Senior Sales Operations Analyst supporting Docker’s developer - tooling SaaS revenue operations in Canada and the United States. Managing field support, Salesforce systems, FP&A updates, onboarding, and data quality.
About the role
- Sales Enablement Leader building content, training, and GTM programs for Caseware’s audit and accounting software. Establishing the enablement function and scaling sales support globally.
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.
- Build the sales enablement function from the ground up at Caseware, a provider of audit and accounting software.
- Shape the broader strategy, operating model, and priorities for sales enablement.
- Improve consistency in the field and scale enablement globally over time.
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 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.
- Candidates must reside in and be eligible to work in Canada.
Benefits
- Flexible work options
- Remote opportunities
- Generous time-off policies
- Competitive salary
- Health insurance
- Retirement plans
- Recognition programs
- Performance bonuses
- Opportunities for career growth
- International projects
- Collaboration with a diverse, global team
- Accommodations during the application or interview process
- Background check exclusion for candidates residing in the Netherlands and Germany
Job title
Job type
Experience level
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Degree requirement
No Education Requirement
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