Head of Engineering

Head of Engineering

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)