Sales Enablement Leader

Caseware•Toronto, ON

3d•CA$100,000 - CA$115,000•Hybrid

About The Position

Caseware is seeking its first Sales Enablement Leader to build the enablement function from the ground up. This is a hands-on role for an individual who can create structure in an evolving environment, partner across the business, and deliver practical tools and training to enhance sales team performance. Initially, the focus will be on building core content, resources, and programs for Sales and Solutions Consulting, collaborating with Product Marketing, Sales Operations, and Training. As the function grows, this role may expand to include direct reports and contribute to the broader strategy and operating model for sales enablement at Caseware. This is a unique opportunity to establish a critical function within a global company with strong market credibility, shaping how sales teams are equipped, improving field consistency, and scaling enablement globally.

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 in a role without immediate team support.
An AI-first mindset and willingness to experiment with new tools and approaches.

Nice To Haves

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.

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.