Burn the ship or build another ship?
Thinking of going enterprise? Get the questions right before you burn your runway. Going after the enterprise segment can mean bigger deals, faster cycles, and more revenue — or a long, expensive detour. Before you make the leap, answer these questions.
1. Is your current PLG motion viable?
If your product-led growth (PLG) motion is broken, that’s easy to diagnose: poor conversion, users stuck before they reach value, or product gaps that block adoption.
Example: I once joined a SaaS startup with PLG aspirations but no real traction. The product had UX friction and required admin-level access to sensitive data. We pivoted to sales-led and grew fast — but only after shutting down PLG.
If PLG is working (even moderately), measure:
ARR growth rate
LTV:CAC
Payback period
GRR and NRR
2. Is PLG still a differentiator?
In some markets, PLG is rare and can be a moat. In others, it’s table stakes. If everyone’s already PLG, a sales-led push may win different, better deals.
Check your funnel:
Lead → PQL → Win conversion rates
Lead volume and quality
Acquisition cost vs. ACV
If the numbers are weak, fix PLG before killing it.
3. What happens to the PLG team?
When you shift upmarket, decide fast:
Keep PLG running independently?
Let it fade over quarters?
Shut it down to free capital?
Each path has risks — especially morale and missed revenue.
4. What does “enterprise” mean for you?
Define it clearly for your team:
Logo list (Fortune 500? 5000?)
Motion (long cycles, big committees)
Deal size (> $100k? land-and-expand?)
Without alignment, you’ll end up chasing different targets.
5. Is the timing right?
Many startups jump too soon — often around $20M ARR and 150 employees — only to stall. Salesforce waited a decade, built a cash cow in SMB/MM, and entered enterprise with $1B+ ARR.
Enterprise is a crowded, competitive arena. Enter only when you have momentum and resources.
6. Is leadership 100% aligned?
Partial buy-in is poison. If even one exec drives a different agenda (e.g., a freemium push while others chase enterprise), execution suffers. Lock in a unified decision, even if not everyone agrees.
7. Do you have the right team?
Winning enterprise requires new skill sets:
Enterprise AEs who can manage 12–18 month, $200k+ deals
Marketers skilled in events, outbound, and partnerships
Customer success managers for low-ratio, high-touch accounts
Hiring takes time. Events can need 6–12 months’ lead.
8. Is the product enterprise-ready?
Don’t hire an enterprise sales team before your product can win enterprise deals. Missing features, security gaps, or slow delivery will sink you — and burn expensive hires.
9. What does success look like?
Pick a North Star and timeline:
$X ARR in enterprise
Y enterprise customers
Improved NRR or LTV:CAC
Track leading indicators (engagement from target accounts, pipeline health) so you don’t panic and pivot too early.
10. Do you have the capital?
Enterprise GTM requires deep investment and long payback. Without strong investors willing to fund the push, you may get outspent and overtaken — even with a better product.
Bottom line: Moving upmarket can transform your company — or burn your runway. Answer these questions honestly, align your team, and secure the capital before you make the leap.
CTA: If you’re debating a move upmarket, run a 60-minute leadership alignment session. The right answers now can save you 18 months of wasted effort.
