HeyDrew! · 1 day ago
VP of Engineering
United States
Full-time
Remote
Mid, Senior Level
$180K/yr - $250K/yr
6+ years expHeyDrew! is a Series A-funded startup that is building an easy-to-use AI tax strategy platform for SMBs. As the VP of Engineering, you will lead the engineering efforts for their Dual Brain platform, overseeing the development from prototype to production-grade while managing a small team of engineers and ensuring engineering excellence.
Financial Services
Responsibilities
Build the platform, hands-on, from scratch (0→1): core architecture, APIs, data model, and foundational services for an AI-first SaaS product
Own agentic AI workflows: orchestration, tool use, stateful workflow design, guardrails, monitoring, and evaluation
Implement GraphRAG: graph-grounded retrieval, knowledge representation, ingestion pipelines, grounding/citations, and quality measurements
Manage outsourced/offshore delivery (LATAM preferred): vendor selection/onboarding, SOWs, sprint cadence, code quality gates, acceptance criteria, and accountability for outcomes
Hire and assess engineers: run technical screens, evaluate skills, and build the early team (2–4, growing to 5–7)
Lead remote/hybrid execution: strong async comms, crisp planning, predictable shipping, and cross-functional collaboration with CEO/product
Establish engineering excellence: testing, CI/CD, observability, incident response, performance, and cost controls
Qualification
Required
6+ years of professional software engineering experience
Startup experience required (Seed/Series A strongly preferred)
SaaS experience required (production systems, reliability, security basics, multi-tenant patterns)
2+ years of people management experience (ideal 2–4), including coaching and delivery ownership
Proven experience hiring engineers and assessing skills (screens, interviews, leveling)
Experience leading remote and/or hybrid teams successfully
Agentic AI and workflow experience shipped to production (not prototypes only)
Experience with LangGraph and/or AutoGen; comfortable with modern AI stacks (LangChain, Semantic Kernel)
GraphRAG experience required (or equivalent retrieval plus structured/graph grounding)
Familiar with LLM evaluation and quality tooling (RAGAS, TruLens) and building for accuracy
Understands the difference between a bug and a compliance failure
Hands-on leader who can architect, code, and review deeply, especially early-stage
Preferred
Experience as a founder in a startup
Production LLM systems experience (monitoring, feedback loops, cost controls, versioning)
Security and compliance readiness (SOC2-type controls, vendor security reviews, access control, audit logs)
Domain exposure in tax, accounting, fintech, compliance, or other high-stakes workflows
Strong data engineering instincts (Postgres, ETL, eventing/queues, structured and unstructured data modeling)
Cloud and infrastructure proficiency (AWS or GCP, Terraform; Kubernetes optional)
Experience with Big 4 innovation groups or TaxTech leaders (Vertex, Wolters Kluwer)
Experience integrating with financial/data APIs (Plaid, Codat, filing/tax platforms or similar)
Document AI experience parsing complex PDFs and forms (OCR and layout extraction)
Knowledge graph depth (designing and operating graph databases in production)
Experience scaling engineering orgs quickly and leading through Managers/Directors (startup growth stages)
Benefits
Equity
Company
HeyDrew!
Most small businesses have a CPA who looks backward. At HeyDrew!, we give them an AI strategist that looks forward.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase