Sales Enablement Leader
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Job Summary
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.
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.
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
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.
About Company
Accounting, audit, analytics and compliance software built by seasoned accountants. Manage your audit and financial reporting more efficiently with less risk.
