Head of Mid Market Sales

<p style="min-height:1.5em">As a <strong>Head of Mid-Market Sales</strong>, you will build and lead our Mid-Market function at Checkatrade.</p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em"><strong>Forget long lists, here’s what you’ll actually spend your time on:</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em"><strong>Revenue &amp; Pipeline: </strong>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</p></li><li><p style="min-height:1.5em"><strong>Playbook &amp; Go-to-Market: </strong>You will define and document the repeatable Mid-Market sales motion while testing and iterating on outbound sequences, messaging, and objection handling</p></li><li><p style="min-height:1.5em"><strong>Team Building: </strong>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</p></li><li><p style="min-height:1.5em"><strong>Insight &amp; Reporting: </strong>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</p></li></ul><p style="min-height:1.5em"><strong>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:</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em"><strong>Proven SaaS sales leadership experience </strong>with some experience managing Mid-Market or SMB+ teams (£10k–£60k ACV)</p></li><li><p style="min-height:1.5em"><strong>Track record of building and scaling teams</strong> — hiring, onboarding, and developing Account Executives in a pre-scale or growth environment</p></li><li><p style="min-height:1.5em"><strong>Consistent delivery through others</strong> — not just personal quota attainment, but driving team performance against target with clear pipeline discipline</p></li><li><p style="min-height:1.5em">Experience <strong>operating in 0→1 or 1→10 environments</strong> — comfortable creating structure, not just following it</p></li><li><p style="min-height:1.5em"><strong>Strong coaching capability</strong> — able to diagnose performance gaps, run effective deal reviews, and improve win rates across the team</p></li><li><p style="min-height:1.5em"><strong>Pipeline and forecasting rigour</strong> — confident running weekly pipeline reviews and delivering accurate, data-backed forecasts through the team</p></li><li><p style="min-height:1.5em"><strong>Structured, value-led selling mindset</strong> — able to embed a repeatable sales methodology across reps</p></li></ul><p style="min-height:1.5em"><strong>We believe great work deserves great rewards. Here’s just a taste:</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em">Competitive salary + commission </p></li><li><p style="min-height:1.5em">Employee Share Program</p></li><li><p style="min-height:1.5em">Health, well-being and learning support</p></li><li><p style="min-height:1.5em">Gym membership, Smart Tech Scheme and Cycle Scheme</p></li><li><p style="min-height:1.5em">Birthday/Special day leave</p></li><li><p style="min-height:1.5em">Buy &amp; sell holiday scheme</p></li><li><p style="min-height:1.5em">1 week’s paid charity leave and much more!</p></li></ul><p style="min-height:1.5em"><strong>How we’ll get to know each other:</strong></p><ul style="min-height:1.5em"><li><p style="min-height:1.5em">Screening call with one of our Talent Acquisition Partners</p></li><li><p style="min-height:1.5em">1st stage interview with the VP of Sales</p></li><li><p style="min-height:1.5em">2nd stage interview with Cross Functional Senior Stakeholders</p></li><li><p style="min-height:1.5em">3rd stage in person case study</p></li><li><p style="min-height:1.5em">Final stage interview with the COO</p></li></ul><p style="min-height:1.5em">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</p><p style="min-height:1.5em"><strong>Want to join our Talent Community and be one of the first to know about our vacancies? Register your interest on our </strong><a target="_blank" rel="noopener noreferrer nofollow" href="https://jobs.ashbyhq.com/checkatrade/form/register-interest"><strong><u>Registration Form</u></strong></a></p><div style="min-height:1.2em;margin-top:0;margin-bottom:0"> </div><div style="min-height:1.2em;margin-top:0;margin-bottom:0"> </div><p style="min-height:1.5em"><strong>About us<br /><br /></strong>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.</p><p style="min-height:1.5em">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.</p><p style="min-height:1.5em"></p><p>Find <a href="https://www.arbeitnow.co.uk">Jobs in United Kingdom</a> on Arbeitnow</a>