Interactive Deal Simulations

Full-Cycle Deal: Enterprise Land-and-Expand

A small initial $90K pilot inside a 22,000-person enterprise. Every move you make is auditioning for a $2M expansion.

The situation

You sourced the deal cold into a single business unit (Customer Operations) at a Fortune 500 financial services firm. The buyer wants to start small — one team, 75 seats, $90K — to prove value. Procurement is heavy, security is heavier, and a separate Strategy & Transformation team is quietly evaluating the same category at the enterprise level. You have to win the small deal in a way that lets you win the big one.

Key stakeholders

Devon Marsh
champion
Director, Customer Ops (Champion)
Wants the pilot. Has limited org influence outside her team.
Renata Vasquez
neutral
VP Strategy & Transformation
Running a parallel, quiet enterprise category review.
Hank Lowell
skeptic
CISO
Has rejected three SaaS vendors this year on data residency.
Procurement Specialist
neutral
Standard contract owner
Tariq Singh
user
End user lead
Will run the pilot day-to-day.

Step 1

Decision point

Devon wants to move fast on the 75-seat pilot. You' heard secondhand that Renata's team is doing an enterprise category review but you have no relationship there.

How do you the initial deal?