The 12–18 Month Trap: Why SaaS Sales Leadership Just Can’t Stick Around Anymore

Advisor, Operator, Believer
Jun 26, 2025
2 min read

Updated: Jul 8, 2025

Just a few years ago, CROs and VPs of Sales could expect a 26-month runway to prove their impact. Today, many don’t even make it to month 12. What was once a strategic leadership role has become the most volatile seat in SaaS.

But let’s be honest it’s not a talent problem. It’s a systemic cycle of unrealistic expectations, reactive decisions, and organizational whiplash.

We’ve Seen This Movie Before

Numbers fall short. The board or CEO loses patience and demands change.

The CRO reacts. They start cutting underperforming reps some of whom deserve it, yes… but many are simply stuck with:

A weak product market fit

Vague or undifferentiated messaging

Pipeline full of “no decisions” due to market noise

The new wave arrives. New reps are hired. New energy hits the floor. But soon the same structural problems resurface poor enablement, misaligned value prop, too much pressure too fast.

Morale drops. The team fractures. The internal narrative shifts to fear and survival.

The CRO is let go. Then the CEO finds a new sales leader and the cycle starts all over again with slightly worse morale and even less trust.

In the end? Same results. Sometimes worse.

What’s Really Going On

SaaS is more competitive than ever and boards expect impossible numbers without acknowledging GTM realities.
AI is raising expectations faster than it’s improving outcomes. Everyone’s supposed to be “more productive” overnight.
And leaders aren’t given the time to fix systemic problems. They’re expected to generate pipeline magic in 1–2 quarters or else.

What Needs to Change

Stop pretending it’s always the people. Sometimes, it’s the system, the GTM structure, the positioning, the product, the pricing, the process.

Building repeatable AI-powered GTM engines Structure matters more than hustle. Sales teams need operating rhythms, not hope.

Measure more than revenue. Use leading indicators deal progression, activity-to-close ratios, AI tool adoption—to evaluate coaching needs, not just output.

Create stability through enablement. New reps won’t succeed if the same broken onboarding, unclear ICPs, and lack of tools still exist.

If You’re a CRO or VP Feeling the Pressure…

Let’s get ahead of the cycle.

We’ll help you: