Fractional Chief Technology Officer (CTO)
Commitment: ~20-25 hours/week
Hybrid Work (mainly remote, 1-2x per month in-person)
Location: Toronto-Hamilton-Waterloo area
About Healthyher.Life
Healthyher.Life is a Canadian women’s health navigator platform dedicated to improving the lives of women managing chronic hormonal health conditions such as Menopause, PCOS, PMDD, Endometriosis, and Thyroid disorders. Our platform connects women to trusted, evidence-based health solutions through 4 pillars of services that include: The Knowledge Center, telehealth physician consults, Hailey™ Your AI Health Concierge™, the Women Talking™ community forum, and the Healthyher Marketplace of quality-assured health and wellness products. Learn more about Healthyher.Life and become a member - visit: https://www.healthyher.life/
We are passionate about creating meaningful change in women’s health. Our team values quality over quantity, accountability, a positive attitude, integrity, and gratitude in everything we do.
The Opportunity
We are seeking an experienced Fractional CTO to architect and lead our technology vision and roadmap, and execute during a critical phase of growth. You also understand the needs of women who struggle to access reliable and trusted health solutions – and you are dedicated to fix it! You will work closely with the Founder/CEO and leadership team to ensure our vision for women’s health navigation technologies are scalable, secure, data-rich and aligned with our mission to support and delight our customers and partners.
This is an ideal role for a technology leader who thrives in startup environments, can balance strategic oversight and resource planning with hands-on execution – in short, a person who wants to make a real and measurable social impact. We are looking for a technical leader with the mindset of a Founder and Builder – for the right person, this role can evolve to a CoFounder opportunity with Healthyher.Life, aligning with the Founder/CEO’s mission to Remodel the Women’s Health Care Journey.
Your Key Responsibilities
· Technology Strategy & Leadership
o Define and execute the long-term technology roadmap, ensuring scalability, security, and innovation in digital health AI solutions.
o Align technology priorities with business goals, customer needs, and B2B market opportunities.
o Provide clear technical direction and collaborative mentoring to internal and external development teams, while maintaining accountability for the assigned performance deliverables
· Product Development & Oversight
o Oversee the ongoing development of our AI technologies, web and mobile platforms.
o Ensure quality over quantity in feature delivery — focusing on solutions that create the highest value for customers.
o Review UX/UI and development work for alignment with product vision and user needs.
· Governance, Compliance & Risk Management
o Ensure adherence to privacy, data protection, and healthcare regulations in Canada and USA.
o Establish best practices for code quality, version control, and documentation.
· Partnerships & Vendor Management
o Manage relationships with technology vendors, development partners, and infrastructure providers.
o Evaluate and negotiate technology solutions, ensuring alignment with budget and objectives.
· Mentorship & Team Building
o Demonstrate your leadership by fostering a culture of integrity, accountability, collaboration, and continuous improvement within the technology function.
o Mentor junior team members and promote knowledge-sharing and continuous learning across the organization.
What You Bring
· Proven experience as a CTO, VP Technology, or Senior-level (Director) Technical Lead in a startup or high-growth tech venture.
· Strong background in web and mobile app development with experience in building and scaling digital health platforms as a service, ideally for women’s health or femtech area.
· Previous experience in architecting complex data integration systems, building AI/ML models (primarily generative) and model integration and optimization with health systems to solve real-world problems.
· Proven experience with building AI application models, cloud based B2B multi-tenanted platforms, API development and integrations.
· Demonstrated ability to lead both strategy and hands-on execution in a lean startup/early-stage company environment.
· Familiarity with data privacy and cybersecurity compliance standards (HIPAA, PHIPA, PIPEDA, GDPR, SOC2) for protecting personal health information (PHI).
· A track record of integrity, accountability, and delivering quality solutions that meet user needs.
· Excellent communication skills, and an eagerness to support the CEO’s fundraising efforts with pitching the tech innovation strategy, and translating technical concepts for investors and stakeholders.
Why Join Us
· Be part of a purpose-driven company making a tangible impact in women’s health.
· Flexible fractional role (approx. 20 hours/week) to fit around other professional or personal commitments; with achieving success metrics, there will be an opportunity to expand the role full-time.
· Opportunity to shape the future of women’s health by scaling our AI-powered digital health platform.
· Collaborative, values-driven team that celebrates diversity, integrity, innovation, and above all, an attitude of gratitude.
Your Compensation:
· Monthly Salary pay for ~20-25 hrs per week (~80-100 hrs per month), working weekdays during regular business hours (9 am to 6 pm).
· Opportunity for stock options or CoFounder equity after completing initial contract period, demonstration of good work performance and leading both technology and team development.
If you are a strategic technology leader who thrives in dynamic environments and wants to help remodel the women’s health journey, we’d love to hear from you.
Contact us at: careers@healthyher.life
Please note that Canadian and Provincial Government funding grants will be leveraged to recruit the right candidate for this career position; therefore only Canadian citizens or permanent residents of Canada will be invited for an interview. Healthyher.Life thanks all applicants who express an interest in this career opportunity, and we are pleased to offer professional development and continuous learning opportunities as well. We are compliant with Canada’s human rights laws and Ontario labour laws, and we ensure that every person is treated equally and fairly for employment, regardless of race, color, creed/religion, gender, sexual orientation, marital status, age, mental or physical disability.
