Senior Director of AI Sales

Singapore Post•Miami, FL

10d•Onsite

About The Position

The Senior 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.

Requirements

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

Responsibilities

Own Revenue Performance: 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.
Build & Scale the Sales Motion: 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.
Lead, Hire & Develop Talent: Recruit 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.
Drive Cross-Functional Execution: 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.
Establish Product & Industry Expertise: Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions.
Enable Specialists to clearly articulate integration value and cross-product business impact to customers.
Build & Scale Best Practices: Develop and document scalable sales playbooks, including: Discovery and call structures, Demo workflows, Expansion strategies, Integration narratives, Objection handling frameworks.
Standardize and scale winning strategies across the organization.
Represent the Function: 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.

Benefits

Novated leasing via salary packaging
Employee Assistance Program (24/7 confidential support on relationships, bereavement, finances)
Generous Parental Leave Program
Paid Volunteer Leave Days
Public Holiday Exchange Scheme
Talent Referral Program – get rewarded for referring a friend to join our team!
Casual dress and relaxed office environment
Fun team camaraderie and events
Opportunities for career progression and development
Diverse training & internal networking opportunities across all of our product lines
Service recognition awards
Responsible Time Off
Comprehensive medical, dental, vision package with 100% employer paid options
Additional benefits including 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
401k/Retirement Plan with 6% employer match