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 closePlaybook & Go-to-Market: You will define and document the repeatable Mid-Market sales motion while testing and iterating on outbound sequences, messaging, and objection handlingTeam 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 cultureInsight & 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 in.