Director, AI Sales — Cross-Sell Growth Leader

USA Simpro Software Ltd.; Miami (FL); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Medical, dental, vision

Employer-paid options

401k with matching

Parental leave

Volunteer leave

Holiday exchange

Wellness apps

Career development

Training & networking

Job summary

Simpro Group is seeking a Director of AI Sales to lead the cross-selling engine across its portfolio. The role focuses on building and scaling a high-performance AI sales team, delivering quota for cross-selling revenue, and driving forecast accuracy with a data-driven, metrics-based approach.

You will hire, coach, and ramp top performers, define playbooks, and partner with Marketing and Enablement to push expansion initiatives.

Qualifications

• 7+ years of B2B SaaS sales experience, including 3+ years in leadership.
• Proven track record building and scaling sales teams.
• Deep expertise in inside sales, cross-selling, and expansion revenue.

Responsibilities

• Own Revenue Performance Carry and hit AI Sales team quota.
• Drive attainment against revenue targets and maintain forecast accuracy.
• Build and scale the sales motion and operating rhythm.
• Hire, coach, and develop AI Sales Executives for high-volume outbound.
• Collaborate with Marketing on campaign plays and expansion initiatives.
• Provide product feedback to shape roadmap priorities.

Skills

B2B SaaS sales

Sales leadership

Inside sales

Cross-selling

Coaching

Salesforce

Pipeline management

Expansion revenue

Data analytics

Executive presence

Tools

Salesforce

Job description

Simpro Group is seeking a Director of AI Sales to lead the cross-selling engine across its portfolio. The role focuses on building and scaling a high-performance AI sales team, delivering quota for cross-selling revenue, and driving forecast accuracy with a data-driven, metrics-based approach.

You will hire, coach, and ramp top performers, define playbooks, and partner with Marketing and Enablement to push expansion initiatives.