Founding Head of Technology (Future CTO)

Job Description

Build From Zero With Proven Founders

We’re an early-stage, self-funded startup operating in stealth mode- founded by two entrepreneurs with multiple successful exits across diverse industries. We’re building a high-impact SaaS platform to disrupt a massive, fragmented market.

We’ve been working on this project for over a year, and we’re getting closer to launch. We’re ready to hire our first full-time team member, and are looking for a rockstar that can step up and play in the big leagues.

This isn’t just another job. It’s a rare opportunity to help shape the product, culture, and trajectory of a company from day one. You’ll work directly with both founders who are extremely active in the business - one a visionary with nonstop ideas and an incredible network, the other a seasoned operator who’s scaled businesses before and knows how to do it again.

We move fast, think deeply, and care deeply about execution. If you’re energized by early-stage chaos, have unending energy and crave a seat at the table, keep reading.

How We Work

We believe in autonomy with accountability. You’ll have the freedom to lead and build—but also the responsibility to deliver and raise the bar. And yes, come on board now and you’ll earn your spot as an owner with equity.

While we support flexibility, we’re big believers in in-person energy. We’ve built our home base in coworking spaces like Industrious and mHUB, because we know the best ideas (and decisions) often come from being in the room together.

We’re keeping the team small and exceptional. No fluff. No politics. Just sharp people doing meaningful work. If that sounds like your kind of place, welcome to the ground floor.

We are seeking a highly skilled and entrepreneurial engineer to lead the development and technical direction of our platform. As the first internal technical hire, you’ll work closely with our external development firm to shape and launch the MVP - and ultimately assume full ownership of our technology stack, internal systems, and long-term roadmap.

You will be responsible for building and scaling a secure, scalable, and elegant platform- either by assembling and managing an internal team or sourcing and overseeing external contributors. You’ll also take ownership of our internal IT systems and tools, ensuring the company is equipped with the infrastructure, automation, and data access it needs to operate efficiently.

You’ll be supported and mentored by a world-class technical advisor: a renowned engineering leader at one of the world’s most respected technology companies. This role will evolve into our Chief Technology Officer, and we are seeking someone energized by that path.

You should be comfortable writing, reading, and modifying production-level code, leveraging AI and automation for both platform features and internal workflows, and constantly exploring new ways to use technology to give the business a competitive edge.

Our current stack potentially includes:

Frontend: Next.js, Tailwind CSS, Zustand

API Layer: Node.js (Nest.js), Express APIs, JWT-based Auth (Auth0/Cognito)

Data Layer: PostgreSQL, Prisma ORM

Cloud Infrastructure: AWS ECS (Fargate) or AWS Lambda for APIs, AWS S3, Redis cache

Hosting: AWS Amplify or Vercel

Third-Party Integrations: Stripe, Twilio, OptaPlanner, Zendesk

Monitoring & Observability: DataDog or CloudWatch

Key Responsibilities

Lead the design, development, and deployment of the platform alongside an external development team

Manage internal IT systems, tools, and platforms, ensuring the team has best-in-class infrastructure

Architect long-term technology strategy, balancing scalability, security, and speed

Oversee vendor relationships for technical services, and evaluate whether to insource or outsource as we scale

Evaluate and implement AI and automation tools for both product and operational efficiency

Serve as the technical thought partner to the founders and eventually own the full technical function as CTO

Build, mentor, and lead a high-performance technical team over time

Some travel to Los Angeles possible to view the market in action

Qualifications

5–10+ years of full-stack engineering experience, preferably in high-growth or startup environments

Proven ability to build, deploy, and scale production-ready platforms

Deep understanding of system design, cloud infrastructure, and DevOps best practices

Experience managing or collaborating with external development firms

Familiarity with AI technologies and a strong interest in using them creatively and effectively

Ownership mindset with a willingness to manage everything from code to cloud to company laptops

Exceptional business judgment, common sense, and the ability to balance technical and strategic priorities

Strong leadership potential with an eye toward stepping into a CTO role

Bonus: Experience in two-sided marketplaces, consumer SaaS, or home services platforms

Compensation

Base salary: up to $125,000 depending on experience with bonus opportunities

Equity: A meaningful stake in the company, with projected value of $2M-$5M at exit and additional opportunities to add to equity ownership

In-person role with flexibility, based at mHUB in Chicago, with access to a vibrant, innovation-focused coworking community

Direct access to founders, early decision-making influence, flexibility and long-term leadership opportunity

Powered by JazzHR

o4b4N1qrGT

Full-time