GigEasy
 is hiring a fractional

Chief Technology Officer

Added 

x

 - Syndicated from 
Wellfound

How Syndicated Job Posts Work

This job was not posted directly to Fractional Jobs. It’s syndicated from another platform
To apply, view the application and follow their guidelines
Please let them know that Fractional Jobs sent you!

This Role is Closed

This company has already made a successful hire.
Fractional jobs get filled quickly. To get alerted when new fractional jobs go live, subscribe to our alerts.

This is a Featured Job

100% guarantee that your intro request will be seen
You’ll receive an update within 14 days
If the company is interested, we’ll intro the two of you directly

Weekly Commitment

10 - 20 hrs

Compensation Range

$3K - 4K / month + equity

Company Stage

Early Stage VC

Industry

InsurTech

Location

Remote
moonlight ok
moonlight ok
convert full-time
convert full-time
equity offered
equity offered
hands-on needed
hands-on needed

Note: We've kept the name of the company private. If you'd like to know the company before requesting an intro, just email us at hello [at] fractionaljobs.io

About Us

GigEasy specializes in pay-as-you-go commercial insurance and healthcare benefits for the 1099 workforce. We use technology to help business, agent, and 1099s get the right coverage for their dynamic needs.

Job Summary

Step into a critical role steering our technical vision and strategy. You will collaborate closely with our engineering team to design scalable systems, integrate advanced AI-driven processes, and streamline insurance API integrations. Starting as an individual contributor (IC), you'll play a hands-on role in building our systems and later help assemble and lead a high-performing engineering team. This opportunity is perfect for an experienced engineering leader looking to make a big impact in a dynamic, startup environment.

Responsibilities

  • Strategic Leadership: Guide the engineering team with technical expertise and forward-thinking strategies.
  • Architecture Oversight: Evaluate and optimize system architecture to align with business objectives.
  • AI-Driven Innovation: Implement scalable AI-based solutions for smart question generation and system efficiencies.
  • API Integration: Oversee the integration of insurance APIs into a unified platform.
  • CI/CD Pipelines: Establish and manage CI/CD workflows to enhance development and deployment processes.
  • Team Growth: Mentor engineers, uphold technical standards, and contribute to hiring top talent.
  • Best Practices: Conduct code reviews and enforce software development best practices.
  • Project Management: Lead development projects, ensuring timely and quality deliverables.

Tech Stack

We work with a cutting-edge stack that includes:

  • Backend: Node.js, Nest.js, TypeORM, Fastify
  • Frontend: React.js, Tailwind CSS, Chakra UI
  • AI & APIs: Zod, Survey.js
  • Databases: MongoDB, Postgres (RDS)
  • Cloud: AWS
  • Tooling: CI/CD pipelines, Pulumi

Qualifications

  • Experience: Proven track record as a Principal/Staff Engineer or CTO, ideally within startups.
  • Technical Expertise: Proficient in Node.js, React.js, and API-driven architectures.
  • AI Integration: Hands-on experience implementing AI solutions.
  • Scalability: Skilled in designing scalable, compliant systems.
  • Compliance: Knowledge of frameworks like HIPAA, SOC 2, or similar.
  • Industry Insight: Familiarity with regulated industries preferably Insurance is a plus.
  • Collaboration: Excellent communication and team-building skills in global and dynamic environments.

How to Apply

Note: This is a syndicated job post, meaning it was not posted to Fractional Jobs directly, so we don't have control over the application process. To apply, click on the "View Application" and follow the application's instructions.


How to Get in Touch

Hit that "Request Intro" button below. Include any relevant links so we can get to know you better.

Your brief intro note should clearly address:


If we think there's a fit, we'll reach out to schedule an intro call. Looking forward!

x
More
Engineering
Jobs

A Boutique Hedge Fund

 - 

Security Leader

 

(
)
20 - 40 hrs
 | 
$250 - $350 / hr
 | 
Remote (USA / Canada only)
Engineering
Syndicated
July 27, 2026
chief-information-security-officer-at-a-boutique-hedge-fund
added 

Lovely Flowers

 - 

Chief Technology Officer

 

12 - 20 hrs
 | 
$200 / hr
 | 
Onsite (Houston only)
Engineering
Syndicated
July 27, 2026
chief-technology-officer-at-lovely-flowers
added 

Revival Group

 - 

Technical Lead & Architect

 

10 - 20 hrs
 | 
Unknown
 | 
Remote (PT only)
Engineering
Syndicated
July 27, 2026
technical-lead-architect-at-revival-group
added 

CG Financial Services

 - 

Chief Information Officer

 

10 - 20 hrs
 | 
Unknown
 | 
Remote
Engineering
Syndicated
July 27, 2026
chief-information-officer-at-cg-financial-services
added 

Reflexion

 - 

Chief Information Security Officer

 

2 - 3 hrs
 | 
Unknown
 | 
Remote (USA only)
Engineering
Syndicated
July 20, 2026
chief-information-security-officer-at-reflexion
added 

Cars & Bids

 - 

Senior Data Engineer

 

20 hrs
 | 
$80 - $120 / hr
 | 
Remote
Engineering
Syndicated
July 20, 2026
senior-data-engineer-at-cars-bids
added 

Rare Beauty Brands

 - 

Shopify E-Commerce Lead

 

10 - 20 hrs
 | 
$12K - $14K / mo
 | 
Remote
Engineering
Syndicated
July 20, 2026
shopify-e-commerce-lead-at-rare-beauty-brands
added 

Just A Start

 - 

Chief Technology Officer

 

10 - 20 hrs
 | 
Unknown
 | 
Onsite (Boston only)
Engineering
Syndicated
July 20, 2026
chief-technology-officer-at-just-a-start
added 

Ando

 - 

Chief Technology Officer

 

10 - 20 hrs
 | 
Unknown
 | 
Remote (USA / Canada only)
Engineering
Syndicated
July 6, 2026
chief-technology-officer-at-ando
added 

Sandbar Health

 - 

Software Engineer

 

10 - 20 hrs
 | 
$90 - $160 / hr
 | 
Remote
Engineering
Syndicated
July 6, 2026
software-engineer-at-sandbar-health
added 

A High Finance AI Startup

 - 

Tech Lead

 

(
)
15 hrs
 | 
$150 - $200 / hr
 | 
Remote (USA / Canada only)
Engineering
Syndicated
June 23, 2026
tech-lead-at-a-high-finance-ai-startup
added 

An Operations Intelligence Startup

 - 

Technical Advisor

 

(
)
15 hrs
 | 
$250 - $350 / hr
 | 
Remote (USA only)
Engineering
Syndicated
June 22, 2026
technical-advisor-at-an-operations-intelligence-startup
added 

Send fractional jobs, 

playbooks, and more to

You’re in! Check your inbox to confirm.
We also post job alerts on
&
Hhmm, try again. That didn’t work.