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GigSafe is the contractor management platform for the future of 1099 work, helping companies pay and insure independent contractors accurately, on time, and compliantly.
Companies running 1099 labor in credentialed industries now need infrastructure that didn't exist a year ago. We're building it.
This year the Supreme Court ruled that companies can be sued for the contractors they engage. Compliance is now top of mind from Fortune 500 companies to small service providers.
We’re a team of 36 highly motivated people, growing fast, and well funded. Come build with us. For more information, visit gigsafe.com.
The RoleGigSafe is looking for a Strategy & Operations Manager to work on GigSafe’s hardest problems and highest priority initiatives. You’ll report to the VP of Business Operations and work directly with the CEO and the executive team.
You will be given significant responsibility - staffed on our most important initiatives and held accountable for their success. We expect you to do whatever is needed to get them done.
Some current initiatives include: repricing the core product, rebuilding the business logic underneath the platform, standing up proactive phone support, rebuilding our internal admin system, ensuring our insurance subsidiary is operationally compliant, and launching into a new vertical.
You will work across product, engineering, operations, compliance, go-to-market and more.
This is a unique opportunity for someone with a demonstrated track record of excellence, who wants responsibility beyond their experience level.
What You'll DoOwn critical initiatives from start to finish, turning open-ended problems into structured analyses, plans, and execution.
Embed with the teams doing the work. Set aggressive timelines and make sure they’re hit.
Deeply understand the business model and the product to answer the unanswered questions.
Work across every function and learn how the whole business actually runs.
Become the person the executive team relies on.
You have a track record of excellence, and have outgrown every role you've held. Traditional paths count (consulting, banking, PE, and product) - so do things like a sport you competed in, an instrument, competitive video gaming, the military, or a side hustle.
You must understand how things actually work. You keep digging until you hit ground truth.
You’re a bulldog. People still really like you.
You give a sh*t. About everything that you do.
You’re extremely organized and detail-oriented.
You use AI seriously.
This job isn't for everyone. Real responsibility and real accountability are hard. The scope changes constantly, and you’ll walk into teams that didn’t ask for your help. You will only be effective if you’re a star on a team full of talented people.
BenefitsMedical, dental, and vision for you and dependents · Unlimited PTO plus company holidays · Competitive base with performance bonus · 401(k) · Meaningful equity · Paid parental leave
GigSafe is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by applicable law.
Skills Required
- Demonstrated track record of excellence (consulting, banking, PE, product, competitive activities, military, side hustle, etc.)
- Deep operational curiosity and ability to investigate until reaching ground truth
- High persistence and ability to influence while remaining well-liked (tenacity with strong interpersonal skills)
- Strong ownership and accountability; comfortable with real responsibility and changing scope
- Extremely organized and detail-oriented
- Proficient use of AI tools in workflows
- Ability to work across functions and embed with teams to drive execution
What We Do
GigSafe gives companies the tools they need to onboard, pay, and stay on top of compliance for their independent contractor (IC) network—all in one place. We work with gig platforms, delivery services, home-service companies, staffing groups, dispatch operations, and any business that depends on a distributed 1099 workforce. Most teams today are stuck juggling a mess of systems: one tool for onboarding, another for compliance, another for payments, another for insurance—and endless spreadsheets in between. It’s slow, manual, and easy for things to fall through the cracks. Contractors feel it too: confusing requirements, repeated paperwork, and delays that keep them from getting to work. GigSafe brings everything together in one simple platform. We automate onboarding, collect and verify documents, keep an eye on ongoing compliance, and sync data wherever it needs to go. We also streamline payments and consolidate reporting so companies always know exactly where things stand with every contractor. Insurance is part of the picture, but it isn’t the whole story. Our platform helps companies track coverage, manage certificates, and meet requirements automatically—without chasing paperwork or relying on manual checks. For contractors, that means a cleaner, clearer experience that gets them up and running faster. Our goal is to make it easier for companies and contractors to work together. By removing busywork and operational friction, we help teams move faster, stay compliant, and operate with confidence—all while giving contractors a more modern and transparent experience. In short: GigSafe gives companies one place to manage onboarding, compliance, payments, insurance, and day-to-day operations for their entire IC network.
Why Work With Us
GigSafe is a small, fast-moving team building tools that make work easier for companies and the contractors they rely on. We live our values—do right by customers, find ground truth, give a shit, build through it—and we want people who care, take ownership, and want to make an immediate impact.
