A CMO Guide to Moving Up Market

Drew: Hello, Renegade Marketers! If this is your first time listening, welcome, and if you’re a regular listener, welcome back. Before I present this episode, I’m thrilled to announce the first-ever in-person CMO Super Huddle that we’re hosting in Palo Alto on November 8, 2024. The theme is “Daring Greatness in 2025” and we’re rocking a full slate of inspiring speakers with ample time for networking. Tickets are on sale now, so grab yours at cmohuddles.com. It’s gonna be flocking amazing!

You’re about to listen to a recording from CMO Huddles Studio, our live show featuring the accomplished marketing leaders of CMO Huddles, a community that’s always sharing, caring, and daring each other to greatness. The marketing leaders in this episode are Allyson Havener of TrustRadius, Sheri Chin of Galileo Financial Technologies, and Jakki Geiger, who most recently was the CMO of Hazelcast, who joined us for a conversation focused on moving up-market from SMB (that’s small and medium-sized businesses) to enterprise. They share hard-earned insights into knowing when to make the shift and how to do it right. If you like what you hear, please subscribe to the podcast and leave a review. You’ll be supporting our quest to be the number one B2B marketing podcast. Alright, let’s dive in.

Narrator: Welcome to Renegade Marketers Unite, possibly the best weekly podcast for CMOs and everyone else looking for innovative ways to transform their brand, drive demand, and just plain cut through. Proving that B2B does not mean boring to business. Here’s your host and Chief Marketing Renegade, Drew Neisser.

Drew: Welcome to CMO Huddle Studio, the live streaming show dedicated to inspiring B2B greatness. I’m your host, Drew Neisser, live from my home studio in New York City. Here’s a common scenario for B2B businesses: You’re in a group, you build a successful company targeting small to medium-sized businesses. You know your customers’ needs, and you fulfill them at every step of their journey. Your pricing, your product, and your promotions are literally on target. Then someone in the C-suite asks, “Hey, what about targeting enterprises? Can’t be that hard, right?” Suddenly, every message, every system, every sales play needs to be revisited. Your staffing needs change. Meanwhile, you still have your original customer base to keep happy. It’s a complicated transition, one fraught with challenges. Fortunately for you, we have two CMOs with us who have recently gone through the process, and another CMO with deep expertise targeting enterprise customers. 

With that, let’s bring on Allyson Havener, Senior Vice President of Marketing & Community at TrustRadius, and a returning guest who previously appeared on the show to discuss product-led growth and B2B buying trends. Hello, Allyson, how are you and where are you this wonderful day?

Allyson: Hi, Drew. Thanks for welcoming me back. I am coming to you from San Francisco.

Drew: Awesome! Actually in the city of San Francisco?

Allyson: Yes, I live in Russian Hill in San Francisco, so in the city proper.

Drew: Wow. Very exciting. Love it. I love San Francisco. So you’ve been through this process at two companies now, in your previous role at LiveRamp and now at TrustRadius. So how do you know when it’s time to move up-market? And were there similar signs at both companies?

Allyson: I think it really starts with your product-market fit. And so when you’re doing that analysis of your kind of addressable market, who do you want to go after? Who are your targets? It’s really thinking about and analyzing your product-market fit. So at LiveRamp, CRM retargeting for digital advertising was very, very new back in 2012, and so we were looking at who would be a good fit for this, who has a lot of media budget, who has big CRM systems, and also who’s in a really competitive market where they have to be innovative, they always have to find that competitive edge. And so we really focused on the persona, and then also the company that they would be at. So we started with retail. We knew that retailers are in a highly, highly competitive market. They have to continually innovate. They also, from a digital advertising perspective, have huge media budgets. They have huge CRMs, and so that’s where we really started to focus and gain some wins there where like, who are some of the most innovative brands in retail? How do we break into those? And then how do we turn them into essentially our ideal customer, build them into advocates, and then kind of use them as our advocates out in the market to get other accounts, other enterprises. So it really started with the persona and where we thought we’d have the best product-market fit.

Drew: And so imagining, though, that as your target, first of all, vertical focus always a good thing. So you’re not saying, “Okay, we’re going after every enterprise. We’re going after this group of people. We can define what their challenges are and get to know them really well.” But I’m still imagining that there are certain things that you just simply didn’t want when you probably didn’t have the expertise on retail or that size. So what kinds of things did you have to do internally to get everybody aligned, to say, “Okay, we’re going after this group”? And you know, right now you have no credibility with them, right? I mean, if you haven’t sold to a new vertical at a different size, how do you make the inroads?

Allyson: I think it starts with the account planning and working with your team. So I think there’s a lot of internal systems that you have to think through as well. And so we decided to kind of build, almost like, we called it an investment map, and we started to understand, okay, where are we going to, you know, if we need to pull in enterprise AEs, you know, if you think about your current AEs that you have right now, who has that experience of breaking into the enterprise, also from your marketing staff, right? Like, who has that expertise, especially in the product marketing sector, right? Your product marketer needs to understand the messaging, the pain points. Does that market analysis, also the analysis around the packaging and pricing is really important too. So there’s some of those internal systems that you need to figure out as well, when you’re doing that external market analysis. And so once we decided we’re like, “Okay, hey, we don’t have a leg to stand on,” you’re totally right. But can we hire some AEs that could break into these accounts? Do we have the right messaging? Do we understand their actual pain points? How do we create content around that? We had a very ABM-targeted approach of very phased approach. To your point, we’re going to go after the enterprise. Well, that’s like, the most broad you could say. So it’s like, what’s the first phase of this? And ours was like, okay, retailers, we hear these five accounts, and we think that we can break into, who’s the enterprise AE that can break into these accounts and knows how to work and multi-thread within a deal. We didn’t put any BDR resources on this at first, it was really AE-focused. And then we had a kind of like, almost like a SWAT-like product marketing team that really focused on vertical-specific messaging and aligning to their pain points, and then obviously positioning our product for that particular persona.

Drew: I did mention at the top that you had new hires because you have to find this expertise. You mentioned the notion of trying to get a couple of wins that you can then leverage to sort of say, “Hey, we’ve got retail.” So let’s talk about, I mean, a lot of that was, I think, LiveRamp. Let’s talk about any things that happened at TrustRadius, and how long does it take to get what you say, “Okay, we’re going to market. We’re going after a particular segment.” How long does it take between planning, we’re going to do it to we landed that first client?

Allyson: Yeah. So I was really fortunate at TrustRadius because we cater to the enterprise. If you think about, you know, the millions of buyers that are coming to TrustRadius to do research, most of them come from the enterprise and mid-market. And so our target audience for our vendors that we work with were already in the enterprise. So I was really lucky, kind of coming into that at TrustRadius. But I think one of the things to think about when you want to move up-market, and like the timing aspect, and you kind of mentioned this in your intro, is your current customer base of if that’s more mid-market or SMB, and then you’re making this transition to really serve the enterprise and doing some of that work internally to say, “Okay, this is kind of like our bread and butter. This has been, you know, how we’ve serviced them, but how are we going to shift resources, add resources to actually go after the enterprise.” And so that was one thing at TrustRadius we worked through because we do have a lot of SMB mid-market companies that are actually trying to move up-market, right? They’re trying to get in front of the TrustRadius enterprise audience, which totally makes sense. And we need to service them and make sure they’re happy customers. But it’s a different service model. So I think when you’re thinking about the enterprise and the resourcing that you put behind it, it’s going to be different. And I think it was really good for us to understand of our current customer base, how much ARR is coming from those SMBs and mid-market, then you can analyze how much it costs to actually service them, and then looking at the enterprise and understanding, okay, our packaging and pricing. How does this scale? How is this going to grow, and how are you going to make up for any lost ARR in the SMB and mid-market sector? So I think it’s kind of like working with your CRO, your CFO, to understand, okay, where are the cohorts of our customer base that we currently have, how much ARR is locked up in that? How do we service them? What does it cost to service them? And then, how are we reallocating for the enterprise? And then what’s the expected growth from that as well?

Drew: So I’m hearing a lot of this is interesting is that it’s impossible to do this without losing somebody because otherwise you’re really creating, “Hey, we have a perfect offering here for small medium, and we have a perfect offering here for enterprises.” It’s not believable, and it’s going to be hard. So if you’re doing it, you’re just going to have to expect you might lose a few people along the way. Is that fair?

Allyson: I think that yes, of course. And I think we’re all working through retention and growth within our customer base, because we know that’s really inefficient. But I think at the executive level and in board, and when you’re talking to the board about a shift and kind of going up-market, is that there will be some retention issues in your SMB and mid-market, and that’s okay. I think it’s about having that focus as well, and that gets really difficult. I think when you get your CEO, your CFO, and your CRO in a room, it’s really hard to say, like, “Hey, we’re going to probably lose X amount in ARR going after the enterprise. But that’s okay, because here’s how much growth potential we’re creating with our pricing model in the enterprise.”

Drew: Yeah. I mean, as you’re talking, I keep wondering. I know there are folks out there that have not done this right, but we’re not talking to those folks today, but I do think there’s some cautionary tales for those folks who try, but we’re going to move on. We’re going to bring on Sheri Chen, and we’ll be back with you, Allyson.

Sheri Chen, who is the CMO of Galileo Financial Technology, who’s joining us for the first time. Hello, Sheri, and welcome. Where are you and how are you this great day?

Sheri: Hi, Drew. I’m in Greenwich, Connecticut, which is right outside your hometown, New York City, and I’m happy to be here with you and Allyson and Jakki. Thanks for including me.

Drew: Oh my gosh, so exciting. So you heard a little bit about what Allyson said. You know, talk a little bit about Galileo. Maybe some folks want to know what Galileo is, and then, what are your motivations for moving up-market?

Sheri: Sure. So Galileo is a financial technology platform company, and we enable a wide range of solutions, everything from digital core banking to payments to lending to risk solutions, just to name a few. And you know, we’ve always served a variety of clients, but we were really best known for partnering with B2C, early-stage fintechs, and there were really sort of three factors that led us up-market. The first was the economic environment, as we all know, unfortunately, fintechs are not getting the access to capital that they once were. The second is we really took a hard look and wanted to diversify and accelerate our revenue stream. So when you go and you go after large established companies, well they don’t need capital markets to fund their innovation, and they come with large customer bases. So once they go live, the time to revenue is a lot quicker. And then the last factor that really drove us up-market was really market demand. Galileo has a really outstanding reputation in the industry. And large banks, non-financial brands and large established fintechs started coming to us because they really wanted to innovate faster, to stay ahead of the competition. And, you know, Galileo’s technology platform is just very well positioned for large brands that either want to leverage our pre-configured solutions or want to do it themselves and build their own through our APIs and technology, etc. So the market really brought us up there, you know, for companies that wanted to innovate with speed and scale.

Drew: Yeah, and what’s interesting about this, and as you’re thinking about your business, if you are thinking, “Oh, maybe we should target enterprise,” one of the good byproducts of being able to offer to multiple targets is the diversification. And as you mentioned, things that are beyond your control, like financing a small fintech that only ended when interest rates went up. So you’re sort of, in some ways, you’re spreading your business risk. However, one of the things that you said is you had already seen the inklings of demand. So this wasn’t like you were going off into territory without “How the heck are we going to do it?” But I do imagine there were still some things that you had to do to put in place to service this group of people versus your smaller fintech. And talk a little bit about the internal preparations required to be enterprise-ready, if you will.

Sheri: Yeah, so you know, everybody gets really fired up when opportunities start coming your way. But you realize, like, you can’t serve everybody the same way, in the same manner, and it really starts to force, it really forced the company to get very client-focused in terms of prioritization and alignment and like, “Who do we really want to serve? Who are we?” And like Allyson said, “What is the right product fit like today, but also where our roadmap is headed?” And so one of the first things was very similar to what Allyson said, is like understanding who is our ideal client profile, who are we going after and getting alignment on that with not only our sales team but across the entire organization, with product Customer Success operations, because serving large enterprise clients is a completely different ballgame than serving, you know, sort of early-stage innovators, entrepreneurs and founders. So, you know, gaining alignment on the ideal client profile and the specific segments was really important. One of the ways we got our heads wrapped around that is we literally have targeted account lists for every segment we’re going after so that everybody is very cognizant of and understanding the segment, but also the specific targets we’re going after. Another thing that we sort of built organically, but then really started to cultivate, was like a Partner Network that could serve the prospects that were out of scope for our ideal client profile. We don’t want to leave prospects who are coming to us high and dry. You know, we may have served them that profile in the past, but we just don’t have the bandwidth to be the best that we can be for everybody. So we had it. We really built out a really strong partner network to refer prospects who didn’t quite meet our sort of upmarket profile. And the really great thing about that partner network is that they also refer clients to us that they can’t serve.

Drew: So many interesting things to unpack. I want to get to partners. But before we do that, can you name a couple of specific things that serving Enterprises was different? I mean, that were, you know, let’s get really tangible here in terms of things that and folks that, if you haven’t done it you might miss and are really important. So talk a little bit about those things that you had to change in order to be able to service this larger customer base.

Sheri: I’ll give you the perfect example. When you’re working with early-stage companies, you are talking to the founder, the CEO, the CSO, the Chief Product Officer, and you can get a decision made relatively quickly if you’re all in the same room and you’re sort of working with two or three people. In large enterprise deals, the deals we go after now, we may have 20 stakeholders across five different functional areas, and really sort of sussing out who are your advocates, who are your detractors, who can help advance the conversation and the deal, really understanding the different roles of all those stakeholders is critical. So really mapping that targeted account or that enterprise account that we’re going after is really important, because pain points and concerns of the Chief Product Officer are probably different than the Chief Financial Officer, and making sure that we speak to the pain points and the solution, you know, sort of those different information needs, and developing content appropriately for the different stakeholders as a large enterprise is really critical to success.

Drew: It’s so interesting. And I just want to sort of, we’re talking about trade-offs here in this show. And you think about enterprises, say, “Oh, well, it’s going to be a million-dollar deal.” And you think about small business, and it might be a $25,000 deal. But here’s the reality is, it takes maybe, 6-10, times longer to close. It takes a lot more resources to close. It takes a lot more resources to service. So when you finally add up all the math, you really better be doing good math. That’s for sure. You know, if you’re used to doing small and they come to the website and they make a decision that’s like, boom, and, you know, cash in the bank. So if you’re going to go after enterprise, you better have some patience.

Sheri: Not only is like the time to close so much longer, but potentially your time to revenue is also longer, right? Because it takes longer to onboard and much more complex large organizations. If you do it right and you have the right product clients, your revenue potential and your revenue realization is like so much larger. So yes, you are making a bigger upfront investment in time and money, but you have to factor all of those incremental costs of servicing a large client into your financial model so you don’t lose your shirt, but also really focusing on that time to revenue, because when you have a larger client base, once it gets turned on, if you have the right product fits, conceptually, you’ll get revenue a lot faster and more of it.

Drew: Okay. Well, we’ll come back to you.

Let’s welcome Jakki Geiger, who’s patiently been waiting. CMO of Hazelcast, who’s been on the show before, to discuss customer-centric marketing. Hello Jakki. Welcome back.

Jakki: Hi Drew. Nice to be back. I really enjoyed the conversation so far, and hearing Allyson and Sheri’s advice.

Drew: Awesome. So first, where are you today?

Jakki: I’m just fresh off of a vacation in Maui, where we spent a lot of time snorkeling, so I’m all refreshed and re-energized. I’m in my home office for two days, and then Friday fly to London because we have our QBR taking place next week.

Drew: Oh, my God, alright, so we’re just spanning the globe here anyway. So you’ve heard the conversation about this, and as an expert in a company that targets enterprises, what were some of the things that you heard so far that sort of really resonated with you?

Jakki: Absolutely. So I’ve spent my entire career focusing pretty much on the global 2000, building brand awareness, creating new logo pipeline. That’s been the area where I’ve spent most of my time. So yeah, the advice absolutely resonated with me. If you’re going after enterprise for the first time, you can’t be everything to everyone. So I really liked Allyson’s point about the ideal customer profile and understanding, like, what are they? Are there industry verticals or a specific use case that you are uniquely positioned to win, and right, like you want to make sure you are in a great position to win those deals. So that really resonated with me. Focus and alignment. It is a team sport, right? Across the entire company, if you’re changing your ideal customer profile and going up to enterprise. So that also resonated with me. The biggest difference I have found is the sales cycles are longer. It’s six to 12 months. The deal sizes, you know, for me, right now, it’s about 100k. At a previous company, 250k. Another one was 750k average deal size, right? So these could be really monster deals. Then, you know, we closed some pretty monster deals this year, or in 2023, at Hazelcast, which was fantastic. The sales cycle is long. It is complex. You know, as Sheri was saying, there’s a lot of different stakeholders involved and understanding those stakeholder needs. What are the questions they’re likely asking throughout the buying process is really, really critical. Having partners who have, like, a really good relationship with your champion or economic buyer can certainly accelerate things.

Drew: And I’m curious. So one of the things as I was hearing Sheri talk about, you know, 20 different decision-makers and buyers. And I kept thinking of Brent Adamson talking about the pain of change versus the gain of change, and the fact that there are some people that you’re selling to, whether it’s the CFO or the technologist who just doesn’t see what’s in it for them, and you know, they’re just gonna resist the change, and we’re seeing that a lot in the conversations and huddles about how hard it is to close an enterprise deal right now. What’s your thought on that? I mean in terms of multiple stakeholders and trying to herd these cats to one place where we can finally pull the deal out in what’s working.

Jakki: In my experience, the best sales reps create a very strong champion who does most of the selling for them. So tapping into that right person who’s motivated, from a business standpoint and a personal standpoint, to adopt that technology and bring it into the organization and to make it a successful project, is, to me, the secret sauce of getting these enterprise deals closed and getting all those 6-10, to 20 people who have a say, who are contributors to that discussion, to get them on board and get them behind it, and get them willing to say, “Yeah, we want to make this investment. It’s going to be good for our business.” And if you can show the ROI or the total cost of ownership going down, right? If you have some kind of financial metrics, so it becomes like a no-brainer, like, why wouldn’t we do this? That makes things easier as well.

Drew: So I’m curious about cultivating these champions, because we hear this a lot, but there’s always risk in change, right? If you’re bringing a new software, you’re bringing in a new system. You’re doing something that is going to bring a new, improved ROI. How do these champions get developed? Is it because they worked with you before? What’s the salesperson doing and what’s happening behind the scenes that would have someone stick their neck out to make the company change and make a big purchase decision?

Jakki: So I like to talk about movers and shakers and campers, right? So a lot of really good reps say, “I’m going to find the movers and shakers.” Maybe someone just recently got hired into a new role, and they want to make a big impact, or they just got promoted, or they want a promotion, right? They want to do something to get their bonus or exceed the target they’re after. So it’s finding those people, those movers and shakers, that I think is critical to the success for a sales rep to get into an enterprise sale and win that deal.

Drew: And it’s so interesting, because it’s about them making their mark, and you become something that, in theory, somehow or other, they got the idea that they’re going to be more successful in their career by bringing this change to the organization, which is really interesting, because other folks may see that, oh, this is all about him or her. So somehow or other, you have these champions, but they still have to bring everybody else along with them.

Jakki: Absolutely. I’d love to just share one of the things that maybe you know, some concrete advice that people don’t think about as they’re going into marketing and selling to enterprise is the impact on the planning and budgeting process, right? So just to give you guys some visibility, our sales cycles could be anywhere between nine and 12 months. So my team right now is building pipeline for the next six months to close in 2024. Starting any opportunities that hit like sales accepted pipeline by August or later, unlikely to close in 2024. That’ll be revenue for 2025. So I need to start, you know, leveraging our sales leader, our sales ops team, my marketing ops team, and we start planning. You know, what do we need to do from a revenue standpoint, back that into pipeline, number of opportunities that we need six months in advance. So that’s something that maybe not everybody thinks about as they’re planning to go into enterprise, is that you actually need to move the planning and budgeting process forward, because those sales cycles are longer.

Drew: Right? I mean, you’re working on deals that right now that aren’t going to close until 2025 and already it’s quite possible, which gets into this whole sort of leading, lagging indicators of what’s, you know, the health of the business, or what marketing is actually doing. And a member of our audience talked about the 95 that are not in the market and the 5% that might be in the market. Thank you for that comment. What’s your thought on that? And how do you balance because, again, the pressure is on everybody to close deals, drive revenue. Marketing needs to drive revenue, but we’re driving the actions you’re taking today, the revenue is going to show up in 2025. How do you manage that? How do you balance that?

Jakki: Right? And we only have so many sellers, and they only have so much time in a day. So for us, you know, finding those intent signals coming from the market is really, really critical for us, because our focus, our energy and time, and our sales team’s time on people who are likely going to buy, not the people who are maybe just, you know, curious or tire-kicking or exploring or trying to get educated. So we’re using intent data quite a bit for these highly engaging campaigns, targeting specific personas with our message where we think we have the highest chance of winning.

Drew: And so that’s going to get you current revenue. What we don’t know is, what about all those other people? Because that’s the sort of 95-5, right? The 5% of the intent signals. And then, just a side note, within that intense signal, you’re hoping that one of those persons is a mover and a shaker, right? So there’s a lot of forensics that goes on here.

Jakki: Exactly. Another interesting challenge that we’ve been facing since COVID and people are working, I like to say, in a distributed fashion, like we are here at Hazelcast as well. Is that idea of like, “Oh, these people must be in headquarters. Let’s do some location-based advertising to those people.” Well, no, these people are distributed all around the globe now, so targeting them is much tougher. So again, using those intent signals, understanding, if there’s 14 lines of business we could possibly strike a deal in. Where are we seeing intent from those different lines like we work with one of the largest credit card companies in the world, we’re currently in 14 lines of business, and there’s so much more opportunity. So finding those people is really, really critical for us.

Drew: Back to this 5 95, I mean, the truth is that those people who are in the market didn’t just accidentally get there. Other things were happening behind the scenes. They may have met you at a trade show so there’s a lot that’s going on before they show up and say, “Hey, I’m really interested.” And that’s this context of where marketing fits in long term, right? Something had to happen to get them to be interested.

Jakki: Yeah. In fact, data shows that it’s probably 12 to 20 things that had to happen before they’re willing to say, “Yeah, I want to see a demo,” or “I want to meet with you,” or “I want to request pricing,” right? There’s a whole bunch of things that they’re doing, interact in points that they’re maybe they see an ad, but they don’t click on and they go to your website directly, or maybe an SDR’s been sending emails, and finally, you’re like, you know what, maybe I do need this technology so attribution is so challenging. But you know, we know that it does take 12 to 20 touches to even get that person to want to engage with us.

Drew: And that’s the thing that I really want to talk about more in CMO Huddles, we talk about the buyer’s journey and tracking, but that usually starts with the first time they click on your website, and then it’s, you know, another 50 touches, or 30 touches. What we really want to see is, what are those 20 touches beforehand, and how can we get at that? Well, we’ll talk about that in a second. We’re going to take a quick break while I talk a little bit about CMO huddles, and then we’ll come back. 

Launched in 2020, CMO huddles is a close-knit community of over 400 highly effective B2B marketing leaders who share, care, and dare each other to greatness. Now, given the extraordinary time constraints on CMOs these days, everything about CMO huddles is designed to help leaders save time and empower them to make faster, better decisions. We got Allyson, Sheri, Jakki, you’re all incredibly busy marketing leaders. I’m wondering if you could share a specific example, if you would be so kind, as to how CMO huddles has helped you. Jakki, you’ve been with us probably the longest. Any thoughts you want to share?

Jakki: Absolutely! So Drew, I was really happy to be one of the founding members of this group. And I think one of the challenges I had as a CMO is I needed to bounce ideas off of people. I needed to hear that other people were going through the same challenges I was. So just having this network of really talented, curious people who want to learn constantly from each other has been an incredibly valuable group for me. I’ve also set up one-on-one meetings with some CMOs where, like, they have an area of expertise, and I want to learn more about that area, or vice versa, I have an area of expertise they’re interested in, and so I kind of share what I can. So for me, that’s been really, really valuable.

Drew: Awesome. I appreciate that, and I appreciate you and your long-term membership. Allyson, any thoughts?

Allyson: Yeah, I totally agree with Jakki in terms of the community building, and that’s been really valuable for me, especially this is my first time being in a CMO role and marketing leadership and reporting to a board. So it’s given me a lot, especially as I’m kind of entering this next phase of my career. I also really enjoy all the industry leaders that you bring in that are not necessarily in marketing, but they are tangential, and it’s really nice to kind of get that industry expertise. And how do you apply that to marketing? How do you apply that to your business? That’s been so valuable, and I’ve really enjoyed those sessions.

Drew: That’s awesome. Okay, Sheri, any thoughts, anything you want to share?

Sheri: Ditto, plus one to what Allyson and Jakki said. I’d also say that I love your recaps because they’re great reference materials, and sometimes I circulate that with my team, if, like, you know, they’re diving deeper into a new topic. And you know, it’s really great reference material and I just really enjoy all of the CMOs that I’ve met and learning from them as well.

Drew: I appreciate that. I was thinking of you as you mentioned partnership, because the last three recaps have all been on partnerships. I hope I haven’t been beating you over the head with it, but it is clearly as through our conversations, it became quite a source of opportunity to just really beef up the partnership part of marketing. 

Thank you, all three of you. If you’re a senior B2B marketer and need a shortcut to B2B greatness, do yourself a favor and visit cmohuddles.com and sign up for our free starter program. 

Okay, let’s get back. Got so much to cover, enterprise marketing and moving up market. So we’ve talked a little bit so far about this balance of moving up market without losing existing business. And, you know, I sort of concluded that’s impossible. But I’m wondering Jakki, or Sheri, any thoughts on it, as you moved up market, how did you make sure that you could keep your existing customers?

Sheri: I mean, I think working closely and again, alignment of strategy and product roadmap across not only new logo sales and operations, but also with our customer success team and figuring out if there’s a path for our existing customers to grow into or take advantage of the new solutions and products and services, and we’ve actually been really successful at cross-selling and in not only helping our existing clients grow, but growing with them together, because they bring new ideas to us as well. And it’s really a really mutually beneficial relationship.

Drew: That’s amazing. And as you said that, I wanted to ask Allyson about this is, as you do add these bigger customers, are you, you know, a lot of folks share their roadmap. Do you sort of confer with them to say, “Hey, what else could we do to support you?” And how’s that work?

Allyson: So we started a customer advisory board for the enterprise, and so all of our enterprise customers sit on that, and they help really guide the roadmap. You know, I think Jakki and Sheri both talked about, you know, when you think about your product roadmap, how are you servicing customers? And it’s much more complicated. And also, how are you going to expand within the customer base as well? And so our customer advisory board has been really, really important to our product roadmap and really helping us, again, define the strategy for enterprise.

Drew: It’s interesting, and I’m wondering, and maybe Jakki, you know this because one of the advantages of the customer advisory board is you can actually roll out or beta test things for them that you might not be able to because, you know, the value of customer is so high. How are you working with your top customers, Jakki, to sort of help develop the future of your product and service?

Jakki: Yeah. So in the past, we, at previous companies, we’ve had very strong beta programs where, you know, we say, here are some new capabilities that we’re rolling out, who is interested in testing it out, giving us feedback, good, bad, ugly, like, how’s it going with this? And there’s always those, you know. So we talked about movers and shakers. There’s also sort of this spectrum, you know, Geoffrey Moore’s law, where you have the visionaries who are willing to just take bets. They want that competitive advantage. They want everything early. They don’t care how raw it is, right? And then you got those people who are like, “Yeah, I’ll just wait till it’s all been tested out and working really well, and then I’ll use it,” right? So finding those people, those visionaries, within the accounts, also is really useful for beta programs.

Drew: So one of the things that occurs to me, we’ve talked about the high value of these enterprise customers, but you’re not the only ones targeting these folks. So the minute you land them, your competitors are going to be going, “Wait, whoa, let’s go get them.” And how much time and what role does marketing play at all in terms of defending right? Because it’s one of the things we talk so much in huddles about getting that net new and getting the next customer. Meanwhile, if you know, if stuff is falling off the back of the truck, we’ve got a problem. How do you sort of defend your stake with the enterprise customers? I’m curious, Sheri, as you’ve sort of gotten into this more, has that even risen up?

Sheri: Yeah. I mean, I think it’s really critical to understand why your prospects and new clients are choosing you right. So really making sure that you have win-loss interviews and getting insights into that has helped us really lean into our strengths and also close the gaps, or perceived gaps. In some cases, there were perceived gaps that we knew we had that technology or we had that capability, but we weren’t doing a good job communicating it. And so I think really understanding why customers are choosing you, helps you show and demonstrate your point of differentiation from your competitors, and why you’re the right fit for what that client needs.

Drew: Yeah, it’s interesting, because we know that with the enterprise, and let’s say there are multiple users, or something like that, that often they’re not taking advantage of it. I mean, we know in CMO huddles that not everybody can take advantage of every aspect of the service that we provide. So how do you track that and Allyson, maybe you could weigh in on this, because we’ve landed the customer, but we got to keep them, otherwise, this whole thing falls apart, right?

Allyson: Right. I think that’s the customer success model. Like the way you keep customers is you make them successful, and we do a lot of buyer research, and buyers are more skeptical, risk-averse than ever before. People are fearing messing up more than missing out. And so people ripping and replacing their tech stack is going to be more and more rare. People are relying on their own prior experience more than ever, and so the best way to make sure that you keep your enterprise customers is to make them successful and make sure that whatever you agreed in the sales cycle, like, here are the results. Here’s kind of the expected ROI. Here’s, you know, even from like implementation timeline, right? It’s really, if you say it’s going to take us three months, six months is when you start seeing results, you know, etc, whatever the timeline is, if you adhere to that, and you start to make your customers really successful, and also helping the actual champion that bought your technology, kind of advocate that within the company, that’s only going to make you more and more stickier. And again, in this environment and its economic conditions, people are going to be way less inclined to actually rip and replace their technology stack, especially if they’re finding success and you have that follow-through. So I think it’s really important that that customer success model is really buttoned up and it’s aligned to whatever your customer marketing and you know your lifestyle marketing strategy is as well.

Drew: You know this is going to make you laugh, but, you know, we’ve been talking about customer success and that as a model and as a service, but I never actually thought about it as making your customers successful. I never did, I know and this is both stupidity and the fact that so many customer success teams are really disguised sales teams that are just making sure that, “Hey, are you using the product, and are you going to renew?” And so nobody has said, “Oh, you’re successful.” And so one of the things I’m curious about, and Jakki, maybe, do you guys provide sort of report cards? Your customers say, “Hey, you’re using a product and you’re getting this value,” so you are having success, or you are achieving success as a result of working with us?”

Jakki: Yes, at one company in particular, we were very diligent about it, because they would say, you know, in the sales cycle, the solution architects would work with the champion to say, well, you’re going to get this kind of return on this investment, right? You’re going to generate $50 million worth of savings or revenue that you didn’t have the year before by implementing this technology. So our customer success team was focused on business value realization. So like onboarding was really critical, setting milestones, having a game plan, a project plan, checking in with the customer, regularly jumping in if they were in trouble and off track, so that at the end of that, you know, go live and value realization journey, they were wildly successful. And then for marketing, it was really helpful, because I could say, awesome. We delivered what we said we were going to deliver. Let’s get them to be a customer advocate for us. So having a really good process in place for making sure you understand what is your customer’s definition of success, and how do we get them there, whether through our own internal resources or through a partner network. Is, I think, for me, like a virtuous circle of goodness.

Drew: Well, and I love the term business value realization. I’m curious, do you need a third party to do that? I know that’s a service that you can pay a lot of money for. How do you actually do that?

Jakki: It’s nice when customers do it internally themselves. That’s the easiest, but they don’t always so yeah, sometimes it’s, you know, basically creating that type of program internally, and sometimes it’s leveraging partners to help build it out for you, where you can actually do an ROI assessment or a TCO calculator.

Sheri: Depends on also the size of the organization and how many key stakeholders. So in a past life, you know, we had smaller—we worked with mid-market, and we had very close relationships with the key decision makers, so we could actually have an advisory board and get the feedback. Today we’re working with like the largest banks, big, you know, brands and large fintechs. It’s very hard for them to get the key people to really be forthright and open up. And so we’ve had better success finding out, you know, getting really great insight and more honest feedback by hiring a third party, but it can get expensive again. Have to do the ROI on it to make sure you’re getting your value from it.

Jakki: I just had a great situation happen where we talked to a new customer who went live, and they’re successful as part of the case study process. And he revealed, he said, “Jakki, great news. We’re saving 30% in operational costs since we’ve gone live and started using Hazelcast platform.” And I was like, that’s fantastic. And we were able to get it just approved and, you know, just posted on the website last week. So when the information just comes from the customers, because they care enough to say, internally, I’m the champion of this, I recommended this technology, and we got these types of results across the company, then it helps them get promoted, get to that next level as well. So I don’t always think of it as just like, how does it help us? But also, how does it help them get to their next level of success?

Drew: This whole concept, I like to call it speed to hero. And if this is, how long does it take for your product or service to make the champion who wants to be a hero become a hero? I love that story, but in enterprise, often, getting testimonials approved can be really hard, because they don’t want to share. They might see your product as a competitive advantage. So I’m curious, and I’ll go to you, Allyson, what are the tricks that you do to get an enterprise customer to actually give you a high-quality testimonial with the data that Jakki’s talking about?

Allyson: So I’ll kind of come at it from like, two angles. So we help a lot of our customers, like, if you think about just TrustRadius, and then them getting their enterprise customers to leave a review on TrustRadius. They can be a hand-raiser, but it’s easy for our customers to do that at scale. So our large enterprise customers, they’re trying to get their customers on the record, most people will leave a review because it’s almost from like an individual standpoint. And they can even do this from like an anonymous standpoint, and so there’s a lot of, like, testimonial, customer stories and quotes that come from reviews.

At TrustRadius we’ve created a program, and we call it Customer Spotlight. So we kind of got away from the scary word of case study, because everyone’s like, “Oh, I don’t want to deal with s case study.” That just feels scary at first. And we made it about instead of, like, the brand that they’re coming from. We made it about the persona and the person, and we gave them like, a very prescriptive like, here’s the template, here’s the use case that you implemented. Here are the metrics that we’re looking for in terms of, like, you know where you were and where you are now.

And then we created this whole program where it like, it goes into our newsletter, it goes into this whole social feed. It goes into—we create content for our scene, we create content that’s more like thought leadership, and do LinkedIn lives like this. So we have, like, a whole program and make it really about the individual, just as Jakki was saying, like, how do you elevate them? How do they use this to get their next job, or whatever it is, or that promotion? And so I think when you make it a program and when you make it about the person, they’re much more inclined, and then also, as much as templatizing as you can so it doesn’t feel as like daunting an extra work because nobody has time for extra work.

Actually, one of our customers used their Customer Spotlight and all the content that we created for them, and they actually used it to get their next job. So they attached it with their resume to show some of the results that they were driving and their customer marketing program. So like I said, I think if you make it about the individual, it’s much easier for them to kind of buy in.

Drew: And that’s so interesting because this conversation has sort of come full circle. We’re selling to an enterprise, but we’re not, we’re selling to an individual, and if we can get that individual and all the way through, I wanted to throw in a couple of other things. So if you’re really struggling, and let’s say the company has a policy that no one could do a testimonial, two things that have worked that I’ve seen, I talk about them in my book. One is an awards program, where you do an awards program, and if they won’t give you the information, you still submit them, and then it’s very hard for them to turn down the opportunity to talk about the award. So that’s one and another is like podcasts and other properties, where they can just talk about themselves and what they’re doing, and then it becomes an implicit endorsement.

The last thing I wanted to say is, if you’re lucky enough to be in a category that is on TrustRadius, you might get these testimonials. Unfortunately, CMO Huddles is not a category we can’t benefit from that, which is why we do it here. That’s all. That’s a lot, a mouthful, I think. And I’m still contemplating the word templatizing.

So we’ve gone full circle. We’ve talked a lot about humans. I’m just wondering for all of you, because I know you prepared, was there something else that you thought in this conversation about enterprise marketers that we haven’t covered just yet? You know, I know, Sheri, you’ve made some notes. Is there something else we should make sure we cover before we wrap up?

Sheri: I mean, I think everybody has sort of acknowledged, you know, enterprise sales are a lot longer and as Jakki said, like a lot of times you’re building pipeline that you’re going to see the benefits of like next year, or in our case, could even be like the following year. So I think having the right sort of measurable milestones to demonstrate that marketing and the company is gaining traction against these enterprise sales and making sure that there’s agreement, not only with the CEO, but with the CFO, is really, really critical, because everybody gets impatient, right? And really being able to quantify how marketing is influencing, you know, your time to close and your time to revenue, I think, really helps, you know, maintain and grow your marketing investment.

Drew: Yeah. I want to throw this out to the group, this notion, and one of the CMOs in our huddles talks about their tiger teams, where, once the deal has started, they have a group of people. It’s a combination of marketing and sales and maybe even customer success. And they’re focused on anything they can do to try to accelerate the deal, which means anticipating everything right and trying to have it to the right person at the right time because deal acceleration right now is like everybody’s dream. I’m wondering. Jakki, any thoughts on that? On deal acceleration?

Jakki: Yeah, so at a previous company, I actually created what was called the revenue acceleration framework. And I mapped out, you know, the funnel, basically from, you know, stage one all the way to close and identify what are the points of friction, right? Is there usually between stage two and stage three? Are there a bunch of security compliance questions that come up? And it usually takes, like, two weeks to schedule the meeting, and then we have to present and then there’s follow-up? Could we just, like, create an FAQ document around security that would just expedite that whole process, right? So, identifying points along the funnel where there are friction points, and saying, is there a program or a piece of content we could create to accelerate that? And that’s worked quite successfully.

Drew: Amazing. Alright? Well, we’re at the point where it’s time for final words of wisdom for other CMOs when it comes to moving up market. We’ll start with you, Allyson.

Allyson: So I wanted to pull on the partner thread a little bit. We talked about it a little bit, but two things. One, if you can partner with somebody and integrate with your systems, and they already serve the enterprise, that is a fast-track way to start breaking into the enterprise. So look into your partner base, where you can partner and build an integration, or maybe there’s another avenue there. But I do think that you could fast track with partnerships. You can also from a serving your SMB and mid-market if there’s a reseller right. Your channel strategy is really important too. So think about your partner network, what you currently have, and where you could go, and how it could help you fast-track into the enterprise, and also serve, continue to serve, through resellers for your SMB and mid-market.

Drew: Thank you so much for coming back to partner. If you’re listening to this live or a show and you have a partner question, just hit me up on LinkedIn, because we just finished, actually four huddles on partnership. I’ve done recaps on all of them, and have a lot of good, fresh thinking. But there’s two things I want to add to that. One is, if in a world of GDPR and privacy laws where you can’t do some of the things that you’re doing, partners are the way into the door. That is really important. Part Two is very few companies actually offer the whole solution. And sometimes it’s, you know, it’s so much better. It’s like a flashlight and batteries. Oh, wait, yeah, because now I can use the flashlight. Okay? Sheri Chin, final words of wisdom.

Sheri: Don’t underestimate sales training. Selling into enterprise is a completely different sales sensibility skill set. Hunting is different than you know, SMB, early stage sales. So sales training is critical to success.

Drew: I love it. Jakki, final words of wisdom.

Jakki: So one thing we didn’t talk about, but it’s very relevant for our business, is that there’s two journeys. There’s the buying journey that our champions, that are economic buyers go down, and we need to make sure we have the content and programs to take them along that journey. But there’s also the trying journey, and that’s a completely different persona and profile for us. So as a marketing organization, we need to be thinking about those personas and what journey are they on, and making sure that they have sort of a seamless experience, and that we can learn as much as possible about each of those journeys to make it more efficient and effective for them. So the aha moment comes a lot faster in the buying journey as well as in the trying journey.

Drew: Yeah. It’s such an interesting thing. And we could go deep on all of them, partnering, sales training, or even the trying journey but we gotta wrap up. So thank you Allyson, Sheri, and Jakki, you’re all amazing sports. And thank you audience for staying with us.

To hear more conversations like this one and submit your questions while we’re live, join us on the next CMO Huddles Studio. We stream to my LinkedIn profile—that’s Drew Neisser—every other week!

Show Credits

Renegade Marketers Unite is written and directed by Drew Neisser. Hey, that’s me! This show is produced by Melissa Caffrey, Laura Parkyn, and Ishar Cuevas. The music is by the amazing Burns Twins and the intro Voice Over is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about B2B branding, CMO Huddles, or my CMO coaching service, check out renegade.com. I’m your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!