Senior Sales Enablement Specialist

About Us

insightsoftware is a global provider of reporting, analytics, and performance management solutions that unlock the potential of business data and transform the way finance and data teams operate. We empower leaders from over 32,000 organizations to make timely and intelligent decisions. Our comprehensive solutions span Financial Planning and Analysis (FP&A), Controllership, and Data and Analytics. We deliver finance teams the insights required to navigate any economic climate and drive greater financial intelligence, while increasing productivity, visibility, accuracy, and compliance.

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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. Beyond training delivery, you'll architect and build all go-to-market collateral (battle cards, playbooks, demo flows, discovery guides, use case narratives, competitive positioning)—and own the sales lift these assets generate.

You'll be data-obsessed about what works, ruthlessly measure enablement ROI, and take personal accountability for your sellers' productivity and quota attainment.

• Partner with the Sr. Manager on enablement strategy; execute the vision across all field-facing initiatives including training design, collateral development, and ongoing coaching
• Design and personally deliver exceptional facilitated training experiences—in-person workshops, Microsoft Teams virtual bootcamps and coaching sessions, and ongoing field support—for enterprise and mid-market sales teams; adapt delivery style and pacing to audience in real-time
• Build all go-to-market collateral from scratch: MEDDPICC and Value Selling‑aligned discovery guides, EPM/equity services battle cards, competitive positioning frameworks, playbooks, demo flows, use case narratives, ROI calculators, and value justification templates—and maintain them as the market evolves
• Own field enablement end-to-end: support sellers before deals (training, collateral access), during deals (coaching, objection handling, complex scenario guidance), and after deals (win/loss analysis, continuous improvement insights)
• Measure enablement effectiveness obsessively: track ramp time, time-to-first-deal, average deal size, win rates, and quota attainment by rep and cohort; correlate training/collateral usage to outcomes and iterate based on data
• Serve as a subject matter expert on EPM platforms (planning, budgeting, analytics, forecasting) and equity services solutions; translate technical features into business impact sellers can articulate to buyers
• Partner with sales managers and reps to diagnose capability gaps; coach underperforming reps individually and guide the team through behavioral change
• Lead new hire onboarding programs; design and deliver bootcamps, field ride‑alongs, and progression frameworks that accelerate ramp and set new reps up to hit quota in year one
• Own major sales moments: lead or personally deliver Sales Kickoffs, product launch training, competitive response programs, and regional training events
• Leverage Claude AI strategically to automate collateral drafts, personalize coaching feedback, analyze win/loss data at scale, and generate dynamic sales scenarios—but own quality and appropriateness of every output
• Track and present enablement metrics to the Sr. Manager and sales leadership: ramp time, quota attainment by cohort, win rate correlation to training, and collateral usage—with clear business impact and recommendations
• Collaborate with the Sr. Manager on enablement platform maintenance (LMS, collateral management, Salesforce reporting, Claude integration) and ensure sellers can access resources when they need them

• 5+ years of progressive Sales Enablement, Sales Training, Sales Operations, or Sales Coaching experience in enterprise software or B2B SaaS; experience supporting…