Hiring a Fractional Sales Leader? Check these before you sign.

The 13 checks

Tick the boxes as you interview. Or print the PDF and bring it to the call.

0 of 13 checked

01They've sat in your chair

Weigh this most

Sales advice from someone who never owned a company is theory. You need someone who has lived your week.

They founded and ran their own company. They owned it. They didn't manage a division.
They made payroll in months when the pipeline ran thin.
They were the only salesperson once, and they built their way out.
They can name three mistakes they made as a founder. Specific ones.

Ask: “When you were the founder and sales stalled, what did you do?”

02They've done this exact job

They built a sales system from nothing at $1M–$10M. They didn't inherit one at a big company.
They show you the work: a playbook, pipeline stage rules, a hiring scorecard.
Reps they hired will take your call. Ask if they'd work for them again.

Ask: “Walk me through the last sales process you built from scratch.”

03They have a plan before execution

They interview your whole sales team, you included, and write up what they find.
They ask about win rates, cycle length and lost deals before they pitch you anything.
They embed. They run pipeline reviews and coach your reps. No deck, then goodbye.

Ask: “What will you install in the first 30 days?”

04They plan to leave

12 weeks minimum to build. 6 to 12 months in all. Then they hand it off.
They put 3 to 5 measurable outcomes in writing before day one.
They commit to checkpoints. Day 30: a playbook on paper. Day 60: you sell less. Day 90: reps run discovery without you.

Walk away if

They never owned a business.
They tell war stories but can't show a document.
A big-company title is their only proof.
"Give it more time," with no plan for what changes.
The engagement has no end date.