When to Call it Quits (on GTM)

One of the most challenging calls to make as a VC or CEO is knowing when to walk away from your current go-to-market strategy.

Most people don't.

They tweak it, adjust tactics, and hang onto the plan because it feels like progress—a new campaign here, a messaging refresh there, maybe a different mix of channels. But here's the reality: tweaking doesn't fix the fundamentals, and sometimes, those fundamentals are broken.

I recently had a conversation with an investor that made me completely rethink how I advise on GTM. We were looking at his portfolio, and the same question kept coming up: How do you really know if your GTM strategy is working? And when do you call time on it?

The truth is most people wait too long.

They hang onto a plan because it looks good in a deck. It's familiar. It worked once. But in today's environment, that's no longer enough. The old way of doing GTM — the annual plan with 10 channels and predictable funnel math — is dying. What worked before isn't working anymore. Why? Because everyone is doing the same thing. The same content plays: digital targeting, ads, partner motion, and LinkedIn thought leadership. It's all become noise.

And when everyone's running the same GTM playbook, nobody stands out.

You see this play out in the numbers. I'm seeing $2–5M ARR companies lose 30–50% of their top-of-funnel performance in a quarter. Not because execution got worse — but because 50 new companies in the category are now running the same playbook. And none of it cuts through.

So what happens?

Most teams do what they've always done: they add more.

More content, more channels, more layers, more tweaks. Because blowing up a GTM strategy feels scary, it's much easier to tell yourself, "We just need to optimize," than saying, "This isn't working."

But here's what's true: continuous tweaking is a false sense of progress. It's not a strategy. It's fear of change disguised as activity.

Sometimes, the move is to strip it back. One of the CEOs I work with made that exact decision. She ditched everything except two channels. She went deep on differentiation, focused her messaging, simplified positioning, and made a bet—four weeks of pain. Then, things started working again.

That's the shift I'm seeing. The funnel is no longer a funnel. It's a cylinder. You don't start wide anymore. You start sharp. You lead right from the top of the funnel with your clearest, deepest expertise. Your TOFU should be as powerful as your old MOFU. If you're not delivering meaningful insight right out the gate, you're just blending in.

Here's how I'd break it down:

First, look at your leading indicators — traffic, engagement, top-of-funnel demand, demo requests, etc.

If those haven't moved in 6–9 months, despite consistent execution, you're likely looking at a GTM strategy problem.

It's not a channel problem. It's not a team problem. A strategy problem. Be honest here as well; it could be a PMF problem, market problem, or something else - it's not always the CMO/CRO to blame, but a wider business problem to be solved.

On the flip side, if your leading indicators are strong but you're not seeing the lagging ones move — revenue, conversion, pipeline velocity — the issue is probably further down the funnel.

Your thought leadership might be solid, but your sales motion, team capability, or bottom-funnel execution is the constraint.

And if neither are moving? That's your sign. Full reset.

Not in your next annual planning cycle. Now.

Because the game has changed, you may need to reset parts of your GTM 3–5 times a year (or more).

Not the strategy itself — that probably needs a single, focused shift.

But the execution layer? That needs speed. That needs reps. And you can't afford to wait quarters to figure it out.

Beyond flat pipeline or weak conversions, here are seven signals I look for that tell me a reset is overdue:

1. You're hitting your activity goals, but revenue isn't moving

You're doing "everything" — emails, content, ads, events — but nothing converts. This usually means your messaging or targeting is off, or you're solving a problem no one prioritizes.

2. Your ICP has changed, but your strategy hasn't

If your customer profile has shifted — upmarket, downmarket, new vertical — but your positioning, campaigns, and channels haven't, it's time to re-align.

3. Sales is rewriting everything

If sales decks, messaging, or value props are being rewritten on the fly, your GTM is broken. Marketing should be giving sales something usable, not just pretty slides.

4. The market has moved — and you haven't

Competitors have changed their story, pricing, or offer. A new trend has emerged. You're already behind if you're still running the same plays from 12 months ago.

5. Your pipeline is thin — or full of junk

You're either not generating enough interest, or you are… but from the wrong people. This suggests a mismatch between campaigns, channels, and ideal buyers.

6. You're growing, but it's not repeatable

If growth comes from the hustle, referrals, or one-off wins, not scalable systems, your GTM might be more luck than the engine—it's time to fix that.

7. You can't answer "Why now?" convincingly

If your pitch lacks urgency—if there's no compelling reason for customers to act now—you'll lose deals. GTM isn't just about what you say but why it matters today.

Action action action:

Investors, Operating Partners, and Heads of Platform, this week's tangible prompt:

If you see two or more of these signals in a portfolio company with an ARR under $10M, it's time to intervene.

Push the CEO to zoom out. Don't ask for another quarterly plan or funnel forecast. Instead, ask:

• What's your sharpest differentiated point of view?
• Are your leading indicators (interest, engagement, inbound) trending up, flat, or down?
• If you had to cut 50% of your GTM effort this week, what would stay — and why?
• If you only had $100,000 to spend on marketing, where would you spend this money?

Encourage a two-week sprint to rebuild the GTM motion from first principles. Strip back to what's working. Push for faster tests and clearer messaging. It's better to do less than keep feeding a bloated engine that isn't driving results.

CEO prompt, this week's tangible prompt:

Have an open conversation with your sales and marketing leads this week.

Ask:

• What are we still doing just because we've always done it?
• Where are we seeing motion — and where are we just making noise?
• If I cut our GTM motion in half tomorrow, what would the high-signal work stay?

Then, decide: is this a messaging problem, a market problem, or a motion problem?

If your leading indicators are flat — reset the GTM.

If your lagging indicators are flat despite solid TOFU, dig into sales and conversion constraints.

If both are broken — reset everything.

And when you do reset, anchor around the only three things that still create unfair advantage:

→ Your point of view

→ Your differentiation

→ Your message

That's it for today.

See you next Saturday.