"You've got 30% more of the sales team missing quota today than six months ago."
Planning Under Uncertainty
The Conservative Forecast + Milestone Playbook
Plan for $9M if you did $10M last year
Set Q1 target of $2.25M
Hit $2.25M? Unlock budget & accelerate
Miss? Revise down for rest of year
Pre-agree on triggers with board & team
The founder bias trap
Founders are biased toward optimism. In downturns, that's a liability, not an asset. Pre-commit to predetermined decision rules so you don't rationalize away Q1 misses.
Sahil's core insight"Don't want to be floundering from 'we're screwed' to 'everything's better.' Set checkpoints that remove emotion from decisions."
New Comp Structure
Realign Incentives for Retention
Shift from purely top-line bookings: Most comp is still "new ACV closed"
Weight expansion & renewal: Upsell, cross-sell, and net retention get real comp points
Change the ratio: If you were 80/20 new-to-expansion, flip to 50/50 or 40/60
Non-linear commission: Hit 50% of quota on new business, 90% on expansion? You still make money
Define "a deal": Pilot contracts, multi-year deals, and small expansion all count differently
Why this works in downturns
Sales teams follow incentives. If you want them hunting expansion, pay them for it. Downturns are when existing customers are most defensible and valuable.
The data signal
Enterprise sales cycles are 115+ days (up from 62). Pilots are trending up. Multi-year deals are rare. Your comp must reflect reality.
Retention
Move Your Best Salespeople into CSM
Cold prospecting is broken. Response rates are at all-time lows
Enterprise sales cycles extended 50+ days YoY
"No decision" = "I like it but won't spend now"
Your existing customers are your only growth lever
Put your best AEs into customer success to defend what you have
Counterintuitive moveIn tough markets, defending your base is more valuable than chasing new logos. This shifts who your A-players should be.
Contrarian Sales Tactics
Five Downturn Myths Debunked
✗Hiring more SDRs will fix pipelineINSTEAD →✓ Cold outreach is dead. Invest in warm intros, account-based selling, and existing customer leverage instead.
✗Compensation should stay all-commissionINSTEAD →✓ Add base salary bump if you shift comp toward expansion. Make retention economically rational for reps.
✗Customers care only about priceINSTEAD →✓ Customers care about getting value and visibility into how peers are navigating the downturn. Be an advisor, not a vendor.
✗Layoffs mean you're doing something wrongINSTEAD →✓ The entire market is missing quota. Layoffs are a symptom, not a failure. Right-size fast and focus on retention.