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. Learn more at insightsoftware.com.

Job Description:

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.

Key Responsibilities

• 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

Required Qualifications

• 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.)—deep enough to explain planning, budgeting, analytics, and forecasting functionality to sellers and buyers

• 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

• Excellent written communication: ability to create clear, persuasive sales collateral and distill complex topics into simple, buyer-friendly narratives

Preferred Qualifications

• Prior experience at an EPM software vendor (Anaplan, Jedox, Vena) in sales, solutions consulting, or sales enablement roles

• Background selling enterprise software to CFO, VP Finance, or Controller personas; understanding of financial planning and analysis (FP&A) workflows

• Experience in equity services, employee stock ownership plans (ESOPs), cap table management, or fintech; strong knowledge of buyer personas and their compliance/reporting requirements

• Hands-on experience with Salesforce reporting, Tableau, Looker, or similar analytics tools; ability to pull and analyze sales productivity data

• Experience designing and running Sales Kickoffs, product launch programs, or regional sales events with 100+ attendees

• Familiarity with sales enablement platforms (Seismic, Showpad, Highspot) and/or LMS systems; ability to manage content libraries and optimize asset discoverability

• Track record coaching and developing other enablement professionals or sales trainers

• Published thought leadership, conference speaking, or content creation on sales enablement, MEDDPICC, Value Selling, or AI in sales

Core Competencies & Values

• Master Facilitation – exceptional presence, adaptability, emotional intelligence; ability to engage diverse audiences and inspire change

• Extreme Ownership – personal accountability for field team success; measure yourself by seller productivity and quota attainment, not completion metrics

• Data-Driven Decision Making – obsessive about measurement; establish KPIs, analyze performance, iterate based on evidence

• GTM Collateral Excellence – ability to build comprehensive, polished, seller-ready assets; attention to detail and consistency across all materials

• Domain Expertise – deep knowledge of EPM platforms and equity services; credibility with both sellers and sophisticated buyers

• Sales Acumen – fluency in enterprise and mid-market deal dynamics; ability to diagnose what's blocking a deal and coach a rep to unblock it

• Sales Methodology Mastery – deep expertise in MEDDPICC and Value Selling frameworks; ability to teach, coach, and integrate both into training and collateral

• AI-Augmented Thinking – strategic use of Claude and tools to scale impact; quality control mindset

• Resilience & Adaptability – comfortable in a fast-moving, high-pressure environment; willing to learn and iterate quickly

What We're Looking For

• You are fundamentally a facilitator—someone who lights up in front of a room or on a Microsoft Teams call. You know how to read an audience, adapt your delivery, handle curveballs with grace, and leave people inspired and equipped. You're skilled at making Teams calls engaging (not just talking heads), and you're equally confident running in-person workshops. You've spent 5+ years doing this, and you're genuinely excellent at it.

• You are fluent in both MEDDPICC and Value Selling frameworks. You don't just know them—you can teach them, coach reps through them, and integrate them into battle cards and playbooks. You understand how to help reps move from discovery (MEDDPICC) into value articulation and justification (Value Selling) seamlessly within complex deals.

• You have deep expertise in EPM platforms and/or equity services. You've either sold them, supported sellers who sell them, or worked at a vendor. You understand the buyer—CFOs, VPs of Finance, Controllers—and their pain points. You can explain why an EPM platform matters in a way that resonates with business leaders.

• You've built comprehensive GTM collateral—not borrowed from competitors, but crafted thoughtfully for your market. Battle cards, playbooks, discovery guides, ROI models. You own the quality and continuity of these assets and update them as the market changes.

• You are obsessed with data. You know your sellers' ramp times, win rates, and average deal sizes—and you track how enablement moves these needles. You present quarterly insights to leadership and iterate your programs based on evidence, not opinion.

• You take extreme ownership of your sellers' success. You don't just run training and hand off—you know your team, their gaps, their wins. You're in the field regularly, coaching reps one-on-one, riding deals, and solving problems. You celebrate their quota attainment as your success.

• You're already using Claude AI to scale your work—drafting collateral, analyzing data, coaching. You think strategically about where AI makes you faster without compromising quality.

• You're resourceful, resilient, and driven. You thrive in dynamic environments and bring positive energy to your team.

The salary range in United States of America for this position is 88,000.00 to 111,000.00 USD Annual.

For sales roles, this range includes the commission target. For non-sales roles, this is a base salary only range; additional bonus eligibility may apply.

Your specific offer within this range will be determined by your skills, experience, and qualifications.

We are committed to pay transparency and fair compensation practices. If you have questions about our compensation approach, please don't hesitate to ask during the interview process.

Additional Information

All your information will be kept confidential according to EEO guidelines.

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