You’re sitting between $2M–$20M ARR. Your growth targets are adding pressure, but the runway feels finite. Then a “whale” shows up in the pipeline with a contract value that would make your quarter.

So... you bend.

A bespoke workflow here, a custom integration there, a pricing exception “just this once”. It feels like you'r being commercial, however, it’s an anti-pattern.

Opportunistic sales is what happens when revenue pressure starts setting product direction. Slowly at first, then all at once.

You’ll recognise it by the trail it leaves:

• Churn is highest among your biggest accounts (because they were never a natural fit, just a big cheque).

• Product strategy constantly shifts to accommodate edge cases and executive escalations.
• Marketing and sales are forced to speak to too many buyer types, with too many narratives, so nothing lands cleanly.

This is the path to a product that’s hard to sell, hard to build, and hard to love.

Why it hurts

April Dunford nails the root of it: your best-fit target customers are the ones who “really care a lot about your unique value.” 

Opportunistic sales pulls you away from that unique value and into a mess of conflicting customer goals:

• The enterprise buyer wants governance, risk controls, and procurement-friendly packaging.
• The mid-market buyer wants speed, templates, and clear ROI.
• The SMB buyer wants a simple setup and a low-friction trial.

Trying to satisfy all of them at once doesn’t create a bigger market, it blurs your market.

The business impact is obvious:

• CAC rises because messaging gets generic and conversion drops.
• Sales cycles lengthen because every deal becomes a bespoke conversation.
• NRR becomes fragile because expansions depend on exceptions and favours, not repeatable value.
• Roadmap focus collapses because your backlog becomes a list of promises.

You end up shipping more and learning less. In reality, that whales make it worse.

Big accounts don’t just request features. They pull your company toward their org chart, compliance requirements, integrations, and internal politics.

Jason Lemkin of SaaStr has a simple warning: selling “90% out-of-the-box is great, butthat 10% custom work can quickly spiral out of control.”

The spiral usually looks like this:

• One-off commitments become “must-haves”
• Engineering time shifts from compounding work to account servicing
• Your core customers stop seeing progress
• Your next 10 customers don’t want those custom features anyway (or they want different ones)

Christoph Janz literally calls out the temptation in his “SaaS animals” framework: “Hail the whale!”

https://christophjanz.blogspot.com/2019/04/five-years-later-five-ways-to-build-100.html

Whales can be a viable strategy if you choose it deliberately. Opportunistic sales is when whales choose you.

What the best products do differently

The companies that scale win by being crystal clear about who they’re for, then expanding without breaking that clarity.

• Atlassian built Jira for software teams shipping work. Enterprise came later as packaging (admin, security, controls), not a rewrite of the core workflow.
• Stripe stayed developer-first. They expanded into billing, fraud, tax, and enterprise needs, but the primitives stayed consistent: predictable APIs, great docs, clean abstractions.
• HubSpot wedged into inbound for SMB/mid-market, then broadened into a CRM platform while keeping one coherent story: help growing businesses acquire and serve customers.

They didn’t “take every deal", they protected the product’s centre of gravity.

How to avoid

1) Have a specific Ideal Customer Profile (ICP)

“Mid-market” isn’t an ICP, neither is “anyone with budget.”

Write it down in a way that a new account executive can use on day one, then treat it as a constraint for product and GTM decisions.

Cover the basics:

• Firmographics: industry, company size, geography, regulatory needs
• Technographics: stack requirements, integration patterns, data maturity
• Use case + urgency: the job-to-be-done, the trigger event, why now
• Buying dynamics: economic buyer, budget owner, typical sales motion
• Disqualifiers: who you don’t sell to (even if they ask nicely)

April Dunford’s positioning advice fits here: you win by being clear about who gets disproportionate value from your product. If you can’t say that in one sentence, your ICP is too fuzzy.

2) Track ICP fit metrics

Most teams measure adoption instead of fit. Fit predicts retention, support load, and expansion.

Track it like you track activation.

Start simple:

• Retention and churn by ICP vs non-ICP
• NRR by segment (expansion looks very different when the customer is a natural match)
• Sales cycle length and win rate by segment
• Support hours per account by segment
• Time-to-value by segment

Add a light-weight fit score in your CRM. Don’t make it academic, make it usable:

• 1–2 points for each core ICP attribute matched
• -3 points for a clear disqualifier (heavy customisation demand, atypical buyer, incompatible stack)
• Flag “out-of-ICP” deals in pipeline reviews the same way you flag discounting

If your non-ICP accounts churn the fastest, you don’t have a “CS problem.” You have a fit problem.

3) Give your sales team permission to say no

Opportunistic sales thrives when account executives feel they’ll be punished for disqualifying deals.

In the end, it's always about incenties. Make “no” a respected outcome when it protects the business.

Concrete ways to do it:

• Reward good “no’s.” Call them out in weekly reviews. Celebrate the deals you didn’t take that would have pulled you off-course.
• Do not allow conditional sales, where feature build is required to get ink on paper. They are not the ICP.
• Coach disqualification language: clear, calm, and commercial
  • “We’re not the best fit for that requirement.”
  • “We can support it through services, but it won’t be in the core product.”
  • “If that’s critical, we should step back.”

Jason Lemkin’s warning is the clearest summary: the last 10% of custom demands can spiral and consume your roadmap. Your sales team needs cover to avoid promising that 10% just to land the logo.

Sustainable growth comes from being choosy

Opportunistic sales feels like momentum. It’s often just motion.

Choose your Ideal Customer Profile. Protect it with deal rules, pricing boundaries, and a roadmap that’s anchored in repeatable value. If whales are part of the strategy, make that a strategy, not a panic response.