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Caseware

Sales Enablement Leader

Caseware

Sales Enablement Leader building content, training, and GTM resources for Caseware’s accounting and audit software. Establishing the enablement function and scaling sales readiness across the United States and globally.

Posted 8/13/2026full-timeRemote • 🇺🇸 United StatesSeniorWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in sales enablement by creating impactful content and delivering training sessions, while effectively collaborating with cross-functional teams to drive alignment and improve sales readiness. Possesses strong execution skills and the ability to adapt materials for regional and global initiatives.

Highest-signal resume keywords
Sales EnablementContent CreationTraining DeliveryCross-Functional CollaborationSaaS or B2B Experience

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Sales Enablement Content DevelopmentPitch Deck CreationObjection-Handling GuidesCompetitive PositioningDemo Script DevelopmentEvaluation Tracker BuildingFeedback Loop ImplementationMarket Insight TranslationEnablement Strategy ContributionOnboarding Support
Soft Skills
Strong Execution SkillsInfluencing Without AuthorityIndependent Outcome OwnershipConfidence in PresentingAbility to Create Structure in Ambiguity
Tools & Technologies
Enablement ToolsContent Management PlatformsKnowledge Hubs
Industry Keywords
GTM SupportSales OperationsProduct MarketingTrainingRegional RolloutGlobal ScalingAI-First Mindset

About the role

Key responsibilities & impact
  • Build and maintain core sales enablement content, including pitch decks, battlecards, objection-handling guides, competitive positioning, demo scripts, evaluation trackers, and FAQs
  • Own the GTM Enablement Hub as the central source of truth for sales-facing messaging, resources, and materials
  • Partner with Product Marketing, Sales Operations, Training, Solutions Consulting, and other teams to align messaging and close enablement gaps
  • Deliver enablement sessions, workshops, and training to the Sales and Solutions Consulting teams
  • Support onboarding, launch readiness, and ongoing sales readiness initiatives
  • Drive localization and adaptation of sales and training materials for regional rollout
  • Extend enablement coverage across North America and support global scaling
  • Build trackers, reporting, and feedback loops to identify gaps, measure usage, and improve effectiveness
  • Translate product updates, market changes, and competitive insights into rep-ready materials
  • Contribute to the long-term enablement strategy, structure, and team design
  • Help build the case for future headcount and potentially hire and lead direct reports as scope expands

Requirements

What you’ll need
  • 4–6 years of experience in sales enablement, sales operations, product marketing, training, or another GTM support role
  • Proven ability to create structure in an ambiguous, fast-moving environment
  • Strong hands-on execution skills, with the ability to build and deliver, not just plan
  • Confidence creating content and presenting or delivering training to sales audiences
  • Strong cross-functional credibility and ability to influence without formal authority
  • Comfort owning outcomes independently without immediate team support
  • Experience with SaaS or B2B trial motions is an asset
  • Familiarity with enablement tools, content management platforms, or knowledge hubs is a plus
  • Experience supporting regional or global rollout is an asset
  • AI-first mindset and willingness to experiment with new tools and approaches
  • Reside in and be eligible to work in the United States

Benefits

Comp & perks
  • Flexible work options
  • Remote opportunities
  • Generous time-off policies
  • Competitive salary
  • Health insurance
  • Retirement plans
  • Performance bonuses
  • Recognition programs
  • Opportunities for career growth
  • International projects
  • Collaboration with a diverse, global team
  • Inclusive workplace and accommodations during the application/interview process