Director of Technical Services

We are seeking a Director of Technical Services to work on service technology in Small Business Services. This is a high-impact director-level position that combines technical leadership, project orchestration, and cross-functional coordination to drive business outcomes through innovation and client obsession. 

The ideal candidate will bring 8+ years of experience in product management or similar fields, with proven expertise in both managing complex internal projects and collaborating with engineering and business teams to deliver customer-facing capabilities. 

Key Responsibilities 

Technical Project & Portfolio Management 

• In partnership with business and engineering teams, define scope, refine requirements, and establish success criteria for technical projects
• Provide thoughtful analysis that tells us what outcomes our work is providing, and where we need to double down
• Maintain visibility into the portfolio of ongoing technical projects and ensure strategic alignment

Cross-Functional Product Coordination 

• Partner with the Service Technology Engineering team to translate business needs into technical solutions
• Act as a product strategist (not a product owner managing backlogs, but a strategic advisor on technical direction)
• Collaborate with business stakeholders, engineering, design, and UX research teams to clarify priorities and unblock work
• Work positively and effectively with internal customers including client service associates, executives, and frontline managers

Stakeholder Management & Communication 

• Serve as a bridge between technical teams, business leaders, and users
• Gather insights from client data, analytics, and direct user feedback to inform service technology decisions
• Communicate technical constraints and tradeoffs to non-technical stakeholders
• Maintain a data-driven approach to prioritization and decision-making

Strategic Leadership 

• Use analytics and customer insights to understand what the business truly requires to achieve objectives
• Develop evidence-based opinions and validate them through research
• Navigate ambiguity and make progress without waiting for perfect information
• Keep teams energized and moving forward with optimistic, collaborative leadership

What We're Looking For 

Core Competencies (Required) 

• Bachelor's degree in a technical, analytical, or business-related field (or equivalent experience)
• 8+ years of proven experience in product management, technical operations, or related roles
• Full SDLC expertise - demonstrated success from discovery through launch and post-launch analysis
• Technical acumen - Ability to engage deeply with engineers on technical decisions, architecture, and system design
• Data fluency - Comfortable with analytics tools, can pull reports, interpretation of data
• Clear communicator - Can write business cases, run productive meetings, and explain technical concepts to diverse audiences
• Comfortable with ambiguity - Make progress without complete information and course-correct quickly
• Naturally collaborative - Works well with engineering, design, business teams; shares perspectives and commits fully once direction is set

Preferred Qualifications 

• Regulated industry experience - Background in payroll, HR, tax, fintech, healthcare, or similar domains where compliance and accuracy are critical
• AI/Automation expertise - Hands-on experience integrating GenAI or LLM tooling into workflows; understands capabilities and limitations
• Technical background - Some hands-on experience with software development, even if not a full-time engineer
• Built something - Created and shipped a product, tool, or side project, preferably using modern development approaches
• Early adopter mindset - Actively learning emerging technologies and applying them to solve business problems

What We Offer 

• Impact at scale - Your decisions drive product strategy and internal operations with direct impact on customer outcomes
• Intellectual challenge - Work at the intersection of technology, product, and business with complex, meaningful problems
• Collaborative culture - Join a team that values courageous conversations, innovation, and continuous learning
• Career growth - Opportunities to develop expertise in emerging technologies and move into broader leadership roles
• Inclusive environment - Work in a culture that embraces diverse perspectives and empowers all associates

How to Apply 

Qualified candidates should submit: 

• Resume with relevant product and technical leadership experience
• Cover letter describing your approach to product strategy and cross-functional collaboration
• Optional: Link to portfolio, side projects, or examples of work you've shipped