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Enablement Specialist

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Brightwheel

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Location:
United States , Des Moines

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Category:
Sales

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Contract Type:
Not provided

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Salary:

65000.00 - 70000.00 USD / Year
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Job Description:

You are a proactive, impact-driven enablement professional who thrives in fast-paced, high-growth environments. You bring a strong ownership mindset and a bias for action — not just building content, but driving real behavior change through coaching, repetition, and practice. You think in systems but act in the moment, adapting your support to meet the needs of early-career reps and fast-moving teams. You value iteration over perfection and are energized by helping others succeed.

Job Responsibility:

  • Own structured enablement support for our Education line of business including, but not limited to upsell reps during Months 1–4 of ramp, bridging the gap between onboarding and full productivity
  • Facilitate high-quality practice environments — including role plays, call reviews, demo walkthroughs, and objection handling — with a focus on capability, not just activity
  • Partner with EDU Upsell leadership to align coaching priorities, extend coaching capacity, and reinforce performance expectations
  • Identify common rep challenges and turn them into scalable enablement moments (e.g., micro-trainings, refreshers, guided practice)
  • Track qualitative and quantitative signals of rep readiness and surface insights to Enablement, Leadership, and Ops
  • Help reduce SME dependency by translating product support needs into repeatable reinforcement mechanisms

Requirements:

  • 2–5 years of experience in Sales Enablement, L&D, Sales/Upsell/CS, or a related function, ideally supporting B2B SaaS or inside upsell sales teams
  • Delivered hands-on coaching or enablement to early-career sellers and built trust through consistent support and feedback
  • Facilitated skill-building programs focused on discovery, qualification, demos, or objection handling
  • Created repeatable enablement content or programs that reduce ad-hoc support needs
  • Navigated cross-functional alignment with sales managers and subject matter experts
  • Demonstrated a strong sense of ownership and the ability to operate independently in a dynamic environment
  • Experience with enablement tools like Gong, Yoodli, WorkRamp, or similar
What we offer:
  • Comprehensive medical, dental, and vision coverage
  • Generous paid parental leave
  • Flexible PTO so you can recharge when you need it
  • Local retirement or savings plans (e.g., 401(k) in the U.S.)
  • Equity & Ownership

Additional Information:

Job Posted:
February 20, 2026

Employment Type:
Fulltime
Work Type:
On-site work
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