Sales Enablement Specialist

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

• Intensive Execution: You own the intensive onboarding program specifically for frontline revenue representatives.

• Live-Action Simulations: You will not just teach them the product; you will run intense, high-pressure simulations focused on outreach, qualification, overcoming initial friction, commercial negotiations, and pitching AI agent add-on solutions.

• The Accountability Gate: You will 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: You are on the sales floor and actively involved in active pipeline and the customer lifecycle.

• Game Tape Breakdown: You will 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: This includes multi-threading into target Leadership teams and/or Owners, all to accelerate deal velocity.

• Strategic Pricing: You will 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 Motions: You will systematize our core execution motions: objection handling, competitor "take-down" strategies, whitespace identification, and strategic cross-department positioning.

• Global Frameworks: You will 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

• Data-Driven Success: You will define success not by "course completion," but by hard data.

• 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

What You Bring

The Track Record: You have genuine, recent selling experience carrying a commercial quota and delivering net-new and portfolio revenue growth. You were in the Top 10% of your previous organization.

The Credibility: You command the room. You can 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.

The Process Mindset: You aren't just a lone-wolf closer or relationship builder; you know how to deconstruct why you win and turn it into a scalable, repeatable playbook.

Radical Candor: You are 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 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. 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.

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.