The Success Trap: When Yesterday’s Wins Become Tomorrow’s Weight

If you’re leading a software, SaaS, services, or tech company, here’s the uncomfortable truth: the strategy that got you here is already going stale. We call it The Success Trap—the quiet slide from proud to stuck, where loyalty to your legacy products, pricing, and GTM playbook crowds out the very investments that would keep you relevant.

This isn’t theory. It’s the pattern behind stalled growth, surprise churn, and the “How did we lose that deal?” postmortem. And yes—too often the first scapegoat is Sales. (“Quit whining and handle the objections.”) Meanwhile, the market has shifted under your feet.

Below are four pointed realities—candid enough to sting, practical enough to use.

1) If you’re not cannibalizing your hits, your competitors will.

Try this: Put a small, protected team in charge of building the product that could obsolete your current flagship—and give the legacy team credit for migrations to defuse internal turf wars.

2) Blaming Sales is a lagging-indicator habit.

Try this: Instrument a ruthless win/loss program, route the signals straight into roadmap and pricing decisions, and make “voice of field” a standing agenda item at the exec table. If the data says you’re losing on “missing capability X” or “price 30% higher,” believe it—and act.

3) Your budget is your strategy—especially in a downturn.

Try this: Lock a non-negotiable innovation floor (e.g., 12–18% of revenue for software; adjust for your model). Split it 70/20/10 across core extensions, adjacent bets, and disruptive options. Track a Vitality Index (% of revenue from offerings <3 years old) and tie leadership comp to it.

4) Pride is not a moat.

Try this: Dual-track your portfolio. Defend the high end with differentiated capability and field a simpler, lower-cost product where “good enough” wins. Refuse to lose the entry segment by default.

Early Warning Lights (ignore at your peril)}

• Win rate down; discount intensity up
• Sales cycles lengthening vs. last year’s cohort
• Renewal/expansion softness in previously “bulletproof” accounts
• Pipeline effort flat, pipeline quality down
• Top-quartile reps leave first


If two or more are flashing, don’t coach harder—change faster.

What to do Monday

• Name the trap. Run a blunt “Success Trap Audit” at ELT: Where are we over-funding yesterday? Where are we under-funding tomorrow?
• Move money. Rebalance toward the next S-curve; protect it from quarterly whiplash.
• Ship the cannibal. Pick one product line and launch the offering you’d fear most if a competitor released it.
• Elevate the signal. Make win/loss and churn reasons as visible as revenue. Roadmap follows evidence, not ego.

Want the full playbook—data, mid-market case studies (wins and wipeouts), leading indicators, and a concrete operating model to avoid or escape the Success Trap?