Sr. Staff Security Engineer

OpenLoop; Toronto; On-site; CAD 140,000 - 190,000; Full time

Benefits offered by this job

Medical, Dental, Vision plans

FSA/HSA

Flexible PTO

401(k) with company match

Life Insurance & Pet insurance

Job summary

OpenLoop is seeking a Sr Staff Security Engineer in Toronto to act as the most senior security authority, shaping architecture across cloud, applications and data. You will drive threat modeling, establish security standards, and guide engineering toward secure-by-default designs.

You’ll partner with CTO/CISO, mentor engineers, and define a zero-trust strategy while translating HIPAA and SOC 2 requirements into concrete controls for PHI handling.

Qualifications

• Bachelor’s degree or equivalent experience in CS or Info Security.
• 10+ years of progressive security experience with 5+ years in security architecture.
• Deep expertise across app, cloud, IAM, network, and data protection.
• Hands-on cloud security, network design, encryption, and PKI management.
• Proven threat modeling leadership (STRIDE/PASTA) across scale.
• Strong SSDLC, OWASP, and secure design patterns knowledge.
• Experience with OAuth/OIDC, SAML, and multi-tenant apps.
• HIPAA/SOC 2/HITRUST/NIST knowledge to design compliant controls.
• Strong ability to communicate architectural risk to technical and exec audiences.

Responsibilities

• Own and evolve security architecture across cloud, apps, and data.
• Lead threat modeling across product, engineering, and infra initiatives.
• Conduct architecture reviews and produce actionable recommendations.
• Design scalable architecture review processes with self-service patterns.
• Partner with CTO and enterprise architecture to embed security governance.
• Define and champion application security standards and data protections.
• Establish zero trust strategy across identity, network, endpoint, and data.
• Oversee key management, secrets management, and certificate lifecycle.
• Lead security reviews for third-party integrations and supply chain risk.
• Mentor security team and elevate architectural thinking.
• Translate GRC/Privacy/Audit requirements into concrete controls.

Skills

Security architecture

Threat modeling

SSDLC

OAuth/OIDC/SAML

Zero trust

Key management

PKI

Cloud security

IAM

Risk communication

Education

Bachelor's degree in Computer Science or Information Security

Job description

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About The Role

OpenLoop's mission is to bring care anywhere by powering telehealth solutions at scale. The Security Architecture & Engineering team defines how security is designed into every system that supports virtual care delivery across all 50 states. As Sr Staff Security Engineer, you will be the most senior technical authority on security architecture at OpenLoop, with approval authority over architecture decisions and responsibility for leading architecture reviews, driving threat modeling, and defining the standards and reference designs that engineering builds against.

What You'll Do

• Own and continuously evolve OpenLoop's security architecture across cloud infrastructure, applications, and corporate systems — defining standards, patterns, and reference architectures that teams build to.
• Lead threat modeling across product, engineering, and infrastructure initiatives, with particular attention to PHI data flows, patient-facing interfaces, and virtual care delivery systems — and coach engineers to threat model their own work.
• Conduct architecture reviews for new and existing systems, evaluating designs against security principles and regulatory requirements and producing actionable recommendations.
• Design and continuously improve the architecture review process itself so that it scales with engineering velocity — including self-service patterns, risk-tiered review paths, and clear criteria for when full review is required.
• Partner with the CTO and enterprise architecture function, embedding security review within existing technical governance rather than running a parallel process.
• Define and champion application security standards, including secure design principles, API security, authentication and authorization patterns (OAuth/OIDC, SAML), and data protection controls — including healthcare interoperability standards such as HL7 and FHIR.
• Establish and maintain a zero trust architecture strategy across identity, network, endpoint, and data layers.
• Architect and govern key management, secrets management, and certificate lifecycle practices across cloud-native environments.
• Own the security architecture for third-party integrations, defining how external systems connect to OpenLoop's environment and ensuring supply chain risk is controlled at the design stage.
• Serve as the primary security partner for product and engineering leaders, embedded in design and planning cycles to shape secure-by-default systems.
• Maintain security architecture documentation, including architecture decision records (ADRs), reference designs, and control frameworks.
• Take security and compliance requirements from GRC, Privacy, and audit partners and translate them into concrete architectural controls — with particular depth in the HIPAA Security Rule's technical safeguards as they apply to PHI architecture.
• Partner with the CISO and security leadership on the long-term architecture roadmap, producing clear metrics and executive-ready reporting on architecture risk posture.
• Mentor and elevate the broader security team, raising architectural thinking and design quality across all security domains.
• Research emerging threats and attack techniques — including threat actors actively targeting healthcare — to keep OpenLoop ahead of the threat landscape.
• Other duties as assigned.

Who You Are

• An architect who has owned the function, not contributed to it — you've built standards other teams actually adopted.
• Someone who scales themselves rather than becoming the queue everyone waits in. You'd rather teach ten engineers to threat model than review ten threat models.
• Comfortable being the most senior security voice in the room, and equally comfortable being overruled and managing the residual risk.
• Cross-domain by instinct: you think about identity, network, application, and data together rather than in isolation.
• Someone who understands that an elegant architecture nobody can operate is a failed architecture — and that a review process teams route around is a failed process.
• An enabler, not a gatekeeper. You've seen security teams become the department of \"no\" and you have opinions about why that happens.
• Self-directed, able to bring structure to ambiguous problems without waiting for it to be handed to you.
• Motivated by the fact that the systems you design protect health information for patients getting care they might not otherwise access.

Required Qualifications

• Bachelor's degree in Computer Science, Information Security, or a related field, or equivalent professional experience.
• 10+ years of progressive security experience, with at least 5 years focused specifically on security architecture across enterprise and cloud environments.
• Deep expertise across multiple security domains: application security, cloud security, identity and access management, network security, and data protection.
• Hands-on experience architecting security solutions in cloud environments, including network security design, IAM, key and secrets management, encryption, and cloud-native security services.
• Proven experience leading threat modeling using structured methodologies (STRIDE, PASTA, or equivalent) at varying scales — from individual features to whole systems — including evaluating others' threat models and training engineers to produce their own.
• Strong command of secure software development lifecycle (SSDLC), OWASP principles, and application security design patterns.
• Proficiency in modern authentication and authorization patterns (OAuth 2.0, OIDC, SAML), including across multi-tenant and patient-facing applications.
• Experience architecting key management, secrets management, and PKI/certificate lifecycle controls in cloud-native environments.
• Working knowledge of HIPAA (including Security Rule technical safeguards), HITRUST CSF, NIST CSF, and SOC 2, sufficient to design controls that satisfy them.
• Demonstrated ability to communicate complex architectural risk to both technical and executive audiences.

Preferred Qualifications

• Experience in healthcare, digital health, or another highly regulated industry.
• Experience designing and evaluating zero trust architectures in production.
• Experience designing or scaling an architecture review process — including risk-tiering, self-service patterns, or integration with an existing technical review board.
• Familiarity with API security architecture and healthcare data exchange standards (HL7, FHIR).
• Familiarity with security architecture frameworks such as SABSA or TOGAF security extensions.
• Experience mentoring senior engineers or establishing architecture practices from scratch.

What Success Looks Like

• First 90 days: Architecture review process documented and running without bottlenecking on the hiring manager. Baseline assessment of current architecture risk delivered. Working relationship established with the CTO org.
• First 6 months: Threat modeling established as a standard design input for net-new initiatives, with at least two engineering teams modeling their own features. At least two published reference architectures adopted by engineering. Risk-tiered review paths in place.
• First 12 months: Architecture-level HIPAA and SOC 2 findings closed. Measurable shift in security findings from late-stage to design-stage. Recognized by engineering leadership as a partner who is invited into design conversations rather than inserted into them.

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans
• Flexible Spending/Health Savings Accounts
• Flexible PTO
• 401(k) + Company Match
• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.