Head of Product

Responsiv; Chicago (IL); On-site; USD 160,000 - 260,000; Full time

Job summary

Responsiv in Chicago is seeking a Head of Product to shape the vision and roadmap of our regulatory platform for compliance, legal, and risk teams. You will lead the product organization, drive AI-driven outputs, and partner with engineering and regulatory data to ensure quality and impact across releases.

You’ll work with design, sales, and customer success to translate complex regulatory requirements into intuitive experiences, setting a high bar for usability and measurable outcomes in a

Qualifications

• 7+ years in product management, including owning strategy and roadmap for a B2B SaaS product, ideally in RegTech, legal tech, or financial services.
• Familiarity with compliance, legal, or regulatory workflows; experience in financial services or similarly regulated industries is a strong plus.
• Demonstrated track record of shipping AI‑driven products and using evals to measure and improve the quality of hard‑to‑measure outputs.
• A high bar for intuitive, beautiful product experiences and the ability to drive customer adoption.
• Experience partnering with engineering teams and domain experts to align on outcomes and ship together, and the ability to communicate vision and priorities

Responsibilities

• Define and communicate the long‑term product vision and a clear, sequenced roadmap that balances innovation, differentiation, and commercial impact.
• Maintain a deep understanding of the RegTech landscape and partner with engineering, Regulatory Data, sales, marketing, and customer success to drive alignment and execution.
• Build a high‑performing product team over time—hiring quality people quickly and ensuring they deliver.
• Lead the product organization and ensure AI-driven outputs are measurable and improve with every release.
• Collaborate with design, engineering, and data teams to elevate product design and user experience.

Skills

Product leadership

Domain knowledge

AI product

Design sensibility

Engineering collaboration

Job description

View all jobs Head of Product Chicago Product In office Full-time

Responsiv Overview

Responsiv is building the leading regulatory operating system for compliance, legal, and risk teams. Too many compliance leaders are still stuck stitching together fragmented alerts, manual spreadsheets, inconsistent sources, and disconnected pieces of advice, just to figure out what a regulation requires them to do. Responsiv solves this end-to-end, giving teams the ability to:

• Build and manage their regulatory universe: Create and maintain registers of the complex laws, rules, and regulations that apply to their business, across every jurisdiction and regulator they answer to.
• Cut through the noise: Filter and route relevant regulatory alerts to the right owners, so teams focus only on the changes that actually matter.
• Turn legal text into action: Translate dense regulatory language into clear, actionable obligations and requirements.
• Find gaps before regulators do: Map new requirements against existing policies, procedures, and controls to surface gaps and recommend the changes needed to close them.
• Move from finding to fix: Automatically draft policy and control updates, and track remediation through a defensible audit trail.
• Get back to the business faster: Understand the regulatory context behind situations existing policies don't cover, so the business can keep moving.

We are entering the market at a genuine inflection point. Nearly half of compliance organizations still use no dedicated regulatory intelligence technology today, and this category now has the highest purchase intent of any compliance technology segment — yet buyers are rightly skeptical of vendors making big AI promises without proof. That's exactly why we built Responsiv — a market‑leading platform designed to deliver high‑impact, defensible results. There's a clear opportunity to become the trusted partner compliance teams need. Backed by Greylock and OnDean Forward (Andrew Sieja, the founder of Relativity).

Head of Product Overview

The Head of Product shapes what Responsiv builds and why. You’ll set the product vision and roadmap, make Responsiv easy to use, intuitive, and beautiful, and ensure product quality—including hard‑to‑measure, AI‑driven outputs—improves measurably with every release. You’ll do this in close partnership with the Head of Regulatory Data, who owns our truth sets and is the arbiter of quality, and AI Engineering, which owns our AI deliverables.

Core Product: Build a Product That’s Easy to Use and Measurably Better

• Elevate Product Design: Make Responsiv easy to use, intuitive, and beautiful. Define the design vision and principles for every module, set and enforce a high bar for intuitiveness, polish, and information hierarchy, and own a unified design system that keeps the product consistent as it scales.
• Eval-Driven Development: Ensure product quality—including hard‑to‑measure, AI‑driven content—improves measurably with every release. Align the team and our legal experts on shared quality rubrics, build regression gates into the development cycle, and report quality trends to the team and leadership. Your job is to make sure the product actually gets better—confirming each release measurably improves against our truth sets, flagging where it doesn’t, and prioritizing the work that closes the gap.

Partner with Engineering and Regulatory Data

• Work alongside AI Engineering and Regulatory Data, who owns our truth sets and is the arbiter of quality, to help the team move even faster. Bring clarity on the problem, who it’s for, and what success looks like, and shape solutions together—trusting engineering’s expertise on the “how.” Provide right‑sized context and keep priorities clear so everyone stays in lockstep.

Lead the Product Organization

Define and communicate the long‑term product vision and a clear, sequenced roadmap that balances innovation, differentiation, and commercial impact. Maintain a deep understanding of the RegTech landscape, partner with engineering, Regulatory Data, sales, marketing, and customer success to drive alignment and execution, and build a high‑performing product team over time—hiring quality people quickly and making sure they deliver.

Qualifications

• Product Leadership: 7+ years in product management, including owning strategy and roadmap for a B2B SaaS product, ideally in RegTech, legal tech, or financial services.
• Domain Knowledge: Familiarity with compliance, legal, or regulatory workflows; experience in financial services or similarly regulated industries is a strong plus.
• AI Product Experience: Demonstrated track record of shipping AI‑driven products and using evals to measure and improve the quality of hard‑to‑measure outputs.
• Design Sensibility: A high bar for intuitive, beautiful product experiences and a proven ability to drive customer adoption.
• Engineering Partnership & Communication: Experience partnering closely with engineering teams and domain experts to agree on outcomes and ship together, and the ability to communicate vision and priorities to internal and external stakeholders.

At Responsiv, our core values are not just words on a page; they are the guiding principles that shape our culture, define our actions, and propel us towards our vision.

• Advocate like you're right. Listen like you're wrong.We communicate ideas with bothpassion and humility. We are all responsible for innovation and believe that ideas can come from anyone.
• Practice extreme ownership: With ownership comes accountability. Deliver on your commitmentsand take individual responsibility for the team’s successes andfailures.
• Measure success:Having clarity on what success looks like is critical toits achievement. Make sure the measurements are meaningful.
• Make an impact:Iterate quickly.Speed over Perfection. Resultsover Activity.
• Do more with less: We value efficiency and resourcefulness. Quality is notdictated by the quantity of resources, but how effectively they are used.
• Celebrate the wins. Acknowledge the losses.Both are important signals to help us steer the ship.Give meaning to the hard work by recognizingthe moments, milestones, stories and people in our joint success.