Senior Director, Product Management

Role Description

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:

• 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.
• 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.
• 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.

Qualifications

• 10+ years in PM, with 5+ years managing and growing PM teams within enterprise B2B SaaS.
• Background in mission-critical platforms (ERP, workforce management, payroll, or high-volume operations software) is strongly preferred.
• Proven success modernizing mature platforms, navigating tech debt, and managing customer change management without business disruption.
• Practical knowledge of how to design and launch AI-assisted, data-driven software capabilities.
• Exceptional ability to influence internal stakeholders, lead strategic customer conversations, and present to executive leadership.
• Bachelor’s degree required; MBA or advanced degree preferred.

Requirements

• $160,000 - $200,000 a year.
• Final offer will be dependent on various factors, including the candidate's qualifications, relevant experience, and the organization's budget.

Benefits

• Casual work environment and remote work flexibility.
• Robust benefits package, including health and dental and 401k with company match.
• 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.