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Open nowPosted 93 days ago

Director, AI Sales

Simpro Software50 open roles

Where
Miami Office
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Your applicationOpen nowDirector, AI SalesSimpro Software · Miami Office

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Simpro Software's own form.

The reply lands in your private mailbox

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market. Simpro Software postings stay open a median of 45 days.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.7%14 days
  5. 35.6%30 days
  6. 58.0%60 days
This job: posted 93 days ago

Simpro Software median: 45 days open

The posting

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

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
  • Click here to find out more about working at Simpro Group!

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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  1. A CV for this posting

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    The review screen in CV Rocket: how each CV was read, round by round.

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    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
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