Fractional Opportunity · CXOwork
Revenue & Sales Enablement
Fractional CRO / Sales Leader
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About this opportunity
We're placing Fractional CROs and Sales Leaders with companies that have found their first customers but haven't yet built the system that creates the next hundred. These are post-seed or Series A companies where the founder is still closing deals and knows that cannot continue.
You will design the revenue architecture, hire the first quota-carrying reps, prove the motion yourself by closing strategic accounts, and stand alongside the founder in board and customer conversations as the senior-most revenue authority. This role is for operators who thrive in the zero-to-one phase of building a revenue organisation — and who can context-switch cleanly across two or three engagements without losing depth in any of them.
Core responsibilities
- Audit the current sales process, pipeline health, and win/loss patterns — deliver a revenue architecture recommendation within 30 days
- Build end-to-end revenue strategy aligned with the company's business model, ICP, and growth stage — defining GTM motions across inbound, outbound, PLG, channel, and enterprise
- Develop pricing, packaging, and monetisation strategy to maximise ARR and LTV — including renewal and expansion mechanics
- Design and implement a repeatable, scalable sales methodology (MEDDIC, SPICED, Sandler, Challenger, or custom) tailored to the company's stage and motion
- Hire, onboard, and ramp the first 3–10 quota-carrying reps — including job descriptions, interview scorecards, ramp milestones, and 30/60/90 plans
- Define territory design, quota allocation, and compensation plans for AEs, SDRs, and SEs
- Personally close 3–5 early enterprise or mid-market accounts to validate the sales motion before handing it off to the team
- Own the weekly revenue forecast and board-level pipeline reporting — accuracy within ±10% by month four
- Build the full revenue tech stack: CRM implementation and hygiene, sequencing tools, conversation intelligence, RevOps automation, and forecasting infrastructure
- Establish Sales–Marketing SLAs: lead handoff criteria, MQL scoring, ICP feedback loops, and demand-gen capacity matched to sales coverage
- Build a customer success handoff process to protect NRR from day one — seamless transitions across Sales → CS → Support
- Surface customer insight into product conversations so the roadmap reflects what's actually closing (and what isn't)
- Serve as trusted revenue advisor to the founder, exec team, and board — present pipeline, strategy, and growth plans with the clarity an investor would expect
- Provide strategic recommendations on hiring, GTM investments, and market-expansion sequencing — and the courage to call out the wrong moves before they're made
Required qualifications
- 10+ years in B2B sales, with at least 3 years as CRO, VP Sales, or Head of Revenue at a startup
- Track record of building revenue from $0 to at least $5M ARR — ideally from scratch, not inheriting a team
- Hands-on experience hiring, coaching, and managing quota-carrying AEs and SDRs
- Deep CRM expertise — HubSpot or Salesforce implementation and administration
- Experience selling to mid-market or enterprise buyers with 3–9 month sales cycles
- Strong financial fluency — able to own a revenue forecast and model compensation plan economics
- Comfort operating in a fractional, multi-client environment — context-switching cleanly between two or three engagements without losing depth in any of them
- Exceptional executive presence and stakeholder communication — can translate revenue mechanics for non-technical founders, boards, and enterprise procurement teams without losing nuance
Nice to have
Not required — but will strengthen your match quality.
- MEDDIC, SPICED, Sandler, or Challenger certification
- Experience building a channel or partnership sales motion alongside direct sales
- Background in pricing strategy, packaging design, or a monetisation rework that materially moved ARR
- Deep RevOps tooling experience (Outreach, Gong, Clari, Vitally) and automation workflow design
- Background in SaaS, marketplace, or API/developer-tool sales
- Prior fractional CRO, advisory, or interim VP Sales experience
Compensation & benefits
- Performance commission on closed revenue — typically 3–8% of net new ARR generated (negotiable)
- Hybrid flexibility — most engagements require 2–3 days on-site per month
- Access to CXOwork's CRO peer network and revenue benchmarks by stage and vertical
- Typical engagement length 4–9 months — often extends through Series B hiring of a full-time CRO
Application process
- 01Application with one sales-build case study: what you inherited, what you built, and the ARR outcome
- 0245-minute panel interview — revenue architecture, hiring, and forecasting deep-dive
- 03Profile approved and matched to active companies
- 04Founder intro call — pipeline and team assessment
- 05Engagement kick-off within 2 weeks
Roles included
- CROs
- Head of Sales
- Account Executives
Key skills