Technology Lead

Remote (Canada)
April 29, 2026
Salary
$
150000
 - 
$
175000
Job Type
Full Time
Years of Experience
8
 - 
12
 years
Industry
AI/Machine Learning

Job Description



Toast is recruiting on behalf of a healthcare technology company operating at the intersection of AI and patient engagement. The company is a growth-stage startup building intelligent automation products for healthcare organizations, with a particular focus on contact center modernization and operational efficiency. Their engineering team is small but technically deep, and they are at a stage where the architecture decisions being made today will shape the platform for years to come. This is a foundational technical leadership hire.
 

Responsibilities

 

  • Lead the end-to-end technical architecture of the platform, spanning backend services, data infrastructure, AI-enabled workflows, and frontend delivery.
  • Manage and mentor a software development team across backend, full stack, data, and DevOps disciplines through hands-on code review, architectural guidance, and clear engineering standards.
  • Own key architectural decisions including technology selection, system design, and integration patterns, with documented rationale and a clear view of long-term consequences.
  • Drive engineering planning in close collaboration with product leadership by decomposing roadmap items into sound technical designs, surfacing risks early, and holding the team accountable to quality.
  • Establish observability, reliability, and security practices as embedded engineering culture rather than periodic audits.
  • Represent engineering in business and client conversations where technical credibility is required, including architecture reviews, compliance discussions, and enterprise onboarding.
  • Recruit and interview senior engineering candidates, with a strong instinct for identifying genuine technical depth.

 

Requirements

 

  • 8 or more years of software engineering experience, with at least 3 years in a senior or technical lead capacity owning architecture and delivery.
  • Strong platform engineering background with proven experience building and operating complex distributed systems.
  • Deep experience with Python-based backend systems and cloud infrastructure, with Azure experience preferred.
  • Hands-on experience with AI and ML adjacent infrastructure including RAG pipelines, vector stores, and agent orchestration.
  • Experience designing systems under compliance-heavy constraints such as healthcare, financial, or similar regulated environments, with attention to security, auditability, and data residency.
  • A track record of setting and maintaining engineering standards that teams actually follow.
  • Strong communication skills with both technical and non-technical stakeholders.
  • Comfort operating in a fast-moving, early-stage environment where priorities evolve.
  • Experience with security and compliance frameworks such as OWASP and SOC 2 practices is an asset, as is prior experience with Graph databases and Neo4j.

 

Benefits

 

  • Competitive base salary reflective of a technical leadership role at a well-funded growth-stage company.
  • Equity participation with meaningful upside as the company scales.
  • Comprehensive benefits package including health, dental, and vision coverage.
  • Direct report to the CEO with full authority to shape the technical direction of the platform from the ground up.
  • Work on a product with tangible patient impact, deploying AI to improve how people experience healthcare at critical moments.
  • High visibility in a small team where your contributions are immediately felt across the organization.
  • The decisions you make now will have lasting consequences on both the product and the people it serves.

Toast's Process

1. Application Review

Submit your application, including your resume and cover letter, through our online portal. Our team will carefully review your qualifications and experiences. We take pride in responding promptly, so if your application aligns with our current opportunities, you’ll hear back from us with next steps. Your journey with Toast begins here, and we’re excited to see what you bring to the table!

2. Vetting Call

If your application is successful, we’ll schedule a vetting call with a member of the Toast team. This 30-45 minute informal conversation is designed for us to get to know you better and assess your skills. Be prepared to discuss your past projects, the challenges you’ve tackled, and the impact you’ve made. This is your chance to shine and show us why you’re a great fit for the roles we offer.

3. Profile Creation

Once you’ve impressed us in the vetting call, we’ll create an unbiased profile that highlights your experience while minimizing common biases. Instead, we focus on your skills, industry experience, and the impact you’ve made. This way, your profile reflects your true potential and accomplishments.

4. Client Submission

After crafting your unbiased profile, we submit it to our trusted clients. We work closely with these clients to ensure they understand the value you bring. Throughout their interview process, we remain by your side, providing support and guidance. Our goal is to help you navigate the hiring process smoothly and confidently, ensuring you have the best chance to secure a role that fits your skills and aspirations.