Your MarTech Stack Is Failing Quietly — Here’s How Enterprise Teams Fix It

Your marketing team is investing in technology. The ROI isn’t showing up.

Tools go underused. Stacks overlap. Every new software rollout feels like dragging people through mud. That’s not a vendor problem. It’s a structure problem — and most organizations don’t realize it until they’ve wasted years of budget.

Jean Guan knows this better than almost anyone. She spent 15 years at CDW building the company’s MarTech enablement team from the ground up — literally from the days when the marketing tech stack ran on a server sitting underneath someone’s desk. By the time she left, she had turned that into a governance function connecting marketing strategy with enterprise IT infrastructure at one of the country’s largest technology distributors.

In this episode of The Human Side of MarTech, Jean breaks down exactly how enterprise companies should approach MarTech vendor selection, drive adoption, manage the human side of change, and build the skills that will matter for the next decade of marketing technology.

The Problem Nobody Talks About: MarTech Without Structure

Most large companies didn’t build MarTech teams on purpose. They built IT departments. MarTech was an afterthought — managed by whoever had bandwidth, running on hardware shoved in the corner.

That was CDW in 2011. When Jean joined, there was no formal MarTech team. Someone pointed her to the server handling marketing systems. It was sitting under a desk.

Why it matters: The marketing technology landscape exploded from roughly 250 solutions in 2010 to more than 20,000 today. General IT teams can’t keep pace with marketing-specific needs — they don’t have the bandwidth, and they don’t understand the process. Companies without a dedicated MarTech function are making high-stakes selection decisions with the wrong people in the room. Getting MarTech vendor selection right starts with having the right people in the room from day one.

“With IT supporting so many departments, asking for the kind of deep analysis that email channel selection requires — how this channel interacts with social, with paid search, with everything else — is just very difficult to get.”

— Jean Guan

CDW’s MarTech enablement team solved this by becoming the connective tissue between marketing strategy and the enterprise IT infrastructure. It covered governance, compliance, IT best practices, and marketing process — all in one function. Not every company needs that level of formalization, but every company needs someone who speaks both languages fluently.

7 Best Enterprise MarTech Vendor Selection Strategies

Inside a large enterprise, the MarTech vendor selection process is never just about features. It’s a cross-functional exercise that touches marketing, IT, legal, procurement, finance, and security. Jean lived this at CDW for 15 years. Here’s what she learned.

1. Document the process before you evaluate any vendor

Before opening a browser to look at demos, map the workflow you’re trying to improve. Understand how it currently operates, why it was built that way, and exactly where the friction lives. This step is skipped constantly — and it’s the reason companies buy tools that don’t fit their actual process. It’s the single most overlooked step in MarTech vendor selection.

2. Bring stakeholders in before you have a shortlist

IT, legal, procurement, security, and finance all have requirements that will shape your decision. If you wait until you’ve already narrowed to two finalists, you’re creating unnecessary friction and risking a veto from a team that could have guided you earlier. Involve them from the start — not as gatekeepers, but as advisors who often have deep vendor exposure you don’t. Cross-functional buy-in early is what separates smooth MarTech vendor selection from a stalled deal.

3. Treat governance teams as research assets

Your security team, your legal team, your procurement team — they’ve seen a lot of vendors. They know which ones have compliance issues, which ones overcharge, and which ones have credibility in the market. Mining that internal knowledge is faster and more reliable than starting from zero with a search.

4. Evaluate ROI, efficiency gain, and security simultaneously

These three factors are often evaluated in separate meetings by separate teams. That’s how you end up with a tool that passes feature review and fails security review — costing you months. Jean recommends building a governance committee that reviews all three together, in the same conversation.

5. Never rush to the best tool in the market

Jean’s answer to the biggest mistake companies make in enterprise MarTech vendor selection: “Rushing to the best tool out there with the best deal. When you rush it, it may not be the right tool for you. Skipping the research steps and jumping into the tool is always very risky.” The fastest path to the wrong answer is skipping due diligence because you’re excited about a vendor’s pitch.

6. Evaluate tools against your specific customer segments

At CDW, healthcare customers carry completely different compliance requirements than small business or federal customers. A tool that works beautifully for one segment may be a compliance liability for another. Your vendor evaluation criteria need to reflect the diversity of your actual customer base — not just the marketing team’s generic wish list. This is where MarTech vendor selection gets specific to your business, not generic to the market.

7. Think about scalability before it’s a problem

Volume kills underspecified tools. Some platforms simply cannot handle hundreds of millions of emails, dynamic segmentation at scale, or multi-channel orchestration across a complex product catalog. Scalability needs to be a first-round evaluation criterion — not something you discover after you’ve already migrated.

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Change Management Is Emotional — Not Just a Project Plan

This is where most MarTech implementations fall apart. The tool is right. The vendor is right. The contract is signed. And then nobody uses it. Good MarTech vendor selection doesn’t guarantee good adoption.

Jean spent time at University of Wisconsin-Madison studying under Professor Urban Wemhoff, a pioneer in change management. She’s applied those frameworks to MarTech implementation ever since — and she’s clear about what most companies miss.

“Tool change has an emotional aspect. People who have worked on a tool for five or ten years get attached. They like the features, the color coding, the workflow. It becomes personal. Then somebody takes it away.”

— Jean Guan

This isn’t a soft problem. It’s the core reason adoption fails. People’s professional identities are bound up in the tools they use every day. When you change the tool, you’re changing how they experience their work — sometimes how they experience their value.

The question leadership needs to answer before a tool launches: If this new software reduces a 500-step process to 200 steps for a 50-person team, what does that mean for those 50 people? Are roles changing? Is headcount affected? These aren’t post-implementation questions. They need to be in the plan before the contract is signed.

Between the lines: The companies winning at MarTech adoption are the ones treating the human side of change with the same rigor they apply to technical requirements. Documentation and training sessions aren’t change management. They’re just documentation and training.

How CDW Approached AI Transformation at Scale

CDW didn’t bolt AI onto their existing strategy. They embedded it into their 360-degree customer strategy from the start — because AI that disrupts the customer experience is just another bad implementation problem.

The mechanism that made the difference: a Center of Excellence around AI governance. Not a marketing initiative. Not an IT project. A cross-functional group including IT experts, legal, developers, directors, VPs, and marketing leadership — all gathered to communicate, socialize, and educate on AI capabilities before rollout.

“The more it’s being communicated, the more understanding people have. That helps with adoption and helps realize the benefits AI can actually bring.”

— Jean Guan

Jean’s concrete proof point: MarTech research. What used to take weeks — meetings with agencies, reading through Gartner and Forrester research papers, vendor demos — AI has compressed dramatically. The efficiency gain is real. But it only materializes when people know how to use the tools and feel comfortable doing so.

The takeaway for your organization: AI is already embedded in the tools your team uses today. The question isn’t whether to engage with it — it’s whether you’re helping your team recognize those capabilities and actually use them. A Center of Excellence model, even a lightweight version, is one of the most effective ways to close that gap.

The 3 Pillars Every MarTech Professional Needs to Master

Jean has seen MarTech careers stall and accelerate. The pattern that separates the two comes down to three pillars — and most practitioners only invest seriously in one.

Pillar 1: Technology

You need genuine passion for and deep understanding of what the technology can and cannot do. Not surface-level familiarity — actual fluency in how systems connect, where they break, and what they were built to accomplish. This is table stakes, and it’s also the pillar most people assume covers everything. It doesn’t.

Pillar 2: Process

Understanding your organization’s specific workflows — and the history of why they were built that way — is what separates people who can select a tool from people who can successfully implement one. Process knowledge tells you what the tool needs to do in your specific environment, not just in the demo environment.

Pillar 3: People and Organization

This is the pillar most MarTech practitioners underinvest in. Understanding team structures, individual pain points, career motivations, and daily workflows is what makes the difference between a tool that gets adopted and one that gets ignored. When you know what an email specialist actually cares about — not just what they do — you can position change in a way that lands.

The glue across all three: communication. You need to speak the language of technical teams, operational specialists, email marketers, and C-suite executives — often in the same week. That versatility is the actual differentiator in a MarTech career. The people who can move fluently between technical and human conversations are the ones who get promoted and get results.

Career advice from Jean: Figure out which pillar excites you most and go deep on it first. Process people (Six Sigma, project management) are already in MarTech — they’re managing large technology transformations. Change management experts are in MarTech. Tech-first people are in MarTech. There are multiple on-ramps. And once you’re in, your skills transfer — to SalesTech, FinTech, HealthTech, and beyond.

The Trend Jean Is Watching: Agentic AI

Jean didn’t hesitate when asked what trend she’s watching most closely: agentic AI ecosystems.

“Imagine you get up and the AI agent has already done your shopping at Walmart — the food is at the door. But what if the AI agent made the wrong payment and overspent your budget for the month? All those kinds of impacts are coming.”

— Jean Guan

For MarTech teams, agentic AI isn’t just about automation. It’s a new layer of the customer experience — one that can create significant positive impact or significant trust erosion depending on how it’s implemented. The governance and change management challenges that apply to software implementation apply here with even higher stakes.

Jean is also watching AI’s potential in healthcare — not as a MarTech story, but as a signal of how transformative the technology can be when applied to genuinely hard problems. The marketers and technologists who understand that scope are the ones who will lead the next wave of transformation.

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Rapid Fire: Jean’s Unfiltered Takes

Most overused MarTech buzzword: CDP. “Almost every technology is claiming to be a customer data platform.” If a vendor’s website says CDP, dig deeper before you accept the label at face value.

Biggest mistake companies make in enterprise MarTech vendor selection: Rushing. “Skipping the research steps and jumping into the tool is always very risky.” The urgency to solve a problem fast is completely understandable — but the cost of the wrong tool is always higher than the cost of a thorough evaluation.

Best career advice for people entering MarTech: Don’t just think technology. Understand what excites you about all three pillars and find your entry point. MarTech is one of the most transferable skill sets in the technology world.

Listen to the Full Conversation

Jean Guan spent 15 years doing this work at one of the country’s largest tech companies. Every answer in this episode is grounded in real decisions, real failures, and real wins inside a complex enterprise environment.

Whether you’re tackling your next MarTech vendor selection, managing a sprawling stack, or trying to lead your marketing organization through AI transformation — this episode is worth your full attention.

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