Regulatory Program Manager, Automation & Intelligence

It all started with an idea at Block in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world’s relationship with money to make it more relatable, instantly available, and universally accessible.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward innovation, collaboration and impact. We’ve been a distributed team since day one, and many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

The Role

As Block has scaled, so has the complexity of our regulatory environment. The Settlements and Supervision Operating Model (SSOM) - is Block's centralised governance and execution engine for managing our most critical regulatory commitments. SSOM exists to bring rigour, consistency, and accountability to how Block engages with regulators, auditors, consultants, and partners across a range of high-priority regulatory matters..

SSOM is led by a lean, fully dedicated cross-functional core team drawn from Compliance, Legal, BizOps, Data Science, and Finance. We move fast, operate with precision, and are deeply committed to getting this right for Block, our customers, and our regulators.

Check out our locations, benefits, and more at block.xyz/careers

The Opportunity

This is not a typical program management role. As a SSOM Program Manager, you'll be the driving force behind how Block uses intelligent tooling, automation, and AI to execute one of its most complex and consequential programs. You'll identify where AI and automation can eliminate manual effort, reduce risk, improve tracking accuracy, and accelerate remediation - and then you'll build it, champion it, and embed it into how the SSOM and its partners operate every day.

You'll partner with Compliance, Legal, Data Science, BizOps, Customer Support and Engineering to bring AI-powered workflows to a high-stakes, high-scrutiny environment. You'll be the person who makes the complex feel manageable, and the possible feel inevitable.

We're looking for someone who deeply understands both the gravity of regulatory execution and the transformative potential of AI — and who can bridge those two worlds with credibility, rigour, and genuine enthusiasm.

You will:

• Champion AI & Automation Adoption: Act as the primary evangelist for AI and automation tools within the SSOM Core Team and across the broader Matrix Team - running demos, enablement sessions, and hands-on workshops that build genuine capability and enthusiasm in a regulatory program context.
• Identify & Build Automation Opportunities: Proactively map SSOM workflows end-to-end to identify high-impact automation opportunities - from requirements tracking and remediation pipeline management to regulatory reporting, escalation workflows, and document generation.
• Own the AI & Automation Roadmap: Partner with SSOM leadership and BizOps to define, prioritise, and deliver a rolling roadmap of AI-powered initiatives that measurably improve the speed, accuracy, and consistency of SSOM execution.
• Drive Tool Optimisation: Oversee the adoption and continuous improvement of program management tooling - ensuring automation, AI-assisted insights, and workflow enhancements are embedded into how the SSOM executes against regulatory commitments.
• Translate AI for a Regulatory Audience: Bridge the gap between technical capability and regulatory program reality - communicating the value of AI tools in plain language, with clear use cases, risk considerations, and practical guidance tailored to Compliance, Legal, and BizOps stakeholders.
• Build Scalable Frameworks: Develop reusable playbooks, automation blueprints, and AI-assisted templates that allow the SSOM to scale governance and remediation execution consistently across settlements, supervision workstreams, and future scope expansions.
• Measure What Matters: Define and track KPIs for AI and automation initiatives - including time saved, error reduction, tracking accuracy, and remediation velocity - and report insights to the Steering Committee with clear recommendations.
• Cross-Functional Collaboration: Work closely with Data Science, Engineering, Compliance Analytics, and external consultants to ensure the SSOM has access to the best tooling, pilots, and AI innovations - and that sensitive regulatory data is handled with appropriate controls.
• Stay Ahead of the Curve: Continuously evaluate emerging AI platforms, agentic tools, and automation technologies - bringing informed, opinionated recommendations on what to adopt, pilot, or watch, with a clear eye on risk and compliance implications.
• Roll Up Your Sleeves When It Counts: Step in as a hands-on generalist when the situation demands it - whether that's troubleshooting a complex workflow breakdown, facilitating a working session to unblock a stalled workstream, or leading a targeted intervention to get a remediation track back on course. You know when to let the tools do the work, and when to get in the room and do it yourself.

You will:
Qualifications: Like us, you'll be deeply committed to delivering positive outcomes for Block, our regulators, and our customers - and passionate about using AI to make that execution faster, smarter, and more reliable.

• You have 8+ years of experience in program management, BizOps, regulatory operations, or a related field - with a clear track record of driving process improvement and technology adoption in complex, cross-functional environments.
• You are genuinely excited about AI and automation - you've used tools like AI assistants, workflow automation platforms, and LLM-powered tools, and you have real opinions about what works and what doesn't.
• You have experience leading change management and enablement initiatives - you know how to bring sceptical stakeholders on a journey and make new technology feel accessible, not threatening, in risk-sensitive environments.
• You're analytically strong - comfortable with program tracking data, remediation metrics, and building business cases for tooling investment.
• Your EQ and ability to influence without authority will be just as important as your technical chops - the SSOM spans Compliance, Legal, Engineering, and BizOps, and you'll need to earn trust across all of them.
• Experience in regulated industries - fintech, financial services, or similar - is a strong advantage. Familiarity with AML/BSA, CFPB supervision, or consent order management is highly desirable.
• You understand the stakes: this program has direct visibility to Block's Steering Committee and Board of Directors. You bring the judgement, discretion, and professionalism the environment demands.

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.

While there is no specific deadline to apply for this role, U.S. roles are typically open for an average of 55 days before being filled by a successful candidate. Please refer to the date listed at the top of this job page for when this role was first posted.