• Skip to primary navigation
  • Skip to main content
  • Skip to footer

Side Hustles

Side Hustles

Side Hustles For All

  • Best Side Hustles
    • Woman sitting on a pile of coins and working on a laptop surrounded by icons representing different side hustle ideas

      31 Best Side Hustles to Earn Extra Money in 2026

    • Bicycle courier delivering food for their side hustle.

      What Is a Side Hustle?

    • Remote worker sitting at his desk making money from home

      18 Ways to Make Money from Home (Online and Offline Jobs)

    • By Category
      • Arts & Crafts
      • Business Services
      • Caregiving
      • Creative Services
      • Digital Freelance Services
      • View All
    • By Lifestyle
      • I’m introverted
      • I’m a man
      • I’m a woman
      • I’m a stay-at-home mom
      • I’m unique
      • View All
    • By Profession
      • Artists & Creatives
      • Musicians
      • Nurses
      • Physicians
      • Teachers
      • View All
    • By Age Group
      • College Students
      • Teens
      • Age 50+
      • Seniors
      • View All
    • By Skills & Interests
      • Get Paid to Lose Weight
      • Get Paid to Play Games
      • Get Paid to Read
      • Get Paid to Sleep
      • Get Paid to Travel
      • View All
  • Best Gig Apps
    • Freelance worker popping out of a phone screen and considering gig apps on the App Store and Google Play

      Top 6 Gig Apps to Make Real Cash in 2026

    • Smartphone surrounded by the icons of different money-making apps

      Top 10 Best Money-Making Apps to Try in 2026

    • two teenagers using job apps on a phone and laptop

      19 Job Apps for Teens to Find Jobs and Make Money

    • By Gig Type
      • Cashback
      • Data Entry
      • Delivery
      • Games
      • Product Testing
      • View All
    • By Payment Method
      • Bingo Games that Pay to Cash App
      • Games that Pay Real Money
      • Games that Pay to Cash App
      • Games that Pay via PayPal
      • Surveys that Pay to Cash App
      • View All
    • By Benefits
      • $20 Signup Bonuses
      • $25 Signup Bonuses
      • $50 Signup Bonuses
      • Best Signup Bonuses
      • Instant Signup Bonuses
      • View All
    • By Skills & Interests
      • Driving
      • Losing Weight
      • Playing Games
      • Product Testing
      • Watching Ads
      • View All
  • Job Hunting
    • Freelance worker browsing a job post on a freelance job board.

      23 Job Boards You Can Use to Find Remote Work

    • Freelance writer sitting at her laptop working on a project

      15 Best Remote Jobs That Require No Paid Work Experience

    • Teenager sitting at laptop working an online job

      14 Online Jobs for Teens (With No Experience)

    • Freelancing
      • Freelance Writing Sites
      • Freelance Writing Job Boards
      • Freelance Writing Platforms
      • View More
    • Gig & Shift Work
      • Gig Work Apps
      • On-Demand Work Apps
      • Shift Work Apps
      • View More
    • GPT (Get Paid To)
      • Microtasking
      • Product Testing
      • Survey Taking
      • View More
    • Remote Working
      • Best Remote Job Boards
      • Top 15 Remote Jobs
      • View More
  • Job Board
    • Work Schedule
      • Part-Time Jobs
      • Per-Diem Jobs
      • Go Search
    • Work Environment
      • Hybrid Jobs
      • Remote Jobs
      • Go Search
    • Employment Type
      • Contractor Jobs
      • Internship Jobs
      • Temporary Jobs
      • Go Search
    • Job Title
      • Accounting Jobs
      • Data Entry Jobs
      • Nursing Jobs
      • Online Teaching Jobs
      • Software Engineer Jobs
      • Go Search
    • State
      • California Jobs
      • Florida Jobs
      • New York Jobs
      • Pennsylvania Jobs
      • Texas Jobs
      • Go Search
    • City
      • Chicago, IL
      • Houston, TX
      • Los Angeles, CA
      • New York City, NY
      • Phoenix, AZ
      • Go Search

Home Flexible Job Board Senior Machine Learning Engineer, Applied AI Quality

$194,500–343,100/yr 52d ago

Senior Machine Learning Engineer, Applied AI Quality

Boost your chances before you apply.

  • ✨ Apply 10x Faster Free

    It takes 30+ tailored applications to land jobs like this one. We'll help you get that done in 1 hour.

    No Credit Card Required

  • Proceed to Application Go directly to the company's job page to apply.
Logo

Block

CA

Full-time Permanent Remote

✨ Apply 10x Faster

Analyze your resume for missing keywords, then one-click optimize it. Don't be anything less than a 100% match candidate.

Free

No Credit Card Required

Summary

Lead the technical strategy and architecture for AI-driven quality and evaluation systems using LLMs and agents. Drive the development of scalable systems to detect regressions and generate actionable product insights across the organization.

Job Description

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

At Block, we believe product quality is foundational to great user experiences, and AI is transforming how we measure, understand, and improve that quality at scale. Our team builds the intelligence layer that evaluates system behavior across millions of real-world interactions, helping ensure our products are reliable, safe, and continuously improving.

We’re looking for a Senior Machine Learning Engineer to lead the technical direction of next-generation quality systems powered by LLMs and AI agents. You’ll drive the architecture and strategy behind systems that evaluate product behavior, surface emerging issues, generate actionable insights, and enable teams across Block to make higher-confidence product decisions.

In this role, you’ll operate across ambiguous, high-impact problem spaces and shape how quality is measured and operationalized across the organization. You’ll work across engineering, product, platform, and leadership teams to define long-term technical direction, establish scalable evaluation frameworks, and build systems that become foundational infrastructure for AI-driven product quality.

You Will

  • Lead the technical strategy and architecture for AI-driven quality and evaluation systems used across products and teams.
  • Drive the development of scalable systems that use LLMs, agents, and behavioral signals to evaluate quality, detect regressions, and generate product insights.
  • Define long-term approaches for evaluation, measurement, and quality intelligence across complex product surfaces.
  • Translate ambiguous organizational needs into clear technical direction, roadmap priorities, and platform capabilities.
  • Influence engineering standards and best practices for building reliable, measurable, and trustworthy AI systems.
  • Lead complex cross-functional initiatives spanning product, infrastructure, data, and applied AI teams.
  • Mentor and level up engineers across the organization through technical leadership, design reviews, and systems thinking.
  • Identify leverage opportunities where AI systems can fundamentally improve how teams understand, debug, and improve product behavior.

You Have

  • 5+ years of experience in software engineering, machine learning engineering or applied AI.
  • Deep experience designing and shipping large-scale AI/ML systems in production environments.
  • Strong expertise with LLMs, agents, evaluation systems, retrieval architectures, and modern AI infrastructure.
  • Proven ability to lead ambiguous, high-impact technical initiatives from concept through adoption across multiple teams.
  • Strong systems thinking and architectural judgment, with the ability to balance experimentation, scalability, and operational rigor.
  • Experience defining technical strategy and influencing roadmaps beyond your immediate team.
  • Excellent communication and cross-functional leadership skills, with the ability to align engineering, product, and organizational priorities.
  • A track record of creating leverage through platforms, frameworks, and systems that enable other engineers and teams to move faster and make better decisions.

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.

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:$228,700—$343,100 USDZone B: $217,300—$325,900 USDZone C:$205,900—$308,900 USDZone D:$194,500—$291,700 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.

Privacy Policy

About the company

Block

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 through Afterpay, 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 helping sellers worldwide do the same.

Square is part of Block, Inc. (NYSE: SQ), a global technology company with a focus on financial services.

Founded

2009

Company size

1,001-5,000 employees

Industry

Software Development

Org type

Public Company

Headquarters

San Francisco, CA

Apply Now

About the company

Block

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 through Afterpay, 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 helping sellers worldwide do the same.

Square is part of Block, Inc. (NYSE: SQ), a global technology company with a focus on financial services.

Founded

2009

Company size

1,001-5,000 employees

Industry

Software Development

Org type

Public Company

Headquarters

San Francisco, CA

Footer

sidehustles.com
Facebook Twitter Instagram LinkedIn Reddit TikTok YouTube

Show Me The Money

  • Side Hustle Basics
  • Side Hustle Job Board (Remote & Part-Time Jobs)
  • Gig App Reviews
  • Job Hunting
  • Manage Your Money
  • The Gig Apple: News & Events

Company

  • About Us
  • Contact Us
  • Become a Contributor
  • Advertising & Sponsorships
  • Partner With Us
  • Editorial Guidelines

Side Hustles © All rights reserved

  • Privacy Policy
  • Terms of Service

Thanks for using our free job board

Your review would mean a lot to us.

If you love that we're just giving away remote jobs for free with no paywall, please spread the word. (You will need to create an account on Trustpilot, for which we'll be eternally grateful.) Good luck out there!

Leave a Review Not yet. Send me to the job post.