3 GTM Tech Stack Sins That Are Wrecking Your Revenue

I’m thrilled to kick off this newsletter and share real-world insights from the trenches of revenue operations. My goal is to help you navigate the complexities of building a scalable, high-performance revenue engine. Each edition will tackle the critical questions RevOps leaders must answer to drive smarter, more strategic growth. I can’t wait to hear your thoughts and experiences—let’s dive in.

Missing the Forest for the Features

A Fortune 500-focused VP of Revenue Operations couldn't tell me their market penetration rate. Another enterprise RevOps leader invested $1.2M in their tech stack annually while unable to articulate their customer acquisition costs by segment. A global sales organization implemented a multi-region sales sequence without baseline productivity metrics.

Taking a step back, this is what fascinates me about enterprise revenue operations in 2025: departments managing eight-figure budgets while missing core business metrics. Before evaluating another enterprise-grade platform, let’s step back and address the core numbers every revenue leader must master—so you’re not just slapping another GTM tool into the mix, hoping it will fix things.

The Non-Negotiable Prerequisites

If I were stepping into a RevOps leadership role today, here are the metrics I’d make sure I know could recite in my sleep in order to build a GTM machine at my organization.

1) Market Penetration & TAM Evolution

• Current penetration rate by account segment – How much of your target market have you actually captured?

• Whitespace analysis within enterprise accounts – Where are the untapped expansion opportunities?

• Account expansion potential by vertical – Which industries offer the highest growth potential?

• Competitive displacement rates in target segments – How effectively are you replacing competitors?

2) Revenue Metrics at Scale

• Enterprise CAC with full cost allocation – What does it actually cost to acquire an enterprise customer?

• Time to revenue by deal size tier – How long does it take to realize revenue across deal sizes?

• Multi-year ROI on enterprise accounts – Are your largest customers delivering sustainable, long-term value?

• Global revenue distribution and growth rates – Where is growth happening, and where are you stalling?

3) Sales Productivity Framework

• Activity metrics across global teams – Are your sellers focused on high-impact activities? What are the manual tasks they do every day that suck their time and energy?

• Pipeline velocity by region and segment – How efficiently does pipeline convert across markets?

• Sales cycle analysis by deal complexity – Where do deals stall, and why?

• Resource allocation across enterprise pursuits – Are your top reps spending time on the right opportunities?

These aren’t just numbers—they should be the compass guiding every GTM decision. If you can’t confidently answer these questions today or have a path to finding those answers, no amount of sales tech, AI-driven scoring, or automated workflows will solve the deeper problem. The obsession with adding more tools—rather than optimizing what already exists—is a core reason RevOps teams struggle to answer foundational business questions. You can’t measure what’s buried under layers of redundant software.

Tech Stack Bloat: The Silent Killer

Look, I get it—enterprise tech decisions are messy. With multiple regions, business units, and stakeholders, it’s easy for things to spiral. Most companies are running their tech stack like a junk drawer—overflowing with tools nobody wants to clean out.

Take a Series B company I worked with recently. They were paying for three different sales engagement platforms at the same time.

Yes. Three platforms.

Annual cost? $150,000 in wasted spend.

Why? Different teams bought their preferred tools, and no one had the courage to consolidate.

From where I sit, here are the three biggest tech stack fallacies sins I see companies commit over and over again:

1. Shiny Object Syndrome

You know the drill. A revenue leader comes back from SaaStr, convinced they need the latest AI-powered sales tool—despite just dropping six figures on a similar solution three months ago. That’s not strategy, that’s FOMO.

2. The P&L Blindspot

Your tech stack should be managed like an investment portfolio, but most teams treat it like a shopping spree. If you’re not tracking these three numbers, you’re flying blind:

• Cost per revenue-generating employee

• Revenue impact per tool

• Time-to-value for new implementations

One of my enterprise clients discovered they were spending $80 per email sent through their sales engagement platform due to low adoption. Another saved $300K annually by eliminating “ghost subscriptions”—tools that hadn’t been logged into for over 90 days. Sheesh.

3. The Echo Chamber

“But our RevOps team loves this tool!” Great—but have you actually asked the sales reps who use it every day? Or the marketing team that needs to integrate their campaigns? Too many tech decisions happen in silos, creating a stack that looks good on paper but falls apart in execution.

The bottom line? More tools aren’t the answer—better strategy is. If you don’t take control of your stack, it will take control of you.

5 Ruthless Moves to Make This Week

Every newsletter I send is designed to move beyond insight and into action—because knowing the problem isn’t enough if you’re not fixing it. If I were in your shoes, here’s what I’d do immediately to take back control of your tech stack:

1. Run the Utilization Audit

Pull your credit card statements and document three key data points for every tool:

• Last login date for each user

• Feature usage in the last 30 days

• Total cost per active user

Kill anything with under 60% utilization. If your team isn’t using it, it’s dead weight.

2. Execute the Feature Overlap Test

Take your three most expensive tools, screenshot their core features (without branding), and show them to your sales team. I guarantee you’ll find redundant functionality—meaning you’re paying for the same thing multiple times.

3. Implement a Tool Freeze

Put a 90-day moratorium on new purchases. No exceptions. No “game-changing” AI sales tools. No shiny new CRMs. Nothing. Use this time to measure the actual impact of your existing tools before adding anything new.

4. Shadow Your Team

Block two hours to silently observe both your top and bottom-performing reps at least once a quarter. Document every single tool interaction.

• Where are they wasting time?

• What tools are actually helping them close deals?

• What’s being ignored completely?

5. Calculate the Real Cost of Your Tech Stack

Most teams drastically underestimate what their tech stack is actually costing them. Run this simple formula to get the true annual cost:

📌 (Monthly tool cost per user) × (Number of users) × (12 months) = Yearly cost

📌 (Hours spent in tool per week) × (48 weeks) × (Average hourly cost of employees) = Time cost

📌 (Training hours required) × (Number of new users) × (Average hourly cost) = Onboarding cost

🔍 True Annual Cost = Yearly cost + Time cost + Onboarding cost

If you can’t justify a tool’s cost against the revenue it’s driving, it doesn’t belong in your stack. Top performers typically use fewer tools—but use them more effectively. Your stack should reflect what actually works, not what looks good on a vendor sales deck. The bottom line? If your tech stack isn’t actively driving revenue, it’s actively wasting money.

Closing Thoughts

After hundreds of conversations with revenue leaders, one insight from a CEO stuck with me:

“Running RevOps from the executive suite means you might not realize your sales team is struggling with basic workflow issues.”

That’s why he includes front-line reps in every tool decision—because the daily experience of the people using these tools matters more than any executive dashboard. It’s the best perspective I’ve encountered in this space, and one that too many companies overlook.

👀 What Should We Tackle Next?

Reply with your vote on what I should write about next:

1. 📊 RevOps Isn’t a Support Function—It’s a Growth Engine

   How to position RevOps as a strategic driver of revenue growth instead of just a backend operations team.

2. 💰 How to Prove RevOps is Worth Every Dollar (to Your CFO)

   Struggling to justify RevOps investments? Learn how to tie every dollar spent to measurable revenue impact—and make your CFO your biggest advocate.

3. 🎯 Your ICP is Trash—Here’s How to Fix It

   Most ICPs are built on assumptions, not data. Let’s break down how to build a high-precision ICP that actually converts instead of chasing bad-fit prospects.

4. 🤖 Is AI Helping or Hurting Your Sales Team? A Brutally Honest Breakdown

   AI is everywhere in sales—but is it actually making your team better? How to separate real AI impact from overhyped distractions.

5. 💡 Your suggestion → What’s keeping you up at night?

I read every response, and the best suggestions shape future newsletters.

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Thanks for reading!

Your GTM Engineer,

Ashley 🤝 Let’s connect: LinkedIn

P.S. If you try any of these moves, let me know how it goes—I’m collecting real tech stack transformation stories. :)