Hiring a Fractional CRO / Head of Sales

Taylor Crane

February 25, 2026

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Quick Answer:

Hire a Fractional Head of Sales when you need senior sales leadership to build or stabilize your sales motion, but you do not need a full-time Head of Sales yet. The goal is a repeatable pipeline-to-close process that the company can run without founder heroics.

Most Common Situations Or Problems That Warrant a Fractional Head of Sales

Founder-led Sales slowing you down: The founder owns sales and the company cannot escape the founder-led motion.
No outbound: There is no formal outbound motion, so growth depends on referrals, luck, or inconsistent inbound.
Low conversion: You have lead flow, but it is not converting (no-shows, long cycles, inconsistent follow-up, unclear qualification).
Bigger deals: You are trying to move up-market or add channels/partnerships, but the current process is built for smaller deals.

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How a Fractional Head of Sales Helps Solve Those Problems

Sales playbook: They define ICP, qualification, messaging, and outreach sequences, then turn it into a playbook the team can repeat.
End-to-end process: They own the sales process from lead through close, tightening the stages, handoffs, and follow-up so deals do not stall.
Pipeline creation: They stand up an outbound engine (or expand new lead sources) that fits your buyer, your cycle, and your team capacity.
Deal coaching: They join critical calls, coach objection handling and pricing, and create structure around late-stage execution so close rates improve.
Team ramp: If you have reps (or want to hire them), they set expectations, run weekly cadence, and train the team so output becomes consistent.

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Fractional Account Executive Or a More Senior Fractional Head of Sales?

If you already have a clear motion and you mostly need coverage (running sequences, managing CRM hygiene, moving deals through a defined process), a strong Senior IC can be enough. If the missing piece is building the motion itself (what to sell, who to target, how to qualify, how to forecast, how to hire/coach) then you want a more senior Fractional Head of Sales who can design the system and own the results.

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A Unique Consideration: Compensation

Fractional Head of Sales / CRO is one of those unique roles that may be an exception to retainer-based pricing or hourly-based pricing. It can be more common to see other compensation models, such as commission based pricing. Read more about it here!

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Fractional Head of Sales Case Study

Fractional Jobs recently helped Raven Health (healthtech SaaS), hire a Fractional Head of Sales. Their sales team was stuck, and leads weren’t converting. To fix this, they brought on a seasoned SaaS expert that made a few tweaks while working with the team 10 hrs per week.

Raven Health’s CEO said: “The amount of demo volume we've had come in has spiked since he arrived, and I've had to jump into inside sales and take a dozen or so demos a week to help the team. Good problem to have though!”

Read the full case study here.

Fractional Jobs also helped:

Resto Labs (restaurant-tech) hire a Fractional Head of Business Development for 10 hours per week.
Cloudticity (IT services) hire a Fractional Head of Sales for 15 hours per week.
Pumpkin Petcare (insurtech) hire a Fractional Sales Lead for 10 hours per week.

All with similar results.

Get help hiring a Fractional Head of Sales for your startup or SMB, learn more here.

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Who Wrote This Guide?

I’m Taylor Crane, founder of Fractional Jobs (the site you’re reading this on!).

I’ve helped 100+ companies hire fractional execs and other fractional talent. I also spent a year as a Fractional Head of Product.

I intimately understand how fractional work works from both sides of the table. And this guide is meant to help everyone get up to speed on the fractional world, quickly.