The Opportunity

Toronto, ON
Can work Remote
Information Technology

Flora is an innovative early-stage startup reshaping the landscape of fertility insurance. We are dedicated to providing individually owned fertility insurance solutions, making the journey to parenthood accessible and stress-free. As we embark on this exciting journey, we're looking for a Fractional CTO to spearhead our technology vision and bring our innovative ideas to life.

As a Fractional CTO, you will play a pivotal role in shaping the technological future of Flora. This is a remote, part-time position based in Canada, with the possibility of evolving into a full-time role. You'll be diving into an extremely scrappy environment, working hand-in-hand with our founders to guide Flora's technological direction. Your entrepreneurial spirit, hands-on experience in software development, and ability to navigate the early stages of a startup will be crucial in this role.

Note: This is not a role at Highline Beta. This is a role at Flora, which is a portfolio company.

What you'll do


  • Strategic Leadership: Collaborate closely with the founders to craft and execute Flora's technological strategy, ensuring it aligns with our business goals.
  • Software Development: Be prepared to roll up your sleeves and code, contributing directly to the development of our platform.
  • Team Management: Lead and manage tech teams, fostering a collaborative and productive environment.
  • Vendor Management: Efficiently manage relationships with software application providers and vendors, ensuring seamless integration and operation.
  • Product Development: Use your experience in building software products from the ground up to lead the development of Flora's offerings.
  • Innovation: Leverage no-code tools and application integrations to bring creative and efficient solutions to our technology stack.

What you'll need


  • Entrepreneurial Mindset: Previous experience in starting a software company is highly desirable. Ready to tackle challenges head-on with a positive attitude.
  • Experience: Proven track record of managing teams and building software products from their earliest stages.
  • Technical Skills: Hands-on coding experience and familiarity with no-code platforms and application integrations.
  • Insurance Experience: Ideally, you have experience working in the insurance industry (or another highly regulated industry)
  • Enterprise Software Experience: Previous experience working on enterprise software products (although Flora is a direct to consumer play, much of the technology will be enterprise-grade in terms of security, complexity for back-end quoting, binding, underwriting of insurance, handling claims, etc.)
  • Leadership: Strong leadership skills with the ability to inspire and guide teams towards achieving shared goals.
  • Communication: Excellent communication skills with the ability to work closely with founders and external partners.
  • Adaptability: Comfortable working in a fast-paced, ever-changing startup environment.

We're looking for

Core Skills

Communication Team Building Strategic Planning Software Development Software Architectural Design Security Management Product Management Problem-Solving Skills Data Management Team Leadership

A little bit about us

Highline Beta

At Highline Beta, we celebrate our inclusive work environment and welcome members of all backgrounds and perspectives to apply. We are committed to providing reasonable accommodations and will work with you to meet your needs. If you are a person with a disability and require assistance during the application process, please don't hesitate to reach out!

Are you interested?

Work With Us

Joining Flora means being part of a passionate team committed to making a difference in people's lives. We value hard work, creativity, and the entrepreneurial spirit that drives individuals to turn ideas into reality. As a Fractional CTO at Flora, you'll have the unique opportunity to shape our technology from the ground up and play a key role in our growth and success.

If you're ready to embark on this exciting journey with us, we'd love to hear from you. Let's revolutionize the fertility insurance industry together!