Director of AI Sales & Cross‑Sell

Simpro Group; Reading; On-site; GBP 150,000 - 190,000; Full time

Benefits offered by this job

Novated leasing

Employee Assistance Program (EAP)

Parental Leave Program

Volunteer Leave Days

Wellness & health programs

Career progression opportunities

Job summary

Simpro Group in Reading, UK, is seeking a Director of AI Sales to lead the cross-sell engine across the customer base. You will build and scale a team of Solution Specialists, drive high‑volume outbound and respond to inbound requests, and partner with Account Managers to close revenue.

This is a builder's seat focused on setting operating rhythm, defining KPIs, and delivering consistent quota attainment. You will recruit, ramp, and develop top talent, coach on discovery, demos, and closing

Qualifications

• Proven track record of leading high-velocity sales teams that consistently exceed quota.
• Experience building scalable sales motions, cadences, and operating frameworks from scratch.
• Strong ability to hire, ramp, and develop top-performing sales talent.
• Deep knowledge of pipeline management, forecasting, and deal inspections.
• Partner cross-functional with Account Management, Marketing, Product, and Enablement.

Responsibilities

• Carry and deliver the Solution Specialists team quota for cross-sell revenue across the Simpro Group portfolio.
• Drive consistent attainment against monthly, quarterly, and annual revenue targets.
• Maintain forecast accuracy and ensure a healthy, well-managed pipeline with no surprises.
• Define and implement the team’s operating rhythm, including daily cadence, pipeline management, call and meeting expectations, and inspection processes.
• Establish measurable KPIs and performance standards across the team.
• Recruit, hire, and develop high-performing Solution Specialists capable of managing volume, delivering compelling demos, and closing opportunities effectively.

Skills

Quota attainment

Leadership

Cross-functional collaboration

Forecasting

Talent development

Sales enablement

Demos & product fluency

Tools

Salesforce

HubSpot

Job description

Simpro Group in Reading, UK, is seeking a Director of AI Sales to lead the cross-sell engine across the customer base. You will build and scale a team of Solution Specialists, drive high‑volume outbound and respond to inbound requests, and partner with Account Managers to close revenue.

This is a builder's seat focused on setting operating rhythm, defining KPIs, and delivering consistent quota attainment. You will recruit, ramp, and develop top talent, coach on discovery, demos, and closing