Senior Product Owner

Points North is looking for a Senior Product Owner to own product decisions and drive hands on execution for an established B2B software application that streamlines complex payroll calculations and compliance reporting for companies with prevailing wage and unionized workforces. This seasoned individual contributor will be responsible for developing a keen understanding and expertise of our existing systems, stabilizing and improving the legacy parts while developing new capabilities, and increasing retention, all while operating in a fast-paced environment with a low tolerance for breaking changes. Sound like a challenge? Absolutely, but is a meaningful and highly visible one. You will work cross functionally with Engineering, QA, Implementation, Support, Sales, Finance, Managed Services, and domain SMEs, and you will have direct customer access. As a result, you will play a critical role in our continued growth, helping our clients work smarter, simplify complex payroll obligations, and ultimately give them back their time. What You Will Do: Influence Product Strategy and Decisions Own product direction and day-to-day product decisions for core platform capabilities in alignment with our overall company objectives. Define measurable outcomes and priorities that balance stability and retention, customer value, and modernization. Partner with Engineering on the overall product roadmap with a focus on determining what will deliver the most value to our clients and our business. Be a Hands-On Executor Write epics, user stories, and detailed acceptance criteria that engineers and QA can build and test against with confidence. Conduct discovery and user research: customer interviews, workflow mapping, pain point validation, and value testing. Maintain an organized product ticket backlog for our client-facing teams, while prioritizing the development backlog, refining continuously in partnership with Engineering and ensuring work is ready for development. Triage defects and production issues in partnership with Implementation, Client Support and Engineering. Prioritize fixes based on customer impact, risk, and business outcomes. Participate in our Agile product development process. Stabilize and Evolve a Critical, Complex Platform Drive improvements in reliability, performance, accuracy, and usability across complex payroll/compliance workflows. Ensure changes preserve the trust we have with our clients by considering and mitigating impacts to their existing workflows. Enable Customer Facing Teams Through Product Improvements Partner with Support and Implementation to reduce friction, improve tooling, and increase effectiveness with clear, measurable outcomes. Use data and feedback loops (support trends, customer escalations, implementation insights, adoption signals) to target improvements that move retention. Lead Integration Related Product Work Own requirements, documentation and outcomes for integrations with our partners. Translate integration needs into clear product workflows, API requirements, data mapping expectations, and operational support considerations. Communicate Releases and Drive Readiness Coordinate and deliver release communications (what changed, who it impacts, why it matters, how to use it). Partner with Marketing on positioning/enablement, while personally owning release comms and internal readiness. What Success Looks Like (First 6–12 Months): You have built strong working knowledge of our platform and the real-world customer workflows it supports. Platform stability improves measurably (fewer high severity incidents, reduced customer pain in top friction areas, improved release confidence). Retention drivers are clearly understood and reflected in a focused, outcome-based roadmap. Modernization begins with a pragmatic plan and sequenced execution without destabilizing the legacy system or forcing breaking changes. What We Are Looking For: Familiarity (not necessarily expertise) with one or more of: Prevailing wage compliance (federal/state/local), certified payroll reporting Union payroll rules, fringes, classifications, rate changes Construction payroll/compliance operations Experience in regulated domains where accuracy and explainability are critical (payroll, tax, HR, compliance, fintech). Experience improving product ops fundamentals: intake/triage, backlog health, release readiness, incident learning loops, customer feedback systems. Working Style Fit, you will likely thrive in this role if you: Like being close to the work: writing, refining, triaging, talking to customers, and shipping continuously. Can balance “keep the lights on” with meaningful forward progress. Prefer influence through clarity and execution over authority or managing a team. Are energized by complexity and can translate it into simple, usable experiences. Required Qualifications Proven, extensive professional experience in product management experience with B2B SaaS products, ideally with complex financial calculations and integrations with payroll or ERP systems. Proven ability to be a strong individual contributor: owning outcomes end to end from discovery to delivery to results. Experience working with legacy systems and improving them incrementally while supporting production reliability. Strong track record partnering closely with Engineering and QA, with comfort going deep into edge cases, tradeoffs, and technical constraints. Demonstrated capability to define and deliver API based integrations, including understanding: Integration patterns (REST APIs, webhooks, file-based interchange where applicable) Data mapping/validation, error handling, reconciliation, and operational support needs Enterprise integration expectations (security, reliability, versioning, backward compatibility) Excellent written communication (clear requirements, decision logs, release notes, stakeholder updates). Comfortable working cross functionally with Support, Implementation, Sales, SMEs, and Finance—driving alignment and momentum At Points North, we believe that taking care of our team is the foundation of our success. That’s why we’ve created a benefits package designed to support you both personally and professionally: Health Insurance: Comprehensive medical, dental, and vision plans are available to keep you and your family healthy. Retirement Savings: Invest in your future with employer-matching contributions to a SIMPLE Traditional and/or ROTH IRA plan. Time Off: Generous PTO, paid holidays, and Volunteer Time Off (VTO) are offered so that you can take time to recharge and give back to what matters to you. Growth Opportunities: Professional development is encouraged whether it be in training, certifications, or other opportunities to boost your career. Flexibility: Depending on the role, remote or hybrid arrangements may be made available to fit your lifestyle and business needs. For this position the base salary range is $100,000-135,000 per year, plus annual bonus eligibility. Final compensation determinations will reflect your unique experience, skills, and the responsibilities of the role. At Points North, you’ll find an energizing, ambitious and supportive workplace where your contributions make a real impact. Ready to join our team? Apply today to take the next step in your career!