About the role

Sales Enablement Leader building content, training, and GTM programs for Caseware’s audit and accounting software. Establishing the enablement function and scaling sales support globally.

Responsibilities

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 team and Solutions Consulting team.
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 simple 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 the development of the long-term enablement strategy, structure, and team design.
Help build the case for future headcount and, where appropriate, hire and lead direct reports as scope expands.
Build the sales enablement function from the ground up at Caseware, a provider of audit and accounting software.
Shape the broader strategy, operating model, and priorities for sales enablement.
Improve consistency in the field and scale enablement globally over time.

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 in a role 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.
Candidates must reside in and be eligible to work in Canada.

Flexible work options
Remote opportunities
Generous time-off policies
Competitive salary
Health insurance
Retirement plans
Recognition programs
Performance bonuses
Opportunities for career growth
International projects
Collaboration with a diverse, global team
Accommodations during the application or interview process
Background check exclusion for candidates residing in the Netherlands and Germany