Sales Enablement Leader

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

What you will be doing:

• 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.

What you will bring:

• 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 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

What success looks like:

• Sales teams have easy access to current, useful, and well-organized enablement content.

• Training is practical, consistent, and aligned to how the team sells.

• Cross-functional partners are aligned and working from the same messaging and priorities.

• Gaps in the sales journey are identified quickly and addressed with clear action.

• The enablement function becomes a trusted partner to Sales, Product Marketing, Operations, and Training.

• The role scales into a broader enablement function as business needs evolve.