Senior Sales Enablement Specialist - EMEA

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

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 frame