Sales Enablement Specialist

About the role

Job Context

About the Role

Simpro Group is targeting a $10B+ global Serviceable Addressable Market, and the window to capture significant share is open right now. We are in a hyper-aggressive market capture phase - scaling a high-velocity sales force designed to decisively outpace the competition and drive net-new logos.

To achieve this at scale, we need more than programs - we need architecture. This role is for a seasoned Sales Enablement professional who knows how to build the systems, coaching frameworks, and methodologies that transform good salespeople into elite acquisition operators.

You won't be measuring LMS completion rates. You'll be measuring close rates, ramp velocity, and win rates.

What You Will Do

• 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.
• Set and enforce readiness gates - if a new hire cannot demonstrate core competencies in live-action simulations, you make the call on next steps. We do not ramp mediocrity.
• Continuously iterate the program based on field outcomes, not trainer feedback.
• Pipeline Coaching & Deal Acceleration
• Embed yourself in team motion - review active pipeline, break down call recordings, and coach on conversion.
• Coach reps on multi-threading into leadership teams and economic buyers to accelerate deal velocity.
• Develop frameworks for creating urgency, leveraging pricing strategically, and handling competitive displacement scenarios.
• Identify patterns across the team's pipeline to surface systemic skill gaps and address them proactively.
• Build & Scale the Sales Playbooks
• Systematize core acquisition motions: objection libraries, competitor take-down strategies, and specialist cross-sell positioning frameworks.
• Build repeatable, globally scalable frameworks so every rep speaks the same high-impact language.
• Embed our structured sales methodologies nto onboarding, coaching, and inspection rhythms.
• Partner with Sales Ops and Revenue Intelligence to ensure playbooks are grounded in real win/loss data.
• Measure Revenue Impact, Not Completion
• Define success through hard data: conversion rate improvement, new logos acquired, ramp time velocity, win-rate against primary competitors, and cross-sell attachment rates.
• Build and maintain an enablement scorecard tied directly to revenue outcomes.
• Report regularly to sales leadership with insight-driven recommendations, not vanity metrics.

What You Bring

Essential Experience

• 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).
• Experience building and facilitating rep coaching frameworks and skills assessments.
• Deep familiarity with structured sales methodologies (MEDDIC, SPIN, Challenger, or equivalent) and the ability to embed them practically into day-to-day selling.
• Proven ability to build playbooks and certification programs from scratch.

What Sets You Apart

• You understand the Sales motion deeply - you may have carried a quota yourself, or have spent significant time embedded with acquisition-focused sales teams.
• You combine strategic thinking with hands-on delivery - you can design the framework and run the session.
• Radical candor: you are comfortable giving tough, direct feedback to experienced sales professionals.
• You measure your own success by the business outcomes you influence, not the programs you deliver.

You are energized by

• Building systems that scale
• Coaching reps to exceed their potential
• Translating field reality into programs
• Owning outcomes, not just activities

You are not right for this role if

• You want to return to carrying a quota
• You measure success by decks delivered
• You need a fully built playbook to execute
• You shy away from direct feedback

What You'll Bring

• Our Core Values
• We Are One Team
• We Are Customer Centric
• We Are Growth Minded
• We Are Accountable
• We Celebrate Success

Additional information

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.