Director Product Management - Workflows & AI

About the role

Ideal candidate will be located in Central or Eastern Time Zones.

Paylocity is an award-winning provider of cloud-based HR and payroll software solutions, offering the most complete platform for the modern workforce. The company has become one of the fastest-growing HCM software providers worldwide by offering an intuitive, easy-to-use product suite that helps businesses automate and streamline HR and payroll processes, attract and retain talent, and build a strong workplace culture. While traditional HR and payroll providers automate basic HR processes such as payroll and benefits administration, Paylocity goes further by developing tools that HR and businesses need to compete for talent and deliver against the expectations of the modern workforce.

Responsibilities

• Product Strategy & Leadership
  • Define and execute customer-centric product strategies that deliver trusted AI and workflow experiences as part of the Paylocity platform and drive customer value for HR, IT, Finance, and business leaders.
  • Set high-level business direction for AI and Workflows platform capabilities, enabling intelligent solutions that can assist users, automate business processes, and act on users’ behalf within appropriate guardrails.
  • Identify high-impact opportunities to co-create innovative AI and workflow solutions with customers, grounded in trusted data practices and measurable business outcomes.
  • Clearly articulate the quantified value of AI and Workflow features to customers, executives, Sales, Customer Success, and go-to-market teams.
  • Define and manage business cases for key initiatives, ensuring alignment on product vision, customer value, user experience, success metrics, total cost of ownership, and corporate objectives.
  • Design and manage performance benchmarks and feedback loops to continuously improve AI and Workflow solutions and communicate what these capabilities can and cannot do.
  • Stay current on AI, workflow automation, agents, analytics, and HCM technology trends, using market and industry knowledge to raise the bar for product strategy and execution.
• Product Development & Execution
  • Translate strategic objectives into sequenced program initiatives with clear scope, resourcing assumptions, risks, dependencies, milestones, and measurable outcomes.
  • Lead a portfolio of AI and Workflows platform initiatives from concept through launch and iteration, driving delivery, removing roadblocks, and actively managing risks and dependencies.
  • Partner with Engineering, Data, UX, Security, Legal, and Compliance to translate capabilities into reliable, scalable product experiences that balance innovation with privacy, compliance, and enterprise-grade quality.
  • Ensure effective use of product development lifecycle processes, including maintaining JIRA hygiene, preparing executive status communications, incorporating early access feedback, and driving launch and go-to-market teams toward key business objectives.
  • Drive outcome- and learning-oriented operating feedback loops using product metrics, experimentation, customer feedback, and post-launch iteration.
  • Promote adoption of platform capabilities to enhance customer value while reducing operational and compliance risk.
• Innovation & Customer Growth
  • Deeply understand customer pain points and identify how AI, agents, workflow automation, and analytics can improve the customer experience and deliver business outcomes.
  • Monitor market trends, competitor capabilities, and emerging AI and Workflow technologies to identify opportunities for differentiation and customer value.
  • Foster a culture of experimentation, innovation, and continuous improvement, ensuring product decisions are informed by customer feedback, real-world usage data, and responsible AI practices.
• Cross-Functional Collaboration & Stakeholder Alignment
  • Align cross-functional partners across Engineering, UX, Data, Legal, Security, Compliance, Sales, Marketing, Customer Success, and Go-to-Market on outcomes, sequencing, dependencies, and launch readiness.
  • Present business cases, portfolio plans, progress, tradeoffs, and product impact reports to executive leadership with transparency on customer value, risk, adoption, and success metrics.
  • Establish strong feedback loops with customers, Sales, Support, Implementation, Customer Success, and early access programs to refine products, address pain points, and improve user experience.
• Governance & Trust
  • Partner with Legal, Security, and Compliance to ensure responsible AI usage, effective data governance, privacy, and retention practices.
  • Define guardrails for data usage and lifecycle management, including classification, access controls, retention policies, explainability, human-in-the-loop workflows, and reliability expectations.
  • Evaluate AI vendor offerings, models, and platforms with a strong risk, value, scalability, and ROI lens.
  • Communicate AI limitations clearly and honestly to internal and external stakeholders.
• Leadership & Team Development
  • Lead, mentor, coach, and develop a team of Product leaders and Product Managers across AI, Workflow, automation, and platform domains.
  • Set clear expectations, priorities, and standards for product excellence, including strong discovery, clear requirements, high-quality decision making, and accountability for outcomes.
  • Act as a multiplier by establishing reusable patterns, frameworks, and best practices for AI product development and responsible workflow automation.
  • Create mechanisms, systems, processes, and strategies that instill Paylocity values within the organization and foster a culture of innovation, continuous learning, and customer focus.

Requirements

• BS degree or higher in a related technical field.
• 8+ years of Product Management experience, with 3+ years in a senior or group product leadership role in a fast-paced SaaS environment.
• Demonstrated experience shipping AI-enabled, data-driven, agent, automation, or platform products in a B2B SaaS environment, preferably external products that operate at scale.
• Demonstrated experience shipping Workflow platform products in a B2B SaaS environment: external workflow products that operate at scale.
• Strong understanding of modern AI concepts, including LLMs, retrieval-augmented generation, agents, automation, analytics, and feedback loops at a product level.
• Proven ability to lead and scale product teams, strengthen product craft, and develop Product Managers and Product Leaders.
• Ability to successfully interface with technical and non-technical stakeholders at all levels, with exceptional executive communication and presentation skills.
• Experience working cross-functionally with Engineering, Data, UX, Design, Legal, Security, Compliance, Sales, Marketing, Customer Success, and Go-to-Market teams.
• Proven success developing product vision and strategy from customer needs, market insight, and business objectives.
• Strong track record guiding products through discovery, delivery, launch, iteration, and lifecycle management using strategic thinking, creative problem-solving, and adaptability to change.
• Strong business acumen with the ability to connect product metrics, adoption, customer outcomes, operational risk, and financial performance to business impact.
• Strong systems thinking and ability to leverage performance benchmarks and feedback loops to improve AI and Workflow performance over time.
• Experience managing competing priorities and aligning multiple areas of the business around common goals, dependencies, sequencing, and tradeoffs.
• Demonstrated ability to influence senior leaders and secure buy-in on product strategies, portfolio plans, and investment priorities.
• A strong sense of curiosity, with a passion for innovation, continuous learning, responsible AI, and staying ahead of industry trends.

Physical Requirements

• Ability to sit for extended periods: The role requires sitting at a desk or workstation for long periods, typically 7–8 hours a day.
• Use of computer and phone systems: The employee must be able to operate a computer, use phone systems, and type. This includes using multiple software programs and inquiries simultaneously.

Pay

The base pay range for this position is $190,000 – $275,000/yr; however, base pay offered may vary depending on job-related knowledge, skills, and experience. This position is eligible for an annual bonus and restricted stock.