Senior Director, Product Management – WinTeam ERP

WorkWave empowers the hardworking service professionals who keep our world safe, clean, and beautiful. We are seeking a Senior Director of Product Management to drive the vision, strategy, and execution for WinTeam —our flagship Enterprise Resource Planning (ERP) platform for the commercial cleaning and security guarding industries. This is not a maintenance role; it is a transformation role. You will lead the modernization of a mature, business-critical ERP, embedding AI, data intelligence, and modern SaaS workflows to power thousands of complex enterprise client sites. WHAT YOU'LL DO: 1. Product Vision & AI Transformation Drive the Roadmap: Own the end-to-end vision, strategy, and execution for WinTeam's core ERP modules. Lead Modernization: Balance technical architecture upgrades with near-term customer value. Shift execution from feature-focused output to outcome-driven business impact. Embed AI-First Workflows: Leverage machine learning, predictive analytics, and automated decision-making to turn rich operational data into customer value. 2. Team Leadership & Craft Build & Mentor: Lead, grow, and empower a high-performing team of Product Managers and Product Owners. Elevate the PM Craft: Instill rigorous discovery practices, sharp requirements writing, disciplined prioritization, and an aggressive bias for action. 3. Cross-Functional Execution & Market Leadership Align Stakeholders: Partner closely with Engineering, Design, GTM, and Executive teams to accelerate delivery speed and go-to-market impact. Voice of the Customer: Deepen customer relationships via advisory boards, site visits, and discovery calls. Act as a key product authority in strategic sales cycles and industry events. Drive Business ROI: Manage product profitability, work alongside Finance on pricing/packaging models, and build data-driven ROI cases for new feature investments. WHAT YOU'LL BRING Product Leadership: 10+ years in PM, with 5+ years managing and growing PM teams within enterprise B2B SaaS. Domain Experience: Background in mission-critical platforms (ERP, workforce management, payroll, or high-volume operations software) is strongly preferred. Transformation Track Record: Proven success modernizing mature platforms, navigating tech debt, and managing customer change management without business disruption. AI & Data Fluency: Practical knowledge of how to design and launch AI-assisted, data-driven software capabilities. Executive Gravitas & Communication: Exceptional ability to influence internal stakeholders, lead strategic customer conversations, and present to executive leadership. Education: Bachelor’s degree required; MBA or advanced degree preferred. WHAT YOU SHOULD KNOW ABOUT US: • We are laid back but buttoned up. We offer a casual work environment and remote work flexibility and have a passion for developing creative, innovative best in class solutions that directly contribute to the success of our customers • We care deeply and deliver service and solutions that make a real difference in the lives of our clients and their businesses • We openly accept others as they are and build strong partnerships based on trust • Teamwork and collaboration is key to help our colleagues and customers solve their challenges • Our team is energetic, fun, naturally inquisitive and eager to make an impact, we invite you to join us! LOVE WHAT YOU DO, NO MATTER WHERE YOU DO IT: • Join our Remote-First Global Work Community: WorkWave provides an innovative and dynamic remote-first Global Work Community that encourages growth, creativity, and collaboration. No matter what stage of your career or where you live, WorkWave is your place to be part of a global company with a startup feel, where your ideas matter and your growth is a priority. A GLOBAL COMPANY WITH A LOCAL PRESENCE: • We know that there are benefits of being in the office and working from home. WorkWave promotes a healthy work/life balance and provides employees with the flexibility of collaborating in the office or the option to work virtually if desired. Our teams are well versed at working collaboratively in a fully virtual environment. • Our HQ is based at our state of the art home office in the historic Bell Works complex located in Holmdel Township, New Jersey. We keep our offices available to all to use when working remotely isn’t feasible, or to help with cross training, team building and/or brainstorming. • We have employees in over 30 states, 7 countries and many regional offices - each with their own set of perks and opportunities to give back to the local community. • Whether you work remotely or take advantage of one of our offices, you’ll find a community of WorkWavers that value diversity, and care deeply about our products, clients, our communities and each other. RELAX, WE'VE GOT YOU COVERED: • Employees can expect a robust benefits package, including health and dental and 401k with company match AND BEYOND... • Find your perfect work/life balance with our Flexible Time Off policy or generous PTO plan (role dependent) and paid holidays • Up to 4 weeks paid bonding leave • Robust Employee Assistance Program through TotalCare offering free counseling 24/7/365, plus financial counseling, legal guidance, adoption assistance services and much more! • 24/7 access to virtual medical care with Teladoc • Regional discounts and perks GROW WITH US: • We understand the impact of attracting and keeping top talent and reward intellectual curiosity and a thirst for personal and professional growth • Encouraging our employees that already have an intimate knowledge of and passion for our products to apply for other roles within our walls just makes sense! • Our employees have access to extensive video libraries for soft skill and role specific training available 24/7 and live trainings are provided throughout the year JOIN OUR WINNING TEAM! • 10 Time winner of Best Place to Work in New Jersey by NJBiz! • WorkWave has been recognized with multiple awards for its outstanding products, growth and culture, including the Inc. 5000, SaaS Award, IT World Awards, Globe Awards, Silver Stevie Award for Employer of the Year, and Best Place to Work Inc. Magazine • Recently named one of The Software Report's 3rd annual list of the Top 100 Software Companies of 2022 (worldwide!) We’re an equal opportunity employer. All applicants will be considered for employment without attention to race, color, age, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status: Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At WorkWave, we are dedicated to building a diverse, inclusive and authentic workplace, so if you feel like you could make a great impact in this role but your past experience doesn't align perfectly with every qualification in the job description, we encourage you to apply anyway. You may just be the right candidate for this or other roles!