Sr. Product Manager - Payroll Tax & Compliance

About ConnectPay
ConnectPay is a compliance-first payroll and people platform built for small businesses. We serve approximately 12,000 clients across all 50 states, combining deep payroll tax and compliance expertise with a high-touch service model that small employers trust. As we modernize our platform and expand through partners, product leadership plays a central role in shaping how we grow.

Job Summary:
We are looking for an experienced product leader to own the Payroll Tax & Compliance domain — the heart of our platform and the foundation of our clients' trust. In this role, you will set the strategy and roadmap for how ConnectPayUSA calculates, files, and remits payroll taxes and stays ahead of an evolving compliance landscape across federal, state, and local jurisdictions.

This role reports to the Chief Product Officer and works under their direction, giving you a direct line to company strategy and executive decision-making. You will define where the domain needs to go, set direction for the product owners driving day-to-day execution, and stay close to delivery by partnering directly with engineering teams in the US and globally. You will also work hand-in-hand with our tax operations team to identify process gaps and turn them into opportunities for automation, efficiency, and a better client experience.

What You Will Do

• Set the direction. Own the product vision, strategy, and roadmap for the payroll tax and compliance domain, aligned with company priorities, our SMB client base, and market trends.
• Modernize the platform. Lead efforts to streamline, modernize, and build out our tax and compliance system capabilities — from tax calculation and filing to notices, amendments, and year-end processing.
• Partner with operations. Work closely with the tax operations team to understand day-to-day processes, identify gaps, and prioritize automation and efficiency opportunities that reduce cost to serve and improve accuracy.
• Guide execution. Set direction and priorities for product owners within the domain, guide their day-to-day execution, and track progress against committed outcomes.
• Drive delivery. Partner with engineering teams in the US and globally to translate strategy into well-defined initiatives and deliver them predictably, sprint over sprint.
• Decide with evidence. Ground decisions in data — client impact, support volume, cost-to-serve, adoption, and regulatory change — and make trade-offs transparent.
• Communicate up and across. Present product strategy, roadmaps, and progress to senior leadership with clarity and confidence, and keep stakeholders aligned across the business.

What You Will Bring

• 7+ years of product management experience, with a track record of setting direction for cross-functional teams and driving work through others.
• Experience in payroll, payroll tax, HCM, fintech, or another regulated, compliance-heavy domain; direct payroll tax experience is a strong plus.
• A track record of building product strategy and seeing it through to shipped outcomes — you are as comfortable in a roadmap review as you are in a sprint planning session.
• Experience partnering with distributed or global engineering teams and driving execution across time zones.
• Strong analytical skills; you use data on operations, adoption, and cost to prioritize and to measure success.
• Excellent communication and presentation skills, with experience presenting to executives and senior leadership.
• A bias for simplifying complexity — you can take an intricate regulatory or operational process and turn it into a clear product plan.

What Will Set You Apart

• Experience directly managing or mentoring product managers or product owners.
• Hands-on experience with payroll tax filing, agency integrations, or compliance operations at a payroll provider, PEO, or HCM platform.
• Experience modernizing legacy systems or leading platform re-architecture initiatives from the product side.
• Familiarity with SMB customers and the service expectations of small employers.

Why ConnectPayUSA
You will own one of the most consequential domains in the company — the one our clients depend on to pay their people accurately and stay compliant. You will have real scope, a talented team, direct access to executive leadership, and the chance to shape how a trusted SMB platform modernizes and scales.

ConnectPay is committed to fair and equitable pay. The expected hiring range for this role is $120,000 - 178,000 , depending on factors such as experience, skills, education, location, and internal equity. In addition to base pay, team members are eligible for equity and participation in an annual bonus plan targeted at 10%, based on company and individual performance.

We also offer a comprehensive benefits package designed to support your health, financial well-being, and peace of mind, including 401(k) with company contributions, medical, dental, and vision coverage, life insurance, short- and long-term disability insurance, and flexible spending accounts.

CP Payroll is an equal opportunity employer. We are committed to building an inclusive workplace where people feel respected, supported, and able to do their best work. All employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, marital status, veteran status, or any other protected characteristic under applicable law.

This is currently a hybrid position based in Mansfield, MA, and we are focusing on candidates who can work in that hybrid environment. Please note that we are not able to sponsor visas for this role at this time.