Sales Enablement Specialist

USA Simpro Software Ltd.; Miami (FL); On-site; USD 80,000 - 120,000; Full time

Benefits offered by this job

Responsible Time Off

Comprehensive medical, dental, vision package

401k/Retirement Plan with 6% employer match

Generous Parental Leave Program

Paid Volunteer Leave Days

Job summary

USA Simpro Software Ltd. in Miami is seeking a Sales Enablement expert to drive performance through elite coaching and enablement strategies. The position requires strong selling experience and effective training abilities.

With responsibilities ranging from running onboarding programs to integrating sales methodologies, successful candidates will enjoy a comprehensive benefits package including generous parental leave and a retirement plan with employer match.

Qualifications

• Proven selling experience with commercial quotas.
• Experience in high-velocity SaaS sales.
• Ability to give direct feedback and improve team skills.

Responsibilities

• Run the High-Velocity Onboarding Academy.
• Conduct live-action simulations for reps.
• Integrate sales methodologies into team's DNA.
• Measure success through hard data and core metrics.

Skills

Sales strategy

Commercial acumen

Coaching abilities

Negotiation skills

Job description

Job Context

Most \"Sales Enablement\" roles are administrative. They build PowerPoint decks, track LMS completion rates, and tick boxes. This is not that role. Simpro Group is staring down a $10B+ global SAM (Serviceable Addressable Market). The scale of this opportunity is staggering, and the window to capture the lion's share is open right now. Because of this massive market opportunity, we are scaling an elite, high‑velocity revenue force designed to decisively outpace the competition, secure our market footprint, and drive commercial success across the entire lifecycle. To achieve this, we don't need \"Trainers.\" We need \"Real‑World Instructors.\" We are looking for an elite top performer—a proven closer and commercial strategist who has consistently crushed revenue quotas in high‑velocity SaaS and now wants to pivot to enablement. Your job is to take raw talent and develop them into elite, Tier‑1 commercial operators. When you coach our reps on complex negotiations, competitive positioning, or strategic expansions, they will listen because they know you have actually carried the bag and won the exact same deals.

What You’ll Do

• Run the \"High‑Velocity\" Onboarding Academy – own the intensive onboarding program specifically for frontline revenue representatives.


• Live‑Action Simulations – run intense, high‑pressure simulations focused on outreach, qualification, overcoming initial friction, commercial negotiations, and pitching AI agent add‑on solutions.


• The Accountability Gate – act as the gatekeeper; if a new hire cannot pass your live‑action simulations (e.g., executing a flawless discovery call, competitive displacement pitch, or value negotiation) following adequate training, you will make the call on next steps. We do not ramp mediocrity.


• Deal Dissection & Tactical Coaching Floor Integration – embed yourself in the frontline motion, break down game tape, and coach reps on how to convert more pipeline into closed‑won bookings.


• Multi‑Threading – multi‑thread into target leadership teams and/or owners to accelerate deal velocity.


• Strategic Pricing – teach reps how to confidently drive financial adjustments, defend against competitor churn, and leverage price and value as a strategic advantage.


• Optimize and Scale Revenue Playbooks – systematize our core execution motions: objection handling, competitor \"take‑down\" strategies, whitespace identification, and strategic cross‑department positioning.


• Global Frameworks – build repeatable frameworks and planning models that scale globally, ensuring every representative speaks the exact same high‑impact language to proactively manage opportunities rather than reacting to friction.


• Methodology Integration – embed sales methodologies (like MEDDIC) deeply into our DNA.


• Measure Revenue, Not Completion – define success by hard data rather than course completion.


• Core Metrics – conversion rate improvement, pipeline created and closed, revenue retention, win‑rate against primary competitors, ramp time velocity, and solution attachment rates.

What You’ll Bring

• Track Record – genuine, recent selling experience carrying a commercial quota and delivering net‑new and portfolio revenue growth. In the Top 10% of your previous organization.


• Credibility – command the room; take the phone from a struggling rep, sit in on a tense commercial call, de‑escalate a situation, handle a hostile prospect, and secure the commitment yourself.


• Process Mindset – deconstruct why you win and turn it into a scalable, repeatable playbook.


• Radical Candor – comfortable giving tough, direct feedback to experienced revenue teams to elevate their commercial acumen.

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 product lines


• Opportunities for career progression and development


• Service recognition awards

Our Core Values

• We Are One Team


• We Are Customer Centric


• We Are Growth Minded


• We Are Accountable


• We Celebrate Success

Equal Opportunity Employer

Simpro, AroFlo, BigChange & ClockShark are equal‑opportunity employers with a best‑of‑class onboarding program and supportive team environments. 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.