Sales Enablement Leader

Caseware is one of Canadas original Fintech companies having led the global audit and accounting software industry for over 30 years with more than 500000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

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 12 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 anExisting vacancyThis is afull-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:

• 46 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$100000 CAD and $115000 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 bedeterminedbased 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.

Whats 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.
About Caseware:Casewares cutting-edge software products are meticulously designed for accounting firms corporations and teams are continually collaborating innovating and building upon our existing suite of products. With a customer-focused mindset we are building technology that is shaping what the future of audits financial reporting and financial data analytics will look like.
With a recent strategic investment from Hg Capital in 2020 Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.
One of Casewares core values is Many Voices One Team and with that in mind were dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process please e-mail our People Operations team at emailprotected.
AI Usage:The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness transparency and oversight.
Background Check:Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residingin the Netherlands and Germany are excluded from undergoing background checks via
Security and Fraud:Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @ and our open positions are always listed on reputable job boards and on our website We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer proceed with extreme caution.We may use artificial intelligence (AI) tools to support parts of the hiring process such as reviewing applications analyzing resumes or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed please contact us.
Employment Type : Full-Time
Experience: years
Vacancy: 1