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
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.
Skills Required
- Proven SaaS sales leadership experience with experience managing Mid-Market or SMB+ teams
- Track record of building and scaling teams
- Consistent delivery through others
- Experience operating in 0 -> 1 or 1 -> 10 environments
- Strong coaching capability
- Pipeline and forecasting rigor
- Structured, value-led selling mindset
What We Do
Checkatrade is one of the UK’s top online marketplaces for home improvements and repairs. Our mission is to be the trusted foundation of every home by connecting people with trades and tools to make home improvements easy – because we believe safe and happy homes improve lives, support livelihoods, and build communities. From our humble beginnings in 1998 to becoming a national household name, we’re on an exciting journey. For more than 25 years Checkatrade has stood for reputation and raising standards – whether that is for our trade members, consumers, or our colleagues. We think big and are passionate about changing the face of home improvements and repairs. Today, we are a modern online marketplace and a force for good. We strive every day to support people to improve their homes and we don’t settle for the status quo – we are evolving, innovating, and growing. With generous investment from private equity partners Brookfield, we have an ambitious growth plan and a robust roadmap to get there. Led by our values – Be All In, Always Customer Obsessed, Get It Done, Be Bold, and Do The Right Thing – we are 500 high-performing individuals working across the UK, with high-spec offices in London and Portsmouth. We are here to be the best and inspire others to do the same, and to get there we need exceptionally talented, bright, and driven people – so if that sounds like you, you couldn’t join at a better time!
