Head of Mid Market Sales

As a Head of Mid-Market Sales, you will build and lead our Mid-Market function at Checkatrade.

This is a 0→1→100 leadership role. You’ll take ownership of a largely undefined space and turn it into a scalable, high-performing revenue engine - defining the motion, closing initial deals, and building a team that can deliver consistently beyond you.

As we evolve from a transactional model to a more structured, value-led and SaaS-oriented approach, you’ll play a critical role in shaping how we win in the Mid-Market: establishing the sales playbook, embedding pipeline discipline, and developing a team of high-performing Account Executives.

You’ll work closely with Product, Marketing, CSM, and Revenue Operations to ensure we’re not just closing deals, but building a motion that drives activation, retention, and long-term value.

This is a high-impact, high-ownership leadership role - where you’ll be expected to lead from the front, build from the ground up, and scale through others.

Forget long lists, here’s what you’ll actually spend your time on

• Revenue & Pipeline: 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
• Playbook & Go-to-Market: You will define and document the repeatable Mid-Market sales motion while testing and iterating on outbound sequences, messaging, and objection handling
• Team Building: 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
• Insight & Reporting: 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

It’s not about ticking every box. It’s about turning up curious, ready to crack on. You’ll do well here if you bring:

• 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

We believe great work deserves great rewards. Here’s just a taste

• 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!

How we’ll get to know each other

• Screening call with one of our Talent Acquisition Partners
• 1st stage interview with the VP of Sales
• 2nd stage interview and case study with Cross Functional Senior Stakeholders
• Final stage interview with the COO

If this sounds like the place where you can do your best work, we’d love to hear from you, even if you don’t tick every box

Want to join our Talent Community and be one of the first to know about our vacancies? Register your interest on our Registration Form