Simpro
Sales Enablement Specialist
Miami Office
Sponsorship not specifiedDetected 22 days ago
SalesCold OutreachOnboardingLeadershipMentoring
About the role
- Simpro Group is targeting a $10B+ global Serviceable Addressable Market, and the window to capture significant share is open right now.
- To achieve this at scale, we need more than programs - we need architecture.
- You won't be measuring LMS completion rates.
Responsibilities
- Design & Run the Onboarding Bootcamp
- Own the intensive onboarding program from day one through ramp.
- Design high-pressure simulations and live coaching scenarios: cold outreach, inbound qualification, competitive positioning, objection handling, and AI add-on solution pitching.
- Develop frameworks for creating urgency, leveraging pricing strategically, and handling competitive displacement scenarios.
- Build & Scale the Sales Playbooks
- Build repeatable, globally scalable frameworks so every rep speaks the same high-impact language.
Requirements
- Radical candor: you are comfortable giving tough, direct feedback to experienced sales professionals.
- You are energized by...
- You are not right for this role if...
- Essential Experience
- Experience building and facilitating rep coaching frameworks and skills assessments.
- Proven ability to build playbooks and certification programs from scratch.
- What Sets You Apart
- You combine strategic thinking with hands-on delivery - you can design the framework and run the session.
- You measure your own success by the business outcomes you influence, not the programs you deliver.
- Building systems that scale
Nice to have
- Report regularly to sales leadership with insight-driven recommendations, not vanity metrics.
- 3-5+ years in a dedicated Sales Enablement, Revenue Enablement, or Sales Effectiveness role - ideally within a high-growth SaaS or technology business.
- Demonstrated track record of designing and delivering enablement programs that measurably improved sales performance (quota attainment, ramp time, win rates).
- Deep familiarity with structured sales methodologies (MEDDIC, SPIN, Challenger, or equivalent) and the ability to embed them practically into day-to-day selling.
- You understand the Sales motion deeply - you may have carried a quota yourself, or have spent significant time embedded with acquisition-focused sales teams.
Skills
- Embed our structured sales methodologies nto onboarding, coaching, and inspection rhythms.
- Measure Revenue Impact, Not Completion
Benefits
- Responsible Time Off
- Comprehensive medical, dental, vision package with 100% employer paid options
- 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
This listing is sourced directly from Simpro's careers page and normalized into a canonical job model.