Director of Product Management and IT Operations

About Self Bill Pro: Self Bill Pro is a rapidly growing startup dedicated to solving one of the most persistent challenges in the employee benefits ecosystem: the complexity of monthly benefits billing. We provide a tech-enabled service where our dedicated team leverages proprietary software to eliminate the administrative burdens of manual invoice audits and costly billing errors. Our mission is to streamline this critical operation, freeing up employers, brokers, and carriers to focus on their strategic priorities. About the Role: Compensation - $130,000 - 160,000 We are seeking a highly motivated and experienced Director of Product Management and IT Operations to lead the strategic direction and operational execution of our proprietary software platform. This is a critical leadership role that requires a unique blend of product management expertise, technical acumen, and operational leadership. You will be responsible for defining and driving the product roadmap while also ensuring the stability and security of our IT infrastructure and systems. Reports to: Chief Operating Officer Key Responsibilities: • Product Leadership: Partner with our global product manager to define, prioritize, and manage the product roadmap, ensuring it aligns with overall business objectives and our long-term technology vision. • Product Development: Lead the product development lifecycle from ideation to launch, including gathering and analyzing user feedback, writing detailed user stories and specifications, and collaborating with our offshore software development team. • Technical Oversight: Provide technical oversight and guidance to the development team on product features, enhancements, and operational issues. • Compliance & Security: Ensure compliance with security standards (e.g., SOC 2, HIPAA) and best practices, working to protect the organization’s data and systems. • Stakeholder Management: Effectively communicate with and manage relationships with various stakeholders, including customers, investors, and internal teams to gather requirements, test ideas, and communicate product progress. • Cross-functional Collaboration: Work closely with the stateside operational team to field feedback and translate business needs into technical requirements. • IT Operations & Helpdesk: Oversee day-to-day IT operations, including helpdesk support and quick resolution of operational issues and hotfixes as new employees are onboarded. • Extensive experience in a product management role, with a strong background in software development and project management. • Direct experience in the employee benefits or benefits administration technology space is a must. • Proven ability to think creatively about building software solutions and features that solve complex, real-world problems. • Strong communication skills and the ability to work effectively with both technical and non-technical stakeholders. • Experience managing and collaborating with a global or offshore development team. • Practical knowledge of IT operations, helpdesk support, and cybersecurity principles. • Familiarity with SOC 2 and HIPAA compliance requirements is highly desirable. • A natural leader with the ability to inspire and motivate a team, foster a positive work environment, and manage a high-volume workload in a fast-paced environment. Why Join Us? At Self Bill Pro, you’ll join a collaborative and ambitious team dedicated to transforming outdated processes through smart, scalable technology. As a key leader in a rapidly growing organization, you will have a direct impact on our product, our clients, and our future. If you are a highly motivated individual with a passion for technology, data, and making a tangible difference in the employee benefits landscape, we enc