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Head of EngineeringPosition OverviewWe are seeking an experienced Head of Engineering to lead an engineering organization through a large-scale platform rebuild while remaining deeply hands-on in the codebase. This is a player-coach leadership role responsible for engineering people, delivery, process, architecture, hiring, reliability, and the successful transition from a legacy platform to a rebuilt production environment.The ideal candidate is an experienced engineering leader who has not fully stepped away from software development and is comfortable making architectural decisions, writing production code, leading engineers, and owning complex technical delivery. This role requires strong judgment around scope, sequencing, technical tradeoffs, migration risk, and operational reliability.The Head of Engineering will report directly to the CEO and work closely with Product, Growth, Finance, and other business leaders.Key ResponsibilitiesPlatform Rebuild &amp; Technical Leadership<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Lead the architecture, sequencing, and implementation of a large-scale platform rebuild.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Remain hands-on in the codebase, contributing directly to load-bearing technical work and establishing patterns for the broader engineering team.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Evaluate architectural decisions and recommend changes when existing approaches no longer serve the needs of the platform.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Ensure technical changes are carefully evaluated, sequenced, and implemented rather than introducing unnecessary complexity or simultaneous changes across the platform.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish clear technical standards and provide architectural direction to engineering teams.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain a practical balance between technical quality, delivery timelines, scalability, and business priorities.</li>
</ul>Product Parity &amp; Delivery<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish and maintain clear capability requirements for each product domain.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Protect the scope required for launch while identifying and managing potential scope creep.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Evaluate whether functionality has genuinely reached production parity before major milestones.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Continuously reassess delivery plans based on actual engineering velocity and changing technical requirements.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain predictable development and release processes with clear milestones and timelines.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Partner with Product and business leadership to communicate technical progress, risks, dependencies, and revised timelines.</li>
</ul>Platform Migration &amp; Cutover<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Own the strategy and execution of a major platform migration and production cutover.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Develop and maintain migration tooling capable of operating against production data and snapshots.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Lead repeated migration rehearsals to identify and resolve issues before the final cutover.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish reconciliation processes for financial, transactional, user, and other critical data.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Define and test rollback procedures to ensure a controlled and recoverable migration process.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish measurable acceptance criteria for the migration and cutover.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Ensure critical historical data and financial information are migrated accurately and completely.</li>
</ul>Infrastructure, Reliability &amp; Operations<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Oversee the reliability, scalability, and operational health of both legacy and rebuilt platforms.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Manage sustaining engineering efforts for the existing platform while maintaining a clear separation between maintenance work and rebuild priorities.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish priorities for production issues, with particular attention to revenue-impacting and critical platform functionality.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain effective on-call, incident response, monitoring, and reliability processes.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Monitor infrastructure performance and maintain visibility into engineering and platform costs.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Identify and address operational risks before they become production issues.</li>
</ul>Architecture &amp; Technology<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Lead development within a modern, minimal AWS-based serverless architecture.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Work with TypeScript across frontend, backend, infrastructure, and testing environments.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Guide development using technologies such as React, Vite, AWS Lambda, API Gateway, Step Functions, AppSync Events, Aurora DSQL, DynamoDB, Cognito, CloudFront, and AWS CDK.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain infrastructure and deployment practices using modern CI/CD workflows and secure authentication mechanisms.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Apply managed cloud services where appropriate and avoid unnecessary operational complexity.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Evaluate requests for new technologies or infrastructure based on demonstrated technical need, scalability, reliability, and maintainability.</li>
</ul>Compliance, Security &amp; Risk Management<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Provide engineering leadership for technical compliance requirements that affect product development and platform launches.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish appropriate security, privacy, data retention, identity verification, and payment-related controls.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Partner with relevant stakeholders to understand compliance requirements and incorporate them into engineering plans.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain strong standards for secure development, testing, code review, and production access.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Identify and mitigate technical and operational risks associated with sensitive data and financial transactions.</li>
</ul>Engineering Management &amp; People Leadership<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Manage and develop the engineering team while remaining actively involved in technical execution.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish clear expectations around engineering quality, ownership, communication, and delivery.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Recruit and hire engineers with the skills required to support the platform rebuild and long-term growth.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Coach engineers and help develop technical leadership within the organization.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish effective code review, testing, documentation, and development practices.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Build an engineering culture focused on accountability, quality, thoughtful decision-making, and continuous improvement.</li>
</ul>Delivery &amp; Engineering Operations<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain a clear engineering roadmap, development workflow, and delivery cadence.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Establish predictable shipping schedules and ensure the business has clear visibility into engineering commitments.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Maintain appropriate engineering processes without creating unnecessary bureaucracy.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Use measurable progress and actual delivery velocity to inform planning.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Ensure engineering priorities remain aligned with product and business objectives.</li>
</ul>Technical Environment<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Language: TypeScript</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Frontend: React + Vite</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
API &amp; Compute: AWS API Gateway, Lambda, Step Functions</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Realtime: AppSync Events</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Data: Aurora DSQL and DynamoDB</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Identity &amp; Edge: Cognito and CloudFront</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Infrastructure: AWS CDK</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
CI/CD: GitHub Actions with OIDC-based AWS authentication</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Architecture: AWS serverless, managed-service-focused environment</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">
Development: Single repository and unified TypeScript codebase</li>
</ul>Required Qualifications<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Significant experience leading engineering teams and complex software development initiatives.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Demonstrated experience remaining hands-on with production code while managing an engineering organization.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Strong software architecture and system design experience.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience leading large-scale platform migrations, rewrites, or modernization initiatives.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience managing complex production cutovers and migration risk.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Strong experience with TypeScript and modern web application development.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Strong understanding of AWS and serverless architecture.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience with cloud infrastructure, CI/CD, production reliability, and incident response.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Strong understanding of databases, APIs, distributed systems, and scalable application architecture.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience establishing engineering standards around testing, code review, security, and development practices.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Strong people management, hiring, coaching, and organizational leadership skills.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Ability to make pragmatic technical decisions while balancing product requirements, business priorities, and delivery timelines.</li>
</ul>Preferred Qualifications<ul style="margin:0px;padding-left:40px;">
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience with AWS services including Lambda, API Gateway, Step Functions, DynamoDB, Aurora, Cognito, CloudFront, and CDK.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience leading a platform rebuild while simultaneously maintaining a legacy production system.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience with high-volume transactional or consumer-facing platforms.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience with payment systems or other systems requiring strong data consistency and reconciliation.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience designing and executing zero- or low-downtime migration strategies.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience establishing engineering organizations and processes during periods of rapid growth.</li>
<li style="line-height:1.2;font-family:Arial;font-size:14px;color:rgb(0, 0, 0);margin:0px;">Experience working closely with executive leadership, Product, Finance, and other cross-functional teams.</li>
</ul>

Head of Engineering

Position Overview

We are seeking an experienced Head of Engineering to lead an
engineering organization through a large-scale platform rebuild
while remaining deeply hands-on in the codebase. This is a
player-coach leadership role responsible for engineering people,
delivery, process, architecture, hiring, reliability, and the
successful transition from a legacy platform to a rebuilt
production environment.

The ideal candidate is an experienced engineering leader who has
not fully stepped away from software development and is
comfortable making architectural decisions, writing production
code, leading engineers, and owning complex technical delivery.
This role requires strong judgment around scope, sequencing,
technical tradeoffs, migration risk, and operational reliability.

The Head of Engineering will report directly to the CEO and work
closely with Product, Growth, Finance, and other business
leaders.

Key Responsibilities

Platform Rebuild & Technical Leadership

* Lead the architecture, sequencing, and implementation of a
large-scale platform rebuild.
* Remain hands-on in the codebase, contributing directly to
load-bearing technical work and establishing patterns for the
broader engineering team.
* Evaluate architectural decisions and recommend changes when
existing approaches no longer serve the needs of the platform.
* Ensure technical changes are carefully evaluated, sequenced,
and implemented rather than introducing unnecessary complexity or
simultaneous changes across the platform.
* Establish clear technical standards and provide architectural
direction to engineering teams.
* Maintain a practical balance between technical quality,
delivery timelines, scalability, and business priorities.
Product Parity & Delivery

* Establish and maintain clear capability requirements for each
product domain.
* Protect the scope required for launch while identifying and
managing potential scope creep.
* Evaluate whether functionality has genuinely reached production
parity before major milestones.
* Continuously reassess delivery plans based on actual
engineering velocity and changing technical requirements.
* Maintain predictable development and release processes with
clear milestones and timelines.
* Partner with Product and business leadership to communicate
technical progress, risks, dependencies, and revised timelines.
Platform Migration & Cutover

* Own the strategy and execution of a major platform migration
and production cutover.
* Develop and maintain migration tooling capable of operating
against production data and snapshots.
* Lead repeated migration rehearsals to identify and resolve
issues before the final cutover.
* Establish reconciliation processes for financial,
transactional, user, and other critical data.
* Define and test rollback procedures to ensure a controlled and
recoverable migration process.
* Establish measurable acceptance criteria for the migration and
cutover.
* Ensure critical historical data and financial information are
migrated accurately and completely.
Infrastructure, Reliability & Operations

* Oversee the reliability, scalability, and operational health of
both legacy and rebuilt platforms.
* Manage sustaining engineering efforts for the existing platform
while maintaining a clear separation between maintenance work and
rebuild priorities.
* Establish priorities for production issues, with particular
attention to revenue-impacting and critical platform
functionality.
* Maintain effective on-call, incident response, monitoring, and
reliability processes.
* Monitor infrastructure performance and maintain visibility into
engineering and platform costs.
* Identify and address operational risks before they become
production issues.
Architecture & Technology

* Lead development within a modern, minimal AWS-based serverless
architecture.
* Work with TypeScript across frontend, backend, infrastructure,
and testing environments.
* Guide development using technologies such as React, Vite, AWS
Lambda, API Gateway, Step Functions, AppSync Events, Aurora DSQL,
DynamoDB, Cognito, CloudFront, and AWS CDK.
* Maintain infrastructure and deployment practices using modern
CI/CD workflows and secure authentication mechanisms.
* Apply managed cloud services where appropriate and avoid
unnecessary operational complexity.
* Evaluate requests for new technologies or infrastructure based
on demonstrated technical need, scalability, reliability, and
maintainability.
Compliance, Security & Risk Management

* Provide engineering leadership for technical compliance
requirements that affect product development and platform
launches.
* Establish appropriate security, privacy, data retention,
identity verification, and payment-related controls.
* Partner with relevant stakeholders to understand compliance
requirements and incorporate them into engineering plans.
* Maintain strong standards for secure development, testing, code
review, and production access.
* Identify and mitigate technical and operational risks
associated with sensitive data and financial transactions.
Engineering Management & People Leadership

* Manage and develop the engineering team while remaining
actively involved in technical execution.
* Establish clear expectations around engineering quality,
ownership, communication, and delivery.
* Recruit and hire engineers with the skills required to support
the platform rebuild and long-term growth.
* Coach engineers and help develop technical leadership within
the organization.
* Establish effective code review, testing, documentation, and
development practices.
* Build an engineering culture focused on accountability,
quality, thoughtful decision-making, and continuous improvement.
Delivery & Engineering Operations

* Maintain a clear engineering roadmap, development workflow, and
delivery cadence.
* Establish predictable shipping schedules and ensure the
business has clear visibility into engineering commitments.
* Maintain appropriate engineering processes without creating
unnecessary bureaucracy.
* Use measurable progress and actual delivery velocity to inform
planning.
* Ensure engineering priorities remain aligned with product and
business objectives.
Technical Environment

* Language: TypeScript
* Frontend: React + Vite
* API & Compute: AWS API Gateway, Lambda, Step Functions
* Realtime: AppSync Events
* Data: Aurora DSQL and DynamoDB
* Identity & Edge: Cognito and CloudFront
* Infrastructure: AWS CDK
* CI/CD: GitHub Actions with OIDC-based AWS authentication
* Architecture: AWS serverless, managed-service-focused
environment
* Development: Single repository and unified TypeScript codebase
Required Qualifications

* Significant experience leading engineering teams and complex
software development initiatives.
* Demonstrated experience remaining hands-on with production code
while managing an engineering organization.
* Strong software architecture and system design experience.
* Experience leading large-scale platform migrations, rewrites,
or modernization initiatives.
* Experience managing complex production cutovers and migration
risk.
* Strong experience with TypeScript and modern web application
development.
* Strong understanding of AWS and serverless architecture.
* Experience with cloud infrastructure, CI/CD, production
reliability, and incident response.
* Strong understanding of databases, APIs, distributed systems,
and scalable application architecture.
* Experience establishing engineering standards around testing,
code review, security, and development practices.
* Strong people management, hiring, coaching, and organizational
leadership skills.
* Ability to make pragmatic technical decisions while balancing
product requirements, business priorities, and delivery
timelines.
Preferred Qualifications

* Experience with AWS services including Lambda, API Gateway,
Step Functions, DynamoDB, Aurora, Cognito, CloudFront, and CDK.
* Experience leading a platform rebuild while simultaneously
maintaining a legacy production system.
* Experience with high-volume transactional or consumer-facing
platforms.
* Experience with payment systems or other systems requiring
strong data consistency and reconciliation.
* Experience designing and executing zero- or low-downtime
migration strategies.
* Experience establishing engineering organizations and processes
during periods of rapid growth.
* Experience working closely with executive leadership, Product,
Finance, and other cross-functional teams.

Head of Engineering - ADULT CONTENT

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