Sales Enablement Specialist

USA Simpro Software Ltd.; Miami (FL); On-site; USD 120,000 - 180,000; Full time

Job summary

Simpro Group is seeking a seasoned Sales Enablement leader to design scalable onboarding programs and coaching frameworks that accelerate ramp times and win rates. The role embeds structured methodologies (MEDDIC, SPIN, Challenger) and partners with Sales Ops and Revenue Intelligence to ground playbooks in real win/loss data.

You will lead onboarding from day one, embed coaching in daily seller activity, and drive measurable revenue improvements through a rigorous enablement scorecard and

Qualifications

• 3–5+ years in dedicated Sales Enablement or Revenue Enablement in a high-growth SaaS/tech business.
• Proven track record delivering enablement programs that improved quota attainment and ramp times.
• Experience building rep coaching frameworks and skills assessments; embeds structured methodologies.

Responsibilities

• Design and run onboarding bootcamp and ramp simulations with readiness gates.
• Coach on pipeline velocity, multi-threading to leadership and economic buyers.
• Build scalable playbooks, objection libraries, and competitive strategies.
• Measure revenue impact with scorecards and data-driven recommendations.

Skills

Sales Enablement

Coaching

Pipeline Review

Multithreaded Selling

MedDIC/SPIN/Challenger

Tools

Sales Ops

Revenue Intelligence

Job description

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.

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

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.

*Please note, no agencies will be accepted in the recruitment of this role.

Welcome to Simpro! Together with AroFlo, BigChange and ClockShark we are one team made up of many nationalities. We are customer‑centric, always putting our customers and teammates first. We take accountability, owning both our innovations and our mistakes. We're growth‑minded, constantly learning and evolving. And most of all, we celebrate our successes together!

Simpro Group provides best‑in‑class SaaS field service management solutions to trade and field service businesses worldwide. The group comprises four industry‑leading companies, Simpro, AroFlo, BigChange and ClockShark, with offices across NorthAmerica, Australia, NewZealand and theUK. Simpro, AroFlo & BigChange provide comprehensive field service management software for growth‑minded trade and field service businesses, while ClockShark specializes in time‑tracking and scheduling software solutions. Together, these companies seek to drive businesses forward with solutions that empower teams to work smarter, provide foundations for business scaling, and offer data‑driven insights to fuel decision‑making.

Simpro Group serves over 22,000 businesses and over 400,000 users worldwide and has a global workforce of more than 600 employees.

Ready to transform your business? Explore our products at simprogroup.com, aroflo.com, bigchange.com and clockshark.com.