Ironclad is a Series E AI contracting platform used by companies to manage contract workflows across the business.
Ironclad sought a legal and product leader who could help embed commercial legal expertise directly into its product. The company needed someone who could translate contract judgment into product systems, structured datasets, evaluation frameworks, and customer-facing AI outputs.
The Search
Ironclad partnered with Kerwin to recruit a Senior Staff Product Manager, Legal.
This was a newly created role designed to bridge Legal, Product, Engineering, and customer needs. The mandate was to help Ironclad turn commercial contracting expertise across NDAs, MSAs, SaaS agreements, vendor contracts, and customer agreements into scalable product capabilities.
The successful candidate needed deep experience as an in-house commercial attorney, along with product ownership, AI fluency, and the ability to build in an ambiguous environment.
Challenges
The profile required a combination that was difficult to find: significant in-house commercial contracting experience, strong product instincts, familiarity with AI and LLMs, and the ability to work effectively across Product, Engineering, Legal, Sales, and Customer Success.
Many candidates had strong legal backgrounds or experience with legal technology. Far fewer had actually helped build products and could translate the judgment of an experienced commercial attorney into something that could work at scale.
The San Francisco-based hybrid requirement narrowed the market further, and compensation became an important consideration as the search reached the strongest candidates.
Our Approach
Kerwin helped Ironclad define the profile for a net-new role spanning legal, product, AI, and operations.
A critical requirement was extensive experience practicing as an in-house commercial attorney. The search focused on candidates who had spent meaningful time negotiating and advising on commercial agreements firsthand, while also developing experience in legal technology, product development, or AI-enabled contract workflows.
Kerwin targeted commercial counsel, product counsel, legal-tech operators, CLM specialists, legal engineers, and product-minded attorneys who had worked directly with Product and Engineering teams.
The assessment went beyond legal credentials. Candidates were evaluated on whether they had owned product work, collaborated directly with engineers, contributed to product requirements, and turned commercial legal judgment into repeatable workflows and product functionality.
This helped distinguish candidates who had advised product teams from those who had actually helped build products.
Results
Kerwin completed the search and placed the successful candidate as Sr. Staff Product Manager (SME), Legal, within two months.
The hire came directly from the legal-tech ecosystem and brought a rare combination of deep commercial legal experience and hands-on product development. The candidate had previously owned AI-native contract intelligence and contract-review products while working closely with Engineering, Design, Sales, and Customer Success in their previous position.
They also brought more than a decade of commercial contracting experience, advanced academic work focused on AI and technology law, familiarity with Ironclad’s product, and repeated experience building new products from the ground up.
Impact
The hire gave Ironclad a legal-product leader who could help turn commercial legal expertise into product logic, AI contract-review outputs, evaluation systems, and scalable workflows.
With the role filled, Ironclad feels it is in a better position to build its legal engineering and legal SME capabilities within Product.
The search also demonstrated Kerwin’s ability to identify highly specialized talent for emerging legal-product roles where success depends on both deep legal experience and technical fluency.