About the role
Job Summary Principal Solution Architect
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 Solution Architecture & Roadmap
- Define, maintain, and communicate the technology architecture roadmap, ensuring alignment with organizational strategy, scalability, security, and innovation goals.
- Collaborate closely with Product, Engineering, and Leadership teams to translate business requirements into robust technical solutions.
- Design and evolve system architectures that are scalable, resilient, and adaptable to future needs.
Technical Leadership & Delivery
- Lead the architectural design and implementation of new features across multi-platform systems (web, mobile, backend).
- Establish best practices for solution design, focusing on usability, performance, security, and regulatory compliance.
- Oversee architectural reviews and ensure adherence to standards and guidelines.
AI & Emerging Technology Integration
- Drive the evaluation and integration of AI/ML technologies (e.g., NLP, predictive analytics, personalization) into Pillway’s platform.
- Stay current with emerging tech trends such as large language models (LLMs), automation, and advanced data platforms.
- Ensure AI/ML solutions comply with privacy, governance, and ethical standards.
Collaboration & Mentorship
- Partner with engineering teams to ensure architectural alignment and provide guidance on complex technical challenges.
- Mentor engineers and technical leads, fostering a culture of innovation, accountability, and technical excellence.
- Facilitate communication between technical and non-technical stakeholders to ensure clarity and shared understanding.
Operational Excellence
- Support DevOps practices including CI/CD pipelines, system monitoring, and incident response to ensure high availability and reliability.
- Ensure compliance with healthcare regulations and data privacy standards such as PHIPA and HIPAA.
- Advocate for security best practices and scalable infrastructure design.
Qualifications Education & Experience
- Bachelor’s or Master’s degree in Computer Science, Engineering, or a related field.
- 10+ years of experience in software engineering with at least 5 years in a solution architecture, technical lead, or systems architect role.
- Proven experience managing architecture and delivery at an organizational scale.
Technical Expertise
- Strong background in modern application development frameworks (React, Node.js, Python, or similar).
- Proficiency in cloud platforms (Azure, AWS, GCP) and infrastructure as code (Terraform, Chef, or similar).
- Deep knowledge of system architecture, scaling strategies, security principles, and compliance requirements.
- Familiarity with AI/ML concepts, frameworks, and tools, especially related to LLMs and generalized linear models (GLM), is a strong asset.
Leadership & Strategic Skills
- Demonstrated ability to define and execute technology roadmaps aligned with business objectives.
- Excellent communication skills, capable of bridging technical and business perspectives.
- Experience mentoring and leading engineering teams toward high performance.
- Knowledge of healthcare regulations and compliance standards is preferred.
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 Principal Solution Architect
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 Solution Architecture & Roadmap
- Define, maintain, and communicate the technology architecture roadmap, ensuring alignment with organizational strategy, scalability, security, and innovation goals.
- Collaborate closely with Product, Engineering, and Leadership teams to translate business requirements into robust technical solutions.
- Design and evolve system architectures that are scalable, resilient, and adaptable to future needs.
Technical Leadership & Delivery
- Lead the architectural design and implementation of new features across multi-platform systems (web, mobile, backend).
- Establish best practices for solution design, focusing on usability, performance, security, and regulatory compliance.
- Oversee architectural reviews and ensure adherence to standards and guidelines.
AI & Emerging Technology Integration
- Drive the evaluation and integration of AI/ML technologies (e.g., NLP, predictive analytics, personalization) into Pillway’s platform.
- Stay current with emerging tech trends such as large language models (LLMs), automation, and advanced data platforms.
- Ensure AI/ML solutions comply with privacy, governance, and ethical standards.
Collaboration & Mentorship
- Partner with engineering teams to ensure architectural alignment and provide guidance on complex technical challenges.
- Mentor engineers and technical leads, fostering a culture of innovation, accountability, and technical excellence.
- Facilitate communication between technical and non-technical stakeholders to ensure clarity and shared understanding.
Operational Excellence
- Support DevOps practices including CI/CD pipelines, system monitoring, and incident response to ensure high availability and reliability.
- Ensure compliance with healthcare regulations and data privacy standards such as PHIPA and HIPAA.
- Advocate for security best practices and scalable infrastructure design.
Qualifications Education & Experience
- Bachelor’s or Master’s degree in Computer Science, Engineering, or a related field.
- 10+ years of experience in software engineering with at least 5 years in a solution architecture, technical lead, or systems architect role.
- Proven experience managing architecture and delivery at an organizational scale.
Technical Expertise
- Strong background in modern application development frameworks (React, Node.js, Python, or similar).
- Proficiency in cloud platforms (Azure, AWS, GCP) and infrastructure as code (Terraform, Chef, or similar).
- Deep knowledge of system architecture, scaling strategies, security principles, and compliance requirements.
- Familiarity with AI/ML concepts, frameworks, and tools, especially related to LLMs and generalized linear models (GLM), is a strong asset.
Leadership & Strategic Skills
- Demonstrated ability to define and execute technology roadmaps aligned with business objectives.
- Excellent communication skills, capable of bridging technical and business perspectives.
- Experience mentoring and leading engineering teams toward high performance.
- Knowledge of healthcare regulations and compliance standards is preferred.
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.