UserTesting

Strategic Projects Lead, AI Training

UserTesting • $110K — $130K *
US-AnywhereRemote in United States
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4+ years of experience in project leadership within operation-focused roles, ideally in AI or related fields.
  • Experience managing large external workforces and contributors, particularly in AI training settings.
  • Strong analytical and project management capabilities to oversee multiple complex projects simultaneously.
  • Proven problem-solving skills with a comfort level in ambiguous environments.
  • Excellent communication skills to collaborate with customers and cross-functional teams.
  • Familiarity with AI training methodologies and processes is a plus.

Responsibilities

  • Lead the complete cycle of AI training projects from initial discussions with customers to successful delivery.
  • Create and implement sourcing strategies to find specialized contributor communities.
  • Recruit and manage contributors, establishing efficient operational workflows for onboarding and task management.
  • Track and evaluate project metrics such as quality and cost to ensure effective execution.
  • Oversee project economics, aligning contributor compensation and staffing with customer expectations and timelines.
  • Serve as the primary liaison for customers throughout project execution, ensuring clear communication of progress and changes.
  • Identify and implement improvements to processes and systems for sustained business growth in the AI training sector.

Benefits

  • Remote work flexibility within the U.S. time zones.
  • Opportunities for personal and professional growth as part of a new business.
  • A commitment to building an inclusive and accessible work environment.
  • Encouragement for diverse perspectives in the hiring process.
Full Job Description

The Opportunity


At UserTesting, we’re the leader in human insight, helping organizations build better products and experiences by connecting them with real human perspectives. As companies increasingly build and train AI systems, our technology, participant network, and expert services uniquely position us to support this rapidly evolving space.


AI Training is a new business being incubated within UserTesting, focused on applying our expertise in sourcing and managing specialized communities to power high-quality AI training initiatives. As one of the early members of this team, you’ll have the opportunity to shape how we operate, build scalable processes from the ground up, and play a key role in growing a new business.


We’re looking for a Strategic Projects Lead to own the end-to-end delivery of AI training projects—from early customer conversations through successful execution. You’ll partner with customers, internal stakeholders, and contributor communities to solve complex operational challenges, delivering high-quality outcomes while building repeatable systems that enable future growth.

Responsibilities

  • Own the end-to-end delivery of AI training projects, partnering with customers from initial scoping through successful execution while assessing feasibility, timelines, operational requirements, pricing inputs, and project risks.
  • Develop and execute sourcing strategies for specialized contributor populations by leveraging UserTesting’s network, external recruiting channels, partner partnerships, and other creative approaches to meet customer needs.
  • Recruit, onboard, and manage contributor communities, designing scalable operational workflows that include onboarding, task distribution, contributor communications, quality assurance, escalations, and delivery.
  • Monitor project performance by tracking key operational metrics—including recruiting progress, activation, throughput, quality, cost, and retention—and proactively adjust plans to ensure successful outcomes.
  • Own project economics by balancing sourcing strategies, contributor compensation, staffing, quality expectations, and delivery timelines to drive efficient execution.
  • Serve as the primary customer contact throughout project delivery, translating evolving requirements into clear guidance for contributors while communicating progress, risks, and tradeoffs with transparency.
  • Continuously improve how the team operates by identifying opportunities to build repeatable processes, scalable systems, and operational capabilities that support the long-term growth of the AI Training business.

Requirements

  • 4+ years of experience leading complex, cross-functional projects in operations, strategic programs, consulting, AI training, marketplaces, expert networks, talent platforms, data operations, or similar fast-paced environments.
  • Proven experience managing projects involving large populations of contractors, contributors, participants, experts, or other external workforces. Experience in AI training or human data organizations is strongly preferred.
  • Strong project management and analytical skills, with the ability to manage multiple priorities, model project performance, monitor operational metrics, and understand project economics.
  • Demonstrated ownership and problem-solving skills, with the ability to thrive in ambiguity, build processes from the ground up, and balance detailed execution with strategic thinking.
  • Excellent written and verbal communication skills, with experience partnering directly with customers and collaborating across cross-functional teams.
  • Familiarity with AI training concepts such as annotation, evaluations, quality assurance, reinforcement learning environments, expert data, or post-training workflows is preferred.
  • Location: Remote within the United States, with the ability to work primarily within U.S. time zones.

Don’t meet every single requirement but excited about the role? We encourage you to apply. Research shows that some candidates are less likely to apply unless they meet 100% of the qualifications—but you may be exactly who we’re looking for. Diverse perspectives drive innovation, and we’re committed to building a team with a wide range of backgrounds, experiences, and skills.

Application Process

  • Meet with a Recruiter

  • Meet the Hiring Manager

  • Participate in a Panel Interview

  • Final Interview (if applicable)

  • Offer Stage

Accommodations

At UserTesting, we’re committed to creating inclusive and accessible experiences for all candidates. We believe diverse perspectives are essential to building exceptional products and experiences. If you require accommodations or would like us to tailor the interview process to better meet your needs, please contact us at .

About UserTesting

UserTesting is a software company that provides a platform for businesses to conduct user experience research and testing. The company was founded in 2007 by Dave Garr and Darrell Benatar. UserTesting's platform allows businesses to get feedback on their products and services from real users, helping them to improve their user experience and increase customer satisfaction. The company's platform offers a variety of testing methods, including remote usability testing, live conversation testing, and survey testing. UserTesting has been recognized as one of the fastest-growing private companies in the United States by Inc. Magazine, and has been featured in numerous publications, including Forbes, The Wall Street Journal, and TechCrunch.
Learn more about UserTesting
Size
500 employees
Market Cap
$1 billion
Industry
Founded
2007
NASDAQ

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