Senior Sales Enablement Specialist

Role Overview

We’re seeking a Senior Sales Enablement Specialist who is fundamentally a master facilitator with extreme ownership of field team success. Reporting to the Sr. Manager, Sales Enablement & Programs, you’ll design and personally deliver world-class enablement experiences—both in-person and virtual—directly supporting enterprise and mid-market sales teams selling EPM and equity services solutions.

What You Will Do

Key responsibilities include partnering with the Sr. Manager on enablement strategy, executing the vision across all field-facing initiatives, designing and delivering exceptional facilitated training experiences, building comprehensive GTM collateral, owning field enablement end-to-end, measuring enablement effectiveness obsessively, and serving as a subject matter expert on EPM platforms and equity services solutions.

Why It Might Be a Fit

You will take personal accountability for field team productivity, celebrate reps’ wins as your wins, and measure yourself by their quota attainment and deal velocity, not training completion. You will be data-driven, leveraging analytics, SQL, dashboards, or Salesforce reporting to establish KPIs, measure program ROI, and communicate findings to leadership.

Requirements

• 5+ years of progressive Sales Enablement, Sales Training, Sales Operations, or Sales Coaching experience in enterprise software or B2B SaaS
• Experience supporting both enterprise and mid-market sales teams required
• Proven expertise in Enterprise Performance Management (EPM) platforms (Anaplan, Jedox, Vena, Adaptive Insights, Oracle EPM Cloud, Planful, Prevedere, etc.)
• Experience selling or supporting sales of equity services, employee ownership solutions, or related financial services; strong understanding of buy-side finance personas and their pain points
• Exceptional facilitation and training delivery skills: natural presence, ability to command virtual and in-person rooms, adapt content on the fly, handle difficult questions with poise, and inspire behavioral change
• Track record building comprehensive GTM collateral from scratch: sales playbooks, battle cards, discovery guides, competitive positioning documents, case studies, demo flows, and ROI/value calculators
• Demonstrated mastery of MEDDPICC and Value Selling frameworks; proven ability to teach both methodologies and coach reps through complex, multi-stakeholder deals; ability to integrate both frameworks into collateral and coaching
• Data-driven mindset: comfortable with analytics, SQL, dashboards, or Salesforce reporting; ability to establish KPIs, measure program ROI, and communicate findings to leadership
• Extreme ownership mentality: take personal accountability for field team productivity; celebrate reps’ wins as your wins; measure yourself by their quota attainment and deal velocity, not training completion
• Practical experience with Claude AI or similar LLMs for content generation, win/loss analysis, scenario simulation, or workflow automation; ability to evaluate AI outputs critically

Benefits

• Salary range: 88,000.00 to 111,000.00 USD Annual
• Commission target included in sales roles
• Bonus eligibility may apply for non-sales roles
• Additional information: All your information will be kept confidential according to EEO guidelines
• Background checks are required for employment with insightsoftware, where permitted by country, state/province