Director, AI Sales
At a glance
Leadership Sales Leadership role at Simpro. Miami Office · full-time.
Pay not stated
Growth Roles summary, based on the employer's posting.
What you'll do
- Own the AI team’s cross-sell quota across the Simpro Group portfolio and deliver revenue targets
- Set the team’s daily operating cadence, pipeline controls, call standards, KPIs, and inspection routines
- Hire, onboard, coach, and develop AI Sales Executives through call reviews, deal reviews, and pipeline checks
- Create repeatable playbooks for discovery, demos, expansion selling, and handling objections
- Coordinate with Account Management, Marketing, Enablement, and Product on opportunities, campaigns, training, and customer feedback
What you bring
- At least seven years in B2B SaaS sales, including at least three years managing or leading sales teams
- A proven record of creating and scaling teams that perform at a high level
- Strong experience with inside selling, customer cross-sell, and expansion revenue
- Working command of Salesforce, sales analytics, and pipeline oversight
- Executive presence, with the ability to bring data-backed recommendations to leadership
Who this fits
You’ll suit a hands-on sales leader who can build systems, improve rep performance, and remain accountable for team revenue. The role is based in the Miami office and centers on leading quota-carrying AI Sales Executives. Experience in field service management, trades, or related SaaS is preferred.
From the employer
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
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
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.
If you'd like to join a fun and progressive organization, where there are opportunities to develop your career, please apply now with your CV/resume.
*Please note, no agencies will be accepted in the recruitment of this role.
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