Director of Engineering

Location: Hybrid 1-2x in office (Austin, TX or Charlotte, NC)Reports to: Head of ProductTeam: ~35+ engineers (distributed / global contractors)About The RoleWe’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.What You’ll Own Engineering Leadership & AccountabilityOwn engineering team performance, delivery, and business outcomes across the organizationLead and develop engineering managers and senior engineers across a distributed teamBuild a culture of ownership, accountability, and continuous improvementHold managers accountable for team health, performance, and delivery Technical Direction & GovernanceSet and guide architecture, technical standards, and key engineering decisionsEstablish strong technical governance across infrastructure, security, and accessEnsure sound system design to support scalability, reliability, and product evolutionTranslate complex technical concepts into clear business impact and tradeoffsExpected to be hands-on enough to guide architecture and unblock teams, without operating as an individual contributor Platform Reliability & InfrastructureOwn system stability, uptime, and performance across all environmentsEstablish best practices for incident response, deployments, and infrastructure healthDrive improvements in security, access management, and risk mitigationOwn infrastructure and platform governance (excluding helpdesk/IT support) Engineering Operating System & Delivery DisciplineInstall and run a consistent engineering operating cadence (planning, refinement, execution)Improve delivery predictability and ensure commitments are credible and visible to the businessStrengthen release quality, testing standards, and deployment disciplineReduce rework and increase confidence in engineering outputEnsure engineering progress, risks, and capacity are clearly communicated and visible to leadership Product PartnershipPartner closely with Product & Design leadership to ensure work is well-scoped, prioritized, and ready for engineeringDrive clear tradeoffs between speed, scope, and qualityImprove cross-functional alignment and reduce churn between teamsCore ExperienceWhat We’re Looking For10+ years of experience in software engineering, with 5+ years in engineering leadership roles managing managersProven experience leading engineering teams in a startup or high-growth environmentExperience managing distributed / global teams (20–30+ engineers)Track record of improving execution, delivery discipline, and team accountabilityExperience partnering closely with Product and executive leadershipCore CompetenciesLeadership & Team DevelopmentExperience managing remote teams and fostering strong culture and developmentStrong talent assessment and coaching capabilities; able to raise the performance barAbility to distinguish and address process vs. talent issuesExecution & Delivery DisciplineHigh standards for quality, accountability, and executionStrong 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 cadencesOperating in Ambiguity & ChangeComfortable operating in scrappy, ambiguous environments and bringing structureProven ability to lead change and evolve team processes, structure, and accountabilityCommunication & Cross-Functional InfluenceStrong ability to translate technical complexity into business impactStrong communicator across technical and non-technical stakeholdersStrong ownership mindset; accountable for outcomes, not just engineering outputAbility to influence cross-functional stakeholders without direct authorityBusiness & Customer OrientationUnderstands and prioritizes customer and business impact in engineering decisionsTechnical Requirements (Must-Have)Software Architecture & Distributed Systems: ExpertDefines system architecture, service boundaries, integration patterns, and long-term technical directionMakes sound tradeoffs across speed, reliability, scalability, cost, and complexityDrives simplification, technical debt management, and maintainabilityCloud & Infrastructure (GCP): ProficientOwnership of Google Cloud environments, APIs, services, billing, and environment strategyStrong judgment on scaling, availability, cost control, and operational resilienceDatabase, Data Systems & Backend Reliability (PostgreSQL / Supabase a plus): ProficientDatabase performance, scaling, backups, failover, migrations, and restoration confidenceData modeling, cross-system consistency, and source-of-truth decisionsExperience with business continuity and disaster recoveryReliability, Observability & Incident Management: ProficientMonitoring, alerting, logging, tracing, on-call readiness, incident response, and postmortemsEstablishes service health standards, operational reviews, and production readiness expectationsCI/CD, Release Engineering & Source Control (GitLab): ProficientPipelines, deployments, release processes, environment management, rollback strategy, and secret managementBuilds safe, repeatable release discipline with clear quality gatesSecurity & Risk Management: ProficientSecure SDLC, IAM/access controls, secrets management, vulnerability remediation, and audit abilityProtects customer and business-critical systems through practical engineering controlsAPI & Systems Integrations: ExpertDeep experience building and managing systems leveraging third-party APIs and internal servicesStrong understanding of integration reliability, failure modes, retry patterns, and downstream impactQuality Engineering & Test Strategy: ProficientAutomated testing strategy, integration and E2E coverage, regression prevention, and UAT readinessImproves quality by building preventive systems, not just reacting to bugsApplication / Product Engineering: ProficientStrong full-stack awareness and product-engineering judgmentCan support fast product delivery while preserving architectural integrityWhat Success Looks LikeEngineering commitments are credible, predictable, and consistently metDelivery is faster, more consistent, and less reactive, with clear visibility into progress and riskReleases are high quality, repeatable, and require minimal reworkPlatform reliability, uptime, and system health measurably improveProduct and Engineering operate with clear alignment, strong partnership, and reduced churnEngineering output is clearly understood and trusted by the businessRole Evolution50% tactical / 50% strategic (stabilize + install systems)