Chief Product Officer

About ConnectPay
ConnectPay provides comprehensive payroll and HR solutions specifically designed for small and medium-sized businesses. Our mission is to simplify payroll processes while enhancing employee experience, and ensuring full regulatory compliance, enabling our clients to focus on growing their businesses.
At ConnectPay, we pride ourselves on combining cutting-edge technology with a personalized, human-first approach. We understand that every business is unique, so we tailor our services—including payroll processing, tax compliance, and HR support—to meet the specific needs of our clients.
We believe that our employees are our most valuable asset. By fostering a culture of innovation, collaboration, and professional growth, we empower our team to deliver exceptional service and create meaningful daily impact for our clients.

Job Summary
The Chief Product Officer will own the Product Vision for the company and be responsible for the development, justification, and acceptance of that vision. He/she will also serve as strategic thought partner to both the CEO and CTO, actively contributing to the growth strategy, technology roadmap alignment, and product-market evolution. This role demands a leader who can bridge business vision, technical feasibility, and market opportunity though collaborative, strategic dialogue. This is an executive-level position with direct accountability for product revenue, sourcing and specifications.

Key Responsibilities:
Executive Leadership & Strategic Partnership

• Serve as strategic thought partner to the CEO and CTO, contributing to company vision, through regular strategic dialogue and collaborative planning sessions while owning the short and long-term product vision and roadmap.
• Develop and communicate quarterly product business performance reviews, strategic roadmap updates, and investment recommendations to the organization and the Board of Directors, demonstrating clear ROI and marketing position.
• Own product P&L with direct accountability for revenue targets, profitability metrics, and resource allocation decisions across the product portfolio.
• Own pricing strategy and monetization models across product portfolio, with demonstrated ability to optimize price-value positioning for our markets.
• Build and maintain executive relationships with strategic customers, partners and industry stakeholders, representing the company at C-level engagements and strategic account reviews.
• Build and maintain executive relationships with the rest of the ConnectPay senior management team.
• Identify strategic acquisition targets to augment the company's product portfolio

Product Strategy and Industry Expert Leader

• Stay abreast of industry trends, identifying opportunities for new products and enhancements.
• Develop and implement a comprehensive product strategy that aligns with the company’s vision and market opportunities.
• Define product requirements, roadmaps, and key performance metrics to guide development and measure success, establishing clear product management artifacts including user stories, acceptance criteria, and success metrics.
• Drive product portfolio rationalization, making data-driven decisions about product investment levels, sunsetting underperforming offerings and resource allocation to maximize portfolio ROI.

Product Execution & Delivery

• Lead the entire product lifecycle, from ideation to market launch, ensuring alignment with business goals and customer needs while maintaining rigorous product management standards and documentation.
• Collaborate across the organization to build innovative products that resonate with target markets, particularly small and mid-size business customers.
• Drive customer feedback loops to ensure product features meet market demands and deliver superior user experiences.
• Foster a culture of continuous improvement, leveraging data and analytics to refine product offerings and institutionalize evidence-based decision making.

Team Development & Culture

• Build, expand, and mentor a high-performing product organization that thrives on innovation, collaboration, and customer focus.
• Define clear roles, responsibilities, and growth opportunities for product and design team members, establishing product management competencies.
• Develop high-performance processes that facilitate both the product management group and the rest of the organization in their ability to design, develop, and deploy critical products and processes for our customers.
• Foster alignment and momentum across teams with a shared focus on delivering client and business outcomes.
• Create a culture of innovation, experimentation, and calculated risk taking that encourages breakthrough thinking while maintaining operational discipline.

Success Metrics
Success in this role will be measured by:

• Achievement of product revenue and profitability targets.
• Product adoption, customer retention, and Net Dollar Retention (NDR).
• Market share growth and competitive win rates.
• On-time delivery of strategic roadmap commitments.
• Quality of strategic insights and recommendations presented to executive team and Board of Directors.
• Enhanced penetration level into customer base

Qualifications

• MBA and 15+ years in tech-enabled services; including 5+ years the VP level or above
• Proven success leading B2B and B2B2C product strategy, management and design through high-growth scaling, with demonstrated experience serving small and mid-sized (SMB) markets
• Deep expertise in product management methodologies, agile development, and user experience best practices, with track record of establishing product management discipline across organizations
• Experience in private equity-backed, venture-backed, or high-growth startups-to-scale environments with demonstrated ability to operate under performance pressure
• Demonstrated ability to serve as strategic thought partner to fellow C-suite executives, contributing meaningfully to business strategy and vision alongside operational excellence
• Experience building and mentoring high-performing product teams, ideally in private equity-backed or startup-to-scale environments
• Must possess a strong sense of urgency with a bias for action and demonstrate a strength in conviction
• High emotional intelligence with a proven ability to navigate organizational complexity, manage conflict and build consensus with peers, the Board of Directors and investors.

CP Payroll believes in fair and equitable pay. A reasonable estimate of this role’s hiring base salary range is $200,000 – 220,000. The actual salary will depend on a variety of factors, including but not limited to a candidate’s education, training, experience, location, and internal equity. In addition to base salary, all CP Payroll team members receive equity and participate in either an annual bonus plan, based on company and individual performance, or a role-based sales incentive plan.

This role is eligible for an annual bonus with a target of 25% of base salary, based on company and individual performance.

At CP Payroll, we are proud to offer a comprehensive team member benefits package, including 401(k) with company contributions, group 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 a work environment free from discrimination and harassment. All employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, marital status, veteran status, or any other protected characteristic under applicable law.