Director of Engineering

Location: Hybrid 1-2x in office (Austin, TX or Charlotte, NC)

Reports to: Head of Product

Team: ~35+ engineers (distributed / global contractors)

We’re looking for a Director of Engineering to lead and scale the next chapter of Olly Olly’s engineering organization. This role owns engineering execution, technical direction, and operational rigor across the organization
. You will own engineering outcomes end-to-end: team performance, delivery predictability, platform reliability, and technical direction, while installing the systems and discipline required to operate as a high-performing, scalable organization.

This is a builder-operator role
, not a maintenance role. You will inherit a fast-moving, scrappy environment and are expected to bring structure without slowing us down
.

• Engineering Leadership & Accountability
• Own engineering team performance, delivery, and business outcomes across the organization
• Lead and develop engineering managers and senior engineers across a distributed team
• Build a culture of ownership, accountability, and continuous improvement
• Hold managers accountable for team health, performance, and delivery
• Technical Direction & Governance
• Set and guide architecture, technical standards, and key engineering decisions
• Establish strong technical governance across infrastructure, security, and access
• Ensure sound system design to support scalability, reliability, and product evolution
• Translate complex technical concepts into clear business impact and tradeoffs
• Expected to be hands‑on enough to guide architecture and unblock teams, without operating as an individual contributor
• Platform Reliability & Infrastructure
• Own system stability, uptime, and performance across all environments
• Establish best practices for incident response, deployments, and infrastructure health
• Drive improvements in security, access management, and risk mitigation
• Own infrastructure and platform governance (excluding helpdesk/IT support)
• Engineering Operating System & Delivery Discipline
• Install and run a consistent engineering operating cadence (planning, refinement, execution)
• Improve delivery predictability and ensure commitments are credible and visible to the business
• Strengthen release quality, testing standards, and deployment discipline
• Reduce rework and increase confidence in engineering output
• Ensure engineering progress, risks, and capacity are clearly communicated and visible to leadership
• Product Partnership
• Partner closely with Product & Design leadership to ensure work is well-scoped, prioritized, and ready for engineering
• Drive clear tradeoffs between speed, scope, and quality
• Improve cross-functional alignment and reduce churn between teams

• 10+ years of experience in software engineering, with 5+ years in engineering leadership roles managing managers
• Proven experience leading engineering teams in a startup or high-growth environment
• Experience managing distributed / global teams (20–30+ engineers)
• Track record of improving execution, delivery discipline, and team accountability
• Experience partnering closely with Product and executive leadership

• Experience managing remote teams and fostering strong culture and development
• Strong talent assessment and coaching capabilities; able to raise the performance bar
• Ability to distinguish and address process vs. talent issues

• High standards for quality, accountability, and execution
• Strong prioritization and tradeoff judgment (balancing speed, quality, and scope)
• Data‑driven approach to engineering management (metrics, delivery, quality, reliability)
• Ability to design and implement scalable systems, processes, and operating cadences

• Comfortable operating in scrappy, ambiguous environments and bringing structure
• Proven ability to lead change and evolve team processes, structure, and accountability

• Strong ability to translate technical complexity into business impact
• Strong communicator across technical and non-technical stakeholders
• Strong ownership mindset; accountable for…