Sr. Product Manager - Payroll Tax & Compliance

CP Payroll, LLC dba ConnectPay•Mansfield, MA

2d•$120,000 - $178,000•Hybrid

About The Position

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. 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.