A CEO’s High-Level Guide to GTM Troubleshooting

Finance blames sales. Sales blames marketing. Marketing blames the macro environment. Everyone blames SDRs.

Scene: You're consistently missing targets.

Finance blames sales. Sales blames marketing. Marketing blames the macro environment. Everyone blames SDRs.

The executive meetings feel like tag-team cage fights. The only thing you can all agree on is: mess.

So, as CEO, what do you do?

Here’s the high-level playbook:

1. Avoid the Blame Game

Speak slowly, focus on facts, and do not cast blame.

And I mean not even subtly to make a point or your case stronger.

When the house is on fire, finger-pointing is fuel. Problem-solving is water.

Focus on the future:

Replace “marketing failed to build enough pipeline”…

…with “when we start with less than 2.5x pipeline coverage, we almost always miss the plan”.

Blameless, factual, forward-looking.

2. Reset the Pipeline Conversation

Relentlessly remind everyone:

• How do you make 16 quarters in a row? One at a time.
  ​

• How do you make one quarter? Start with enough pipeline coverage.
  ​

• Then convert at your target rate.

This focuses everyone on one quarter – the right horizon if you’ve missed three in a row.

Then dig into the numbers:

• Define what “sufficient” starting coverage actually means based on your historical conversion rates.
  ​

• If conversion rates aren't viable (e.g., you need 5x coverage to hit the plan), you're facing both a coverage and a conversion problem.

3. Build A Cross-Functional Pipeline Task Force

You need a team of senior people – marketing, sales, alliances, SDR leadership, all laser-focused on one goal:

Start every quarter with sufficient pipeline coverage.

• Forecast pipeline for next quarter (and ideally the quarter after).
  ​

• Take action when forecasts miss targets.
  ​

• Shift resources as needed (e.g., pause AE hiring to boost demand generation).

Think: “We’re $2M short for next quarter. Who can move fastest to cover it?”

4. Mind the Real Goal — Not Just Upstream Metrics

Pipegen targets matter, but hitting pipeline coverage targets is what really matters.

• If marketing misses pipegen goals but you still hit pipeline coverage – that's a win.
  ​

• If you miss pipeline coverage, no amount of "but our MQLs were up!" matters.

Tracking upstream metrics is good, but starting coverage is the scoreboard.

5. Watch Out For This Dysfunction

Sometimes you’ll see this:

• Sales hit plan (barely).
  ​

• Marketing consistently misses pipeline targets.
  ​

• Sales demanded more pipeline than actually needed (e.g., asked for 5x coverage but only needed 4x).

This is toxic long-term.

It kills marketing morale, drives turnover, and eventually hurts pipeline generation – just not immediately. If your sales function is hitting the plan consistently, marketing is doing its job — even if the "official" targets say otherwise.

Final Thought

Pipeline generation is a team sport.

It’s not about blaming functions. It’s not about protecting ego.

It’s about saying together: "We’re off plan. What are we going to do about it?"

Just a team that solves the problem – quarter by quarter.

📰 News, Updates, and Resources Worth Your Time

​FCF margins are improving...but efficiency is worsening?, OnlyCFO

Despite record-high free cash flow (FCF) margins in public cloud companies, go-to-market (GTM) efficiency is in sharp decline. The current margins are a lagging benefit from more efficient customer acquisition years ago – not a reflection of today’s performance. While sales and marketing (S&M) costs as a percentage of revenue appear to be improving, the actual cost to acquire $1 of new ARR has been rising steadily.

​The nasty side effects of bad PLG, Leah Tharin

Five key pitfalls: capping revenue potential, high credit card fees and risk exposure, missing critical customer insights, scalability limits without sales, and the myth that top PLG companies rely solely on PLG.

Leah Tharin builds on these points, arguing PLG should complement, not replace, sales – especially when moving upmarket. Strong PLG motions support growth, reduce CAC, and improve product quality, but reaching enterprise scale requires high-touch sales. In short: PLG gets you started—sales takes you further. You need both.

​Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better, First Round Review

Timeless wisdom for startup leaders from four execs who have led planning at Stripe, Notion, Vanta, Linktree, and more. They candidly address why the annual planning process is so painful and how to improve it, especially in today’s unpredictable environment of constant AI disruption. From re-thinking one-size-fits-all formulas to balancing top-down vs. bottom-up goal setting, this piece is packed with strategic insights to make planning a more effective (and less excruciating) exercise.

​Dear SaaStr: What is a Good Benchmark for SaaS Revenue Per Employee by Stage?, SaaStr

A quick gut-check on efficiency metrics for founders. Jason Lemkin’s Q&A post breaks down rough ARR-per-employee benchmarks from early stage (~$100K–$150K per employee at <$10M ARR) to scale-up. It’s a handy yardstick for CEOs to gauge their team’s productivity and ensure they’re scaling headcount in line with revenue growth.

✍️ Become A Better Writer: Buzzwords don’t sell. Outcomes do.

This week, I’d like to take a moment to look at one of the biggest missed opportunities in SaaS and product writing: being too vague.

When you say your product “improves productivity” or “streamlines workflows,” you might think you’re making a strong point.

But to your reader, it’s just noise – abstract, empty, and interchangeable with a hundred other tools they’ve already seen that day.

If you want your copy to land, you must make it concrete. Show what your product does, not just what it represents.

Abstract Language Doesn’t Stick

Let’s start with a few real-world examples of conceptual phrases that feel polished, but say very little:

• “Helps boost collaboration”

• “Makes processes more efficient”

• “Delivers a better customer experience”

• “Provides actionable insights”

All of these are perfectly fine ideas. But the problem is – they’re ideas, not outcomes.

Your reader doesn’t want to be told that your product is powerful. They want to see how it solves their problem.

Make It Tangible

Let’s bring these phrases down to earth:

Concrete language doesn’t just explain – it demonstrates. It helps your reader visualise using the product, not just buying into an idea.

Practical Tip: Use This Sentence Structure

A simple trick to move from vague to specific:

Instead of:
👉 “[Feature] helps you [broad benefit].”

Try:
👉 “With [feature], you can [specific action or result].”

Example:

Instead of: “The automation engine helps you work more efficiently.”

Try: “With our automation engine, you can trigger emails based on user behaviour without writing a single line of code.”

Why This Works

Concrete language improves:

• ✅ Comprehension (the reader understands what the feature does)

• ✅ Trust (the claim feels real and grounded)

• ✅ Conversion (the benefit feels attainable and useful)

In fact, studies in consumer psychology consistently show that specific details improve credibility and recall. Your reader is more likely to believe, remember, and act on your message if they can clearly visualise what you’re talking about.

Final Thought

Every time you write a feature description, product page, or onboarding message, ask yourself this:

“Can the reader picture what I’m talking about?”

If not, make it concrete. Make it real.

Because “helps improve productivity” is forgettable. But “lets your team edit the same document in real time, without emailing versions back and forth”? That’s what gets remembered – and what gets results.

– Justin

😅 Something fun

Because we all need something to take off the edge a little :)

Thank you for reading, have a great weekend, and see you next week!

Meanwhile, keep doing the work that matters.

Yours,

– Alex, Justin, and Naman at ScaleMath 💌