Director, Software Engineering

Cast & Crew

5d•$180,000 - $225,000•Remote

About The Position

We're looking for a Director of Software Engineering to lead multiple engineering teams within our Onboarding and Timekeeping product line — one of the most active and strategically important areas of the business. This is a role for a leader, not just a manager. You'll cultivate ownership and decision-making at the team level, develop strong engineering anchors, and create an environment where your teams don't wait for direction — they are empowered to move. You'll own the engineering execution of a robust product roadmap that includes mobile applications in a rapid growth phase, drive deep collaboration with Product and QA, and connect your teams into the broader engineering organization through a Spotify-inspired model of Squads, Tribes, Chapters, and Guilds. You'll also champion our initiative to embed AI meaningfully into how we build software. We're in the middle of a cultural shift — moving faster, owning outcomes, celebrating wins, and holding each other to a high bar. We work hard and play hard. This role requires someone who can get up to speed quickly, lead with empathy from day one, and immediately begin delivering impact.

Requirements

10+ years in software engineering, with 4+ years in engineering leadership managing managers
Strong technical background — you can engage credibly on system design, architecture tradeoffs, and engineering quality
A proven philosophy of developing leaders, not just managing reports — you know the difference and live it
Experience leading or scaling mobile application engineering, ideally in a high-growth context
Track record of shortening delivery timelines and improving quality through process, culture, and tooling — not heroics
Hands-on familiarity with the Spotify model (Squads, Tribes, Chapters, Guilds) and experience operating within or building toward it
Experience leading globally distributed teams across multiple time zones
Strong cross-functional collaboration instincts — especially with Product and QA
Experience with AI-assisted development tooling and enthusiasm for applying it to improve team productivity
Excellent communicator; comfortable at the executive level and equally comfortable listening at the team level

Nice To Haves

Experience in workforce management, payroll, timekeeping, or HR tech domains
Experience managing teams with heavy external integration complexity
Familiarity with engineering metrics frameworks (DORA, SPACE, etc.)
Prior experience driving a meaningful cultural transformation

Responsibilities

Build a culture of distributed ownership — push decision-making down to the team level and develop strong team anchors who lead with confidence
Coach and grow engineering managers, QA leads, and senior engineers into well-rounded technical leaders
Embody the distinction between leadership and management: inspire, develop, and get out of the way
Champion a work hard, play hard team culture — high standards, fast feedback, and genuine celebration of wins
Lead and align multiple Squads — autonomous, cross-functional teams each owning a slice of the Onboarding and Timekeeping product line — ensuring they have the clarity, resources, and psychological safety to self-organize and deliver
Operate as a Tribe leader across these Squads, driving coherence, shared mission, and cross-team coordination within the product line
Actively develop Chapters — communities of engineers who share a discipline (e.g., mobile, backend, QA) — ensuring members grow in craft, adopt consistent practices, and carry excellence across Squad boundaries
Grow and support Guilds as voluntary communities of interest that spread knowledge and innovation across the broader engineering organization
Use this structure not as org-chart formality, but as the engine for building well-rounded, continuously improving team members
Guide engineering strategy and execution for mobile applications that are in an active rapid growth phase — balancing speed, quality, and scalability
Partner with mobile chapter leads and senior engineers to establish strong mobile engineering practices, CI/CD pipelines, and quality standards
Anticipate the unique challenges of scaling a mobile product: release cadence, device fragmentation, app store pipelines, and performance at scale
Attract and develop mobile engineering talent to match the growth trajectory of the product
Own engineering delivery against a demanding roadmap — shorten delivery timelines, improve delivery quality, and build the practices that make both sustainable
Set clear commitments, surface risks early, and consistently ship with quality
Involve QA leads as first-class collaborators in planning, not an afterthought at the end
Work shoulder-to-shoulder with Product to refine priorities, scope tradeoffs, and translate business goals into engineering plans
Navigate a complex integration landscape — your teams touch and are touched by multiple other product lines; you ensure those relationships are healthy, proactive, and unblocking
Drive alignment and coordination across internal product teams and with peer engineering leaders in other product lines
Represent your teams well in cross-functional forums and escalate and resolve dependencies with urgency
Own the strategy and execution of our AI-Driven SDLC initiative — define how AI tooling is adopted, measured, and continuously improved across your teams
Establish metrics that demonstrate real gains in velocity and quality, not just adoption theater
Stay ahead of the tooling landscape and bring informed, opinionated recommendations to the organization
Maintain strong technical engagement — able to get into architecture decisions, unblock teams, and give meaningful feedback on system design and engineering quality
Partner with architects and senior engineers to ensure decisions align with long-term platform goals
Drive engineering quality through observability, incident response, code standards, and post-mortems