VP of EngineeringAdvocate • San Francisco, CA, United States

VP of Engineering

Advocate • San Francisco, CA, United States

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VP of Engineering

VP of EngineeringPlatform Architecture & Scale

About Advocate

Advocate is transforming how Americans access government benefits. Using cutting‑edge AI technology, we're reducing months‑long disability application processes to days, helping vulnerable citizens get the support they deserve. After 2.5 years of rapid growth, we've built systems with increasing scale and complexity. Now we need an architectural visionary to design our next‑generation platform.

The Opportunity

We're seeking a VP of Engineering who sees elegant simplicity where others see overwhelming complexity. You'll partner with our CTO to head architecture and engineering, reimagining how case development platforms should work in an AI‑first world. This role is for an architect who finds simple elegance in design, creating minimal technical surface area to deliver maximum value. You understand that the best systems grow incrementally but are guided by a coherent vision from day one - not through endless complexity or components without consideration for the whole.

The Role

You'll lead and mentor a team of engineers while partnering with our CTO to define platform architecture. This uniquely combines deep technical architecture, strategic thinking, and hands‑on engineering leadership. You'll need world‑class system design skills paired with the ability to inspire brilliant engineers toward a unified vision.

The Person We're Looking For

Essential Background You're an accomplished architect and engineering leader who has designed sophisticated platforms that model human workflows with AI to transform facts into meaningful insights. You've led teams through platform transformations and built best‑in‑class user experiences. Most importantly, you've fully integrated AI into your workflow - it's not a tool you use, it's a partner that amplifies your capabilities 10×.

Location & Work Requirements

This position requires candidates who are currently authorized to work in the United States without sponsorship and are based in the US. The role requires travel to our SF and NY office locations at least 6 times per year for strategic planning sessions, team collaboration, and key company events. Unfortunately, we are unable to consider international applicants or provide visa sponsorship at this time.

Core Responsibilities

Architectural & Engineering Leadership : Partner with the CTO to design enterprise‑grade systems that seamlessly blend event‑driven architectures, stream processing, workflow orchestration, and AI pipelines. Build and mentor a high‑performing engineering team, creating a culture where engineers grow while delivering exceptional results. Your architectural reviews are teaching moments; your pair programming sessions demonstrate AI‑amplified development
AI‑Native Development Culture : Champion the use of AI in every aspect of development. At Advocate, we believe in human intellectual amplification through AI partnership – we'll never be “vibe coders.” You'll establish workflows and practices that make AI collaboration second nature for the entire team, teaching others to achieve 10× productivity through AI partnership
Platform Evolution : Design systems that handle data changing over time through human and machine steps. As humans review data and AI generates insights, your architecture must elegantly handle cascading changes while maintaining perfect audit trails. Transform existing systems into clean, scalable patterns while maintaining 99.99% uptime
Simplicity Through Sophistication : Create architectures that are profoundly simple despite underlying complexity. The best solution to a 10‑component problem might be 3 elegant abstractions, not 20 micro‑services

Technical Excellence

AI & Architecture Mastery : You've developed a profoundly effective personal workflow with Claude Code, Codex, GPT‑5, and other AI systems. You understand the difference between “vibe coding” and true AI partnership. You're equally fluent in distributed systems patterns (event sourcing, CQRS, saga patterns), know when to use Kafka vs. Kinesis vs. neither, and understand AWS services deeply without being dependent on them

Framework & Performance Expertise : Experienced with modern orchestration (Temporal, Airflow), data processing (Spark, Flink), and application frameworks – understanding their internals, not just usage. You predict bottlenecks before they exist and design security‑first systems where protection is inherent, not added

Cognitive Approach

Systems Thinker : You see connections others miss – between data points, algorithms, and human processes. You question every assumption from first principles. Your designs start from fundamental truths, not industry conventions

Right, A Lot : Your instincts about what will work are correct more often than not. You have a track record of successful bets on architectural decisions that seemed risky but proved transformative

Extreme Ownership : You're obsessively driven to solve problems. When you take on a challenge, it becomes yours completely. The problem stays with you in the shower, on walks, in dreams. You wake up at 3 AM with breakthrough ideas and immediately test them

Intellectual Humility : You understand AI may produce insights beyond human comprehension and build systems that account for this. You admit when wrong and change course quickly

Communication Clarity : You can explain distributed consensus to an intern and data sharding to a board member. Your architecture documents are clear, visual, and impossible to misinterpret

Leadership Excellence

Technical Influence : Engineers follow your vision because your designs are obviously correct. You lead through clarity and competence

Team Builder : You identify talent, develop potential, and create teams greater than the sum of their parts. You elevate every engineer, teaching them to think architecturally and collaborate with AI effectively

Decisive Under Uncertainty : You make architectural decisions with 70% information and adjust as you learn. You build consensus without compromise

Unique Qualifications

Interdisciplinary Background : Your expertise spans multiple fields – software engineering, data science, user experience, organizational behavior

Speed & Outcome Obsession : You measure iterations in hours and days. A working solution today beats perfection next quarter

Invention Track Record : You've created novel architectural patterns and think in terms of “what’s possible” not “what’s been done”

Technical Environment

Event‑driven architectures (Kafka / Kinesis / EventBridge)

Multi‑tier data platforms (Aurora, DynamoDB, OpenSearch, S3)

Orchestration (Temporal, Step Functions, custom engines)

Real‑time processing (Flink / Kinesis Analytics)

Container orchestration (ECS / EKS)

Infrastructure as Code (CDK / Terraform)

AI / ML pipelines throughout – You'll have full authority to evaluate, adopt, or replace any part of our stack.

AI Orchestration (LlamaIndex, LangChain)

Are You Ready?

A complex system you've architected and your key design decisions

How AI has transformed your development workflow

Your approach to building AI‑native engineering teams

This role is for those rare individuals who can hold an entire platform in their mind while inspiring others to build it – those who see AI as a partner in invention, not just automation.

Join us in building the platform that will revolutionize government services.

Synonym Inc. • San Francisco, CA, United States

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