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.

Key Responsibilities

Technical Project & Portfolio Management

· 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

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 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

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, 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

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

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

Day-to-Day Activities

This is a varied, dynamic role with no two days alike:

· 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 findings and recommendations to leadership

· Mentor team members and build technical capacity within your organization

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