Shorten enterprise sales cycles

Who this is for

Founder led lower-middle market companies with 5 to 50 million in annual revenue selling into complex accounts.

The quick answer

Map how the customer buys. Confirm the problem, value, economic buyer, and the legal and security steps early. Co write a mutual action plan with dates. Use paid pilots that include the next order on success. Bring delivery leaders into late stage calls to reduce risk. Keep a short risk log and clear blockers each week.

The method in eight steps

Map the buying team
Sponsor, economic buyer, users, procurement, legal, and security. Ask how similar purchases were approved and capture lead times.
Qualify for urgency and value
Put a number on the problem and the cost of delay with the sponsor. Park deals without urgency.
Write a mutual action plan
Tasks, owners, and dates from now to signature and go live. Use it as the agenda at every meeting.
Run paid pilots with a success line
Define a tight use case and a measurable success line. Include the next order in the pilot terms if the line is met.
Remove legal and security friction
Share a standard data protection addendum and a security pack early. Keep internal redline rules simple and quick.
Build the economic buyer case
One page in their language that covers problem, options, value, price, risk, and timeline. Include the cost of delay.
Hold a weekly large deal review
Inspect next steps by date, ageing, and stage conversion. Clear blockers fast.
Use executive help at key moments
Have an executive call when confidence or risk removal will move the deal.

Example

A software firm moved to paid pilots with a four week success line and added a mutual action plan template. Median cycle dropped and win rate rose.

Pitfalls and fixes

Free pilots with no end. Keep them paid and time bound.
Legal surprises late. Share the pack early.
Single thread deals. Add two more contacts by the second meeting.

Checklist

Buying map complete
Mutual action plan in use
Paid pilot template ready
Legal and security pack ready
Weekly review and risk log