Strategy, Focus, and Culture: Lessons from Martech Leaders in Times of Change
In this conversation with Rachel Gray—Sr. Enterprise AE at Optimizely and founder of That Martech Girl—we cover her journey from science labs to martech leadership, the three essentials for thriving in economic downturns (strategy, focus, culture), and why businesses can’t afford to ignore AI strategy. Rachel also shares her sales framework, lessons from leaders who’ve navigated scarcity, and what agentic AI means for the future of organizations well beyond marketing.
Here are some hot points from the interview:
The 3 keys to surviving downturns: strategy, focus, and culture.
Businesses must develop an agentic AI strategy—ChatGPT alone isn’t enough.
Sales success comes from consultative conversations and aligning with the client’s timeline.
By 2026, agentic AI will reshape entire organizations, not just marketing.
Bria Porter: So Rachel, for those who do not know you, can you share a bit about your journey into martech and what inspired you to start That Martech girl?
Rachel Gray: Um, how much do you want?
Bria Porter: whatever.
Rachel Gray: Okay, well, I originally started my career in biology and chemistry, so mark technology is a far cry from biology and chemistry, right? However, I was looking for a job during grad school in Chicago, and the one that I found was in sales. So while I was there, I got to shadow this amazing man who became my mentor. He taught me all about sales. He taught me all about account management, etc. I was his rev ops manager, and I got to build out a CRM. That was back 10 years ago when CRMs weren't like a thing, and I got to build out like a Salesforce CRM for him and digitize his processes from completely paper to completely digital. So it was my first entrance into, like, marketing technology. And I took that wherever I went, and I became, like the expert in marketing operations. And then from there, I, like, started to blend both my sales knowledge and my MAR tech knowledge, and eventually it led me to a Mar tech firm, and I started doing the full sales cycle for them. And then fast forward, 10 years later, now I am an enterprise account executive at Optimizely, which is the leading marketing operations platform or digital experience platform in the market. So, yeah, that is, like, high level my journey into martech, and thus far in my career,
Bria Porter: It's giving leader the whole time throughout I like it. Yeah, from your vantage point at Optimizely and as a podcaster, what excites you the most about marketing technology and where it's headed right now,
Rachel Gray: I think for me as a consumer, I've always been fascinated with marketing, even just dabbling in social media. So being on the inside of that and seeing, like, the pace of innovation and how fast things are moving, especially with AI, it's so interesting to me, especially with that consumer perspective of like, where things are going. And then, you know, I'm doing the MBA at Vanderbilt, and it's just like having the perspective of like economic change, and how companies who have survived economic change have done so in the past. Now having like that interest as well as the consumer interest, like together, it's just, I don't know, both on a philosophical and a consumer point of view, and also in my day to day work, it's completely interesting to me. Yeah, so that's, that's my perspective on it.
Bria Porter: I completely agree. I think it's moving fast, and especially with AI, we're moving at a pace that's faster, you know, it's like a gold rush, almost, with how quickly it's moving. Now we're in this place where we're headed towards a recession, and you have to be very careful. What are you learning about leaders of organizations and what they've done when there's a [time of] scarcity or concern or conservatism when it comes to the economy, what do you see that they're doing?
Rachel Gray: So it's interesting you asked that because yesterday, that was all we were talking about in class. And it's this fascinating perspective we actually had. We had this CEO come in who's a three time CEO of tech companies, and he came in, he was talking about that, and how he's changed companies during times of economic downturn and the changes he's made. Also looking at Amazon, Blockbuster, X.com, and why some of them failed, versus why some of them survived during economic downturn, that was the topic of conversation, and he really like brought it down to several things. And the first was like strategy, like really having a clear strategy, having the ability to pivot during times of economic downturn.. Making sure that there is a strategy, because a bad strategy is better than no strategy, literally coming from the CEO's mouth. So that's number one. Number two, he was talking about focus, like how Yahoo, for instance, during the "dot com" era had no focus, and who has a Yahoo email address now, right? They're doing all sorts of things. They had no focus. So they were scattered in their approach, and they didn't really put energy into things that they found was sustainable. They just kept saying yes to everything, so being really focused in your approach. And then another thing he said was culture. And that one was the one that like stuck out to me the most. And the case study had to do with Costco, where, like during covid 19, retailers took a huge dip, right? But it seems like Costco has survived and is thriving, actually. And why is that? And so a question I asked was like, okay, if I'm Sam's Club and I see Costco doing so well, why not just replicate what Costco has like? It's the business model isn't that complex from an outsider perspective and what that was like. Sure, it doesn't seem complex, but culture is very hard to replicate, so even in times of economic downturn and scarcity, like maintaining that culture really, really, really, really matters, because consumers can also feel that, right? So it's not only in the internal operations, but it has an effect on externally, how that company performs, especially economic downturn. And that was something like, I get like, I didn't think of right? I was just like, culture, whatever. You know, let's, let's go in a circle and say Kumbaya. It's not going to have that much of a difference, but it does. It really does. And like, you could see that difference in actuality, with like company like Costco. So that was interesting.
Bria Porter: That's real. I mean, I think internal and external culture. What are you doing with your employees? What's your ESG look like? What are you doing with your with your customers and your clients, and how you treat the internal side of the business, I think really affects. Um, what bleeds outside, like you're saying so, um, so strategy, culture,
Rachel Gray: strategy, focus and culture.
Bria Porter: I like it. Yeah, those are the big threes. As we're heading into Q4 What do you think business owners should be laser focused on to finish out the year strong,
Rachel Gray: AI strategy. But maybe I'm saying that because Optimizely is so focused on AI right now. But you know, I can only speak from my lens, but I think like in the context of what I learned yesterday in class, like, I think those three things are important as you look towards next year and planning for, like, a new year, if it's your new fiscal, etc, those things are important. But like, also your AI strategy is extremely important because, as we said before, like the pace of innovation is moving so quickly, and if you're not doing anything, if you have no strategy, that's it's unacceptable. You cannot do that.
Bria Porter: So when you think about like aI strategy for a small to mid size business, are you talking about. How they're using AI to push forward, you know, internal operations. Are you thinking about what kind of AI tools they're creating for customers?
Rachel Gray: I'm thinking about all of it. Yeah, I think that there needs to be a strategy holistically. Like, it shouldn't just be, like, with one section of the business. It should be for all.
Bria Porter: So what's in your AI Rolodex? what are the essential tools that people should have?
Rachel Gray: I mean, it depends on the type of organization it is, right? I think it's not a one size fits all, but I think just like focusing on chat, I mean, chat, GPT and everybody knows about that, but I don't think that's enough anymore. I think that, like, the pace of innovation has gone towards agentic so that really needs to be a focus. And we not only need to understand it, but we need to, like, have a strategy of how to implement it, because it will not only help with, like, propelling the business forward, but it will also help with customer acquisition as well. So like, I just think, I don't, I don't necessarily say, like, here is my rolodex, because not, it's not a one size fits all. But like, based on the type of business, I do think you need to be looking not only at chat solutions, but also at agentic solutions as well.
Bria Porter: Got it? Okay, okay, so I'm going to move along into a framework for closing deals, because you're the closer. So what are your big three rules for moving in from consideration into a solid yes?
Rachel Gray: and we're talking purely software sales, tech sales. Perspective, Medic is extremely important to me. That's how I was taught. That is how my leader, my past leader, has taught me. I don't know if you know about medic in the medic framework
Bria Porter: not at all.
Rachel Gray: So it's basically like having an internal list of what exactly is important for that deal to move across the line and making sure that, let's see all your bases are covered and you have all of the information necessary. So metrics, economic buyer, and you can look this up on your own time, but just these specific things that you have internally to be able to say, okay, here is what I need to have. I know that I have all of the informations. All my T's are crossed, all my eyes are dotted. Because if you don't have this information, especially in a like complex sale, then there is no way you can move that conversation forward, right? And so this information is should have been being collected throughout those conversations. You can't just, like, have a conversation, show off your product and then expect somebody to buy, especially when it's a complex sale, you really need to be able to understand, like, why is this important to you? Right? I always think like asking questions is more important than just trying to shove a product down someone's throat, right? We need to be consultative and why that person's even having the conversation with you. So that's number one. Also, like, when you get medic, then you will also understand, like, why it's important for the business and what their timeline is. It's not always your timeline, it's their timeline. So if you can match up your deal cycle to their timeline as like the timing that they have within their business and what's important to them, then you will be able to be in sync with their deal cycle. So if it's like, for instance, we're in September, it's end of quarter. Next month is October. A lot of fiscals are starting in October, so some people have some budget that they need to get rid of by the end of October. So most times that's like, maybe an indicator that we need to get this deal done by the end of September, because then our budgets expire, we have new budgets in October, right? So that's just an example. That's one of many. But like being able to ask those questions to say, like, "Okay, well, why is buying this product important to you? Is there a specific time that you need it by?" It's not your timeline. It's their timeline. So being able to match up your process to theirs and like have a mutual plan to get that accomplished. So it's more like a partnership, rather than just like me trying to shove something down your throat for you to buy something from me, right? So then it feels more consultative and less like just a slimy salesperson trying to get their deal done.
Bria Porter: 100% I was going to say it gives like concierge. It gives more bespoke I'm here for you and what you need and how I can service you. The product is just how we get that done, you know, right? Okay, so one last question for you. What's one trend or shift in Mar tech that you think will define 2026 something business owners should be preparing for right now.
Rachel Gray: I mean, I said this before, yeah, but, like, it's so important, and I don't think we understand the gravity of agentic AI, like really being able to have a workforce do your work for you, and then creating a strategy around that like this has never been accomplished before. We actually talking about this yesterday in class. The reason why this innovation has moved forward so quickly is because super computers have gotten this innovation and got into this place, and it hasn't been done before. So, like, this has never happened before, and this way of thinking is completely new. So I don't think it's only a shift in marketing. I think it's a shift in, like, digital transformation, organizational transformation, where everything is going to change. It's not just confined to marketing, and I think that's a big piece of what we're doing wrong. And like, how businesses are thinking about this wrong, where they're just thinking, Okay, well, let marketing suss out their AI tools. Let HR suss out their AI tools. Let you know each section of the business try to figure out what they want to do with AI and that type of thinking is completely wrong, because think about this, if you have agents in each portion of the business with workflows that are completely connected. How can each organizational unit suss out their own tools? That is like a recipe for disaster? That's why I think the strategy starts at the top, and it's like, you know, we need to have a holistic strategy, rather than just like, go figure it out on your own. That's not going to work. So I don't be, I think, like, more than anything, my advice would be, really understand what agentic AI is and what it can do, and then with that knowledge, then come back to the table and start thinking about the strategy, because it's like, if we're saying, how is that going to change marketing, I think we're asking the wrong question. It's more like, how is it going to transform the organization, and how will marketing fit into that? So yeah, that would just be my last pieceof advice.
Bria Porter: We recently did a blog post about the importance of not working in silos interdepartmentally, and how that really can shifting. So right on par with you there.
Thanks, Rachel.
Rachel Gray: You're welcome.