Director, AI Sales

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

Job Context

Ready to lead a high-growth sales motion and earn at the highest level? As Director of AI Sales, you will own the cross-selling engine across the Simpro customer base. This is a high-impact, fast-paced opportunity for an ambitious, high-energy sales leader looking to maximize their earning potential while building and scaling an elite sales team. You will lead quota-carrying AI Sales Executives running high-volume outbound strategies to turn warm pipeline into closed revenue. If you thrive in a true builder's seat and want your compensation to reflect your impact, this is your role. The Mission: You'll set the bar for intensity, deal execution, and product fluency across the team. You are personally accountable for the team's contribution to Group cross-selling revenue. You hire exceptional sellers, coach them to close, and build the systems that make winning repeatable.

What You’ll Do

• Own Revenue Performance Carry and deliver the AI Sales team quota for cross-selling 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 — daily cadence, pipeline management, call expectations, and inspection processes
• Establish measurable KPIs and performance standards across the team
• Continuously optimize processes to improve conversion, productivity, and revenue outcomes
• Develop and document scalable sales playbooks: discovery structures, demo workflows, expansion strategies, objection handling frameworks
• Lead, Hire & Develop Talent
• Recruit and develop high-performing AI Sales Executives capable of managing volume, delivering compelling demos, and closing at speed
• Make timely and decisive talent decisions to maintain a high-performance culture
• Create a scalable onboarding and ramp program that accelerates time-to-productivity
• Conduct live call coaching, deal reviews, and pipeline inspections — improve team performance in discovery, demo execution, and closing
• 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
• Represent the Function
• Serve as the voice of the AI Sales organization in Revenue Leadership discussions
• Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations

What You’ll Bring

• 7+ years of B2B SaaS sales experience, including 3+ years in a sales management or leadership role
• Demonstrated track record of building and scaling high-performance sales teams
• Deep expertise in inside sales, cross-selling, and expansion revenue motions
• Exceptional coaching ability — you make every rep measurably better within their first 30 days
• Strong command of Salesforce, sales analytics, and pipeline management
• Experience in field service management, trades, or adjacent SaaS industries strongly preferred
• Executive presence — you represent this function at the leadership table with data and conviction

What We Can Offer You

• 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
• 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!
• Diverse training & internal networking opportunities across all of our product lines
• Opportunities for career progression and development
• Service recognition awards

Our 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. This means that we want everyone to feel welcome with us and to provide equal opportunities for everyone, regardless of age, disability, gender reassignment, marriage and civil partnership, pregnancy and maternity, race, religion or belief, sex or sexual orientation, or any other non-performance factor.

Please note, no agencies will be accepted in the recruitment of this role.

Simpro Group provides best-in-class SaaS field service management solutions to trade and field service businesses worldwide. The group comprises four industry-leading companies, Simpro, AroFlo, BigChange and ClockShark, with offices across North America, Australia, New Zealand and the UK. Simpro, AroFlo & BigChange provide comprehensive field service management software for growth-minded trade and field service businesses, while ClockShark specializes in time-tracking and scheduling software solutions. Together, these companies seek to drive businesses forward with solutions that empower teams to work smarter, provide foundations for business scaling, and offer data-driven insights to fuel decision‑making. Simpro Group serves over 22,000 businesses and over 400,000 users worldwide and has a global workforce of more than 600 employees.

We are customer‑centric, always putting our customers and teammates first. We take accountability, owning both our innovations and our mistakes. We're growth‑minded, constantly learning and evolving. And most of all, we celebrate our successes together!

Ready to transform your business? Explore our products at simprogroup.com, aroflo.com, bigchange.com and clockshark.com.