Director Of AI Sales

Date: 2026-09-28T00:00:00

Location: Reading, Berkshire, GB, RG1 2

Application Deadline: 2026-12-28T19:00:26.003

What You'll Do

The Director of AI sales owns the cross-sell engine across the Simpro Group customer base. This leader builds, runs, and scales a team of Solution Specialists who carry quota, run high-volume outbound and respond to inbound requests. They also partner with Account Managers to convert opportunities into closed revenue. This is a builder's seat. The Director sets the bar for intensity, deal execution and product fluency, and is personally accountable for the team's contribution to Group cross-sell revenue.

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.

Continuously optimize processes to improve conversion, productivity, and revenue outcomes.

Recruit, hire, and develop high-performing Solution Specialists capable of managing volume, delivering compelling demos, and closing opportunities effectively.

Make timely and decisive talent decisions to maintain a high-performance culture.

Create a scalable onboarding and ramp program that accelerates time-to-productivity.

Coach to Close: conduct live call coaching, deal reviews, and pipeline inspections.

Improve team performance in discovery, demo execution, objection handling, and closing strategies.

Ensure every Specialist becomes measurably more effective within their first 30 days.

Partner closely with Account Management leadership to convert qualified opportunities into revenue.

Collaborate with Marketing on campaign plays and expansion initiatives.

Work with Enablement on onboarding and ongoing training programs.

Provide Product teams with customer insights and market feedback that influence roadmap priorities.

Build and scale best practices: develop and document scalable sales playbooks, including discovery and call structures, demo workflows, expansion strategies, integration narratives, and objection handling frameworks.

Standardize and scale winning strategies across the organization.

Serve as the voice of the Solution Specialists organization within Revenue Leadership discussions.

Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations.

Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions.

Enable Specialists to articulate integration value and cross-product business impact to customers.

Qualifications

Proven track record of leading teams that consistently exceed quota and deliver high-performance results.

Experience leading high-velocity inbound, outbound, or expansion sales teams.

Demonstrated success building sales motions, cadences, and operational frameworks from scratch.

Strong experience hiring, ramping, and developing sales talent.

Ability to lead through metrics, accountability, and operational discipline.

Strong technical aptitude with the ability to independently run product demos and coach others effectively.

Deep understanding of pipeline management, forecasting, activity metrics, and deal inspection processes.

Experience partnering cross-functionally with Account Management, Marketing, Product, and Enablement teams.

Excellent communication and leadership skills with a direct, decisive, and accountable management style.

Additional Requirements

This is an in-office leadership role focused on building and scaling teams through in-person collaboration.

Benefits

Novated leasing via salary packaging.

Employee Assistance Program (24/7 confidential support).

Generous Parental Leave Program.

Paid Volunteer Leave Days.

Public Holiday Exchange Scheme.

Talent Referral Program.

Casual dress and relaxed office environment.

Fun team camaraderie and events.

Opportunities for career progression and development.

Diverse training & internal networking opportunities across all product lines.

Service recognition awards.

Comprehensive medical, dental, vision package with 100% employer paid options.

Health Savings Account; Flexible Spending Account; Critical Illness Insurance; Hospital Insurance; Accident Insurance; Life Insurance and AD&D; and Disability Insurance available to purchase.

Wellness Challenge App, Diabetes Prevention App, and Health Hub App.

401(k)/Retirement Plan with 6% employer match.

Core Values

We are One Team.

We are Customer Centric.

We are Growth Minded.

We are Accountable.

We celebrate Success.

Simpro, AroFlo, BigChange & ClockShark are equal opportunity employers with a best-of-class onboarding program and supportive team environments. We embrace and support culture diversity and Equal Employment Opportunity. Aboriginals, Torres Strait Islanders and minority groups are encouraged to apply.

#s1-Gen

What You'll DoThe Director of AI sales owns the cross-sell engine across the Simpro Group customer base. This leader builds, runs, and scales a team of Solution Specialists who carry quota, run high-volume outbound and respond to inbound requests. They also partner with Account Managers to convert opportunities into closed revenue. This is a builder's seat. The Director sets the bar for intensity, deal execution and product fluency, and is personally accountable for the team's contribution to Group cross-sell revenue.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.Continuously optimize processes to improve conversion, productivity, and revenue outcomes.Recruit, hire, and develop high-performing Solution Specialists capable of managing volume, delivering compelling demos, and closing opportunities effectively.Make timely and decisive talent decisions to maintain a high-performance culture.Create a scalable onboarding and ramp program that accelerates time-to-productivity.Coach to Close: conduct live call coaching, deal reviews, and pipeline inspections.Improve team performance in discovery, demo execution, objection handling, and closing strategies.Ensure every Specialist becomes measurably more effective within their first 30 days.Partner closely with Account Management leadership to convert qualified opportunities into revenue.Collaborate with Marketing on campaign plays and expansion initiatives.Work with Enablement on onboarding and ongoing training programs.Provide Product teams with customer insights and market
feedback that influence roadmap priorities.Build and scale best practices: develop and document scalable sales playbooks, including discovery and call structures, demo workflows, expansion strategies, integration narratives, and objection handling frameworks.Standardize and scale winning strategies across the organization.Serve as the voice of the Solution Specialists organization within Revenue Leadership discussions.Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations.Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions.Enable Specialists to articulate integration value and cross-product business impact to customers.QualificationsProven track record of leading teams that consistently exceed quota and deliver high-performance results.Experience leading high-velocity inbound, outbound, or expansion sales teams.Demonstrated success building sales motions,
cadences, and operational frameworks from scratch.Strong experience hiring, ramping, and developing sales talent.Ability to lead through metrics, accountability, and operational discipline.Strong technical aptitude with the ability to independently run product demos and coach others effectively.Deep understanding of pipeline management, forecasting, activity metrics, and deal inspection processes.Experience partnering cross-functionally with Account Management, Marketing, Product, and Enablement teams.Excellent communication and leadership skills with a direct, decisive, and accountable management style.Additional RequirementsThis is an in-office leadership role focused on building and scaling teams through in-person collaboration.BenefitsNovated leasing via salary packaging.Employee Assistance Program (24/7 confidential support).Generous Parental Leave Program.Paid Volunteer Leave Days.Public Holiday Exchange Scheme.Talent Referral Program.Casual dress and relaxed office environment.Fun
team camaraderie and events.Opportunities for career progression and development.Diverse training & internal networking opportunities across all product lines.Service recognition awards.Comprehensive medical, dental, vision package with 100% employer paid options.Health Savings Account; Flexible Spending Account; Critical Illness Insurance; Hospital Insurance; Accident Insurance; Life Insurance and AD&D; and Disability Insurance available to purchase.Well-ness Challenge App, Diabetes Prevention App, and Health Hub App.401(k)/Retirement Plan with 6% employer match.Core ValuesWe are One Team.We are Customer Centric.We are Growth Minded.We are Accountable.We celebrate Success.Simpro, AroFlo, BigChange & ClockShark are equal opportunity employers with a best-of-class onboarding program and supportive team environments. We embrace and support culture diversity and Equal Employment Opportunity. Aboriginals, Torres Strait Islanders and minority groups are encouraged to apply. #J-18808-Ljbffr

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