Director, Software Engineering

Director Of Software Engineering

At Cast & Crew, we've empowered creativity and supported the global entertainment industry for decades. Together with our family of brands, we operate as a combined entertainment technology and services provider offering industry standard screenwriting accounting software, digital payroll products, data & reporting, and a host of creative tools. The industry continues to move faster than ever, and the need for our expertise, our technology, and our people has never been greater. We are a production's best ally every step of the way. #OneCastOneCrew

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.

Core Responsibilities

Servant Leadership & Team Development

• 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

Spotify Model: Squads, Tribes, Chapters & Guilds

• 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

Mobile Applications & Rapid Growth

• 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

Product Delivery & Quality

• 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

Cross-Product Collaboration

• 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

AI-Driven SDLC

• 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

Technical Direction

• 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

Key Qualifications

• 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

Preferred Qualifications

• 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

Special Work Conditions

• Sedentary – Involves sitting most of the time but may involve walking or standing for brief periods of time. Some positions may entail exerting up to 15 lbs. of force occasionally and/or a negligible amount of force to lift, carry, push, or pull.

#LI-REMOTE

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Benefits

Cast & Crew provides a comprehensive package of employee benefits including: Medical, Dental, Vision, PTO, health and wellness programs, employee discounts, and more! Note: Cast & Crew benefits are subject to eligibility requirements.

Cast & Crew is an equal opportunity employer committed to hiring a diverse workforce and sustaining an inclusive culture. It is our policy to provide equal employment opportunities to all individuals based on job-related qualifications and ability to perform a job, without regard to age, gender, gender identity, sexual orientation, race, color, religion, creed, national origin, disability, genetic information, veteran status, citizenship or marital status, and to maintain a non-discriminatory environment free from intimidation, harassment or bias based upon these grounds.

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Compensation is commensurate with various factors including, but not limited to, relevant experience, qualifications, skills, training, licensure, certifications, geographic cost of labor, and other business and organizational needs. Compensation range for candidates in other locations may differ based on the cost of labor in that location. The compensation range for this position is: $180,000.00 - $225,000.00 per year.