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.
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
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
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)
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
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
Leadership & Team Development
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
Execution & Delivery Discipline
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
Operating in Ambiguity & Change
Comfortable operating in scrappy, ambiguous environments and bringing structure
Proven ability to lead change and evolve team processes, structure, and accountability
Communication & Cross-Functional Influence
Strong ability to translate technical complexity into business impact
Strong communicator across technical and non-technical stakeholders
Strong ownership mindset; accountable for outcomes, not just engineering output
Ability to influence cross-functional stakeholders without direct authority
Business & Customer Orientation
Software Architecture & Distributed Systems: Expert
Defines system architecture, service boundaries, integration patterns, and long-term technical direction
Makes sound tradeoffs across speed, reliability, scalability, cost, and complexity
Drives simplification, technical debt management, and maintainability
Cloud & Infrastructure (GCP): Proficient
Ownership of Google Cloud environments, APIs, services, billing, and environment strategy
Strong judgment on scaling, availability, cost control, and operational resilience
Database, Data Systems & Backend Reliability (PostgreSQL / Supabase a plus): Proficient
Database performance, scaling, backups, failover, migrations, and restoration confidence
Data modeling, cross-system consistency, and source-of-truth decisions
Experience with business continuity and disaster recovery
Reliability, Observability & Incident Management: Proficient
Monitoring, alerting, logging, tracing, on-call readiness, incident response, and postmortems
Establishes service health standards, operational reviews, and production readiness expectations
CI/CD, Release Engineering & Source Control (GitLab): Proficient
Pipelines, deployments, release processes, environment management, rollback strategy, and secret management
Builds safe, repeatable release discipline with clear quality gates
Security & Risk Management: Proficient
Secure SDLC, IAM/access controls, secrets management, vulnerability remediation, and audit ability
Protects customer and business-critical systems through practical engineering controls
API & Systems Integrations: Expert
Deep experience building and managing systems leveraging third-party APIs and internal services
Strong understanding of integration reliability, failure modes, retry patterns, and downstream impact
Quality Engineering & Test Strategy: Proficient
Automated testing strategy, integration and E2E coverage, regression prevention, and UAT readiness
Improves quality by building preventive systems, not just reacting to bugs
Application / Product Engineering: Proficient
Engineering commitments are credible, predictable, and consistently met
Delivery is faster, more consistent, and less reactive, with clear visibility into progress and risk
Releases are high quality, repeatable, and require minimal rework
Platform reliability, uptime, and system health measurably improve
Product and Engineering operate with clear alignment, strong partnership, and reduced churn
Engineering output is clearly understood and trusted by the business
