About the role
Job Summary Tech Lead
Pillway
Full-time
In-Office | Brampton, ON, Canada
About Pillway Pillway is a digital-first pharmacy and health technology company building patient-centric healthcare solutions. Our mission is to make medication management simple, accessible, and effective by leveraging technology, pharmacy expertise, and personalized care.
As Pillway scales, we are investing in core platform features, AI-driven healthcare solutions, and modern infrastructure to support patients, providers, and partners nationwide.
Role Overview The Tech Lead will serve as the organizational-level technical leader, owning the technology roadmap, engineering standards, and innovation strategy across Pillway.
This role requires a strong technical foundation, with the ability to balance AI/ML innovation, core feature development, and long-term architecture decisions. You will guide engineering teams, collaborate with leadership, and ensure Pillway’s technology aligns with business growth and compliance needs.
Key Responsibilities Technology & Roadmap
- Define and maintain the technology roadmap, balancing feature delivery, scalability, security, and innovation.
- Partner with Product & Leadership to align tech initiatives with organizational goals.
- Drive system design and architectural evolution, ensuring platforms remain robust and adaptable.
Feature Development
- Oversee design and delivery of new features across web, mobile, and backend systems.
- Ensure features meet standards for usability, performance, and compliance in healthcare.
- Introduce practices for continuous improvement and product scalability.
AI & Innovation
- Lead integration of AI/ML solutions into Pillway products (NLP for pharmacy, predictive adherence, personalization, etc.).
- Stay ahead of emerging technologies (LLMs, automation, data platforms) and assess their fit.
- Ensure AI initiatives follow privacy, governance, and ethical guidelines.
Team Leadership
- Mentor engineers, growing technical depth across the org.
- Lead technical discussions, code reviews, and architectural reviews.
- Foster a collaborative culture of innovation, accountability, and excellence.
Operational Excellence
- Champion DevOps practices, CI/CD pipelines, monitoring, and incident response.
- Establish data privacy and compliance standards (PHIPA/HIPAA).
- Ensure systems meet high availability, security, and scalability requirements.
Qualifications Education & Experience-
- Bachelor’s/Master’s in Computer Science, Engineering, or related field.
- 5+ years of software engineering experience, with 2+ years in a Tech Lead/Architect role.
- Experience managing technology at org scale (roadmaps, architecture, delivery).
Technical Expertise-
- Strong background in modern application development (React, Node.js, Python, or similar).
- Proficient in cloud platforms (Azure/GCP/AWS) and infrastructure as code (Terraform, Chef).
- Experience in system architecture, scaling, and security.
- Familiarity with AI/ML concepts(LLM, GLM and trending frameworks) is a strong asset.
Leadership & Strategic Skills-
- Proven ability to define and execute technology roadmaps.
- Strong communicator, able to translate between technical and business priorities.
- Experience mentoring engineers and building high-performing teams.
- Knowledge of healthcare regulations and compliance standards preferred.
Why Join Pillway?
- Lead the technology direction at an organizational level.
- Build solutions that directly impact patient care and healthcare delivery.
- Opportunity to work on both core feature development and AI innovation.
- Grow with a fast-scaling healthtech company into senior leadership roles.
About Pillway
Pillway is a tech-first, full-service virtual pharmacy that offers best-in-class service for individuals that require prescription medication, with a specialized focus for those who manage multiple medications per day. Reimagining the pharmacy experience, Pillway is revolutionizing today's traditional model through the thoughtful use of technology. It is the first of its kind in Canada that connects doctors, pharmacists and patients resulting in a full circle of care. Pillway has built a multifaceted technology platform that provides solutions for patients, pharmacists, and healthcare providers with complete end-to-end vertical integration across all pharmacy services. This connected ecosystem provides patients with an unmatched healthcare experience through the power of Artificial Intelligence.
Simpill Health Group is reimaging the healthcare experience through the thoughtful use of technology. Simpill is a Canadian health-tech company focused on creating industry disrupting technologies that optimize and simplify the healthcare experience and enable patients to live their best life. Current products of the company include Pillway, a full-service digital pharmacy and PillExchange, an enhanced e-Prescribing platform connecting doctors, pharmacists and patients.
About the role
Job Summary Tech Lead
Pillway
Full-time
In-Office | Brampton, ON, Canada
About Pillway Pillway is a digital-first pharmacy and health technology company building patient-centric healthcare solutions. Our mission is to make medication management simple, accessible, and effective by leveraging technology, pharmacy expertise, and personalized care.
As Pillway scales, we are investing in core platform features, AI-driven healthcare solutions, and modern infrastructure to support patients, providers, and partners nationwide.
Role Overview The Tech Lead will serve as the organizational-level technical leader, owning the technology roadmap, engineering standards, and innovation strategy across Pillway.
This role requires a strong technical foundation, with the ability to balance AI/ML innovation, core feature development, and long-term architecture decisions. You will guide engineering teams, collaborate with leadership, and ensure Pillway’s technology aligns with business growth and compliance needs.
Key Responsibilities Technology & Roadmap
- Define and maintain the technology roadmap, balancing feature delivery, scalability, security, and innovation.
- Partner with Product & Leadership to align tech initiatives with organizational goals.
- Drive system design and architectural evolution, ensuring platforms remain robust and adaptable.
Feature Development
- Oversee design and delivery of new features across web, mobile, and backend systems.
- Ensure features meet standards for usability, performance, and compliance in healthcare.
- Introduce practices for continuous improvement and product scalability.
AI & Innovation
- Lead integration of AI/ML solutions into Pillway products (NLP for pharmacy, predictive adherence, personalization, etc.).
- Stay ahead of emerging technologies (LLMs, automation, data platforms) and assess their fit.
- Ensure AI initiatives follow privacy, governance, and ethical guidelines.
Team Leadership
- Mentor engineers, growing technical depth across the org.
- Lead technical discussions, code reviews, and architectural reviews.
- Foster a collaborative culture of innovation, accountability, and excellence.
Operational Excellence
- Champion DevOps practices, CI/CD pipelines, monitoring, and incident response.
- Establish data privacy and compliance standards (PHIPA/HIPAA).
- Ensure systems meet high availability, security, and scalability requirements.
Qualifications Education & Experience-
- Bachelor’s/Master’s in Computer Science, Engineering, or related field.
- 5+ years of software engineering experience, with 2+ years in a Tech Lead/Architect role.
- Experience managing technology at org scale (roadmaps, architecture, delivery).
Technical Expertise-
- Strong background in modern application development (React, Node.js, Python, or similar).
- Proficient in cloud platforms (Azure/GCP/AWS) and infrastructure as code (Terraform, Chef).
- Experience in system architecture, scaling, and security.
- Familiarity with AI/ML concepts(LLM, GLM and trending frameworks) is a strong asset.
Leadership & Strategic Skills-
- Proven ability to define and execute technology roadmaps.
- Strong communicator, able to translate between technical and business priorities.
- Experience mentoring engineers and building high-performing teams.
- Knowledge of healthcare regulations and compliance standards preferred.
Why Join Pillway?
- Lead the technology direction at an organizational level.
- Build solutions that directly impact patient care and healthcare delivery.
- Opportunity to work on both core feature development and AI innovation.
- Grow with a fast-scaling healthtech company into senior leadership roles.
About Pillway
Pillway is a tech-first, full-service virtual pharmacy that offers best-in-class service for individuals that require prescription medication, with a specialized focus for those who manage multiple medications per day. Reimagining the pharmacy experience, Pillway is revolutionizing today's traditional model through the thoughtful use of technology. It is the first of its kind in Canada that connects doctors, pharmacists and patients resulting in a full circle of care. Pillway has built a multifaceted technology platform that provides solutions for patients, pharmacists, and healthcare providers with complete end-to-end vertical integration across all pharmacy services. This connected ecosystem provides patients with an unmatched healthcare experience through the power of Artificial Intelligence.
Simpill Health Group is reimaging the healthcare experience through the thoughtful use of technology. Simpill is a Canadian health-tech company focused on creating industry disrupting technologies that optimize and simplify the healthcare experience and enable patients to live their best life. Current products of the company include Pillway, a full-service digital pharmacy and PillExchange, an enhanced e-Prescribing platform connecting doctors, pharmacists and patients.