Head of Mid Market Sales

🕒 May 12

Apply Now

Find Similar Remote Jobs

Receive Emails For Remote Jobs

📊 Check your resume score for this job

Improve your chances of getting an interview by checking your resume score before you apply.

Upload Resume

Checkatrade

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 1998

👥 B2C

🛍️ eCommerce

🛒 Retail

B2C • eCommerce • Retail

Checkatrade is a platform that connects homeowners with trusted tradespeople for various home improvement projects. Whether it's plumbing, electrical work, roofing, or gardening, Checkatrade helps homeowners find reliable and reviewed professionals ready to assist them. The service includes a comprehensive advice center, job categories, and guarantees on trades professionals' work, ensuring a seamless process for home improvements and repairs.

📋 Description

• 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 • You will define and document the repeatable Mid-Market sales motion while testing and iterating on outbound sequences, messaging, and objection handling • 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 • 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

🎯 Requirements

• 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

🏖️ Benefits

• 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!