How to Close Bigger SaaS Deals: Practical Steps From SaaStr

# Why closing bigger deals is different

# Hire the right sales leader

Bring in a CRO or VP of Sales who has closed deals consistently at the price point you want to reach. This hire brings practical experience: how to price, structure negotiations, and avoid common mistakes that make customers feel overcharged. Lemkin points to hiring carefully — the right senior seller will shorten the learning curve and raise your win rate at the high end.

# Build enterprise-grade product capabilities

# Staff to support land-and-expand

Post-sale engagement drives upsell. Invest heavily in forward-deployed engineers, pre-sales support, and customer success. Lemkin recommends aiming for as much as one customer success manager (CSM) per $500k in ARR if you can afford it. Engaged, well-supported customers are more likely to expand organically and less likely to churn.

# Adjust expectations on sales cycle and patience

Bigger deals typically take longer to close. A smart VP of Sales will shorten cycles where possible, but a newly upmarket company should expect longer timelines. Be zealous about removing friction and shortening cycles, but accept that multi-month processes are normal when the dollar amounts are higher.

# Use in-person engagement deliberately

Travel to meet top prospects and customers. In-person meetings increase deal size, speed, and likelihood of long-term success. You can close some large deals remotely, but they will often be smaller, slower, and higher risk compared with deals where teams have met face-to-face.

# Be aggressive, but earn the right

Push for full-seat, full-revenue commitments where appropriate, but don't push customers past what your brand and track record justify. Overreaching too early can break deals or damage relationships. As you accumulate enterprise references and product capabilities, you'll be able to ask for more up front.

# The process is deliberate

Going upmarket is a sequence: hire seasoned sellers, build enterprise features and integrations, staff customer-facing roles for post-sale success, accept longer sales processes, and add in-person selling for key accounts. Bring in one or two veterans who already sell at your aspirational price point and use those hires to accelerate the rest of the organization.