Tag: go-to-market

What AI Is Doing to Marketing
I’ve been working with large language models since 2021, and in various forms of AI tooling for most of my career before that (including graph databases, for anyone who remembers when those were the interesting frontier). So when I wrote a piece early last year about AI tools in marketing, it wasn’t my first time thinking about the question. It was, in retrospect, still too optimistic about some specific bets.
I highlighted RB2B as a tool worth watching; it identifies individual visitors to your website, surfaces them in Slack, lets your sales team follow up while the signal is warm. My enthusiasm was genuine. What I underestimated was fit. Visitor identification tools turn out to work best for the organizations that need them least: teams with high traffic, tight sales processes, and reps who act fast. For everyone else, you get a notification and an awkward non-conversation. I’ve moved from recommending it broadly to recommending it selectively. That’s not a criticism of the product. It’s the kind of calibration that only happens after you’ve watched something in practice.
That recalibration is a small example of something larger. The question in early 2025 was still mostly evaluative: which tools are worth trying, what are the risks, how do you avoid getting burned. It made sense then. The field was genuinely new and very uncertain. That frame is less useful now, because most organizations have tried things, formed opinions, and started to see where the returns are real and where they aren’t. The more interesting question is where AI has actually changed the work, as opposed to where it’s been inserted into the work without meaningfully changing it. There’s quite a bit of the latter.
Some of the most durable changes are happening at the operational edges, in places that don’t generate much coverage. AI tools that connect to calendars, email, and file systems have gotten quietly good at surface-level relationship management: flagging follow-ups that have gone cold, surfacing context before a call, noting when a client hasn’t heard from you in a while. I use Copilot for this daily. Working across multiple client relationships, the question “did this person ever get back to you on that thing you asked three weeks ago?” is a real problem, and AI solves it in a way that a well-configured CRM never quite did (and I am, for the record, a genuine advocate for CRMs). It doesn’t require disciplined prompting or careful setup. It just works.
More interesting to me is AI’s usefulness as a thinking partner at the senior level: not for producing outputs, but for stress-testing ideas when the right person isn’t available. If you want to know how a skeptical CFO might receive a pricing proposal, or what a competitor would likely say about your positioning, or whether a strategy has obvious holes you’ve stopped seeing from too close, a well-framed conversation with a capable model is a surprisingly useful substitute. This isn’t a replacement for real colleagues or real judgment. It’s a workaround for the moments when the right conversation isn’t accessible, and in practice it’s more useful than people who haven’t tried it would expect.
The content production side is where I’d urge the most precision about what you’re actually trying to accomplish. AI can generate SEO-oriented copy at scale, and for some organizations that’s a legitimate choice. If the goal is volume and broad keyword coverage, and you’re willing to accept mixed quality in exchange for low cost per piece, AI handles that reasonably well. Most SEO agencies produce similarly inconsistent results at significantly higher cost. If that’s genuinely your strategy, AI is probably the better procurement decision. But it’s not a strategy I’ve ever advocated for, because it describes a race to produce content readers didn’t ask for in order to rank in searches that AI intermediaries are increasingly answering before anyone clicks. Search behavior has changed materially, and more queries are being resolved inside AI interfaces entirely, which means the volume playbook is producing fewer returns even when executed competently. The organizations that appear to be navigating this more successfully are investing in content that demonstrates genuine expertise and earns cited presence in AI-generated answers, rather than content optimized to rank. That’s harder to produce, and AI is a less reliable tool for it, because it requires organizational knowledge and a distinct point of view.
That raises a different set of questions, and a pattern I’ve been watching with growing interest.
Across a number of organizations right now, AI is being deployed as an IT initiative. Agents are getting rolled out through the infrastructure function, often without meaningful input from marketing, sometimes without input from sales or customer support. The parallel that keeps coming to mind is the early internet, when IT was given ownership of the company website. Those websites worked, technically. What they frequently didn’t reflect was any coherent sense of organizational purpose, customer communication, or marketing intent. They were websites in the sense that they existed and loaded. The same dynamic is playing out now, but faster and with more organizational surface area.
Social media went through a version of this too. Companies would hire someone to “do the social media,” and the goal would be expressed in the metrics the platform made visible: followers, likes, reach. Rarely was there a clear connection to business goals. The work was real; the direction was often missing. AI deployment without a coherent owner and clear intent tends to produce the same category of problem.
Sales has been among the most active self-directed adopters of AI tools. Clay, Instantly, and similar platforms are genuinely powerful: they can enrich prospect data at scale, automate personalized outreach, identify buying signals, and run sequences that would have required a team of SDRs a few years ago. There’s a legitimate case for all of it. There’s also a real failure mode, which is that sales teams running these tools independently tend to be operating without the organizational context that would make the campaigns actually work. Who is the ICP? How does the product solve their specific problem? What’s the right language for the moment the prospect is in? Are existing customers getting accidentally included in future-focused outreach that doesn’t reflect their current relationship with the company? These are questions sales often doesn’t know to ask, because they’re marketing questions. And when you add AI scale to outreach that’s imprecise at the targeting level, you get volume applied in the wrong direction: very much its own kind of problem, separate from annoying people (though it does that too).
The enterprise picture is different, and worth watching even for those of us who don’t primarily work there. Large organizations are rolling out AI initiatives, often because a CEO heard about it at a conference or a board member asked about it. What’s striking is that the definition of “AI” in many of these conversations is remarkably uneven. Many haven’t fully used what they already have. Copilot is embedded in tools that hundreds of millions of employees use daily, and yet active adoption remains shallow. When employees have access to both Copilot and ChatGPT, only 18% choose Copilot voluntarily — when Copilot is the only available tool, that figure rises to 68%. Stackmatix That gap says something about the difference between distribution and genuine utility.
Meanwhile, the conversations happening inside those organizations about AI often land somewhere unexpected. When I ask people in enterprise settings what they’re actually getting value from in their AI tools, the two things I hear most often are: help writing emails, and help navigating internal politics. In highly matrixed organizations, heavy on bureaucracy, permission structures, acronyms, and stakeholder management, knowing how to word something to subtly achieve a purpose, or understanding the terrain before a difficult conversation, can be genuinely valuable. No judgment there. (Well, a little.) But it’s a narrow slice of what modern AI tools are capable of, and if most people in a large organization are converging on the same use case, the marginal value of that use case compresses over time.
What all of these patterns share is a common structural problem: AI deployed without a coherent owner, in service of goals that were never made clear before the tools were turned on. The IT team rolling out agents, the sales team running outbound at scale, the enterprise initiative that can explain the vendor but not the objective: these aren’t technology failures. They’re organizational failures that technology is making more visible.
The piece I wrote in early 2025 reflected an honest read on a fast-moving and genuinely uncertain moment. What I’d add now, a year and change later, is that the pace of the tools has continued to outrun most organizations’ ability to integrate them with any coherence. The limiting factor was never access to AI. It was always clarity about what you were trying to accomplish before you turned it on, and that’s not a new problem. Too many organizations have asked too much of marketing for too long, with insufficient resources and loosely defined goals. AI doesn’t resolve that condition. In some cases, it just makes the ambiguity faster.
2026-04-29
Why Your Funnel Isn’t the Problem (Even If It Looks Like It Is)
When conversion rates start to slip or pipeline slows down, most teams end up in the same place. They turn their attention to the funnel. It is the most visible system they have. It has stages, numbers, drop-off points, and a clear sense of where things appear to be breaking. That makes it feel like the right place to work.
So the fixes begin there. Landing pages get reworked, forms get shortened, sequences get added, attribution gets cleaned up. There is usually a clear owner and a set of metrics that can be improved incrementally, which reinforces the sense that progress is happening even when the underlying pattern does not change very much.
Part of what makes this difficult is that funnel issues are rarely imagined. They are real. You can see where people are dropping off. You can measure where conversion weakens. The mistake is assuming that those points of friction originate inside the funnel itself, rather than treating them as the place where something else is surfacing.
A common version is strong top-of-funnel activity paired with weak conversion into qualified opportunities. Traffic is there, leads are coming in, engagement looks healthy, but sales ends up questioning the quality of what is being handed over. Marketing can point to volume and activity, sales can point to low close rates, and both perspectives hold up on their own. The tension comes from the fact that neither explains why the gap exists.
Another version shows up closer to the point of conversion. People begin the process of reaching out and then stop. They fill out part of a form, or spend time on a contact page, but do not complete the step. It is easy to interpret that as friction in the interface. Sometimes it is. Often it is hesitation that the funnel is not equipped to resolve.
In one case, a services firm had exactly this pattern. A meaningful number of visitors were reaching the contact page, but very few were submitting the form. The page itself was minimal. It presented the form clearly, but did not do much else. It assumed that by the time someone arrived there, the decision to engage had already been made.
Shortening the form helped slightly. The more meaningful change was adding context that should have been present earlier but was not. What working with the firm actually involved, what kinds of problems they were well-suited to solve, and why a prospective client might choose them over other options. Once that information was in place, submissions increased quickly, not because the funnel had been optimized in a technical sense, but because the decision being asked of the user became easier to make.
Where B2B Funnel Problems Start
That pattern shows up in different forms across companies. Funnels tend to function as a kind of compression point for the rest of the go-to-market system. They carry assumptions about who the audience is, what problem is being solved, and how clearly that problem has been communicated. When those assumptions are weak or inconsistent, the funnel becomes the place where that inconsistency is exposed.
This is why incremental improvements often have limited impact. You can reduce friction, adjust sequencing, and improve conversion rates at the margins, but those gains do not compound if the inputs are misaligned. If the audience is too broad, the funnel fills with people who were never a strong fit. If positioning is vague, the funnel has to do more explanatory work than it is designed for. If marketing and sales are operating with different definitions of the customer, the handoff between them will continue to feel uneven.
None of these issues originate in the funnel, but all of them appear there.
That makes the funnel a useful diagnostic tool, but a misleading starting point. It tells you where something is breaking, not necessarily why. When teams focus exclusively on fixing what they can see, they can spend a long time improving a system that is accurately reflecting deeper uncertainty.
There is a point at which funnel optimization becomes powerful. When the rest of the system is coherent, small improvements in conversion and flow begin to matter more, and the work starts to compound. Before that, the funnel tends to behave more like a mirror than a machine. It reflects the clarity of the decisions that sit around it.
If those decisions are still unsettled, the funnel will continue to look like the problem, even as it faithfully reports on what is actually happening.
2026-04-17
Why Your Marketing Feels Busy but Not Effective
Every so often, I’ll talk to a team that is clearly doing a lot of marketing.
Not theoretically. Not “we should probably do more.” They are in motion. Campaigns are running, outbound is happening, content is going out the door, tools are in place. There is real effort behind it.
And still, something feels off.
It usually shows up as a kind of background frustration. The numbers are not terrible, but they are not convincing either. Pipeline exists, but it is uneven. Sales conversations feel harder than they should. There is no obvious failure point, just a sense that nothing is quite landing.
At that stage, most companies assume they need to improve what they are already doing. Tighter messaging. Better channels. More output. Sometimes all three.
That instinct makes sense. It is also where things start to drift.
Why Marketing Isn’t Working: When Activity Replaces Direction
Because the issue is often not how the work is being done, but what the work is meant to accomplish in the first place. Marketing exists inside the company, but not as a clearly defined function. It is a collection of activities rather than a system with a job to do.
When that happens, activity becomes the default way to make progress. If something is not working, you add more. More campaigns, more experiments, more surface area. It feels responsible. It looks like effort.
It also creates a kind of internal noise that is hard to diagnose.
You can see it in how targeting gets discussed. There is usually an idea of the audience, but it is broad enough to accommodate almost anything. The definition shifts depending on the campaign or the person running it. Over time, that flexibility starts to erode any real sense of focus.
The same thing happens with measurement. Data exists, but it does not accumulate in a way that sharpens decisions. Different tools tell slightly different stories. Reports get reviewed, but they do not resolve questions. They just confirm that something is happening.
Even the website tends to reflect this. It explains the company, sometimes in detail, but it does not carry much weight in the buying process. It is there, but it is not doing any real sorting or guiding. When someone reaches out, the real work begins from scratch.
So sales absorbs it. Which is fine, up to a point.
But when sales becomes the place where positioning, qualification, and clarity all get figured out at once, the system is already under strain. Every conversation has to do too much work. Some deals close, but it is hard to tell why. Others stall, and the reasons stay fuzzy.
From the outside, none of this looks broken. It looks like a team that is trying hard and staying active.
From the inside, it feels like effort that never quite turns into momentum.
Lately, AI has started to accelerate this pattern. It makes it easier to produce, easier to test, easier to scale activity. For teams that already lack a clear definition of what marketing is supposed to do, that can feel like validation. The systems are running. Output is high. It looks like progress.
But more activity does not create structure. It just fills the space faster.
At some point, the question shifts. Not “are we doing enough marketing,” but “what is marketing actually responsible for here.”
That answer is usually less obvious than it sounds. It is not a generic definition. It depends on the stage of the company, the sales motion, the shape of demand, and what the rest of the organization expects to happen after someone shows interest.
Until that is clear, everything tends to carry the same weight. Campaigns, content, outbound, partnerships. There is no real hierarchy, so there is no consistent way to decide what matters more or what should change.
That is when marketing starts to feel busy instead of effective.
And it is also when adding more rarely helps.
2026-04-08
Swag Isn’t the Point. Memory Is.
What PPAI Expo 2026 reinforced about merch and brand
In January, I attended the PPAI Expo in Las Vegas, the largest promotional products conference in North America, alongside Wendy Addiss of Addiss Enterprises, our longtime promotional products partner.
I didn’t go because Cedar Collab is becoming a swag shop. I went because more of our clients are asking a better question than they used to: How should merch actually work as part of a serious brand or go-to-market strategy?
After a few days on the floor, and conversations with distributors, suppliers, and industry leaders, one thing stood out. Most organizations still get merch wrong. Not because it’s cheap or generic. But because it’s disconnected from intent.
Fewer, better things beat louder things
The strongest signal this year was not novelty. It was restraint.
The merch that actually performs now looks less like promotional product and more like retail. Better materials. Subtle branding. Objects people would choose for themselves.
This isn’t a trend. It’s a correction.
In an environment where every conference bag is full, one well-chosen item can do more brand work than a dozen forgettable ones. If the object doesn’t fit naturally into someone’s life, it doesn’t matter how clever the logo is.
Good merch is worn, used, or kept. Everything else is landfill.
But sometimes, loud is exactly the point
That said, subtle isn’t always the goal.
On the PPAI show floor, Wendy Addiss-Dellar of Addiss Enterprises shared a story about a client who, year after year, ordered enormous bright yellow rulers. They were impractical. They were hard to miss. People joked about them.
And they worked.
Not because anyone wanted a ruler that size, but because people stopped, laughed, and asked, “Where did you get that?” The rulers created conversation. They broke the ice. They made the brand memorable in a crowded room.
That kind of merch isn’t right for most companies. But for that client, attention was the strategy.
The lesson isn’t that novelty wins. It’s that fit matters more than taste. Good merch isn’t always subtle. It’s appropriate.
The moment matters as much as the object
Another pattern that kept showing up was experiential merch. Live personalization. Customization tied to a specific event or interaction.
Not because customization is new. Because meaning is contextual.
The same object lands very differently when it’s tied to onboarding, a milestone, a thank you, or a real conversation. Merch works when it anchors a moment people already care about. When it’s handed out with no context, it becomes clutter.
Sustainability has shifted from messaging to credibility
Sustainability is no longer a differentiator on its own. That was obvious across PPAI and ASI.
What has changed is the standard of proof. Executives and buyers are less interested in vague claims and more interested in specifics. Materials. Sourcing. Tradeoffs. What is actually defensible.
That mirrors what we see across modern marketing. Broad virtue signaling has less impact than concrete choices made with intention.
The brands winning with merch treat it as infrastructure
The most effective use of merch today isn’t decorative. It’s structural.
The organizations getting real value from it treat merch as part of a system. Onboarding. Account-based marketing. Conferences. Partner relationships. Internal culture.
They start with questions like: Who is this for? What moment does this support? What do we want someone to remember?
They don’t start with a catalog. They start with intent.
What this means for Cedar Collab clients
At Cedar Collab, we don’t start with merch. We start with intent.
Sometimes the right answer is a thoughtfully chosen object that carries your brand into someone’s daily life. Sometimes the right answer is no merch at all.
When we do recommend it, we look at audience psychology, context, timing, and brand signal. We care more about long-term memory than short-term impressions.
That’s why we pay attention to industry signals like PPAI and ASI. Not to chase what’s new, but to validate what actually lasts.
One last story
Years ago, as part of an early account-based marketing effort, a client sent custom socks to a small group of prospects. This was long before branded socks were everywhere.
Five years later, one of those prospects called. They remembered the company after finding the socks in the back of a drawer. They finally had budget and were ready to move forward.
That wasn’t because socks are magic. It was because objects, chosen with care, can outlast campaigns.
That’s the real opportunity with merch.
Not swag. Memory.
2026-02-18
Why Your Martech Stack Isn’t the Problem
It’s that time of year when LinkedIn fills up with “here’s my tech stack” posts.
I don’t mind them. Tools are useful. I work with a lot of them. Clay. HubSpot. Marketo. Systems that promise leverage, automation, or a little bit of magic if you configure them just right.
What’s stood out to me this year isn’t the tools themselves. It’s how often teams swing between extremes. One month, it’s a heavy AI martech stack held together by hope. The next, it’s Excel, because everything else feels too expensive, too complex, or too brittle to manage.
That whiplash isn’t a tooling problem. It’s a clarity problem.
When teams don’t have a shared understanding of what they’re trying to accomplish, tools become substitutes for strategy. AI doesn’t fix that. It accelerates it. A million automations without direction aren’t meaningfully different from older models of brute-force growth. Lots of activity. Plenty of cost. Very little coherence.
At Cedar Collab, we can implement just about any stack a client brings us. But we rarely start with software. We start with questions that don’t show up in a demo. Who is your ICP, really? What are you actually selling, and how is that different from what customers think they’re buying? How is your brand experienced by real humans, not personas? Where do you want this company to be in one year, five years, ten years? And just as important: what needs to stay human, and what truly deserves to be systematized?
Those questions sound abstract, but they’re practical. When the answers are clear, tools get boring again. They fit. They cost what they should. They can be owned and managed without drama. When the answers aren’t clear, automation starts replacing judgment. Efficiency replaces care. And no amount of AI fixes the underlying drift.
This is why so many teams feel burned by martech right now. It’s not because the tools don’t work. It’s because they’re being asked to compensate for decisions that haven’t been made yet. Strategy, positioning, pricing, audience focus, and long-term intent are all upstream of software. When those are unresolved, every new tool feels both promising and disappointing.
There’s a broader pattern here too. As more brands optimize relentlessly for speed and scale, customers feel less connected, not more. Perfectly templated interactions. Chatbots that answer quickly but say nothing. Systems optimized for response time rather than felt experience. Others have named this tension clearly, and they’re right to do so. Efficiency without care doesn’t build trust. It erodes it quietly.
The most expensive martech decision a company can make is buying software to compensate for unanswered internal questions. Not because the software is bad, but because it delays the work that actually matters.
Good strategy makes technology supportive. Bad strategy makes it exhausting.
That’s the difference.
2025-12-19
The Wasted Space of Legitimacy Messaging
When I walk to Lumen Field for a Sounders match, two very different ads always stick out to me. One is a giant pickup truck suspended above the crowd, a steel frame looming over thousands of fans. The other is Sound Transit’s gameday message warning people not to stand too close to the platform edge. Lime runs a similar campaign in The Urbanist: “Ride streets not sidewalks.”
Most of my day is on foot, but I also bike, ride buses and trains, and occasionally rent a car. That perspective makes the contrast hard to ignore. Car ads almost never waste time on safety warnings. They sell lifestyle and identity. But transit or micromobility providers often spend their limited ad space on reminders that sound more like disclaimers than vision.
The incumbent vs. the challenger
This same dynamic plays out in B2B marketing. Incumbents like Salesforce don’t waste ad dollars proving they are legitimate. They assume legitimacy, then sell vision: efficiency, growth, freedom. Challengers often get stuck spending precious airtime on reassurance. They fall back on messages like “we’re secure” or “we’re enterprise-ready” instead of telling the bigger story.
Okta offers a better model. Rather than leading only with compliance or safety, it told a story about speed and empowerment: identity made simple so teams can move faster. The reassurance was still there, but it was not the headline.
And that’s what effective challengers do. They bake legitimacy into the product and the proof points, while leading with aspiration.
The wasted space
Operational messaging is not bad on its own. It becomes a problem when it is divorced from vision. A platform sign telling people not to fall into the train gap is technically correct, but it reinforces danger instead of trust. The same is true for SaaS startups that flood their marketing with compliance or uptime claims but forget to tell buyers why they exist in the first place. It is wasted space.
The constraint of having to include a safety or compliance message is not a limitation so much as an opening for creativity. The message itself can carry the brand story if it is framed right. For example, instead of “don’t stand too close,” Sound Transit could have run “Yellow keeps you safe” alongside an image of riders chatting with coffee in hand, relaxed behind the yellow line that demarcates the platform. The safety rule is still clear, but it is also part of a bigger promise: reliability, ease, and community. Lime could do the same: “Streets are for riding. Sidewalks are for sharing.” A simple directive that doubles as a brand statement about respect and balance in the city.
The lesson applies directly to B2B. Compliance and security requirements will always demand space, but the way you phrase them can either reinforce fear or highlight trust. Okta, AWS, and Slack showed how the safety line itself can become shorthand for empowerment, speed, and belonging. That is the difference between a disclaimer and a brand story.
Doing both
The truth? Many organizations will always have to include some of these messages. A safety budget might require it. A compliance officer might insist on it. But that does not mean the message has to sit apart from brand and strategy. The work is to integrate it. Safety reminders can sit inside the larger frame: you are safe here, you belong here, this is a system built for you. In B2B terms, the company can meet procurement’s security checkbox while still speaking to the executive’s vision. The safety note is part of the chorus, not the only lyric.
We see this with cloud software providers. AWS and Azure may meet compliance requirements by default, but their ads focus on speed, scale, and transformation. They reassure, but they do not waste the headline. Slack did this too: while it had to prove security to IT teams, its outward message was about changing how teams work together. Legitimacy was required, but aspiration won the market.
The creative opportunity
For founders and CMOs, the lesson is clear. Challenger brands do not win by apologizing for existing. They win by combining reassurance with aspiration. Legitimacy is the baseline, not the story. Buyers expect you to be safe, secure, compliant, reliable. That is table stakes. What earns attention is the bigger promise.
If you are a challenger, do not spend your budget repeating the disclaimer. Use that space to show who your buyers become when they choose you. Blend the necessary with the aspirational. Incumbents may own the status quo, but challengers have the chance to define the next story. That is not a disadvantage. It is an opening for creativity.
2025-09-30