Context Is the New Strategy: Chae O’Brien on AI, Signal vs. Noise & the Future of Go-to-Market

ICYMI: Chae O’Brien catches up with 10 Minute Martech on why AI without context is just noise.

“Look at five to ten AI-generated options, and you should instantly be able to see what’s incoherent and what aligns with your vision.”

In this episode of 10 Minute Martech, Chae O’Brien, Principal Strategist at Thought Bakery, joins host Sara Faatz to explore one of the most pressing challenges facing marketing teams today: navigating the rapid rise of AI while still building thoughtful, effective go-to-market strategies.

From startups trying to balance lean growth with AI mandates to the changing behavior of modern B2B buyers, Chae unpacks how marketing teams can maintain clarity and direction when the pace of technology feels overwhelming.

Chae’s Big Idea: Context Is the Infrastructure for AI-Driven Marketing

Chae reframes the AI conversation around a simple principle: technology only creates value when it is grounded in context.

AI can generate endless campaigns, messaging ideas and strategies, but without a clear understanding of the customer, the company’s roadmap and the broader go-to-market strategy, those outputs quickly become noise.

Her advice to marketing leaders is to treat context as shared infrastructure. When teams deeply understand their customers’ day-to-day reality and align around a clear strategic vision, they can use AI to accelerate execution. Without that foundation, even the most powerful tools will struggle to produce meaningful results.

10 Memorable Moments with Kevin Hein

1. AI Mandates Are Overwhelming Teams

Startups and marketing teams are being pushed to adopt AI while also reducing budgets, shrinking teams and building leaner go-to-market strategies.

2. Marketing Leaders Are Facing Hard Questions

The biggest question Chae hears from clients is simple: What measurable result will this actually deliver?

3. Leaders Need a Bird’s-Eye View

Before diving into tactics or AI adoption, organizations need to step back and understand the broader strategic picture.

4. Simulate Your Customer’s Day

Chae often asks leaders a deceptively simple question: Can you stimulate the day-to-day life of your ideal customer?

5. The B2B Buying Journey Is Mostly Autonomous

By the time buyers engage with vendors, most of their research is already done.

6. Generative Search Will Reshape the Funnel

As AI becomes a research tool, even more early-stage discovery will happen through generative interfaces rather than traditional search.

7. ‘Taste’ Defines Strategic Clarity

Chae describes “taste” as a company’s ability to know what fits its strategy, messaging and brand.

8. Context Should be Shared

Organizations should maintain shared context files or knowledge systems that allow teams to stay aligned when using AI

9. Discernment Becomes a Core Skill

When AI generates multiple campaign options, marketers must be able to quickly identify which ideas support their goals and which are simply noise.

10. AI Adoption Is Moving at Unprecedented Speed

C-suite adoption of AI is accelerating faster than almost any technology shift seen before.

Chae’s Martech Hot Take

“AI should be treated like science. Some experiments will fail, some will succeed. But we have to keep testing to understand what actually works."

For Chae, the biggest mistake organizations make is expecting immediate answers. AI adoption is happening during a messy middle where experimentation, iteration and learning are all essential.

Chae’s Inspiration List

Chae draws inspiration from thinkers and researchers who are studying AI adoption in real-world environments:

• Allie K. Miller – AI strategist and educator
• Conner Greenan (NYU) – AI and innovation expert
• Ethan Mollick (Wharton) – Researcher on AI and organizational adoption

Their work bridges the gap between emerging AI capabilities and practical implementation in organizations.

Listen to the 10 Minute Martech Episode

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Next Up in the 10 Minute Martech ICYMI Series

Kyle Lacy, Chief Marketing Officer at Docebo, joins us to unpack how his team is generating multimillion-dollar pipeline from tools built in just a week, and why the real difference comes down to whether leaders invest in upskilling or simply issue AI mandates.

Want to Keep Reading in the Meantime? Full Transcript: Chae O’Brien

Here’s the full transcript to keep you transfixed. Every insight, every quote, unedited and unforgettable.

Sara Faatz: I’m Sara Faatz, and I lead community and awareness at Progress, and this is 10 Minute Martech.

Chae O’Brien: Look at 5 to 10 AI-generated options, and you should instantly be able to see what’s incoherent and what is aligned to the vision and product roadmap or growth roadmap of your firm. You should be able to discern which ones will support your goals and which ones would rather fall more in the bucket of noise versus signal.

Sara Faatz: That’s Chae O’Brien, principal strategist at Thought Bakery. Let’s get started. Chae, let’s just dive right in. Can you tell me what is your deep thought, or what is keeping you up at night right now?

Chae O’Brien: Startups today are really, really overwhelmed by the mandate to lean harder into AI whilst trying to figure out how to build lean go-to-market stacks, while trying to figure out how to get to know their customers better, while trying to figure out, in the age of mass content or great content of a very high value being provided en masse because of AI, how do we cut through the noise? Most of the time when I work with clients, the biggest question is, what result is this going to deliver?

Chae O’Brien: And the challenging part about that is I am at a place many times now… I’m very comfortable with saying I’m not sure. And two years ago, if someone told me this would be me, I would say that doesn’t sound like me, right? Because for me, marketing does not work if we cannot measure it. I am one of those that believe in measurable marketing, but that’s really what’s keeping me up. The fact that we’re having all these very abstract conversations and mandates that are affecting the workforce in a very real, debilitating way of use more AI, do more with less, cut the budget, be more lean, be more efficient.

Chae O’Brien: The world is also a little bit on fire globally. So, we do need to take a step back, and most of the time at night I’m thinking, okay, how do I get leadership to take a step back and see the bird’s-eye view before we can get into those tactical conversations of go-to-market?

Sara Faatz: There is a lot of change happening right now, and you’ve even said that we have to think about how we measure differently, and you have different teams that are thinking about things differently than they ever have before. How do you facilitate that change management?

Chae O’Brien: Part question that I feel just cuts straight through the argument is, can you tell me, in the day-to-day, can you simulate your customers or your top ICP personas? Can you simulate their calendar, a day in the life of them? And many times I get pushback and they’re like, “Oh, what kind of silly question is that?” or like “Yeah, I know what you’re getting at.” I’m like, “No, I’m being very serious. I’m not trying to be a thought leader.”

Chae O’Brien: Because for us to really have that discernment to know what should be part of our customer experience and what just doesn’t represent who we are and how we want to serve our customers and future buyers, you need to intimately know what their day-to-day looks like. What we’re not addressing, and I don’t think we could address it in 10 minutes, is fundamentally the way people behave with their digital interactions, it’s decomposing. The top of the funnel now… I am not gonna read 10 blogs, I am not gonna read 50-page PDFs. So, people are changing in how they trust, in how they research. They want to be more autonomous.

Chae O’Brien: We saw that 80% of the B2B buying journey. I think 6th Sense in their report about a year or two ago said that 80% or 75% up. It’s an autonomous journey. So, by the time they make it to that choice, they already sort of know who they want to go with. And when we think about generative search and what we can do, I imagine that’s gonna tick up aggressively as more people become doing their top-of-the-funnel research with generative search. So, when I talk to leaders and I ask them that question and they cannot answer, or they give me abstract answers, I say, “Right, if we really want to understand the taste of this firm or invest in it where it is formidable and it is the connective tissue that lives and breathes in all of our go-to-market, we have to admit how much we know or don’t know about the audiences we’re really trying hard to show value to, to educate.”

Chae O’Brien: Using the word taste, a lot of people are like, “I still don’t get what she’s talking about.” It’s really context. In the age of AI, we should all have shared context in.md files that everyone can feed into their enterprise AI safely and then communicate in a way that same company, different teams, slightly different goals, but same roadmap is being followed, right? Several moving as one. When you treat context as infrastructure, you decide who owns the truth, how it’s updated, and how it propagates. You invest in fewer systems so that you’re better connected.

Sara Faatz: So, what if somebody wants to determine if their organization has that, or even try to figure out where on the taste journey they are, what are a handful of things they can be looking at to say, “Okay, we should be pulling levers over here and thinking differently on this, but we’re okay in this area”?

Chae O’Brien: Let’s say we’re looking at go-to-market strategy for a specific segment, and we want to build evergreen campaigns to support different go-to-market motions for that segment. Look at 5 to 10 AI-generated options, and you should instantly be able to see what’s incoherent and what is aligned to the vision and product roadmap or growth roadmap of your firm. You should be able to discern which ones will support your goals or support it with edits, and which ones would rather fall more in the bucket of noise versus signal. So, discernment between what the AI is giving you and the context that you have is what’s really important, because if you can’t discern between all the options, then you’re not really sure yet about what specifically, where specifically your brand plays when it comes to the type of motion, the way the campaign would be built, the way the persona would be educated, engaged, attracted, nurtured… All of that.

Sara Faatz: Wonderful. I have one more quick question for you. You’ve talked a little bit about some people that you follow, but who do you follow for inspiration or information?

Chae O’Brien: I feel like Allie K. Miller, who worked at Amazon… Now she’s the CEO of Thinking Machine. I find the way she gives tutorials, the way she shows enterprises to look at AI in small use cases first at the individual’s persona level has been very powerful. Connor Grennan at NYU, they’re also, they seem to be friends because many times they speak together. And then Ethan Mollick, he’s at Wharton. I think his studies are phenomenal.

Sara Faatz: Absolutely.

Chae O’Brien: I think in this space, many times it’s a little bit incestuous in B2B. We do follow everybody else and we egg each other on, which is a good thing. But when it comes to AI, we should treat it like a science. And, if we were in school, we would know that within science, there’s a lot of experiments that can fail, and there’s a bunch of them that do really cool things that lead to positive outcomes. So, I like to look at the people that are sort of influencing my thoughts. Definitely academics, but academics who are not testing it in an abstract form. They are testing it with organizations of different sizes. I think one of the biggest things that stood out to me is Ethan had said there’s been so many phenomenal technologies, but he’s never seen C-suite leaders adopt AI in the aggressive growth adoption rates he saw with C-suite executives. He was surprised by it.

Chae O’Brien: Then we saw people like Jensen Huang three, four years ago talking about PDF GPT, and now people be like, “PDF GPT? What?” Because it’s moving so fast. So, I find when you… For me, those three people, I do pay attention to a lot of what they say because it can feel like whiplash with a model coming out all the time. I mean, Claude, Co-Work, Gemini, Co-Intelligence… These are phenomenal new ways to use AI within team-wide workflows. But to really leverage that, we have to understand what’s happening on the human side, what is changing in the expectation of us working, right? The future of work is very much hinged on leadership’s ability to recognize we are in a messy middle, and time needs to be taken to do a skill inventory, figure out how that needs to evolve and translate it into an AI-forward way. And there are going to be roles that are still analysis-heavy and AI will do some automation, but the human is still very much eight to six in the office.

Sara Faatz: Yeah. Yeah.

Chae O’Brien: Taking it for granted that it will demolish and cannibalize the intellectual capacity so many of us have built up, I think, is a bit ignorant. So, that’s where I hope leadership really tunes in a little more to the sensitivities of what this means for the future.

Sara Faatz: Thank you so much for your time today. I really appreciate it, and I really enjoyed our conversation.

Chae O’Brien: Indeed. Thank you, Sara.

Sara Faatz: Thanks for tuning in. Make sure you like and subscribe wherever you get your podcasts. Until next time, I’m Sara Faatz, and this is 10 Minute Martech.

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