About the Role

We are creating a dedicated Payroll Integrations Team and are seeking a strong Technical Lead who combines deep Ruby engineering expertise with strong business acumen and executive-level communication skills.

This role is not just a senior engineer—it is the technical owner and business liaison for our payroll integration strategy.

You will lead a team of Ruby integration engineers while serving as the primary bridge between engineering, clients, internal business units, implementation teams, and executive leadership. You must understand both the technical architecture and the business outcomes required to deliver successful payroll and benefits integrations.

This person will help define priorities, guide architecture, support client conversations, and ensure our integrations across payroll platforms are scalable, accurate, and aligned with business objectives.

Supported platforms include:

• Workday
• Paycom
• Dayforce
• ADP Workforce Now
• UKG Pro
• Paylocity
• Paycor

What You’ll Do

Technical Leadership

• Lead the design, architecture, and delivery of payroll and benefits integrations across major payroll providers
• Provide technical leadership and mentorship to a dedicated team of Ruby engineers
• Establish engineering standards, code quality expectations, and integration best practices
• Review architecture decisions and guide complex technical problem-solving
• Own technical prioritization, backlog planning, and delivery execution for payroll integrations
• Drive continuous improvements across reliability, scalability, and supportability

Business & Client Leadership

• Serve as the primary technical liaison between engineering, clients, implementation teams, operations, and executive leadership
• Participate in customer calls, implementation discussions, escalation management, and solution design sessions
• Translate business requirements into technical solutions and communicate technical tradeoffs clearly to stakeholders
• Partner with product and executive leadership to align technical priorities with business goals
• Help define integration strategy, roadmap planning, and client delivery expectations
• Support pre-sales, implementation planning, and strategic client conversations where needed

Engineering Responsibilities

• Write and review production-quality Ruby on Rails code
• Build secure, scalable APIs and integration services
• Support complex data mapping, transformation, and workflow orchestration
• Troubleshoot and resolve critical integration issues across clients and vendors
• Ensure operational excellence across integrations and platform stability

What We’re Looking For

Required Experience

• 10+ years of professional software engineering experience
• 7+ years of Ruby on Rails development experience
• Significant experience leading complex payroll/HRIS integrations
• Proven experience with one or more:
• Workday
• Paycom
• Dayforce
• ADP Workforce Now
• UKG Pro
• Paylocity
• Paycor
• Previous experience in a Technical Lead, Solutions Architect, Integration Lead, or Engineering Leadership role
• Strong client-facing experience with the ability to lead business and technical discussions confidently
• Deep understanding of payroll systems, benefits administration, deductions, eligibility, and enrollment workflows
• Expertise in API architecture, file integrations, ETL workflows, and enterprise integration patterns
• Strong knowledge of relational databases, Rails architecture, and distributed systems
• Experience working directly with executive stakeholders and cross-functional business leaders

Nice to Have

• Experience in benefits administration, HR Tech, InsurTech, or payroll platforms
• Experience supporting enterprise implementations and customer onboarding
• AWS, Redis, Docker, Kubernetes experience
• Observability and production operations experience
• Exposure to compliance and security requirements in payroll/benefits environments

What You’ll Bring

• Strong executive presence and excellent communication skills
• The ability to lead both technically and strategically
• Confidence in customer-facing environments and high-visibility business discussions
• Strong decision-making skills and ownership mentality
• A builder’s mindset with the ability to create structure where it doesn’t yet exist
• Deep technical credibility combined with practical business judgment
• A strong bias toward action, accountability, and measurable outcomes