What are the responsibilities and job description for the Forward Deployed Engineer position at iWellniss OS?
FOUNDING TECHNICAL LEAD, AI SYSTEMS & ENGINEERING
Direct Path to Chief Technology Officer
Company: iWellniss OS
Initial Product: Ida
Location: Jersey City or New York City preferred; exceptional remote candidates considered
Reports to: Founder & CEO
Employment: Full-time preferred; contract-to-hire or founding-partner structures may be considered
ABOUT iWELLNISS OS
iWellniss OS turns ambitious ideas into secure, reliable operating products by combining exceptional human judgment with AI-powered development systems.
Our first product and proving ground is Ida—“I Do Anything.”
Ida began as a personal AI assistant and is evolving into a personal operating system. It is designed to understand a person’s conversations, projects, schedule, health, business, files, relationships, and priorities—then help that person make decisions and take supervised action.
Ida is not an idea waiting for a prototype. A functioning product already exists, including:
• Separate Test and Production environments
• Voice, memory, projects, and a personal Library
• Deployment controls and security boundaries
• An active AI-assisted development system
iWellniss OS is the larger company and operating model behind Ida. Our long-term goal is to create and operate software companies through small, highly capable human teams directing fleets of AI development systems.
THE OPPORTUNITY
We are seeking a founding technical leader to take ownership of technical execution while the Founder & CEO continues to lead product vision, customer experience, company strategy, capital allocation, and major authority boundaries.
This is not a ceremonial CTO role or a management-only position.
The right person must be able to enter an evolving codebase, determine what is real, correct what is weak, make sound architectural decisions, direct human and AI builders, and safely move work from product vision into Production.
The central objective is straightforward:
Build a technical organization that allows the Founder to focus on vision, customers, strategy, capital, and company building—without personally coordinating every prompt, branch, test, deployment, and technical decision.
WHAT YOU WILL OWN
Technical Architecture and Execution
• Own the technical architecture for Ida and the broader iWellniss OS development system
• Translate the Founder’s product vision into technical priorities, build plans, and release sequences
• Make decisions across application architecture, infrastructure, data storage, security, access control, integrations, reliability, and scalability
• Maintain clear distinctions between planned, built, tested, accepted, deployed, and Production-ready work
• Establish a roadmap that balances speed, usability, security, and long-term maintainability
Hands-On Engineering
• Personally inspect, review, debug, and improve production software
• Evaluate AI-generated code for correctness, security, maintainability, and release readiness
• Step directly into the code when critical issues require it
• Identify fragile tests, weak abstractions, security gaps, unnecessary complexity, and technical debt before they become operational problems
• Remain technically current and actively involved in implementation
AI Development Operations
• Direct development across Claude Code, Codex, and other AI engineering systems
• Create workflows that allow multiple builds to proceed without branch collisions, duplicated work, or unclear ownership
• Build supervised systems that can plan, implement, test, review, recover, and prepare releases with minimal Founder involvement
• Ensure AI-generated tests prove that failures are detected—not merely produce green results
• Continuously improve how human judgment and AI execution work together
Team Leadership
• Lead existing contributors and future engineers, contractors, technical operators, and AI builders
• Assign clear outcomes, authority boundaries, acceptance criteria, and deadlines
• Hold contributors accountable without requiring daily supervision from the Founder
• Determine which capabilities should be automated, contracted, hired internally, or retained by leadership
• Recruit and develop the future iWellniss OS engineering organization
Infrastructure, Security, and Reliability
• Own the reliability of Development, Test, and Production environments
• Establish secure credential management, access controls, backups, monitoring, storage practices, and incident response
• Protect personal information, business information, intellectual property, and future healthcare data
• Ensure Production changes are deliberate, traceable, evidence-based, and reversible whenever possible
• Lead incident response and create clear recovery and prevention plans
Founder Partnership
• Convert verbal product ideas into executable technical plans
• Bring the Founder clear decisions, tradeoffs, risks, and exceptions—not constant technical narration
• Challenge ideas or sequencing when they introduce unnecessary risk, complexity, or distraction
• Protect the product vision while preventing the Founder from becoming the technical bottleneck
• Communicate directly and honestly, including when the correct answer is no
WHO WE ARE LOOKING FOR
The ideal candidate has:
• Personally helped build and launch a software product from zero to one
• Recent experience writing, reviewing, and shipping production code
• Experience with AI applications, autonomous agents, language models, evaluation systems, or AI-assisted development
• Broad architectural experience across application code, databases, cloud infrastructure, authentication, security, integrations, and deployment
• Experience leading engineers, contractors, or technical teams
• Strong product judgment and an understanding of how software should feel to the person using it
• Experience with sensitive information or security-conscious systems; healthcare or regulated-software experience is valuable but not required
• The ability to move quickly without becoming careless
• The confidence to challenge a fast-moving Founder constructively
• The ability to create clarity in an ambitious, rapidly evolving environment
A specific degree, former employer, or traditional career path is not required. Demonstrated ability matters more than credentials.
THIS ROLE IS NOT RIGHT FOR SOMEONE WHO
• Wants a CTO title without remaining technically hands-on
• Has only managed mature teams and has never built from the beginning
• Requires perfectly organized requirements before taking action
• Treats AI-generated code as automatically trustworthy
• Confuses additional meetings or documentation with meaningful progress
• Avoids difficult conversations with the Founder
• Requires the Founder to make every meaningful technical decision
• Prioritizes technical elegance while ignoring the user experience
• Moves recklessly and expects security, testing, and reliability to be repaired later
INITIAL SUCCESS MEASURES
During the initial operating period, you will be expected to:
• Reconstruct and clearly explain Ida’s actual technical state
• Audit the application, infrastructure, security model, development process, environments, and technical debt
• Produce a prioritized plan defining what should remain, change, simplify, or be removed
• Take one meaningful product outcome from the Founder’s spoken vision through verified release
• Direct human and AI builders without creating collisions or duplicated work
• Demonstrate a controlled incident-response and recovery process
• Produce a six-month technical roadmap and engineering organization plan
• Measurably reduce the Founder’s involvement in daily technical coordination
PATH TO CTO
This position has a direct path to becoming Chief Technology Officer of iWellniss OS.
The title will be earned through demonstrated ownership, judgment, execution, leadership, and alignment.
The successful candidate will ultimately own architecture, engineering, infrastructure, security, technical hiring, AI development operations, release readiness, and incident response across iWellniss OS and its products.
WHY THIS OPPORTUNITY IS DIFFERENT
This is an opportunity to help build both a category-defining personal intelligence product and a company designed to create many products like it.
You will not simply inherit an established engineering team. You will help define a new type of technical organization—one in which a small number of exceptional people supervise powerful AI systems and produce at a level that previously required a much larger company.
The role offers substantial responsibility, direct access to the Founder, meaningful influence over the company, and the opportunity to grow into a true founding executive.
HOW TO APPLY
Please include:
- A product you personally helped take from idea to Production
- The exact technical responsibilities you owned
- An example of a serious technical or operational failure you handled
- How you currently use AI in software development
- How you evaluate and safely operate AI-generated code
- Why this stage of company building and level of ownership appeal to you
Please do not submit a generic résumé without answering these questions.