Chief Technology Officer

Posted 9 Days Ago
Be an Early Applicant
Hiring Remotely in Chicago, IL
In-Office or Remote
200K-250K Annually
Senior level
Artificial Intelligence • Cloud • HR Tech • Business Intelligence • Generative AI • Automation
HYRD is building the Career OS - automating job search for millions of professionals globally
The Role
As CTO, you'll lead the development of an AI-powered career operating system, transforming an MVP into a scalable platform while building and managing a technical team.
Summary Generated by Built In

THE OPPORTUNITY

HYRD is seeking a Technical Co-Founder/CTO to architect and build the Career Operating System that will revolutionize how millions navigate their professional lives. This is a co-founder opportunity to own a significant equity stake while building category-defining technology.

We're creating the infrastructure for careers - an AI-powered platform that automates job applications, personalizes skill development, and matches talent with opportunities. With paying customers already using our MVP, we're ready to scale from hundreds to millions of users.

Location: Remote (US-based preferred)
Compensation: 2.5-4% founder equity (RSA), transitioning to $200-250K salary upon Series A funding
Start Date: Immediate

WHAT YOU'LL BUILD

As CTO, you'll transform our validated MVP (currently on Airtable, Make.com, Softr) into a scalable platform supporting millions of professionals. You'll architect three interconnected products:

HYRD Core - The Application Engine

  • Automated job application system processing thousands daily
  • AI-powered resume optimization for each opportunity
  • Real-time application tracking and response management
  • Integration with major job boards and ATS systems

SKILLD - The Learning Layer

  • Personalized skill assessment and gap analysis
  • AI-driven learning path recommendations
  • Course platform integrations and progress tracking
  • Certification and credential management

SOURCD - The Talent Marketplace

  • B2B2C matching algorithm connecting talent with enterprises
  • Company portals with analytics dashboards
  • Talent pipeline management systems
  • Payment processing and SaaS billing infrastructure

The AI Intelligence Layer

  • NLP for resume-job matching
  • Career trajectory prediction models
  • Salary optimization algorithms
  • Personalized recommendation engines

YOUR RESPONSIBILITIES

First 30 Days:

  • Complete technical audit of current no-code system
  • Design architecture for scalable Career OS platform
  • Create migration strategy maintaining zero downtime
  • Begin recruiting first 2 engineers on equity packages
  • Deploy immediate improvements to current system

First 90 Days:

  • Launch MVP of new platform architecture
  • Integrate all three products into unified system
  • Build initial engineering team (3-4 engineers)
  • Achieve 99.9% uptime and <200ms response times
  • Prepare infrastructure for 10,000+ users

First Year:

  • Scale platform to support 100,000+ users
  • Build and lead team of 8-10 engineers
  • Implement advanced AI features and automations
  • Launch mobile applications
  • Establish HYRD as technical leader in career tech

Team You'll Build:

Immediate Hires (Months 1-3):

  • Head of AI/ML - Lead all AI initiatives
  • Senior Full-Stack Engineers (2-3) - Core platform development
  • DevOps/SRE - Infrastructure and scaling

Second Wave (Months 3-6):

  • Data/Integrations Engineer - API and data pipeline
  • Product Designer - User experience ownership
  • Product Manager - Product strategy and roadmap
  • Additional Full-Stack Engineers as needed

WHAT WE'RE LOOKING FOR

Technical Requirements:

Essential Skills:

  • 8+ years software development experience
  • 3+ years in technical leadership roles (CTO, VP Engineering, Tech Lead)
  • Full-stack expertise (React, Node.js, Python, PostgreSQL)
  • System architecture for high-scale platforms
  • Experience with AI/ML integration (OpenAI, Claude APIs)
  • DevOps and cloud infrastructure (AWS/GCP)

HYRD-Specific Needs:

  • Experience migrating from no-code (Airtable, Zapier) to scalable architecture
  • Knowledge of web scraping at scale and API integrations
  • Background in marketplace or SaaS platforms
  • Understanding of job boards, ATS systems, or HR tech helpful

Leadership Experience:

  • Built and scaled products from 0 to 50K+ users
  • Recruited and managed engineering teams of 5+ people
  • Hired engineers on equity-heavy packages
  • Comfortable with technical debt trade-offs
  • Experience in resource-constrained environments

Mindset & Personality:

  • Excited to work for equity until funding (critical requirement)
  • Hands-on coder who still builds alongside the team
  • Believes in democratizing career success
  • Thrives in ambiguity and moves fast
  • Makes pragmatic technical decisions
  • Customer-obsessed problem solver

WHY JOIN HYRD

Massive Opportunity:

  • $400B career services market growing 23% annually
  • First-mover advantage building the Career OS category
  • Clear path to unicorn valuation

Real Traction:

  • Revenue-generating with paying customers pre-launch
  • Proven product-market fit
  • Strong customer demand overwhelming current systems

True Ownership:

  • 2.5-4% founder equity stake with RSA structure
  • Additional milestone-based equity (0.1-0.25% per milestone)
  • Direct partnership with CEO
  • Shape technical vision from day one

Impact:

  • Solve a problem affecting 3 billion professionals globally
  • Democratize access to career opportunities
  • Build technology that changes how the world works

COMPENSATION STRUCTURE

Immediate (Equity-Only Phase):

  • 2.5-4% founder equity (Restricted Stock Award)
  • 4-year vesting with 1-year cliff
  • Milestone top-ups (0.1-0.25%) for:
    • Successful platform migration
    • Reaching 10K users
    • Series A close
    • Key feature launches
  • Minimal stipend possible for critical expenses

Post-Series A (Target: 12-18 Months):

  • $200-250K base salary
  • Maintain full equity stake
  • Performance bonuses
  • Comprehensive benefits
  • Additional equity grants at funding milestones

THE INTERVIEW PROCESS

  1. Initial Call (30 min) - Mission alignment and vision discussion with CEO
  2. Technical Deep Dive (90 min) - Architecture discussion and system design
  3. Leadership Assessment (60 min) - Team building and culture fit
  4. Final Round (Half day) - Present 90-day plan, meet advisors, finalize terms

REQUIREMENTS CHECKLIST

Must-Haves:

  •  Can work for equity-only until Series A funding
  • 8+ years coding experience with recent hands-on work
  • Built and scaled consumer platforms before
  • Previous startup experience (not just FAANG)
  • Available to start within 30 days
  • Based in US or compatible time zones

Nice-to-Haves:

  •  HR tech or career services experience
  • Previous successful exit
  • Strong engineering network for recruiting
  • AI/ML expertise beyond API integration
  • Experience with no-code tools

HOW TO APPLY

Send the following to [[email protected]] with "CTO - Career OS" in subject:

  1. Your Story: Why does democratizing career success matter to you?
  2. Technical Proof: Link to something you built that scaled (GitHub, live product, case study)
  3. 90-Day Vision: How would you approach the migration from no-code to scale?
  4. Availability: Confirmation you can work for equity and your start date
  5. LinkedIn/Resume: So we can see your journey

Priority given to candidates who:

  • Can start immediately
  • Have built HR tech or marketplace platforms
  • Bring a network of engineers willing to work for equity
  • Show passion for the mission beyond just the technology

A NOTE FROM THE CEO

"We're looking for a true technical co-founder who sees the massive opportunity in building the Career OS. You'll have complete technical autonomy, significant equity, and the chance to build something that impacts millions of lives.

Our current MVP is generating revenue with paying customers. Now we need someone who can transform this early traction into a platform that scales to millions while building a world-class engineering team.

The technical challenges are real (scaling job applications, AI matching, marketplace dynamics), the impact is massive (every professional needs this), and the opportunity is once-in-a-lifetime.

If you want your work to define your legacy, this is it."

-Drake, CEO & Founder

ABOUT HYRD

HYRD is building the operating system for careers - the platform every professional will use to navigate their work life. We automate job searching, personalize skill development, and match talent with opportunities. With the job market in chaos and AI transforming every role, professionals desperately need what we're building.

We're a remote-first team obsessed with solving the broken job search process. Revenue-generating pre-launch and preparing for Series A, we're positioned to become the definitive platform for career management.

Ready to build the Career OS? Apply now.

HYRD is an equal opportunity employer committed to building a diverse and inclusive team.

Top Skills

AWS
Claude Apis
GCP
Node.js
Openai
Postgres
Python
React
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The Company
4 Employees
Year Founded: 2025

What We Do

HYRD is revolutionizing how professionals navigate their careers by building the first Career Operating System. We're solving the broken job search process where 73% of professionals spend 3+ months applying to hundreds of jobs with minimal success.
Our AI-powered platform includes three integrated products:

HYRD Core: Automates job applications while you sleep, optimizing resumes for each role and managing the entire application process
SKILLD: Personalizes skill development by identifying gaps and recommending exact learning paths
SOURCD: B2B marketplace connecting verified talent directly with enterprises

We handle the tedious parts of career management so professionals can focus on their actual work. Our platform submits personalized applications, tracks responses, schedules interviews, and provides real-time insights on market opportunities. Think of us as having a personal career assistant that never sleeps.

Currently, we're transforming lives for early customers who are landing interviews at 10x their previous rate. We're venture-backed, revenue-generating, and building toward becoming the definitive platform every professional will use to manage their career - similar to how Salesforce transformed CRM or Slack transformed communication.

The career services market is $400B globally with no unified solution. LinkedIn owns networking, Indeed owns listings, but nobody owns career management. We're filling that massive gap by building infrastructure that will power how 3 billion professionals worldwide navigate their work lives.

Why Work With Us

We're not hiring employees - we're recruiting co-founders. You'll ship code that impacts millions, not optimize ad clicks. We're remote-first forever, work async, and judge only on output. Join us to democratize career success and build generational wealth.

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