---
title: 'Sales Enablement Program Manager at Block'
canonical: 'https://feeny.ai/job/sales-enablement-program-manager-block-toronto-tpbq7v67xcr5'
type: 'job'
last_seen: '2026-10-19'
---

# Sales Enablement Program Manager at Block

- **Company:** Block
- **Location:** Toronto, Canada
- **Work type:** remote
- **Posted:** 2026-10-15
- **Last confirmed live:** 2026-10-19
- **Apply:** http://block.xyz/careers/jobs/5442203008?gh_jid=5442203008

## 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](https://block.xyz/news/inclusion). Application Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

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](https://privacy.block.xyz/privacyportal/form) 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.](https://block.xyz/employee-benefits)

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. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

[Privacy Policy](https://block.xyz/en/legal/applicant-privacy-notice)

## About Block

## Company Overview
- **One-liner**: Block, Inc. builds technology for economic empowerment, providing financial services and tools for merchants and consumers through brands like Square, Cash App, Afterpay, Tidal, Bitkey, and Proto.
- **Entity Type**: Public (NYSE: SQ)
- **Headquarters**: Oakland, California, United States
- **Founded**: 2009
- **Founders**: Jack Dorsey, Jim McKelvey, Tristan O’Tierney

## Core Business
- **Primary industry**: Financial services, payments, and financial technology (fintech)
- **Target customers**: B2B (merchants, sellers of all sizes) and B2C (consumers, music listeners, bitcoin users)
- **Mission**: To build simple, powerful tools that make progress toward an economy that’s truly open to all — helping create a financial system that is open to everyone. [block.xyz](https://block.xyz/)

## Products & Services
- **Square**: Point-of-sale system and commerce platform that enables sellers to accept card payments, manage operations (bookings, e-commerce, inventory, payroll, banking), and access business loans. [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Cash App**: Digital wallet for consumers to send, receive, save, or borrow money; access a debit card; invest in stocks and bitcoin; and file taxes. [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Afterpay**: Buy now, pay later service that lets customers manage spending over time. [block.xyz](https://block.xyz/)
- **Tidal**: Music streaming platform that empowers artists to thrive as entrepreneurs. [block.xyz](https://block.xyz/)
- **Bitkey**: Simple self-custody bitcoin wallet. [block.xyz](https://block.xyz/)
- **Proto**: Suite of bitcoin mining products and services. [block.xyz](https://block.xyz/)

## Market Standing
- **Valuation/Market Cap**: $96.3 billion (as of 2025/2026, per LinkedIn). [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Key Metric (Public)**: Annual revenue of $24.2 billion (latest fiscal year). [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Notable Investors/Partners**: Jack Dorsey (founder, chair, CEO) owns ~10% of the company; other major institutional investors. Key partners include Amazon, Meta, Google (as talent sources). [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Growth Signals**: Serves 57 million users and 4 million sellers, processing $241 billion in payments annually. Operates in 34 countries. Headcount of 3,223 (though down 25.4% YoY). Active job postings increased 614% quarter-over-quarter (50 open roles). [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)

## Competitive Advantages
- **Ecosystem moat**: Multiple interconnected brands (Square, Cash App, Afterpay, Tidal, Bitkey, Proto) that cross-sell and deepen user engagement across payments, banking, music, and bitcoin.
- **Market leadership**: Dominant U.S. point-of-sale market share and strong consumer adoption of Cash App.
- **Bitcoin & crypto focus**: Early and deep integration of bitcoin (Bitkey wallet, Proto mining, Cash App crypto trading) differentiates Block from traditional fintechs.
- **Distributed work culture**: Allows global talent acquisition and flexible work arrangements that reduce real estate costs and increase employee satisfaction. [block.xyz/employee-benefits](https://block.xyz/employee-benefits)

## Strategic Focus
- Expanding the bitcoin ecosystem through self-custody (Bitkey) and mining infrastructure (Proto).
- Deepening financial inclusion with Cash App (banking, lending, investing) and Afterpay (credit alternatives).
- Growing the Square merchant platform internationally and into larger enterprise accounts.
- Leveraging AI in hiring and operations to improve efficiency and reduce bias. [block.xyz/careers/our-ai-hiring-principles](https://block.xyz/careers/our-ai-hiring-principles)

## Why Work Here
- **Culture**: Block emphasizes a “distributed work” model — employees choose where they work (home, office, hybrid) unless a role requires specific geography. Up to 45 days of international work flexibility across 150+ countries. [block.xyz/employee-benefits](https://block.xyz/employee-benefits)
- **Benefits**: Competitive pay, equity (Employee Stock Purchase Plan at 15% discount), matching 401(k), flexible PTO, comprehensive health/wellness (medical, dental, vision, mental health support), family leave, and family planning support. [block.xyz/employee-benefits](https://block.xyz/employee-benefits)
- **Engineering culture**: AI is used to augment hiring (not replace judgment). Strong emphasis on open source, bitcoin, and building for economic empowerment. Teams work across Square, Cash App, Afterpay, Tidal, Bitkey, and Proto — offering broad career mobility. [block.xyz/careers/our-ai-hiring-principles](https://block.xyz/careers/our-ai-hiring-principles)
- **Remote/Hybrid**: Fully distributed; offices available in Oakland, San Francisco, New York, Melbourne, London, Toronto, and more. [linkedin.com/company/joinblock](https://www.linkedin.com/company/joinblock)
- **Perks**: Employee stock ownership, wellness stipends, career growth programs across the ecosystem.

## Sources
1. [block.xyz](https://block.xyz/)
2. [block.xyz - Careers](https://block.xyz/careers/jobs)
3. [block.xyz - Employee Benefits](https://block.xyz/employee-benefits)
4. [block.xyz - AI Hiring Principles](https://block.xyz/careers/our-ai-hiring-principles)
5. [LinkedIn - Block](https://www.linkedin.com/company/joinblock)

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- [Implementation Specialist - Bilingual (Spanish) PST Timezone](https://feeny.ai/job/implementation-specialist-bilingual-spanish-pst-timezone-block-bay-area-ca-nmhpkxhyj8e0) — Bay Area CA United States of, United States
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