Technical Support & Enablement Program Manager

Block is one company built from many blocks, all united by the same purpose of economic empowerment. The blocks that form our foundational teams - People, Finance, Counsel, Hardware, Information Security, Platform Infrastructure Engineering, and more - provide support and guidance at the corporate level. They work across business groups and around the globe, spanning time zones and disciplines to develop inclusive People policies, forecast finances, give legal counsel, safeguard systems, nurture new initiatives, and more. Every challenge creates possibilities, and we need different perspectives to see them all. Bring yours to Block.
The Role
We're building an AI-first culture at Block - aiming for 95% of employees using AI daily, with G2 (our internally built AI platform) becoming the default interface for how we work. We're looking for someone who can balance technical support with learning & enablement design and deliver to help make that happen.
The role sits within Block's BizOps Change & Adoption team. You'll be a strategic partner to the G2 and BizOps teams - building the technical support infrastructure, designing learning programs that drive behavior change, and managing the programs that keep our AI champions equipped to scale AI adoption across their functions.
You Will

• Be the primary responder in G2 support channels - troubleshooting issues, helping people solve technical problems and creating a safe and engaging culture of knowledge sharing
• Design and facilitate office hours and other troubleshooting sessions
• Triage complex issues to Product team or escalate to super users
• Track common technical issues and feed insights to Product team
• Build and maintain technical documentation (how-tos, troubleshooting guides, product release notes etc)
• Keep all materials, documentation, and knowledge base current and accessible
• Design and deliver learning programs that shifts mindsets from "AI is a tool I use sometimes" to "AI is how I work"
• Create learning pathways for different skill levels (beginners → power users → Guild members)
• Develop instructional materials (guides, tutorials, videos, workshops) and technical toolkits
• Coordinate and facilitate enablement sessions and learning programs (office hours, workshops, Guild technical sessions)
• Measure and report on adoption metrics (workflow creation, tool usage, capability growth)

You Have

• 5+ years of program management experience, ideally with a technical background
• 2+ years of experience with automation tools, workflow builders, APIs
• Experience building, debugging, and troubleshooting AI workflows
• Comfortable with MCP integrations (Slack, Gmail, Sheets, Airtable, etc.)
• Understanding of LLM and AI tool capabilities
• Experience designing learning programs or enablement content
• Understanding of adult learning principles and instructional design
• Strong facilitation skills - running engaging workshops and sessions
• Experience measuring learning effectiveness (not just completion)

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 a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to identity or other legally protected class. 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 .
Block is a globally distributed company and this role will require working with other employees in multiple time zones. You may be required to perform work outside of normal business as part of this role.
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 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. 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.