Head of AI-Driven Engineering & Platform Security

Juniper Square; United States; On-site; USD 230,000 - 285,000; Full time

Benefits offered by this job

Health, dental, and vision

Life insurance

Mental wellness coverage

Fertility and family support

Flexible time off

Paid family leave

Retirement savings plans

Home office setup allowance

Professional development stipend

Job summary

Juniper Square is seeking a Director of Engineering to lead the vision and execution of foundational systems, with emphasis on modularizing the Python/FastAPI monolith and enabling AI-powered features. You will drive security, data pipelines, and SDK/tooling to empower product teams and reduce technical debt.

You will manage engineering managers and staff engineers, shaping an ambitious, secure, high-velocity platform across the org with strategic influence and collaboration.

Qualifications

• 15+ years of software engineering experience and 5+ years in engineering leadership.
• Proven experience architecting AI features (LLMs, RAG, tool calling).
• Experience migrating monoliths to modular architectures at scale.
• Deep security principles, IAM, OAuth 2.0/OIDC knowledge.
• Strong Python/FastAPI fluency and guiding senior engineers.

Responsibilities

• Direct the multi-year strategy to decouple legacy monoliths into modular FastAPI architecture.
• Lead AI-native SDLC adoption and measure developer productivity.
• Develop internal SDKs, data pipelines, and tools for AI-powered features.
• Champion AppSec with shift-left security and automated scanning.
• Oversee shared services for identity, auditing, and high-throughput gateways.
• Collaborate across teams on refactoring timelines and platform capabilities.
• Build and mentor a high-performing engineering organization.

Skills

AI fluency

AI features architecture

Staff engineering leadership

OAuth/OIDC security

Python/FastAPI

Executive communication

Job description

Juniper Square is seeking a Director of Engineering to lead the vision and execution of foundational systems, with emphasis on modularizing the Python/FastAPI monolith and enabling AI-powered features. You will drive security, data pipelines, and SDK/tooling to empower product teams and reduce technical debt.

You will manage engineering managers and staff engineers, shaping an ambitious, secure, high-velocity platform across the org with strategic influence and collaboration.