Director of Engineering

| Remote
Employer Provided Salary: 120,000-150,000 Annually
Salary data is provided by the employer. Please note this is not a guarantee of compensation.
Sorry, this job was removed at 7:56 p.m. (EST) on Monday, June 24, 2024
Find out who’s hiring remotely
See all Remote jobs
By clicking Apply Now you agree to share your profile information with the hiring company.

OS BENEFiTS helps independent hospitality businesses support their teams with affordably priced preventative care, crisis insurance, and lifestyle services. Today, many independent hospitality businesses struggle to navigate the needs of their teams and their margins at the same time. The result? A hardworking community of hospitality professionals is left underserved and underinsured. According to a 2021 report by the Bureau of Labor Statistics, there are over 400,000+ independent restaurants and 11,000,000 hospitality workers in the US, but only 32% of hospitality workers have healthcare coverage, compared to 77% of private industry workers. This is an issue of care as well as recruitment and retention in the hospitality industry. 

Great hospitality means taking care of our guests’ every need. So, shouldn’t it be easier for owners to do the same for their teams? With OS BENEFiTS, small businesses have an accessible way to provide affordably priced preventative care, crisis insurance, and lifestyle services to their teams. It’s the simplest way to empower this community with everything they need to succeed.

The OS BENEFiTS Director of Engineering is a unique opportunity to be the first engineering hire for a growing benefits company where they will be able to flex initially executing and delivering as a solo player and later spearhead the growth and leadership of an in-house technical team. As the primary technical contributor, this role will oversee all software development processes from ideation through execution, focusing on our platform's integrations with external partners. The right candidate is a hands-on tech expert with a keen sense for management and scaling technical startups. As a "startup within a startup", autonomy, ownership, and adaptability are crucial. This remote position directly reports to the CEO.


  • Collaborate with the Head of Product and CEO to design compelling product experiences on the platform to boost engagement.
  • Align with the Head of Product on the evolution of our Product Roadmap, architecting and executing innovative features to achieve business goals while ensuring stringent adherence to security protocols.
  • Lead both front-end and back-end development initiatives including establishing and upholding system functionality, focusing on testing for efficiency and minimizing maintenance overhead.
  • Partner with the Head of Product and Program Manager, focusing on delivering a top-tier user experience incorporating user feedback.
  • Develop and manage a dynamic tech team, offering direction, feedback, and scalable solutions on behalf of OS BENEFiTS.
  • Specialize in crafting real-time big data infrastructures, capable of processing vast data amounts for various purposes like analysis and visualization.
  • Translate stakeholder needs into precise system requirements and software components with clear requirements, goals, and timelines.
  • Systematically identify and address software and organizational issues.
  • Architect a robust build/CI system, integrating a service for error logs in prioritization.
  • Stay updated with industry trends, ensuring our platform remains at the forefront in terms of performance, security, and cost-efficiency.



  • 4-6 years of full-stack software development experience, inclusive of senior engineering or technical leadership roles with a player/coach perspective.
  • BA/BS in CS or equivalent professional experience.
  • Proficient in system integration, infrastructure, and architectural designs.
  • Expertise in agile development leadership.
  • Proven ability to foster relationships in a remote work setting.
  • Empathetic, patient, with strong listening skills.
  • A problem-solver with a keen eye for scalable solutions.
  • Highly autonomous yet a collaborative team player.
  • Passion for hospitality, health care innovation, and/or benefit management.


  • Familiarity with MVC-style web architectures and PHP frameworks like Laravel.
  • Frontend development experience using a CMS like Directus.
  • Expertise in building product integrations, encompassing third-party email services (e.g., Mandrill/Mailchimp), CRM tools (like Nutshell), and enhanced customer support (via chatbots like Intercom).

Insatiable curiosity
Endless creativity
Boundless optimism
Steady empathy
Balanced confidence

Position: Director of Engineering 
Department: OS BENEFiTS 
Reports to: CEO 
Classification: Exempt, full-time
Location: Remote within US
Compensation: $120K + equity TBC

OS BENEFiTS provides equal employment opportunity to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local laws. 

Read Full Job Description
Apply Now
By clicking Apply Now you agree to share your profile information with the hiring company.

Similar Jobs

Apply Now
By clicking Apply Now you agree to share your profile information with the hiring company.
Learn more about OS BENEFiTSFind similar jobs