Lead end-to-end machine learning initiatives for Block’s conversational support systems. Responsibilities include developing and maintaining chatbot and recommendation models, researching LLM, RAG, fine-tuning, and real-time inference architectures, shaping long-term ML roadmaps, and guiding cross-functional teams. The role also requires communicating technical strategy and outcomes to leadership and external stakeholders while delivering scalable, production-ready AI solutions across Cash App, Square, and other Block products.
Block builds simple, powerful tools that make progress towards an economy that's truly open to all. 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. Join us.
The Role
Block's Support ML Modeling team is a central driver of innovation in customer support experiences across our entire ecosystem-including Cash App, Square, and other business units. We are dedicated to advancing the state of intelligent, automated support through machine learning and generative AI. From customer-facing chatbots to smart internal tools for agents, our team builds high-impact, scalable systems that improve support quality, efficiency, and accessibility.
We're building the future of support at Block: one powered by AI, voice interfaces, and smart automation. We're looking for candidates with a passion for intelligent systems, practical ML experience, and a desire to build product-driven solutions. Our ideal candidate is a leader in the field, with a proven track record of building ML systems that can accelerate our ability to scale our conversational AI initiatives.
You Will
You Have
Technologies We Use and Teach
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 .
Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.
To find a location's zone designation, please refer to this resource . If a location of interest is not listed, please speak with a recruiter for additional information.
Zone A:
$276,800 - $415,200 USD
Zone B:
$276,800 - $415,200 USD
Zone C:
$276,800 - $415,200 USD
Zone D:
$276,800 - $415,200 USD
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.
The Role
Block's Support ML Modeling team is a central driver of innovation in customer support experiences across our entire ecosystem-including Cash App, Square, and other business units. We are dedicated to advancing the state of intelligent, automated support through machine learning and generative AI. From customer-facing chatbots to smart internal tools for agents, our team builds high-impact, scalable systems that improve support quality, efficiency, and accessibility.
We're building the future of support at Block: one powered by AI, voice interfaces, and smart automation. We're looking for candidates with a passion for intelligent systems, practical ML experience, and a desire to build product-driven solutions. Our ideal candidate is a leader in the field, with a proven track record of building ML systems that can accelerate our ability to scale our conversational AI initiatives.
You Will
- Lead the end-to-end delivery of multiple ML initiatives, from planning and design through rollout, documentation, and long-term maintenance
- Partner strategically with risk, product, engineering, design, and operations leaders to define and drive long term ML roadmaps, informed by domain expertise and industry trends
- Guide the team's direction, identifying new ML/AI opportunities and advising leadership on strategic tradeoffs and opportunities
- Drive R&D efforts exploring next-generation chatbot architectures using LLMs, RAG, fine-tuning, and real-time inference
- Design, deploy, and maintain ML models powering conversational agents including support chatbots across Cash App, Square, and other Block products
- Develop ML-powered tools and real time recommendation systems that enhance support agent effectiveness and customer outcomes
- Act as the technical representative for your team's systems and programs, clearly communicating work and results to stakeholders, cross-functional partners, and external audiences
You Have
- 10+ years of experience in machine learning, applied AI, or product ML roles, with deep technical expertise
- Demonstrated leadership capabilities, with the ability to influence and align cross-functional teams while directly shaping the work of peers through communication, context sharing, and technical guidance
- A track record of delivering organizational wide impact, shaping systems, frameworks, or initiatives that raise the bar across multiple teams or functions
- Proven ability to ship end to end ML features from problem framing through deployment and long-term maintenance
- Demonstrated experience with language models, dialog systems, or generative AI in production
- Strong foundation in NLP, deep learning, or ML infrastructure best practices.
- Excellent communication skills, with the ability to represent the team's work to leadership and stakeholders
- Enthusiasm for R&D and pushing the boundaries of applied AI to transform conversational systems
Technologies We Use and Teach
- Python, PyTorch, TensorFlow, or JAX
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 .
Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.
To find a location's zone designation, please refer to this resource . If a location of interest is not listed, please speak with a recruiter for additional information.
Zone A:
$276,800 - $415,200 USD
Zone B:
$276,800 - $415,200 USD
Zone C:
$276,800 - $415,200 USD
Zone D:
$276,800 - $415,200 USD
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.
Block Chicago, Illinois, USA Office
Chicago, IL, United States
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