Director of Technical Services

We are seeking a Director of Technical Operations 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 teams to deliver customer-facing capabilities.

• Manage the intake and prioritization of data science, tools, and feature requests from internal stakeholders
• Define scope, refine requirements, and establish success criteria for technical projects
• Partner with product owners to deliver
• 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

• 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

• 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

• Use analytics and customer insights to understand what he business actually needs
• 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

• 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, interpret data, and act on insights independently
• Clear communicator
  - Can write business cases, run productive meetings, and explain technical concepts to diverse audiences
• Comfortable with ambiguity
  - Makes progress without complete information and course-corrects quickly
• Naturally collaborative
  - Works well with engineering, design, business teams; shares perspectives and commits fully once direction is set
• Client obsessed
  - Stays close to real users through calls, session recordings, support tickets, and ongoing research

• 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
• Technical trend awareness
  - Follows technology industry developments through blogs, podcasts, books, and industry resources

• Collaborate with engineering and business teams to align on priorities and unblock technical work
• Review analytics reports and client feedback to identify patterns and opportunities
• Facilitate discussions between technical teams and business stakeholders to solve complex problems
• Create clear business requirements with a point of view on technical approach
• Conduct or coordinate customer research and usability validation
• Present…