Incentives eat your strategy for lunch

Photo credit: FaithMag

Nature abhors a vacuum

In a typical B2B SaaS startup, product managers obsess over customer goals, strategic roadmaps, and viable business outcomes. Designers prioritise user needs, problem clarity, and tested sustainable solutions. Engineers focus on feasibility, quality, and scalability. Salespeople care about turning leads into revenue by closing deals.

These groups overlap in mission but not always in incentives.

We’re all attempting to build something people need and will pay for, but the daily levers we pull to get there are different. Product orgs have built strong tools and processes for product management 🗘 design 🗘 engineering collabs, but sales usually don't get the same treatment, despite being just as critical.

That gap creates a lot of risk. Commission-driven salespeople without the right support default to desperation and improvisation.

Overselling features that don’t exist. Promising one-off builds that won’t scale. Signing contracts with unrealistic terms. The result is ever increasing off-roadmap requests with impossible timelines.

They may win lucrative contracts in the short term, but this quickly drains engineering capacity, erodes cross-team trust, sets customers on a path to disappointment and churn, and quietly hijacks the roadmap, tilting strategy toward the loudest deals on the table.

Sales off the rails

Salespeople, in my experience, fall on a spectrum.

At one end are the deep learners: they work hard to understand the product, sell to the right customers, and represent it with integrity. With enough knowledge, and armed with great sales collateral, they become powerful allies for the product org—closing the right deals and providing relevant timely feedback from target customers.

At the other end are the say-anything closers. They move fast, bring in big revenue, and hit targets. But they also overpromise, push for custom builds, and sign terms that can easily derail a roadmap. Managed well, they can be a highly effective sales force. Left unchecked, they’re extremely dangerous to progress.

Most sales teams have both types. Without being set up for success, neither operates at their best. The reckless create chaos. The more capable are left uninformed, underpowered, and unmotivated.

The outcome isn’t just a messy sales pipeline—it’s organisational dysfunction: shaky deals, confused messaging, conflicting narratives, teams drained by unplanned work, and a product strategy going off the rails.

The problem isn’t the sales team. It’s the absence of strong structures that align sales incentives with strategic goals. Without them, the gap widens—and costs compound fast.

Incentives eat strategy

The root cause is incentives.

Product orgs optimise for long-term value, but sales is paid on short-term revenue gains. Non-technical founders often oversell a vision they don’t fully understand in the details. Add VC pressure for hyper-growth, and the gravitational pull towards easy sales and quick wins becomes overwhelming.

Information gaps only deepen the problem.

Product knows what’s real, what’s in progress, and what’s unlikely to ever happen. Even well-intentioned salespeople—rarely hired as technical experts—can struggle to keep up with the rate of change in a product development cycle and so are left to improvise. A rational response to a dysfunctional system.

When clarity and enablement are missing, improvisation is not negligence; it’s often the only option available.

Staff turnover rates further compound issues.

Sales roles can churn quickly, and with each departure institutional knowledge evaporates. Good salespeople burn out and leave. The reckless ones thrive unchecked.

Without solid onboarding and collateral, teams waste energy re-explaining the basics and watching the same mistakes repeat.

The failure lies in the sales culture and systems leadership has chosen—or neglected—to build. Unless those systems change, the outcomes are inevitable: wasted cycles, broken trust, customer churn, and 'success' dominated by short-term gains.

Making sales work for strategy, not against it

The solution isn’t to blame sales—it’s to redesign the interactions between the product org (product management, design, and engineering) and the sales org.

Design 🗘 engineering gets attention because it’s visible. But product org 🗘 sales is where strategy collides with market realities.

Get it wrong, you bleed money and trust, and bend the roadmap to the loudest customers. Get it right, and sales becomes a real force multiplier—your strongest ally in turning vision into reality.

Treat sales as a partner, not an afterthought

Help to create playbooks: clear collateral, usable demos, and plain-language documentation that explains what the product does and why it matters to customers.

Make communication two-way

Push updates downstream, but also pull feedback upstream. Filter aggressively so one-off customer demands don’t hijack the roadmap.

Frame in Jobs to Be Done

Customers don’t care about technical stories; they care about outcomes. Give sales a language rooted in real customer goals, not product backlog items.

Provide roadmap clarity

Be explicit: what’s available now, what’s coming soon, what’s future-but-uncertain, and what’s never. Remove ambiguity before it becomes false promises. Be prepared to negotiate, but not compromise for quick cash.

Enable the good, contain the reckless

Reward salespeople who invest in understanding the product. Protect strategy from those who’ll say anything to close. This isn’t about being “nice”—it’s about defending the mission.

Hire and reward wisely.

Don’t bring in or incentivise salespeople who chase quick deals without understanding SaaS dynamics or scalable products. They’ll trade your strategy for commission every time.

Above all: build for sustainability, not sugar highs.

Short-term wins burn trust, drain teams, and derail the roadmap. Long-term sales culture fuels compounding, sustainable success.