Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.
So we expanded into software and started building integrated, omnichannel solutions - to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.
We're looking for a proactive and highly organized Sales Enablement Program Manager to help drive clarity, consistency, and continuous learning across Block's global sales and Account Management teams. This role requires a strong blend of content operations, learning science, stakeholder management, and sales context awareness.
Support ongoing learning initiatives by helping to plan, build, facilitate, and maintain scalable sales enablement content beyond onboarding.
Curate and maintain centralized knowledge resources, partnering with subject matter experts (SMEs) across Product, Marketing, and Sales to ensure accuracy and consistency.
Help operationalize the everboarding strategy, coordinating timelines, deliverables, and stakeholder communications.
Organize and update internal learning assets, ensuring documentation is easy to find, up-to-date, and aligned with sales priorities.
Manage internal communications related to enablement, such as newsletters, training calendars, training decks,
and update broadcasts to reduce noise and increase clarity.
Collect feedback and track program impact, using data to assess adoption, knowledge retention, and performance improvements.
Support regional Canada enablement needs, ensuring content is localized and relevant for diverse sales teams across markets.
Promote knowledge-sharing practices, including documenting playbooks, building FAQs, and contributing to internal wikis or LMS content.
4+ years of experience in Sales Enablement, Sales, or Account Management.
Robust understanding of adult learning theories and experience applying them to training design, content delivery, or knowledge-sharing systems.
Excellent stakeholder management and communication skills, with an ability to influence and collaborate across functions and levels.
Proven ability to prioritize effectively, manage competing demands, and maintain clarity under ambiguity.
Background in instructional design, content strategy, or sales operations.
Exposure to coaching methodologies such as GROW to support learner development and behavior change.
We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.
These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.
Contact us here with hiring practice or data usage questions.
📌 Head of Programming Sales (Toronto)
🏢 Block
📍 Toronto