Caseware is hiring its first Sales Enablement Leader to build the enablement function from the ground up. This is a highly hands-on role for someone who can create structure in an evolving environment, partner across the business, and deliver practical tools and training that help our sales teams perform at a higher level.

In the near term, you will be responsible for building the core content, resources, and programs that Sales and Solutions Consulting rely on every day. You will work closely with Product Marketing, Sales Operations, Training, and other cross-functional partners to close gaps across the pre-sales, sales, and onboarding journey.

As the function grows, this role may expand to include 1-2 direct reports later this year. Over time, you will also help shape the broader strategy, operating model, and priorities for sales enablement at Caseware.

This is a rare opportunity to build a critical function from the ground up at a global company with strong market credibility. You will help shape how Caseware equips its sales teams, improves consistency in the field, and scales enablement globally over time.

This is an Existing vacancy

This is a full-time, permanent position.

This role is hybrid (working from Toronto office) or remote depending on candidate location and open to candidates who reside in and are eligible to work in Canada

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.

Salary Range:

The annual base salary for this position is between $100,000 CAD and $115,000 CAD per year.

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

What's in it for you:

• Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.

• We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.

• Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance.

• We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans.

• We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success.

• Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth.

• We embrace global opportunities. Work on international projects and collaborate with a diverse, global team.