Sales Enablement Specialist

SIMPRO•Miami, FL

About The Position

Simpro Group is hiring a Sales Enablement Specialist to build the systems, coaching frameworks, and methodologies that help its sales force acquire new customers in a competitive market. The role focuses on measurable revenue outcomes, including close rates, ramp velocity, and win rates, rather than learning-platform completion rates. The specialist will own onboarding from a new hire’s first day through ramp, using simulations, live coaching, and readiness gates to assess core sales competencies. They will also coach representatives on active pipeline and recorded calls, develop deal-acceleration frameworks, and create globally scalable sales playbooks and certification programs. Enablement programs and recommendations should be grounded in field outcomes and win/loss data, with success tracked through a scorecard tied to revenue results. The role combines strategic program design with hands-on facilitation and direct feedback to sales professionals. Simpro, AroFlo, BigChange, and ClockShark describe themselves as equal opportunity employers and note that they offer an onboarding program and supportive team environments.

Requirements

3–5+ years in a dedicated Sales Enablement, Revenue Enablement, or Sales Effectiveness role.
A track record of designing and delivering enablement programs that measurably improved sales performance, such as quota attainment, ramp time, or win rates.
Experience building and facilitating representative coaching frameworks and skills assessments.
Deep familiarity with structured sales methodologies such as MEDDIC, SPIN, Challenger, or equivalent, and the ability to embed them in day-to-day selling.
Proven ability to build playbooks and certification programs from scratch.
Ability to combine strategic thinking with hands-on delivery, including designing frameworks and facilitating sessions.
Comfort giving direct, candid feedback to experienced sales professionals.
Focus on business outcomes influenced rather than programs delivered.

Nice To Haves

Experience in a high-growth SaaS or technology business.
Prior quota-carrying experience or significant time embedded with acquisition-focused sales teams.

Responsibilities

Own and continuously improve the onboarding program from new hires’ first day through ramp.
Design and run high-pressure simulations and live coaching scenarios covering cold outreach, inbound qualification, competitive positioning, objection handling, and AI add-on solution pitching.
Set and enforce readiness gates based on new hires’ ability to demonstrate core competencies in live simulations, and determine next steps when they do not meet expectations.
Iterate onboarding based on field outcomes.
Review active pipeline and call recordings, and coach representatives on conversion.
Coach representatives on multi-threading into leadership teams and economic buyers to accelerate deal velocity.
Develop frameworks for creating urgency, using pricing strategically, and handling competitive displacement.
Identify recurring pipeline patterns and skill gaps, and address them proactively.
Build playbooks for acquisition motions, including objection libraries, competitor strategies, and specialist cross-sell positioning.
Develop repeatable, globally scalable frameworks that promote consistent, high-impact sales messaging.
Embed structured sales methodologies into onboarding, coaching, and inspection rhythms.
Partner with Sales Ops and Revenue Intelligence to ground playbooks in win/loss data.
Define and track enablement outcomes such as conversion improvement, new logos acquired, ramp time, competitor win rates, and cross-sell attachment rates.
Maintain an enablement scorecard tied to revenue outcomes and report insight-driven recommendations to sales leadership.