Ironclad is the leading AI contracting platform that transforms agreements into assets. Contracts move faster, insights surface instantly, and agents push work forward, all with you in control. Whether you’re buying or selling, Ironclad unifies the entire process on one intelligent platform, providing leaders with the visibility they need to stay one step ahead. That’s why the world’s most transformative organizations, from Rivian to the World Health Organization and the Associated Press, trust Ironclad to accelerate their business.
We’re consistently recognized as a leader in the industry: a Leader in the Forrester Wave and Gartner Magic Quadrant for Contract Lifecycle Management, a Fortune Great Place to Work, and one of Fast Company’s Most Innovative Workplaces. Ironclad has also been named to Forbes’ AI 50 and Business Insider’s list of Companies to Bet Your Career On. We’re backed by leading investors including Accel, Y Combinator, Sequoia, BOND, and Franklin Templeton. For more information, visit www.ironcladapp.com or follow us on LinkedIn.
About the Role
Ironclad is accelerating its investment in AI to redefine how legal teams manage and understand contracts. As part of this effort, we are hiring an AI Evaluation Engineer to work within our AI Pillar. This role is focused on unlocking insights from our training data, designing feedback loops, and ensuring the continuous improvement of our agentic and ML or LLM-based systems through data-driven evaluation and iteration.
You’ll partner closely with AI Engineers and Product Managers to drive better model quality through systematic analysis, experimentation, and the curation of high-leverage datasets. Your work will directly impact the effectiveness of features like Smart Import, contract understanding, and agentic workflows.
What You'll Be Doing
Analyze training and evaluation datasets to identify distributional gaps, labeling inconsistencies, and long-tail opportunities.
Design and execute labeling campaigns, including development of golden datasets and annotation guidelines.
Build and maintain dashboards that track model accuracy, regression trends, and product-specific KPIs like success rate or answer helpfulness.
Investigate failure modes via prompt clustering, error taxonomy development, and user intent classification.
Operationalize feedback loops: mine product telemetry and human-in-the-loop reviews for signal, then translate into data-driven model improvement strategies.
Partner with engineers and PMs to run structured A/B tests and human evaluations for new models or features.
Support the development of scalable data and evaluation infrastructure for LLMs and agents.
Work with product, engineering and legal to create clear & transparent processes for the handling of customer data in AI training, fine-tuning and evaluation
About You
Bachelor's or Master's degree in a quantitative field (e.g., Statistics, Computer Science, Data Science, Applied Math).
8+ years of experience in applied ML or data science, preferably in NLP or LLM-based applications.
Strong SQL and Python skills; experience with Jupyter, Pandas, and experiment tracking tools.
Comfortable navigating ambiguity, slicing large datasets, and communicating insights clearly to cross-functional stakeholders.
Experience with prompt analysis, clustering, or user behavior modeling is a plus.
Bonus: familiarity with LLM eval techniques, Reinforcement Learning from Human Feedback (RLHF), or agentic system design.Experience with program management.
Why This Role Matters
AI is critical to the value Ironclad customers get from their contracts, allowing their business to manage risk, close revenue faster and operate more effectively. None of this is possible without reliable and accurate data. This role will lead these efforts, becoming a key contributor to the development of AI solutions in an industry that is likely to be transformed by the new generation of models.
What We Value
Bias for action and data curiosity
Ownership mindset and team-first attitude
Comfort in fast-paced, iterative environments
Passion for building AI products that solve real-world customer problems
US Full-Time Employee Benefits at Ironclad:
100% health coverage for employees (medical, dental, and vision), and 75% coverage for dependents with buy-up plan options available
Market-leading leave policies, including gender-neutral parental leave and compassionate leave
Family forming support through Maven for you and your partner
Paid time off - take the time you need, when you need it
Monthly stipends for wellbeing, hybrid work, and (if applicable) cell phone use
Mental health support through Modern Health, including therapy, coaching, and digital tools
Pre-tax commuter benefits (US Employees)
401(k) plan with Fidelity with employer match (US Employees)
Regular team events to connect, recharge, and have fun
And most importantly: the opportunity to help build the company you want to work at
**UK Employee-specific benefits are included on our UK job postings
Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.