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Reinventing Legacy Companies in an AI-First World

C-Suite Sales & Marketing Perspectives · 2026-08-04 · 24 min

0:00--:--

Key moments - from our scoring

Substance score

58 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality10 / 20
Guest Caliber14 / 20
Specificity & Evidence11 / 20
Conversational Craft11 / 20

In a market flooded with AI-native startups claiming credibility, legacy companies face pressure to prove relevance. Cynthia Gumberg, CMO, argues this isn't the first technology wave to disrupt incumbents - the cloud transition and dot-com era proved that bridges from old to new are possible. Her approach centers on what she calls the company's 'pedigree' (deep market knowledge built over years) rather than positioning as legacy, combined with a structured Voice of Customer program that systematically captures and amplifies customer stories, feedback, and advocacy. Unlike vendors who contact customers only at renewal or upsell, her team maintains ongoing relationships through advisory boards, surveys, case study support, and conference speaking opportunities. This creates compounding ROI: customers become more credible marketers than any vendor can be, Gong and Salesforce tracking shows measurable pipeline impact, and importantly, it grounds leadership against reactive feature chasing when competitors announce weekly. The program also addresses change fatigue - customers report overwhelm from constant AI tool experimentation and model releases, so vendors who simplify messaging and offer calm, trusted guidance become invaluable partners for risk-averse B2B buyers.

Key takeaways

  • →Establish a dedicated Voice of Customer team to systematically capture and amplify customer stories, which creates measurable pipeline impact and ROI greater than any marketing campaign.
  • →Position legacy company advantages as 'pedigree' - multi-year deep market knowledge and proven reliability - rather than trying to out-innovate AI startups on features.
  • →Use customer advisory boards and steering committees to validate marketing messaging, product direction, and competitive positioning, preventing reactive zigging-and-zagging based on competitor announcements.
  • →Maintain relationships with customers when you have something to give them, not only during renewal or upsell cycles, to build trust and stay top-of-mind in a fast-moving market.
  • →In an era of AI feature parity and constant change fatigue, be the calm, trusted voice that helps customers focus on what truly matters rather than absorbing every new tool and model.

Guests

Cynthia Gumberg

Topics in this episode

Edelman Trust BarometerForrester customer obsession studyVoice of Customer programCustomer advocacy and reference strategiesLegacy company positioningAI innovation vs. feature parityBrand trust and customer relationshipsAdvisory boards and steering committeesCustomer success and retentionGong and Salesforce sales intelligence

Questions this episode answers

How does a legacy company compete with AI startups when buyers expect AI-native solutions?

Legacy companies can leverage their pedigree - multi-year deep knowledge of the market and customer needs - while building on the latest AI models. Success requires walking the talk through product innovation, maintaining long-standing trusted customer relationships, and helping customers avoid complexity and change fatigue rather than just chasing feature parity.

What is a Voice of Customer team and how does it impact revenue?

A dedicated Voice of Customer team systematically captures customer feedback, stories, and advocacy through advisory boards, surveys, case studies, and conference speaking opportunities. The program creates measurable ROI by turning customers into advocates (proven more credible than vendor marketing), and Gong and Salesforce tracking shows direct pipeline impact from customer references and stories.

Why do customers make better marketers and salespeople than vendors?

Customers are more trusted than vendors; Edelman's trust barometer shows 67% of buyers believe business leaders are intentionally misleading, while peers and advocates carry far more credibility. Customers tell authentic stories about real value received, which sales teams find invaluable for getting into conversations and shortlists.

How does staying connected to customers help CMOs avoid reactive competitive responses?

Customer advisory boards and steering committees provide grounding feedback to prevent zigging-and-zagging based on competitor announcements; customers often say 'just keep doing what you're doing' even when competitors' messaging sounds polished, keeping focus on proven value rather than reactive positioning.

How should vendors approach customer relationships in a market experiencing AI change fatigue?

Maintain ongoing contact with customers when you have insights or value to give, not just during renewal or upsell; simplify messaging around core benefits and stability rather than bombarding them with new AI tools; position yourself as the calm voice helping them navigate complexity and focus on what matters.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode delivers some solid framework-level thinking - particularly around customer advocacy as differentiation and the concept of 'pedigree vs. legacy' positioning. However, much of the substance is repetitive and surface-level; the guest restates the same core idea (customers are better marketers) multiple times without deepening it with new angles, mechanics, or surprising data. The Forrester and Edelman statistics are useful but well-known in CMO circles.

customers are better marketers than we are. We will never Be as good a marketer as a customer who's an advocate telling up here to buy our product
we're calling it pedigree, not legacy that has some connotations of being old, but we've got this multi year pedigree of history

Originality

10 / 20

The 'voice of customer' team structure is presented as novel, but the underlying logic - that customers are your best advocates, trust matters, and you should listen to buyers - is conventional B2B wisdom. The guest recycles familiar tropes ('walk the talk,' 'be the calm in the storm') and well-established case studies (cloud transition, dot-com era). There is minimal contrarian thinking or first-principles argument; mostly confirmation of what CMOs already believe.

this is not the first wave of transformation
customers are better marketers than we are

Guest Caliber

14 / 20

Cynthia Gumberg is a credible CMO with multi-company experience and has held the role at scale. She brings practitioner legitimacy and has implemented an operational structure (voice of customer team) she can speak to firsthand. However, she is not a founder or CEO; she is a functional leader, which limits her vantage point on broader business transformation or board-level strategy. Her track record and specific company challenges are not detailed.

I've been in B2B tech my entire career, marketing as well as product management early days and way back as an engineer
you've been a chief marketing officer four different times over

Specificity & Evidence

11 / 20

The episode is largely anecdotal and abstract. Guest mentions 'Gong and Salesforce' for tracking but provides no concrete metrics, timelines, or ROI numbers from the voice of customer program. References to 'weekly competitor entrants' and 'two cycles of AI tooling over 1.5-2 years' are vague. The 'reference calls on short lists' claim lacks specifics: which deals, what uplift, what conversion metrics? Forrester and McKinsey studies are cited but without deep analysis or applied examples.

80% of it is probably getting their input and distilling it
we can track it in Gong and Salesforce and all the tools so you can see the impact of it

Conversational Craft

11 / 20

The host asks reasonable opening questions and connects dots between customer trust and pipeline, but rarely pushes back or probes beyond surface answers. When the guest says 'customers are better marketers,' the host agrees rather than asking for evidence or exceptions. Follow-ups are polite and affirming rather than challenging. The conversation reads as collaborative validation rather than an investigation; the host's final comment ('I call you a pioneer') is praise without critical examination of claims or limitations.

I'd like to play deeper into that world of trust
If there was one thing that you wanted, the C Suite executives that we're going to be consuming this podcast to take away from our conversation today, the most important thing, what would that be?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A54%
  • Speaker B46%

Most-used words

customer25customers16voice15team14trust13conversations12product11different10market10important10marketing8world8call7long7relationships7study6

Episode notes

Episode #321: Cynthia Gumbert, Chief Marketing Officer at Litera, explains how established companies can compete confidently in an AI-first market. She shares how customer trust, long-range innovation, and a dedicated Voice of the Customer program strengthen brand relevance and revenue growth. Cynthia also reveals why customer advocates often outperform traditional marketing and sales messages. “Get customers to be your advocates and spokespeople, and never lose sight of the fact that they are your best marketers. They can be your best salespeople. In this age of AI, it is easy to get distracted by product innovations and features, but those customer connections are most important.” - Cynthia Gumbert Cynthia explores how established B2B technology companies can compete with AI-native startups by treating their history as market pedigree, not baggage. She connects long-range product strategy, customer trust, and a dedicated Voice of the Customer program to stronger positioning, shortlist access, and measurable pipeline impact. The conversation also shows why simpler messaging and continuous customer value help leaders navigate AI fatigue without losing focus.

Full transcript

24 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign. Welcome everyone to the C Suite Sales and Marketing Perspectives podcast. I'm Steve McDonald, your host and today we have a phenomenal guest, Cynthia Gumberg. Now, Cynthia, what I love is the richness of our conversations. You're a Chief Marketing officer, you've been a chief marketing officer four different times over. That means being a part of four different executive committees, four different companies, B2B tech, right? But every company has its own personality and its way that it approaches marketing and the whole go to market strategy. And one of the things that I just love that you've done, you started it in your last company and you brought it over here, is you actually dedicated within your team, a team that you call voice of the customer. And one of the things that is so important about that there was one study that was done by Forrester that I think just accentuates what you're doing and the importance of it. They did a customer obsession study and we all say we're customer obsessed, we all say we're customer first. But it's the actions, it's the deliberate actions to learn and execute on the voice of the customer that really matters. And they showed that only 3% of companies were actually customer obsessed with. But the ones that are had, I think if I, uh, remember this correct, 41% faster revenue growth, 49% faster profit growth, and retained customers 51% longer. This is actually tied in a big way to revenue and growth of the business. In CMOs, we have been asked to be more revenue focused for a long time and we tend to think that that has to be core pipeline, demand generation, has to be more leads coming in. But there's an ecosystem that we live within and we're going to get into that today because we're going to be talking about right now you're inside of a really strong, well positioned legacy company. But in this AI world, there's all these startups, right, that are uh, those tiny objects that we all of a sudden have to compete with in really big ways. And so we're going to put all that together and we're going to talk about how you're approaching the market, how you think about that. But I would love to just give you a few seconds to expand a little bit on your background. What I didn't say there before we dig right in.

Speaker B: Yeah, absolutely. I've been in B2B tech my entire career, marketing as well as product management early days and way back as an engineer. I came at marketing with the very quantitative mindset and I have expanded a lot since then to, you know, it's not just the numbers, it is the relationships, it's the brand, it's how people feel about you. So being full stack cmo, you've got to flex both sides of the world. You know, a lot of my playbook is really not a playbook, it's just what is most needed and where are the biggest gaps that we need to fill. Sometimes it is the numbers, sometimes it's the relationship or the brand or the message. The one thing I'm bringing to the table is just it. This is a big Swiss army knife, multi tool kind of role and that's what makes the CMO job a lot of fun.

Speaker A: So I want to start us out with and I'm finding this more and more. I'm talking to a lot of CROs and CEOs and CMOs that all of a sudden are feeling like, wow, we got to reinvent ourselves in this world of AI. There's these AI startups and they seem to be getting all the cred. It's kind of like our kids looking at us and going, dad, you don't get it right. You've been around too long, you're not in the cool crowd anymore. Why are we as legacy companies, why are we not given the credibility that we need and what do we start to do about that?

Speaker B: AI is the latest wave of technology innovation or just a uh, big technology transformation. But this is not the first wave of transformation and this is not the first time this kind of massive transition has happened that's generated a ton of startups with a lot of companies that you know, were kind of in the old way either had to bridge or become irrelevant. And there are plenty, plenty of success stories from history of companies that have been around, bridged the gap and accelerated out of it, beating out some of these newer startups. This was transition to the cloud way back 20 something years ago. Dot com era transition from brick and mortar to Internet. So this is nothing new and there's some very tried and true ways to. You've got to innovate, you've got to walk the talk. Not just talk the talk, but it comes down to beyond product vision, just the relationships you have with those customers and how much they trust you and trust that you are there for the

Speaker A: duration where you ended there trust. At the beginning of the year, end of last year, Forrester came out and they their whole prediction for this year was that trust was the currency to get into the deal, win the deal, keep the deal. It was all about trust, which Underpins all about the relationships. Right. And you have longstanding trusted relationships, but yet AI is one of these things that we've just bequeathed to that it's going to change the world. Right. Everybody's being asked by their board, our buyers are being asked, what are you doing, what are your AI strategies? Right. When you're looking at new vendors and partnerships and what is their AI strategy, how is it going to help us? How are we going to compete? It's almost like this feeling like if we don't make the right AI decisions that all of a sudden we're going to be a step behind. So all of a sudden then these AI native companies have all this credibility. Right. So first off, what are the kind of conversations that you're having to have internally about trust? The relationships we have, the way that we're working with our customers to develop the AI solutions that are tested and we know we're right for the market. A lot of the startups, they don't have the big customer base that we have. We don't have, they don't have the ability to do that. Start from the inside, if you could, about the conversations that you're helping steer and then how does that make it into go to market strategy?

Speaker B: Yeah, the conversations are really start with a product strategy. So it starts with our engineering and our product team and looking at what we're developing, which is now completely AI native. Just the benefits of what we call, we're coming up with the words of how to talk about it. So we're calling it pedigree, not legacy that has some connotations of being old, but we've got this multi year pedigree of history, deep knowledge, understanding of our market and everyone has access to the latest models and we're innovating on top of it, but maintaining what's worked well for me as a marketer and for my team. It is that conviction and just confidence that what we are coming up with is of more benefit to customers based on knowing what they need. We're not looking at the next year of playing and piloting, uh, or the next six months when I look at just my own teams. Over the past year and a half, two years it was all chatgpt, then it's oh, let's try Gemini, then cloud these models and the AI tooling. I've cycled now through twice two cycles of different AI tooling within my own organization and I feel like that's a lot of what's happening now is just piloting, testing, playing. We have Got to bridge our customers for not just the next six months of playing. It's got to be a five year, 10 year, 15. We're looking at the long horizon of where they will be in many years from now and what is the right situation for them in their technology stack. But as a vendor partner for them as well, to last them for the long run. We've got a long horizon view of this and confidence that we know what they need the most. And that is the trust that we built with human to human and the trust we built in our products as well.

Speaker A: So I'd like to play deeper into that world of trust because here's where it's so important these days. The short list forms and our buyers walk in on average four to five vendors and then they pick from that group 95% of the time. So if we're not in on day one, we're not in. Getting on that list isn't about. And you and I both come from the tech world, the SaaS world. We know how can fall in love with our own technology and our own products. But building the trust, being known and trusted is about knowing them more than it is having the right tech and the right product features. And especially in a world of AI where new features roll out, they're copied, they're, you know, they're like AI can develop a road map at lightning speed. Right.

Speaker B: And so vibe code, a roadmap in 15 minutes.

Speaker A: Absolutely. So in a lot of respects with AI, we're having to rely heavier and heavier on relationships, heavier and heavier on our understanding of the customer. And so that's why I wanted to ask you, you've created this team within your team that is the voice of customer team. Just if you wouldn't mind taking us through why you did that.

Speaker B: Yeah.

Speaker A: And how it's actually making a difference.

Speaker B: Right.

Speaker A: So when you're in a board meeting or um, you're meeting with your CEO or the CRO, you're putting time and effort and resources dedicated to this team. So the first thing that like CFO or CEO is going to want to know is, okay, how's it impacting the bottom line? How's it going to help me sell if you can I connect all those dots? That was like five questions.

Speaker B: No, it, absolutely. It made sense. So. So the statement that I tell my own organization that annoys them the most and they hear it from me probably at least once a month and they hear me tell the sales team this is, customers are better marketers than we are. We will never Be as good a marketer as a customer who's an advocate telling up here to buy our product hands down, period. Sales cannot get enough of customer stories, reference calls, connections. That's just the bottom line of having a voice of customer team is creating a, uh, environment where our customers are able to bring up their stories. We are doing this for them. We're helping to support not just, hey, tell us your case study, but we're supporting them along the way and making the connections through customer success organization advisory boards. We do surveys, we do polls, we ask them if they want to see, speak on our behalf at conferences and events, or just take that reference call once in a while. There is no bigger ROI than we took the reference call, or there isn't even an rfp or you're on the short list of one before there even is a short list being created. If a customer is a good reference, it is very important. It is measurable in the sense of these stories, these case studies, these references are connected to our opportunity pipeline. We can track it in Gong and Salesforce and all the tools so you can see the impact of it. But just the snowball effect of having more and more customers and then see each other talking about what we're doing and see themselves or each other on stage is compounding and critically important.

Speaker A: It was amazing. And this has been happening for a long time. But if you were to go look at just the most recent Edelman Trust barometer of, I think it was 32,000 worldwide respondents, 67% think that business leaders like you and I are being intentionally misleading. That's the exact words out of the study. Two thirds of our buyers are thinking we're being intentionally misleading. And so the idea that you say the customers are better marketers than we are is because they're more trusted. Right. We trust peers at the same level. We trust scientists. I remember seeing that in a study.

Speaker B: Right, exactly.

Speaker A: And so, uh, the idea of bonding, our voice that should be leading the marketplace. Right. Understanding their challenges, navigating, making recommendations, not being a vendor that supplies just technology. Very important. But also helping them wade these waters. Right. And being looked upon as somebody who has that kind of credibility and that kind of a background, and we have to work at maintaining that credibility every day and we have to learn about it every day. I'm sure that if you said, uh, you know, what we're finding from our voice of customer team vs a year ago vs a year ago is very different. We can't just write an ICP out a definition, hand it to everybody. Uh, we got it covered. Right? Uh, it's always changing. Like do you find that. And I'd look to evolve into that question, do you find that evolving? Always changing. We need to constantly be in front of the customer. Let's start with that.

Speaker B: Absolutely. So when we look at the voice of customer program as well, 80% of it is probably getting their input and distilling it for us to become better marketers, salespeople, product product developers, product managers. It's their voice coming internal to us. And it's of course what I mentioned earlier, their voice to other customers to help us sell as advocates. The words we use and the way we talk about what we do is heavily impacted by our advisory boards, our steering committees. We have different titles and functions and different steering committees of customers. And we bounce not just product ideas, but marketing. We said it this way, are you going to believe it or how do you talk about this thing and what do these stats mean to you? So there's so much interaction and so much benefit from just having a forum to listen to them. They'll love talking. We can send a quick 2 question poll and they'll answer it back to us. And it does change. We have new competitor entrants probably weekly in this market that I'm in, probably every week there's a new announcement about somebody getting into the market with a lot of these competition. It's very grounding, I would say, to hear from our customers though there's so much noise. Just keep doing what you're doing. Because it's tempting to say to be very reactive and just keep zigging and zagging based on, oh, this competitor said this and they say it really well and it looks good. Let's copy that. And we have customer. No, no, just please stop copying. Just stay your course because it's working. Even if it might not sound quite the same. It's also a grounding function for us to again keep bridging that. This wave and this transition.

Speaker A: I was talking to a CRO yesterday about in a day and age where we're having harder time getting into conversations and those conversations are fewer and farther between and they're shorter than they've ever been before. And so we were talking about then, how do you get into those conversations? How do you make the most out of those conversations? And it very, uh, quickly came back to we have the best insights in the industry because when we get into the conversation, we prove that was worthwhile. It's worthwhile spending longer on that conversation and having Another conversation. So what you're doing inside of the voice of the customer team, it's yes, it's absolutely about creating better demand gen campaigns, pretty better thought leadership. But it's also about empowering our entire sales force. Right. And customer success organization about what's true and what's meaningful. The voice of the buyer is supposed to be our North Star and I think it was 2023. McKinsey came out with a study and they said only 15% of companies actually use the voice of the customer to help them make decisions. It's crazy, absolutely crazy.

Speaker B: This is beyond a, uh, marketing initiative too. It's so important for our CEO to work on sentiment, work on brand with capital. B. It's not branding, it's our brand is how they think about us, how they feel about us. This has been a very top down across the entire leadership team initiative for us. And when you say just giving them a reason to want to take your call. The default for many SaaS companies that I've seen or been exposed to or on the receiving end of is you hear from them when they're selling to you and you hear from them when it's renewal time or they want to sell something more to you.

Speaker A: Yes.

Speaker B: And that's another benefit of having this voice of customer organization. They're hearing from us when we have something to give to them, not when we're asking something of them or when we just want to talk and get feedback and get input. So it just gives us a lot of opportunities to maintain a relationship even when there's no active, we need to renew, we need to sell you something. More conversations. That alone is such a benefit. And I don't see many vendors. I'm a buyer of a lot of technology and I can name only few on one hand to really maintain that relationship over time.

Speaker A: Yes. Maintaining the relationship you and I talked about before we started here about really a big part of the decision to hire partner with a new company is what's it going to be like when I actually start working with you? Right. It's that relationship that is so important. And it's interesting because I have so many conversations with C suite executives and I always ask, and I asked you this question too, what are your two greatest challenges for creating long term sustainable growth? And what's really interesting, I've seen a shift over this last year that the challenges are coming more and more into. How do I keep up with the pace of the market? How do I stay relevant faster? How do I provide value faster? Like all of our clients are expecting more in a shorter period of time. Right. They're expecting more with less and in less time. And so staying grounded in the buyer truth and staying grounded in those relationships and keeps us connected, keeps us top of mind, keeps us relevant while we're learning. Like, that's what I'm. That's a huge part of many things that I'm taking away from what you just said. Is that a good takeaway?

Speaker B: That's a great takeaway. And I think that's the balance. The tightrope that we're all walking in this market right now and where AI is just what you said. There's so many new things coming at people so quickly and the pace to keep up with the changes. Everybody's running fast. Our customers are, our vendors are, our employees are. Everyone's running really fast. But yet there is change fatigue as well. How many new AI, uh, tools do I need to bring in and experiment with until there's some stability? How many new release a day? There's a new model here, there's a new model. It's come out and here, play with it. There's so much fatigue with AI. I cannot absorb all of this coming at me. I just need to do my job well and thinking, putting ourselves in our customer shoes and also in what we do best. There's a common thread that goes across that we're going to try to avoid complicating things with so many new changes and just have a, uh, through line of. Here are the benefits that we provide you today, that we will always provide you and continue to increase in the value you're getting from our products and just simplifying the message and the story and our mission and our position is so important because, yeah, I think everybody's just really a little bit overloaded. It's overwhelmed right now and it always comes back to home base. This is what we do best. They're going to like us for that.

Speaker A: If we, yes. If we can be the calm in the middle of that storm of everything that's coming at them, the constant change and a trusted voice saying, within all of that, here's where you really need to focus. Right.

Speaker B: Yeah.

Speaker A: That's a huge benefit. That wasn't really even around a couple, uh, of years ago. Right. But now that's a major challenge that they're all facing is how do I make sense of all of this and make the right decisions? Because we know B2B decisions are about risk avoidance. Right. As much as anything else. So a huge emotional factor into that. If there was one thing that you wanted, the C Suite executives that we're going to be consuming this podcast to take away from our conversation today, the most important thing, what would that be?

Speaker B: I think it is getting customers to be your advocates and sports books people and never losing sight of the fact that they are your best marketers, they can be your best salespeople. In this age of AI, it's very easy to get distracted by the product innovations and the features. But those connections with customers and what you are actually doing for them at the end of the day is most important.

Speaker A: I have to tell you, that's my number one takeaway from everything you talked about here. And it seems like sometimes such a basic thing. And we get very familiar with our customers because we talk about them all the time, we track them all the time, and we have sales conversations with them all the time and we do surveys and we have customer success conversations. So it's very easy just to say, hey, through our normal go to market process, we know a lot. What we really have is just a lot of familiarity. And what you've proven here is something I'm going to call you a pioneer in this because I talk to a lot of C Suite executives and I have never talked to anybody. We've recorded our 300, I think 22nd podcast and I've never talked to anybody that had a dedicated team that they called Voice of the Customer. And I just want to call out. That's a huge accomplishment. I hope you're really proud of it and I hope that you're Board on down is proud that you've done that for the organization and a teaching moment for all of us. Because this whole podcast, the whole mission is how do we learn from each other. We all have different experiences, different perspectives, different insights that we can bring and if we all share it with each other, then that's the Rising Tide that lifts all boats. And you were an amazing part of that Rising Tide today. And I just wanted to say thank you, Cynthia, for coming on.

Speaker B: Thank you, Steve, really appreciate it. It's been a pleasure. A few minutes talking to you.

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