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Head of Mid Market Sales
Checkatrade. You will own the Mid-Market revenue target across both leads and non-leads segments, while building and maintaining 3–5× pipeline coverage with clear visibility and control.
About the role
Key responsibilities & impact- You will own the Mid-Market revenue target across both leads and non-leads segments, while building and maintaining 3–5× pipeline coverage with clear visibility and control.
- You will also run end-to-end sales cycles: discovery → demo → pilot → commercial close
- You will define and document the repeatable Mid-Market sales motion while testing and iterating on outbound sequences, messaging, and objection handling
- You will hire, onboard, and coach two Account Executives and define performance standards, ramp plans, and quota frameworks.
- You will also act as a player-coach — carrying a personal number while building the team and set the tone for a high-accountability, high-performance culture
- You will own pipeline reporting and forecasting, presenting weekly updates to leadership (TradeAI Steering Committee).
- You will also feed real-time market and customer insights back into Product, Marketing, and leadership
Requirements
What you’ll need- Proven SaaS sales leadership experience with some experience managing Mid-Market or SMB+ teams (£10k–£60k ACV)
- Track record of building and scaling teams — hiring, onboarding, and developing Account Executives in a pre-scale or growth environment
- Consistent delivery through others — not just personal quota attainment, but driving team performance against target with clear pipeline discipline
- Experience operating in 0→1 or 1→10 environments — comfortable creating structure, not just following it
- Strong coaching capability — able to diagnose performance gaps, run effective deal reviews, and improve win rates across the team
- Pipeline and forecasting rigour — confident running weekly pipeline reviews and delivering accurate, data-backed forecasts through the team
- Structured, value-led selling mindset — able to embed a repeatable sales methodology across reps
Benefits
Comp & perks- Competitive salary + commission (role dependent)
- Employee Share Program
- Health, well-being and learning support
- Gym membership, Smart Tech Scheme and Cycle Scheme
- Birthday/Special day leave
- Buy & sell holiday scheme
- 1 week’s paid charity leave and much more!
ATS Keywords
✓ Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
SaaS salespipeline reportingforecastingsales methodologyobjection handlingdeal reviewsperformance standardsquota frameworksteam performance managementdata-backed forecasts
Soft Skills
coachingleadershipcommunicationteam buildinghigh-performance cultureaccountabilitystructured thinkingproblem-solvingadaptabilityinterpersonal skills