Head of Mid Market Sales

Other

• 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.
• 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
• 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!
• 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
• About us We’re Checkatrade – the UK’s leading platform for finding a tradesperson. With more than 50,000 trades listed and over 6 million reviews, we help homeowners get jobs done right and help tradespeople grow their business.
• We’re growing fast, with big plans to become the go-to brand for home improvements. If you care about great work, take pride in the details, and want to make an impact, you’ll fit right in.