Director of Technical Services

Job Description 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…