Sales Enablement Program Manager

Block, Inc.; Toronto; Remote; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning benefits

Job summary

Block, Inc. is seeking a proactive Sales Enablement Program Manager in Toronto to drive clarity and learning across global sales and account management teams.

You will operationalize everboarding, manage content, and coordinate with SMEs in Product, Marketing, and Sales. You will champion scalable enablement, maintain learning assets, and measure impact while supporting Canada-specific enablement across markets.

Qualifications

• 4+ years of experience in Sales Enablement, Sales, or Account Management.
• Strong understanding of adult learning theories and 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.

Responsibilities

• Plan, build, facilitate, and maintain scalable sales enablement content beyond onboarding.
• Curate centralized knowledge resources, partnering with 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.

Skills

Sales Enablement

Stakeholder Management

Adult Learning Theory

Communication

Job description

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. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.
Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

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. You’ll play a critical role in operationalizing our everboarding strategy—ongoing education beyond onboarding. This role requires a strong blend of content operations, learning science, stakeholder management, and sales context awareness.

You Will

• 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.

You Have

• 4+ years of experience in Sales Enablement, Sales, or Account Management.
• Strong 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.

Nice to Have

• 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. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build a workplace that is fair and square? Check out our I+D page .

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. 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.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people.Squaremakes commerce and financial services accessible to sellers.Cash Appis the easy way to spend, send, and store money.Afterpayis transforming the way customers manage their spending over time.TIDALis a music platform that empowers artists to thrive as entrepreneurs.Bitkeyis a simple self-custody wallet built for bitcoin.Protois a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.