In short
Building “trust” to move upmarket into enterprise buying committees; how Okta reworked messaging and go-to-market to win against Microsoft, plus a messaging critique of Rippling.
Guest backgrounds
Kevin Goff, first PMM for Google Cloud (launched Google Workspace and business/education Chromebooks). Later led category-defining efforts at Okta, Asana, and Grammarly. Earlier founded a digital accessibility compliance company acquired by KKR in 2022.
Key claims
Trust must be marketed like a product; enterprise buyers define trust differently (e.g., uptime guarantees vs API stability). Win rates lagged despite superior product, due to market perception and competitor credibility. Build a “trust ecosystem” with third-party proof, customer outcomes, analyst strategy, and deputize the whole go-to-market org.
Notable examples
trust.okta.com uptime dashboard (3 nines), SOC 2/HIPAA/FedRAMP compliance content, “Velvet Alliance” partnerships (Box/Slack/Zoom), analyst “Magic Quadrant” seeding to become leader in access management, JetBlue case study (1,000 flights/day). Rippling critique: strong employee-focused header (“Employees get more done”), but site is demo-form heavy; suggest more interactive workflow storytelling and buyer-specific landing pages.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding the Upmarket Challenge
0:35 to 1:17
Discussion on the complexities of moving up market and the importance of trust.
“In the world of B2B, moving up market means landing larger, more complex customers.”
Introducing Kevin Goff
1:18 to 2:06
Introduction of guest Kevin Goff and his achievements in product marketing.
“So Kevin is one of the most creative problem solvers in the product marketing community.”
Okta's Journey to Trust
2:07 to 3:15
Kevin shares insights into Okta's strategy to overhaul messaging for trust-building.
“A little bummed we're not digging into the Edward Scissorhands experience.”
Facing the Goliath: Competing with Microsoft
3:16 to 4:28
Exploring the challenges Okta faced against Microsoft and the need for trust.
“So first off, you know, it's funny we're on a product marketing show, but this is not a product, right?”
Analyzing the Need for Trust
4:29 to 6:28
Discussion on sales data and market research leading to the emphasis on trust.
“So how do we improve those and then increase win rates against Microsoft specifically in that enterprise category?”
Defining Trust for Different Stakeholders
6:29 to 8:00
Understanding how different members of the buying committee perceive trust.
“but also looking at the state of our product.”
Creating a Trust Ecosystem
8:01 to 9:19
Strategies for building a trust ecosystem and third-party validation.
“So if we were to market a product, if we were going to go to market with a product, what are the components of an amazing product launch or product messaging?”
Integrating Proof Points into Messaging
9:20 to 11:03
How to incorporate third-party data and certifications into marketing strategies.
“So I would love to now turn this into a playbook and say that I'm a PMM facing some kind of like, maybe it's like late stage friction or trying to move up market, whatever.”
The Velvet Alliance: Collaborative Marketing
11:04 to 14:00
Kevin discusses partnerships formed to compete effectively against Microsoft.
“and let's say if we move from version 1.2 of the API to 1.4, that it wouldn't break any of their code or any of their integration.”
Building Trust Through Validation
14:00 to 15:06
Learn how to validate your product through third-party certifications and collaborations.
“It's, it's that trying to say without saying like, don't just take it from us.”
Show all 20 chapters
Engaging Customers for Better Outcomes
15:06 to 18:08
Discover strategies for framing your product offerings around customer business outcomes.
“So not about efficiency, but really about those business outcomes and how they're really trusting you to help deliver those business outcomes.”
The Role of Analysts in Trust Building
18:08 to 19:49
Understand the importance of analysts in establishing market trust and vendor perception.
“core bits of differentiation that we have against a competitor, especially one like Microsoft, where they've probably had a long-term lucrative relationship with a Microsoft-type vendor.”
Implementing a Long-Term Analyst Strategy
19:49 to 24:18
Learn how to create a sustained analyst strategy and its impact on vendor perception.
“you know, some of these things are happening in parallel, right?”
Creating a Cohesive Go-to-Market Strategy
24:18 to 27:22
Explore how to align your go-to-market organization to ensure a unified messaging approach.
“could move were aligned with the metrics that they were gold upon.”
Metrics for Evaluating Success
27:22 to 28:00
Learn how to measure the effectiveness of your go-to-market strategies and trust initiatives.
“So quick recap on everything we talked about so far.”
Measuring Success in Product Marketing
28:00 to 31:30
Learn how to assess the effectiveness of product marketing strategies through various metrics.
“What are the metrics that you use to make sure that a strategy like this is working?”
Messaging Critique of Rippling
31:30 to 42:01
Explore a detailed critique of Rippling's messaging strategies and suggestions for improvement.
“So closing out that segment and moving on to the next, next segment of our show is the messaging critique.”
Shout Outs to Influential PMMs
42:01 to 43:06
Learn about key product marketing mentors and their impacts.
“And I'd love to now turn it over to you.”
Exploring Professional Connections
43:06 to 43:30
Discover how to connect with experts and access their knowledge.
“We were trying to figure out the product-led sales motion, which kind of takes the best of product-led growth and sales-led growth and combines them together in innovative ways.”
Closing Remarks and Inspirations
43:30 to 43:59
Reflect on the insights shared and the journey ahead for listeners.
“Where else can we access your expertise?”
Transcript
Automatic transcript. May contain errors.0:02Hi friends, welcome to Product Marketing Adventures, the only show that takes you beyond theory and into the real execution of product marketing. My name is Elle Grossenbacher, your trusted guide and host of this show. In each episode, I bring in expert product marketers to co-host two segments of this show. First, a case study example of their work, followed by a messaging critique for companies we admire. So if you're a PMM looking for practical guidance and inspiration, you're in the right place. Are you ready? Let's go.
0:41In the world of B2B, moving up market means landing larger, more complex customers. Think like Fortune 1000 or global enterprise accounts. These deals are often high value, high stakes, and come with really long sales cycles. And they're really complex with multi-threaded buying committees. And in my experience from scrappy startups to scaled enterprises, cracking into that world is never easy. It takes way more than just a great product. It takes trust, which brings me to our topic for today, how to build trust with that up market segment to unlock growth. With that, it is my pleasure to welcome Kevin Goff to the show.
1:20So Kevin is one of the most creative problem solvers in the product marketing community. He was the first PMM for what's known today as Google Cloud, where he launched game-changing products like Google Workspaces and Chromebooks for business and education. Since then, he's led category-defining efforts at companies like Okta, Asana, and Grammarly, helping each one to rethink how they show up in the market and build trust with customers. And before all of that, Kevin actually stepped out of college to start a digital accessibility compliance company, which went on to be acquired by KKR in 2022.
1:57Oh, and fun fact, he also sang on the Edward Scissorhands movie soundtrack as a kid. Kevin, I'm thrilled you're here. Welcome to the show.
2:07Kevin Gough:Thanks so much, Elle. Excited to dig in? Yeah, likewise. A little bummed we're not digging into the Edward Scissorhands experience. We'll have to chat about that another time. I know. Well, maybe this will be a good voice warm-up for me. I love it. All right. Well, let's dive right in. I can't imagine anyone would not know this, but just to keep listeners up to speed, can you give a brief overview of Okta for us? Sure. So Okta makes it easy to sign into all your workplace applications. It keeps them secure and makes sure the right people have access to the right applications. Awesome. Thanks. So Okta, of course, is part of the case study that we'll be discussing today.
2:49So with that, the topic that we'll be diving into around that case study is building trust with the upmarket segment. And I'll just say this isn't a fluffy brand topic that I think a lot of marketers may think it is. So for the first segment of the show, let's talk through that case study a bit more. What was going on at Okta when you realized you needed to completely over all the messaging and the go-to-market strategy for that upmarket segment?
3:18Kevin Gough:Yeah, definitely. So first off, you know, it's funny we're on a product marketing show, but this is not a product, right? Trust is not a product per se, but it is something that we are kind of insight was we need to market trust the concept just like we market a product. So some of the same tools and techniques. And so to walk you through what you said, Okta was doing great in the bid market, but we were trying to move up market to really sell to those large enterprises. And Microsoft was our main competitor. They had 20-year relationships. They had earned credibility. Some people had built their careers on it.
3:54Kevin Gough:And so our deals were stalling because our target customers really weren't willing to make the jump to a relatively new vendor. So we really had to gain the trust of the buying committee. And what we did was really a holistic approach. So this was a company-wide initiative. There was something, everything from brand to sales. But the question was, how can product marketing contribute to it? And so that's where we came in and we could walk through some of those activities. And ultimately, the goal was really how do we uplift conversions across the funnel? We actually did a before and after measurement of brand trust scores.
4:31Kevin Gough:So how do we improve those and then increase win rates against Microsoft specifically in that enterprise category? I love that. So, man, talk about going up against a Goliath. Like Microsoft is huge. And while Okta, of course, now has a very respectable brand and really strong recognition in the market, I could imagine how back then, not that that was that long ago, but could have been pretty hard if you're trying to win with those big enterprises. And you mentioned so much that I want to dig into. You talked about how it was a holistic approach and it was a company-wide initiative. And you didn't just slap on, you know, hey, we're secure, some kind of badge, right?
5:10You went so much deeper than that. It sounds like you tackled this from like product, sales, marketing, and potentially even, you know, analysts and so many different angles, all while staying consistent on a core narrative. So I want to dig a little bit deeper on how you landed on this. I guess, like, what was part of that analysis for assessing the situation? Like, why did you why trust was the main core value that you wanted to anchor on as a company?
5:39Kevin Gough:Yeah, certainly. Well, you know, I think it was it was looking at our sales data. And what we saw was we had a superior product. If you even did kind of side-by-side comparisons, people preferred our product capabilities. But we saw just our win rates were not where we wanted them to be. We also did some market research and understood sentiment analysis of Okta compared to Microsoft. And we also looked at some of the claims that competitors were making in the market, claims about uptime or compliance. And we recognized that we weren't really at parity with some of these claims, even though maybe our product could deliver the same amount of compliance or same amount of uptime.
6:25Kevin Gough:So it was really looking at both market signals, but also looking at the state of our product. And we really felt our product was ready for the enterprise. So how do we make market perception match market reality? Got it. Okay. And it sounds like multiple members of the team and potentially even third parties, you did so much analysis and it's analysis from sales and feedback from sales, looking at your win rates. All of that told a story that, hey, we have our product can do this. Our product can solve the problem that the customer has. We just need to step up to the plate so that they can rely on us for the long haul like they can with a big beast like Microsoft.
7:11Kevin Gough:Right. There was I mean, there was kind of a vendor consolidation. Right. People wanted to choose a few strategic vendors. So our idea was how could we be one of the top five vendors that someone chooses to have a long-term and hopefully million-dollar relationship with? Yeah, right. Absolutely. So when you think about it with your team, then focusing on, I guess, product marketing's role moving forward, you have this very compelling assessment with all this data. And the team across the entire, when I say the team, I mean the entire company is rallying around this. What was, I guess, the task at hand just for product marketing?
7:54I guess, how did you get started? What was the big question in your mind? Well, really, it circles back to thinking about trust as a product, right?
8:03Kevin Gough:So if we were to market a product, if we were going to go to market with a product, what are the components of an amazing product launch or product messaging? And taking that, you know, something that's very tangible, like product marketing, and applying it to something that's a little bit less tangible, like trust. So really, it starts just like when you're starting to market a new product with thinking about the buying committee. and who are you actually trying to sell to and what do they actually care about? And that's true for products, but it was also true for trust. So different members of the buying committee, which we had mapped out, from engineering to product to finance and compliance, we realized they had different values or different things that they cared about when you talked about the concept of trust.
8:51Got it. Okay. I want to talk more about the buying committee process. And I feel like it's worth saying again, when you thought about product marketing's role and looking at this non-tangible thing like trust and looking at it as a product, like what's required, that dedication to, I guess, like redefining that experience from the customer's perspective and how the customer may experience what trust looks and feels like. So I would love to now turn this into a playbook and say that I'm a PMM facing some kind of like, maybe it's like late stage friction or trying to move up market, whatever. And I've done that research and benchmarking and that big assessment that maybe you've done or done in partnership with various folks across the team.
9:40And now I'm realizing I need to build out a go-to-market strategy and some messaging around some key value, whether that's trust or quality or even authenticity. Like, where do I start? What's step one? It sounds like mapping something. You started to talk about buying committees, but I don't want to get too far ahead. Like, what's step one?
9:57Kevin Gough:Sure, certainly. So I really think it is about, you know, we all talk about ICP and then firmographics and personas, but it's really understanding as you move up market, especially to the enterprise, there's a broader set of people in the buying committee as compared to mid-market. So one, we were really expanding our buying committee. It might have been different layers within the IT team, not just the directors, but the VPs and the CIOs. It was also expanding cross-functionally. So you had chief compliance officers, for example, and chief legal officers. You had very sophisticated procurement teams.
10:32Kevin Gough:So first we had to kind of map out this broader set of buyers and then that contextualization. So I'll just give you a couple examples. When we talk about trust for the product team, they actually cared about uptime guarantees. So they cared that the product was going to be up 99.99 % of the time. So if they had a big spike in traffic on their brand new Uber competitor, that they wouldn't lose any of those signups. So, you know, that was their kind of definition of trust. Whereas the engineering team actually cared about APIs and API documentation. and let's say if we move from version 1.2 of the API to 1.4, that it wouldn't break any of their code or any of their integration.
11:16Kevin Gough:So that's what they meant by trust. And so we came to realize that different stakeholders really had different metrics for trust. So we really had to contextualize that kind of fuzzy concept and a lot of specificity for the various stakeholders. Yes. And what you're saying makes a lot of sense too, because I think earlier in our conversation, just a few moments ago as we were talking about what does it mean to move up market and what that challenge is. You mentioned that in the up market segment, these companies are really looking for consolidation and they're looking to get more with this idea of best of breed.
11:53And I know we're going to get into more of that a little bit later, but what you're saying, it makes a lot of sense now then to dig deeper into this more complex, sophisticated buying committee and looking at it from each perspective of, you know, how does this person think about trust? And what about this person? It makes a lot of sense. Okay. So let's say as a PMM, I'm, you know, on this journey, and I've accomplished step one, I've done all of the mapping and analysis on that buying committee. What's next? What's step two?
12:22Kevin Gough:Yeah. So step two, I really think is creating, I call it like a trust ecosystem or your ecosystem around your organization. So you've all had seen the cliche of like a used car salesperson saying, hey, trust me or something like that. The reality is your brand, your statements can only go so far. So you need to start to develop and cultivate these third party proof points or very data grounded proof points. So an example would be a product level proof point. So we launched an updated trust.okta.com site that had historical information about our uptime and had an updated guarantee. I think it was three nines instead of two nines.
13:04Kevin Gough:And even that uptime guarantee was something that we had to actually go to bat for internally. So we had to talk to the engineering team. We had to talk to the legal team. We had to talk to the finance team because there were some risks in terms of service level agreements and we might have to credit back some amount of the purchase price if we didn't actually meet those uptime guarantees. So product marketing, we really need to make the case that this would help increase sales and move into the enterprise to offset any financial risk or legal risk that we might be exposing by being more specific in even our uptime, for example.
13:43Yeah, got it. It's so helpful. So there's all kinds of different validation points from maybe third parties that you can look at. I love, by the way, and I know this too, We're going to get into more later, but building out a separate site to house all the strong validation that you're, that you're building makes a lot of sense. And right. It's, it's that trying to say without saying like, don't just take it from us. Like, don't just take my word for it. Okay. So once you get that validation going, how do you take all that work that you've done with the persona and the buy team and put it all together in a story that's, you know, backed by evidence, you know, in addition to that, all that third party data and like, you know, even bringing customers into the net mix?
14:24Like, what's the next step?
14:26Kevin Gough:Yeah, so you know, you raise a good point. So I'd say it's more than just you providing that proof. It's things like any third party certifications you have, you think of FedRAMP or HIPAA type of certifications that we also had to kind of advocate as product marketing to get its brand association. So we actually forged some partnerships in collaboration with partner marketing with other companies who are actually competing with Microsoft. So you think of Box or Slack or Zoom. I think we called ourselves the Velvet Alliance, right? And we were kind of the best of breed. And so we also got some validation of, hey, if someone used Zoom and they liked it, maybe they'd want to use Octa.
15:05Kevin Gough:So that also helped in that kind of trust ecosystem. And then I'd say step three is not just those third parties, but really how to get your customers engaged and really kind of trying to tie your trust points that you're trying to demonstrate with some of the business outcomes that your customer actually cares about. So not about efficiency, but really about those business outcomes and how they're really trusting you to help deliver those business outcomes. I love that. I love that. So it's, there's so many opportunities for the third party component, but then taking what the customer, what's meaningful to the customer and framing of all of your capabilities and, you know, the differentiator of your product, rather than starting with that, starting with, well, what's really meaningful to our customer and their business and what they're trying to achieve.
15:56We do that a lot at Cisco as well, across the company, or at least across marketing. We always frame everything that we're doing around business outcomes for the customer. So I can attest that that is a very effective strategy from a PMM perspective. Okay. So bringing it back to our step-by-step process, we've got mapping and contextualizing. We've got the buyer team. We've got building out the validation points. Maybe that's with third parties and maybe it's with metrics that you can provide with the, like you gave the uptime example. And then we have the bringing customers on board, getting them engaged and really framing the story around their business outcomes.
16:39I guess as you're thinking about all of this, and especially with the validation with third parties and customers, we'd be remiss if we didn't talk about analysts. So tell me, what role do analysts play in all of this?
16:56Kevin Gough:Sure, certainly. Well, as you move up market, analysts are increasingly critical. large companies, one, maybe don't have the time to evaluate all the different vendors in an ecosystem. And so they look to their hopefully well-paid analysts to do some of that vetting for them. And there's a little bit of risk mitigation, honestly, too, where you can say, hey, I made this choice because Gartner or Forrester also put them in the leaders quadrants of the magic quadrant. So there's a little bit of bias towards that as well. So I'd say analysts is definitely a long game. My strategy that I've found works well, and also I think works well for the analysts, is you both want to listen and share.
17:39Kevin Gough:So analysts do have a broad-based insights into a market. They're talking with all of your competitors. They're talking with all of your customers. So they can share a lot of insights in terms of product roadmap, differentiation, even things like messaging. They can say, well, this message is dead. People aren't interested in that. So I always want to listen and learn from them up front. But I'm also, to be honest, always planting little seeds, even in those listening sessions, to try to tease out those core bits of differentiation that we have against a competitor, especially one like Microsoft, where they've probably had a long-term lucrative relationship with a Microsoft-type vendor.
18:21Kevin Gough:So I'd say it's a long game in terms of changing vendor perception, but one of the tricks or tips, I would say, is really focus on trying to get a question or two that you can influence in one of the magic quadrants. For example, for Okta, we really did a great job with integrations. We had literally thousands of integrations, which made it very easy to sign in to all these new cloud apps. And that was something that we were much better than our competitors on. So we were successful in getting that question in one of the magic quadrants that really helped improve our score and our perception. And ultimately, we became a leader in the access management magic quadrant.
19:04That's so strategic. So I totally agree. The magic quadrant strategy from a vendor perspective, it starts way before you actually get the questionnaire from Gartner.
19:17Kevin Gough:or, you know, magic quadrant or whatever equivalent. Forest or wave. Yeah. Yeah. IDC. Yeah, all of them. And I think it's so strategic to think about when you plant those seeds and the way that you were able to do it with your differentiators so that you ended up getting your differentiator as a question on the questionnaire as just really smart thinking. Okay. So it sounds like step four would have been like building out that analyst strategy, strategy, which maybe you should, from a timeline perspective, now that I'm thinking about this, you know, some of these things are happening in parallel, right?
19:52It's not like you do one check, then you do the other one check. Like you have to be thinking from a timing perspective, some of these things are happening, you know, either earlier on in the process. I can imagine, for example, like planting those seeds with Gartner. It's an ongoing strategy. You just have to make sure all that goodness that you're doing in the first few steps with like mapping out the buyer team and building out the validation and the customer objectives, right? Like you're bringing that into the analyst strategy, right? Like, is that kind of what you guys did at Okta?
20:24Kevin Gough:Yeah, well, you know, honestly, I think it became a year-long initiative for us because there are things, I mean, you think of some other long lead times, like to do the uptime guarantee, engineering needed to do a little work to get the certifications. we actually had to apply and get audited for SOC type 2 or HIPAA or FedRAMP. So I think that there is, of course, there's some quick wins. I think the customer stories like a JetBlue case study that says they trust us with 1 ,000 flights a day, that's something you can do in a month, whereas some of these other things are longer lead time. So I wouldn't say don't start until you have everything, but I think it's probably going to be a little bit more of a rolling thunder as you're rolling this out.
21:11Yeah. Yeah. Helpful tip. Okay. So once you get all of this strategy in place and you have some of those quick wins, as well as the long-term plan all in place, what does this look like from a customer's perspective?
21:25Kevin Gough:Sure. So I think really to make this or any initiative of successful. It's about how to deputize the entire go-to-market organization. So you're kind of getting the same message across all surfaces. I mean, very explicitly and visually, we read it our website, we chose some really rich purples, you know, and kind of financial services type imagery that said, hey, you know, trust us, we're serious. But it was also about the sales team and giving them a trust playbook with specific assets and collaterals around compliance that they could actually present to customers. It was partnering with the customer success team as well.
22:08Kevin Gough:So how could we give the customer success team information around these enhanced capabilities that might drive improved renewal rates or expansion into areas of the business that they hadn't quite been comfortable trusting Okta previously. So that I think was part of the success was everyone was kind of a trust ambassador for the company. I love that. Everyone was so involved. And when you do that, especially earlier on, as it sounds like you guys did this with building out the go to market strategy, everyone got to, I guess, like see that plan as it was coming to fruition. And And I would be willing to assume that even take part in shaping it.
22:51So then as you go and do that step five of, to use your words, deputizing the entire go-to-market organization, it's not the first time they're seeing or hearing it. As in, I don't know about you, but I've certainly experienced, I would say, even mistakes that I've made, like not looping sales in early enough when I'm building a strategy. And then I go to do some sales enablement and they're like, whoa, whoa, whoa, hang on. And then I get great feedback, but it's feedback I should have and wish that I would have gotten earlier on. So it's good then because then by the time you go and launch, they're eager, willing, and they have an appetite for this great content that you're putting together like that playbook, the trust playbook you mentioned, which sounds really cool and helpful for the team.
Read the full transcript
23:38Kevin Gough:Yeah, well, I think what was particularly important there was showing the other cross-functional partners metrics that would be meaningful to them that we could move or we believe we can move with this. So corporate marketing and customer marketing, it was brand perception. We could move that. We believe we could move lead generation and conversion rates and win rates in the enterprise market. So that meant our enterprise sellers were more engaged. And we believe we could improve renewal rates as well by this in the enterprise segment. So that meant our customer success team was engaged because the metrics we thought we could move were aligned with the metrics that they were gold upon.
24:21Kevin Gough:So there was a symbiotic relationship there. Yeah. Okay. And can you talk a little bit more about the microsite that you or the Okta team built? I guess, like, what was the goal of that microsite? And what kind of content did you put on there? I know earlier in our chat, you mentioned that you put some of that validation content on there. What else did you use that site for? Sure. So, I mean, I'd say some net new aspects of it was one, the kind of visual dashboard of our uptime over time. So it was literally a heat map, you know, where you saw green and yellow and red and hopefully not a lot of red, right?
24:56Kevin Gough:They kind of said, hey, we're being, it was a transparency. So we're being transparent with you over six months. And so you can actually be confident that what we're claiming is actually what we're delivering. So that was one. The second was kind of fun is we actually had increasingly been hiring security researchers and regional chief information security officers. So we use this as a launchpad for publishing security research to improve our thought leadership and credibility. That is so smart. I love it. Yeah. And then the third one, which was kind of low-hanging fruit, and I actually think a lot of companies might have this, is there was a lot of documentation that we had to go through for these various certification processes, SOC Type 2 or HIPAA or FedRAMP.
25:46Kevin Gough:And typically that lives in some shared folder. And if some customer asks for it, you send it as a PDF. So you don't get a lot of marketing value from it. But we actually put that all online. And so we had a whole compliance section. And so it enabled us to be much more front footed and tackle those questions and conversations earlier because customers could discover it themselves or sales reps could just kind of link to it. And it just once again, it forced kind of that we were buttoned up and the transparency to remove friction in the process. That's the exact word I was going to use, transparency.
26:21It's like you removed all the blockers that typical B2B intentionally puts there. customers or prospective customers to get all this information and do some of the diligence themselves up front. I mean, even when I'm doing buying for marketing tools, I want to do as much research I can before I have to pause my own buying process to wait to talk to a salesperson for them to do their pitch. And then we go back and forth. I just want to do as much diligence on my end as I can to make my shortlist before I go forth having some engagements. So it's helpful to arm your prospective customers with that information so they can get it themselves.
27:04And then the other thing that you mentioned, that strategy that you did of hiring these security experts to author some content, it all helps to build that trust that you're trying to achieve. So I just wanted to call that out as being really helpful. Very cool. Yeah. Okay. So quick recap on everything we talked about so far. So step one, we talked about mapping out the buying committee and contextualizing around that buy team. You talked about step two of building out the validation points that could be everything from your own product validation to third parties. um step three you talked about tying everything to business outcomes for your customers and then step four having an analyst relation strategy and then step five to deputize the go-to-market org and all of these steps maybe you know are happening in parallel so not necessarily a one after the other type of thing but uh a lot of goodness here and i guess like the one thing that i don't know if we talked about yet is when all this is said and done, you've got your story in the market, you've got this brilliant microsite up.
28:17What are the metrics that you use to make sure that a strategy like this is working?
28:23Kevin Gough:Sure. So we had done a brand study. So we were able to do a measure of increased in brand perception. So that's kind of the top of the funnel as much as anything. We were also able to measure win rates, so increased win rates specifically against Microsoft or other competitors in the enterprise segment. Also, we saw an uplift in those renewal rates in the enterprise segment. So we weren't losing deals back to Microsoft. And then we were looking at a lift in pipeline, specifically in the enterprise segment. So really, it was an initiative that, as you said, it was multi-threaded, but was able to deliver on a number of different dimensions across the buyer journey.
29:04Yeah, I could imagine being part of a team And as you're doing maybe teen check-ins or a roadshow of some sort on some of the results, maybe it's even like a company all hands. I could imagine the celebration when you see some of those, all that hard work that everyone had been working towards for so long pay off. That's really awesome. Okay, so final question for you on this topic, Kevin. So for any PMM out there who's trying to move their product up market and maybe they're focusing in on some non-tangible value like trust. What's one piece of advice that you have for a PMM who's in that situation?
29:44Kevin Gough:I think it was really the unlock was getting much more specific on the buying committee and really contextualizing this idea of trust or really any product feature to have it be specific to either the KPI or the strategy or the value that that specific member of the Vine committee was pursuing. And so that allowed us to really be crisp in terms of the value that we were going to deliver to them on trust. And it also kind of created these new work streams with collaborative partners like engineering, like sales, like customer success that enabled us to expand the initiative beyond just being a product marketing initiative or marketing initiative to truly a company-wide initiative.
30:33Yeah, yeah, I think so too. So, and I really appreciate how you and the team thought about what trust looks like across that buyer team. And it made it so much more personal and more genuine when you do it that way versus just applying to what you want trust to be and then slapping it across all the content. You know, it sounds like from the very beginning, you, when I say you, I mean you and the rest of the Okta team, You did all this research around really understanding what signals gave customers that confidence to move forward and what proof they needed to do that. It obviously speaks that it was very successful by doing that approach.
31:13And you didn't just throw some generic trust signals into the mix either. Again, not just like splapping a badge on the website. You actually built something that's personal and human. So I love that. it's, it's really helpful and appreciate you taking the time to walk us through this playbook.
31:30Kevin Gough:All right. Okay. So closing out that segment and moving on to the next, next segment of our show is the messaging critique. Okay. So this is where we as product marketers get to analyze real world market or messaging. And the fun part is Kevin, you, my guest get to pick the company. So before we get started, I'm going to walk through some quick round rules. So you're going to tell us what the company is that we're going to analyze today. And then once we do that, you're going to walk us through the messaging. You're going to tell me one thing that you're loving about the messaging, something that stood out about the product.
32:03And then you're going to tell me something that you wish the PMM would have done differently as they were building out that messaging. And then finally, we're going to do a quick fun brainstorm around how could this PMM take it to the next level? How, you know, maybe they could create some fun content or a new creative campaign, something that the PMM could think about. This is all about refining our craft, no negativity, just a thoughtful, constructive critique. So let's get into it. What is the company that you would like to analyze today? Yeah.
32:37Kevin Gough:So the company I want to look at today is Rippling. It's kind of an everything in one tool for small businesses. It does HR, IT, financial things like spend management, payroll. So I think it's interesting because it's kind of a platform, but the buyers are pretty different. Typically, an HR person versus an IT person versus a finance person, they really have to try to reach a really diverse set of buyers. But for a system or tool that pitches itself as all in one. Yeah. You have really distinct buyers that you mentioned, right? I think you said IT, HR, finance. Those are very distinct buying centers.
33:19Okay. So for those of you who want to follow along, check out rippling.com. It's R-I-P-P-L-I-N-G.com. Okay. So tell me about their messaging, like right off the bat, no, I guess just starting at like with their header and subheader, what are you seeing here and what's working and not working?
33:36Kevin Gough:Yeah, so their header is employees get more done with Rippling. And here's what I like about it is they're not because they have such a diverse set of buyers, they're not trying to get something that touches every single buyer. They're talking about the end consumer, which is the employee. So HR, IT, finance, ultimately, they in some ways have to be in service of the employee. And if they can help the employee get more done, then that delivers value across the business. So I like how they've kind of thread the needle where this is something that all three of those buyers probably want to have happen.
34:16Yeah. So it's kind of like uniting these very distinct buying centers around one common goal. And I heard this, maybe I heard it from a different guest on my show. I can't remember, but I heard this one time where you can tell how good a product is by like when you take it away from your end user and how they react to you taking it away. Like Slack is an example of that. Like when you take away the, like, like every employee is not the buyer of Slack as an example. But if you take that tool away from them, they're going to be really bummed about it. So applying that same similar idea here, obviously I don't, I've never used dripling.
34:54I'm not really sure, you know, not speaking on it from that perspective, But the idea is that like uniting all of these different buying centers around giving a tool that employees appreciate or like, ideally, right, they're getting more done. That's maybe a good a good way to test how effective that tool is. And, you know, so definitely a consideration for those different buying centers. So you like that aspect about it. OK. And what's something that maybe the PMM could have done differently as they were building out some of their messaging? Sure.
35:27Kevin Gough:So it's interesting just looking at the site itself. There are many calls to action, which is see rippling, get a demo. All of those drive to a reg form. So to me, it's really clear that this site is owned by demand gen. It's designed to perform. You know, and so in some ways you kind of see like the org chart when you look at a website and sometimes it's very brandy and sometimes it's very producty. Well, this one is very revenue marketing. And that I mean, this is a hyper growth company. So and it's also SMB. So the cost per acquisition is key to the profitability of the product. So again, what I would love to see as just a visitor of the site is surfacing a little bit more of the interactivity and engagement, just a little teaser demo or a teaser quote from an existing customer.
36:26Kevin Gough:Just something that kind of, I'd say, humanizes the product a bit more is, I think, what I'd love to see on the site. I completely agree. And I was thinking that as you were saying. So for example, on their website here, they've got this great headline, this really strong message and please get more done with rippling. And then on the side, they have a step like right next to that. They have a static image and it's I think it's a replication of what their product looks like. And that's not bad. In fact, I like seeing what the product looks like. I liked product imagery. I just think they could have done, there's so much more opportunity with that real estate to tie the imagery directly back to employees getting more done.
37:13And maybe they're trying to show that with showing the, you know, they've got talent, benefits, like IT, spend, payroll, like all in that one image. So maybe they're trying to show an all-in-one. In my opinion, it's a little too much. And it makes your customer, your ICP, have to work a little too hard, I think, to make that connection. So I would like to see them maybe do some brainstorming around how could they make it easier for visitors of the site or their ICP to make it easier for them to draw the connection with whatever imagery they use with that really strong messaging that they have.
37:53So curious what you think about the imagery.
37:56Kevin Gough:Yeah, I mean, I'd love to see if their site supported it. I mean, that could be an animated GIF. It could be a little carousel. It could be something that kind of has some action or activity around it. Because the workflows are interesting. I mean, you see enrolling in benefits, assigning a computer, assigning a corporate card. You know, once you zoom in two times and you see some of the capabilities, you're like, oh, this looks good. So I think that surfacing these workflows in an engaging fashion and maybe a couple of these workflows, I think, could really kind of add a little bit more specificity to the product.
38:35I completely agree. I think some kind of like animated GIF or something that showed like a process, because as you're saying it, like showing it as a story would be really effective. I do love that they have all the proof points with all of the star ratings that they have. So that's really effective, too. And they've got great customer stories on here as well. So what's something that the PMM could consider to take it to the next level?
39:01Kevin Gough:You know, I would be curious about how they use this landing page, because part of me says maybe there's a bunch of microsites that they've created for IT, for HR, for, you know, So maybe there's a whole play of you're actually targeting specific ICPs, bringing them to an IT or an HR specific landing page, having more specific messaging, and then kind of over time expanding into these other areas. So I would be curious about their land and expand strategy and maybe go deeper on some more targeted microsites or landing pages specific to those buyers. Yeah. You know, when I click, I clicked on each one of those CTAs, those call to actions for each of the buying centers.
39:50And it looks like IT has a special one and the others don't. There's just like immediately looks and feels different. And the actual URL is different as well. So it's really interesting. I wonder if something that, as you're saying, is kind of a strategy, but maybe there's another way that they could be thinking about it, as you said, to take it to the next level.
40:14Kevin Gough:Very cool. Any thought, any quick, like, last thoughts on Rippling? Well, you know, the other thing I like that it was pretty popular a while back, but I'd say it's fallen out of favor. But I like that they have that what's new at Rippling carousel. I think if you have enough news that if people are coming back to the site or have a little time to explore, I do like how they're surfacing the latest and greatest. It's case studies. It's launches. And so this also just gives, honestly, PMM more surface area to do a little bit of promotion while keeping the site fresh without having to do an entire site redo, which can be time consuming and expensive.
40:56Oh, my gosh, I know. And hard. just hard for a PMM to try to get, even if you will update messaging, for example, or you have a new creative story to tell and you want it featured on the site. Oh my gosh, could take forever, especially getting it on a homepage. So yeah, that's a really good call out.
41:13Kevin Gough:Okay, cool. Well, hey, Rippling PMMs, great work. We like your strong messaging and we've got some ideas for you if you're open to it. All right, so that concludes the messaging critique segment. And so, Kevin, there's one thing I want to do before we go. I like to make space for what I call a moment of gratitude on the show because in product marketing, none of us get here alone. We always learn from each other, definitely building on each other's work, and we're all better for it. So before we wrap up, I want to say a genuine thank you for your time and effort, all the preparation that went in on your side ahead of the show and sharing your playbook on Okta and all the time and insights you shared.
41:57Thank you so much. I really, really appreciate it.
42:00Kevin Gough:Thanks. It was a lot of fun, Elle. Yeah, of course. And I'd love to now turn it over to you. Who's maybe one or two PMMs who's made a real impact on your career? This is a great time to give them a little shout out. Sure. I definitely have a few shout outs from across my career. So I want to give a shout out to Jeremy Milo from my time at Google. He was instrumental in helping me think about kind of zero to one product marketing. So I think we launched 13 different products during my time there. And so really just building up that muscle of understanding the ICP and taking it to market and figuring out what channels to sell it through.
42:36Kevin Gough:I want to give a shout out to Ed Sama from my time at Okta. Ed is kind of a master craftsman of product marketing, and he has a blog that's taught me a lot, but also we work together closely. So kind of all of the fine tuning of the craft, especially around pricing and packaging, which I think is something that's increasingly important, especially with AI workloads and cloud workloads. We're kind of innovating new ways to price and package offerings. And then Pooja Rahmani from my time at Asana. And this was a really fun one. We were trying to figure out the product-led sales motion, which kind of takes the best of product-led growth and sales-led growth and combines them together in innovative ways.
43:21Kevin Gough:So I really enjoyed my time working with her on that. I love it. You really had some amazing mentors across your career. That's awesome. And this is my last question for you, I promise. Where else can we access your expertise? Is it best to find you on LinkedIn? Sure. Happy to have a chat. I always like talking to people starting companies. So if you ever want an hour of free time to riff, I'm all for it. That's awesome and very generous of you, as is with all the rest of the effort and time that you've already given us. So thank you so much. And thank you, PMM listeners, for coming on this adventure with us today.
43:58I hope this episode leaves you with inspiration to take in the next step of your own journey.
From the publisher
Moving upmarket to Fortune 1000 accounts isn't just about great products—it's about building trust with complex buying committees. Kevin Gough joins us as one of the most creative problem solvers in product marketing, from launching Google Cloud products to leading category-defining efforts at Okta, Asana, and Grammarly. Today he's sharing how he built trust strategies that opened enterprise doors and helped Okta beat Microsoft at their own game.
Kevin reveals his approach to mapping each stakeholder's unique trust requirements—treating trust like a product with features and proof points. We explore Okta's "trust ecosystem," including their genius microsite showcasing uptime data and compliance documentation usually buried in legal folders. This wasn't transparency theater; it was demonstrating trust with actual receipts that transformed market perceptions.
The magic happened when Kevin mobilized the entire go-to-market team around trust, transforming it from marketing message to company-wide mission. His approach proves platform storytelling isn't about louder claims—it's about earning trust one stakeholder at a time, proving even Microsoft-sized giants become beatable when you get trust right.
LINKS
Rippling (messaging critique): https://www.rippling.com/
Connect with Kevin:
LinkedIn: https://www.linkedin.com/in/kevingough/
Connect with Elle:
LinkedIn: https://www.linkedin.com/in/elle3izabeth/
