VP Engineering | Head of Engineering

Olelo Intelligence; United States; Remote; USD 220,000 - 250,000; Full time

Job summary

Join a pioneering AI startup as the VP of Engineering, where you'll lead a high-performing team and shape the future of innovative AI solutions. This fully remote role offers significant equity and the chance to make a substantial impact in a fast-paced environment.

Benefits

Equity Stake

Remote Work

Occasional Trips to Hawaii

Qualifications

• 10x developer with hands-on technical leadership.
• Proven track record of leading engineering teams.

Responsibilities

• Provide hands-on technical direction and grow the engineering team.
• Oversee end-to-end development lifecycle of AI products.
• Design scalable, well-architected systems.

Skills

Technical Excellence

AWS Expertise

Leadership Experience

Execution Discipline

Architecture Skills

Innovation Balance

Startup Mindset

Communication

AI/ML Understanding

Tools

Python

React

TypeScript

CI/CD

Infrastructure as Code

Job description

Direct message the job poster from Olelo Intelligence

Learner | Builder | AI Entrepreneur | Excellence Through Conversational Intelligence

VP of EngineeringAbout Olelo

Olelo is an innovative AI startup at the forefront of developing cutting-edge artificial intelligence solutions. We're building a revolutionary product that requires exceptional engineering leadership to reach its full potential.

The Opportunity

We're seeking a hands-on VP of Engineering who is a 10x developer themselves to drive our product engineering efforts and lead from the front. This is a foundational leadership role for a technical expert who wants to shape not just code, but the future of an ambitious AI company.

Role & Responsibilities

• Technical Leadership: Provide hands-on technical direction while leading and growing our engineering team
• Product Development: Oversee the end-to-end development lifecycle of our AI products
• Architecture Design: Design and implement scalable, well-architected systems
• Team Building: Recruit, mentor, and develop a high-performing engineering team
• Execution: Drive development velocity while maintaining high code quality standards
• Cross-functional Collaboration: Work closely with product, design, and business stakeholders
• Strategic Planning: Contribute to technical roadmap and long-term company vision

Ideal Qualifications

• Technical Excellence: An exceptional developer (10x) who leads by example and leverages AI-enabled coding tools to maximize productivity
• AWS Expertise: Deep understanding of AWS architecture and services, preferably with AWS Well-Architected Framework certification
• Leadership Experience: Proven track record of leading engineering teams in fast-paced environments
• Execution Discipline: Strong bias toward lean teams and efficient delivery with a focus on results
• Architecture Skills: Experience designing highly scalable, cloud-native architectures
• Innovation Balance: Ability to drive innovation while maintaining solid engineering fundamentals
• Startup Mindset: Comfortable with ambiguity and rapid iteration
• Communication: Exceptional ability to translate technical concepts for non-technical stakeholders
• AI/ML Understanding: Knowledge of AI/ML concepts and implementation (preferred)

Why This Role Is Special

This is a unique opportunity for an exceptional developer who knows how to leverage AI-enabled coding tools, has deep AWS expertise, and is ready to lead from the front in a fast-paced startup environment. Working remotely with occasional trips to Hawaii, you'll build and lead a lean, high-performing team that prioritizes innovation balanced with strong engineering fundamentals.

We're offering a significant equity stake because we're looking for someone who's ready to be a key player in building something truly special - someone who values ownership, impact, and the chance to shape an AI company from its foundations.

As VP of Engineering, you'll be a core member of our leadership team with substantial influence over company direction and culture. While initial cash compensation may be modest compared to larger companies, the equity package reflects our commitment to finding a true partner in building Olelo's future.

Our Technology Stack

• Cloud Infrastructure: AWS (extensive usage across services)
• Backend: Python
• Frontend: React, TypeScript
• DevOps: CI/CD pipelines, Infrastructure as Code
• AI/ML: Python-based ML frameworks

Location & Work Style

This is a fully remote role with occasional trips to our Honolulu, Hawaii headquarters for strategic planning and team collaboration. We believe in focused work from anywhere while maintaining strong team connection through periodic in-person sessions in one of the world's most beautiful locations.

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Engineering and Information Technology

• Industries

  Technology, Information and Internet

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