Sales Enablement Leader

1 month ago
Full-time
Mid Level
Sales and Business Development
Caseware

Caseware

CaseWare International Inc. provides cutting-edge software solutions for accounting firms, corporations, and governments, enabling users worldwide to work smarter and transform insights into impact.

Internet Software & Services
251-1K
Founded 1988

Description

  • Build and maintain core sales enablement content such as 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 for 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 as the function matures.
  • Build trackers, reporting, and feedback loops to identify gaps, measure usage, and improve enablement effectiveness.
  • Translate product updates, market changes, and competitive insights into clear, rep-ready materials.
  • Contribute to long-term enablement strategy, structure, and team design.
  • Help build the case for future headcount and hire and lead direct reports as scope expands.

Requirements

  • 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 the 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.
  • An AI-first mindset and willingness to experiment with new tools and approaches.

Benefits

  • Remote role open to candidates in and eligible to work in the United States.
  • Full-time, permanent position.
  • Flexible work options and remote opportunities.
  • Generous time-off policies.
  • Competitive salary.
  • Comprehensive benefits including health insurance and retirement plans.
  • Performance bonuses and recognition programs.
  • Opportunities for career growth and international collaboration.

Interested in this position?

Apply directly on the company website

Apply Now

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