SyndicatedFractional CPOChicago, Illinois, United States
Full-time CPO, Responsiv
FULL-TIME CPO JOB · SAAS SECTOR · CHICAGO, ILLINOIS, UNITED STATES

Full-time CPO at Responsiv, based in Chicago. Full posting below, with the day rate stated or estimated with its basis.
Full-time CPO — the posting in full
~/original-posting · verbatimsource: gem
What the posting asks · quoted from the listing
- Years
Product Leadership: 7+ years in product management, including owning strategy
- Must-have
Product Leadership: 7+ years in product management, including owning strategy
- Must-have
and roadmap for a B2B SaaS product, ideally in RegTech, legal tech, or
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 both passion 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 commitments and take individual responsibility for the team’s successes
- and failures.
- Measure success: Having clarity on what success looks like is critical to its
achievement. Make sure the measurements are meaningful. ·
- Make an impact: Iterate quickly. Speed over Perfection. Results over
- Activity.
- Do more with less: We value efficiency and resourcefulness. Quality is
- not dictated 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 recognizing the
moments, milestones, stories and people in our joint success.
Same role · same category
Similar Fractional CPO jobs
Same sector
Other fractional jobs in saas
Our own roles first · then the latest
Featured fractional roles
Explore the category
Browse every fractional leadership role
not quite the right fit?
Tell us what you're actually looking for.
Browse the UK fractional and interim roles on our board — each day rate stated, estimated with its basis, or marked not stated — flagged when a role is worth a fractional pitch.
Hiring for a role like this? We undertake a shortlist of 3–5, five-stage vetting and an IR35 position on every brief.