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Enablement Manager

OpenSesame provides enterprise training content and learning solutions to hundreds of Global2000 customers. As the company scales from a single-product firm into a multi-product SaaS business, we seek an Enablement Manager to build and operate a repeatable, AI-enabled enablement function that equips Sales, CSMs, SDRs, and Partners to drive cross-sell, upsell, and product adoption across a complex portfolio.

Skills

  • Proven experience managing enablement programs and tools (Highspot preferred).
  • Strong familiarity with GTM tech stack: Salesforce, HubSpot, Gong, Looker, Gainsight, 6sense, Crossbeam.
  • Experience designing assessments, certifications, and measurable enablement KPIs.
  • Practical experience implementing AI-enabled workflows to improve coaching, scoring, and automation.
  • Ability to create concise, executive-facing playbooks and training materials.

Responsibilities

  • Design and launch an integrated enablement framework for Sales, CSMs, SDRs, and Partners focused on onboarding, continuous learning, and certifications.
  • Own Highspot as the field enablement hub: audit, organize, and drive adoption of content, playbooks, and toolkits.
  • Partner closely with Product Marketing to translate messaging, personas, and competitive positioning into training, playbooks, and executive-ready assets.
  • Deploy AI-enabled workflows (e.g., Gong coaching, predictive scoring, RFP automation) and train GTM teams on their use.
  • Measure and report enablement impact on ramp time, quota attainment, pipeline, retention, and expansion; present quarterly scorecards to leadership.
  • Establish cross-functional cadences for alignment, feedback, and continuous optimization of enablement programs.
  • Build certification programs tied to productivity outcomes and manage partner onboarding improvements.

Education

  • Bachelor's degree preferred or equivalent practical experience.
  • Continuous learning mindset with relevant enablement, sales, or product training certifications considered a plus.

Benefits

  • Comprehensive health insurance
  • 401(k) matching
  • Incentive stock options (ISOs)
  • Paid time off and professional development support
  • Remote-first company with mandatory all-company meetings several times a year
  • Up to 15 days of travel per year (up to 35 days for senior leadership roles)
To read the complete job description, please click on the ‘Apply’ button
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CEO of OpenSesame
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Don Spear
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Average salary estimate

$127500 / YEARLY (est.)
min
max
$110000K
$145000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

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We help companies develop the world’s most productive and admired workforces.Our vision: A world where everyone can easily access the training they need to advance their purpose.

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SALARY RANGE
$110,000/yr - $145,000/yr
EMPLOYMENT TYPE
Full-time, remote
DATE POSTED
August 29, 2025
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