Sales Enablement Specialist

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.

What You’ll 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.

How You Work

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

What You’ll Bring

• 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 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.
• 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.