. It's a hard one, right? Because you have some people that are so excited to use it and to level up. And you have others that are fairly terrified of it, or really just quite adverse to it, and they wanna stay with what they know. And so we try to make it kind of a cultural shift as a company where we, a few things that we do. One is on Fridays we have, we call it highs, lows, and demos. And before AI came back, it was just like, show us what you built this week. But now it's, show us what you built and show us also how you used AI to do that. And that's not just engineering teams by the way, but it's also our Go-To-Market teams, like, show us what you built. And so trying to move everybody into a builder. Essentially the other piece is just measuring success, right? Like, okay, maybe you used to send a hundred emails a day. Well now you're sending a thousand, right? And we're gonna have to measure that every week, right? And getting people to realize, they're not gonna actually be successful in their role if they're not using AI, because that's the norm now and that's what you're competing with. So there's a little bit of education and definitely measuring that that go along with that. Adil Saleh 38:40 Absolutely, because we never know what's gonna, what AI is gonna do next, like what outcomes. And so it's always equally important for us as leaders, as well as those team members that are responsible for those outcomes, to measure it at all times, every single function. So thank you very much, Sarah, for taking the time. The energy was infectious. I loved this conversation. It seems like it. I'm just talking to a colleague who was willing to get in trenches and willing to share all the problems and all the wins and stories and everything. Thank you very much for being such a person and never lose this heart. Sara Wyman 39:14 Yeah. Thanks for having me. Intro 39:17 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.