Head of Engineering

Head of Engineering

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

Reports to: CEO (Liz) with dotted-line alignment to Head of Product

Team: ~20–30 engineers (distributed / global contractors)

About the Role

We’re looking for a Head 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

1. 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

2. 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

3. 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)

4. 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

5. 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

6. Organizational Scaling

• Evaluate team structure, talent mix, and management effectiveness
• Make changes needed to raise the bar on performance and scalability
• Build systems that enable engineering to scale without creating chaos

What We’re Looking For

Core Experience

• 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

Core Competencies

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

• Understands and prioritizes customer and business impact in engineering decisions

Technical Requirements (Must-Have)

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

• Strong full-stack awareness and product-engineering judgment
• Can support fast product delivery while preserving architectural integrity

What Success Looks Like

• 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

Role Evolution

• First 3–6 months: 80% tactical / 20% strategic (stabilize install systems)
• After stabilization: Transition to 50% tactical / 50% strategic (scale optimize)