Head of Engineering

  • 222 W Merchandise Mart Plaza, Chicago, IL 60654, USA
  • Full-time

Company Description

The employee engagement space is a $74B market growing at about 12% year over year with companies seeking to make the link between work culture and business success. However, less than 10% of companies actually know the ROI on their engagement efforts. Five to Nine is positioned to solve for this gap by leveraging employee feedback and providing insights on initiatives to better understand their results. We’re an award-winning VC-backed HR Tech startup looking to hire a Senior Software Engineer who wants to create a product that is influencing the future of work. We are founded by two diverse women who are passionate about cultivating belonging in the workplace.

We’ve been invested in by top VCs such as Kapor Capital (who’s also invested in companies such as Uber and Twilio) and by financial institutions like Morgan Stanley (who’s advisory board helped Slack & Zoom go enterprise). We’ve been featured in Vice, Business Insider, Yahoo Finance, Marketwatch and others.

Our software helps companies manage and measure the impact of their employee engagement programs. Think of us as large companies’ SurveyMonkey meets Eventbrite. We’re revolutionizing the future of work by giving organizers and HR managers visibility into their employee engagement initiatives. We’re based in Chicago and New York City (on-site opportunities in either location are available, with some travel opportunities.)

We’re a B2B SaaS platform and our clients include universities, and public companies, among other large enterprises.

Job Description

You'll be developing our core product (architecture, quality, user experience, etc.), working directly with the C-suite and clients, overseeing the junior coders and being the face of our tech. You’ll need to be able to design, code and test software in addition to leveraging agile tools for continuous integration/delivery.

As Head of Engineering, you will own all aspects of the product and technology end-to-end, including: 

1) Developing the product from the current MVP state to a scalable, enterprise-grade SaaS platform.
2) Ensuring successful execution of ongoing pilots with clients and codifying early user feedback into product's roadmap.
3) Evolving the technology’s vision, strategy and architecture.
4) Leading and building a fantastic technology and product team; creating a unique Five to Nine developer culture that focuses on innovation while having fun.

If this sounds like you, we’d love to hear from you. You’ll be joining an exceptionally talented and motivated team of equals, helping us drive demand for the Five to Nine platform. We are creating massive value for our customers and we’re just getting started!


You’re a self-starter and enjoy taking ownership. You’re someone who has a track record of building web applications (software-as-a-service or product-oriented). You can effectively manage tasks, projects and problem solve. You know your tech and have a strong grasp of object-oriented design practices that promote efficiency and maintainability of the code. You’re a dynamic engineer who is an effective communicator and enjoys an environment of collaboration.


  • Ruby on Rails

  • Javascript (jQuery/React)

  • PostgreSQL

  • Product runs on AWS using services like Elastic Beanstalk, EC2, S3, and others

We understand every engineer has a different stack. Please consider applying even if you check 3/4 of these boxes. We care more about finding the right person and we’re open to you learning on the job.

Additional Information

All your information will be kept confidential according to EEO guidelines.