Withflex Inc. logo

Director of Operations

Job Overview

Location

United States

Job Type

Full-time

Category

Operations

Date Posted

May 8, 2026

Full Job Description

đź“‹ Description

  • • As the first operations hire at Withflex Inc., you will build the operational infrastructure and compliance foundation from the ground up for a healthtech venture focused on enabling HSA/FSA payments for wellness brands.
  • • You will own the operational backbone from concept through execution, drive regulatory readiness in a healthcare environment, design and improve workflows, establish recruiting and performance management systems, define key operational metrics, and partner with product and engineering to align platform needs with operational requirements.
  • • You will join a mission-driven team backed by First Round, Core VC, and Rethink Capital, working with brands like Equinox, Dermstore, Therabody, and Ultrahuman to unlock $150B in annual HSA/FSA spending potential by making healthcare spending effortless.
  • • In this role, you will have the opportunity to shape the company’s growth from day one, build scalable playbooks and policies, work in a high-trust transparent culture, and gain end-to-end ownership of operations in a fast-moving, early-stage healthtech startup.

🎯 Requirements

  • • Proven experience building or scaling operations, ideally as one of the first operations hires at an early-stage healthtech company
  • • Experience working with outside counsel to translate legal and regulatory guidance into actionable operational decisions without sacrificing speed
  • • Demonstrated ability to design workflows that balance compliance, user experience, and operational speed, with a track record of measuring and improving them
  • • Strong ownership mindset, clear written communication skills, and ability to make sound decisions with incomplete information
  • • Passion for greenfield builds, lean teams, and thriving in ambiguous, fast-paced environments

🏖️ Benefits

  • • Competitive compensation and equity package
  • • Flexible, remote-friendly work environment
  • • Mission-driven work making healthcare spending effortless for consumers and brands
  • • Early-stage impact — your contributions will directly shape the company’s growth and success
  • • Collaborative, high-trust, and transparent team culture

Skills & Technologies

Remote

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Withflex Inc. logo
Withflex Inc.
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About Withflex Inc.

Withflex is a technology company focused on revolutionizing the way businesses manage their flexible workforce. Their platform provides a comprehensive solution for hiring, onboarding, managing, and paying contingent workers, freelancers, and contractors. By centralizing these processes, Withflex aims to streamline operations, ensure compliance, and reduce administrative overhead for companies. They cater to businesses of all sizes looking to leverage flexible talent efficiently and effectively, offering tools for talent sourcing, contract management, time tracking, and automated payments. Withflex operates within the HR tech and gig economy enablement sectors.

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