Staff Security Engineer, Application Security (Hybrid)

Homebase•Toronto, ON

102d•Hybrid

About The Position

At Homebase, you’ll join a team that’s bold, fast-moving, and obsessed with helping small businesses thrive. We build with empathy, act with urgency, and take big swings that drive real-world impact. Here, every Homie shows up to raise the bar, support one another, and celebrate wins as a team. We’re not just building an app—we’re building unstoppable teams. So what do you say, are you in? We’re looking for a hands-on Staff Security Engineer to own and shape Homebase’s Application Security domain. This is a technical leadership role at the E5 level—you’ll define the multi-quarter strategy for how we secure our products, set architectural direction, and pioneer new capabilities that keep pace with our rapid growth. Homebase’s product suite spans scheduling, payroll, time tracking, HR, team communication, and a growing ecosystem of AI-powered features. That breadth creates fascinating security challenges, from protecting sensitive workforce and financial data to securing the AI models and pipelines that are becoming central to our product experience. You’ll be the recognized expert our engineering organization turns to for application security decisions. You’ll work at the intersection of security, product, and engineering, partnering with engineering leaders to embed security into architecture from the ground up, while building the platforms and tooling that let developers ship safely at speed. These are the key ways you’ll contribute and create impact in this role:

Requirements

10+ years of progressive experience in Application Security or Security Engineering, with demonstrated impact at the Staff or Principal level.
Deep software engineering experience in production environments, you write code, build tools, and think like an engineer first.
A proven track record of leading architectural changes and complex cross-team initiatives that reduced security risk at scale.
Hands-on experience securing AI-native applications, including LLM integrations, model pipelines, or ML infrastructure.
Strong expertise in web application security, cloud-native security (AWS), and modern DevSecOps practices.
Proficiency in languages and frameworks relevant to our stack: Ruby, Python, React, and Rails.
Experience designing and implementing modern vulnerability management systems and embedding security tooling within CI/CD pipelines.
Exceptional ability to evaluate security trade-offs, make pragmatic risk-informed decisions, and communicate them clearly to technical and non-technical stakeholders.
Demonstrated curiosity about emerging AI capabilities, with a track record of leveraging new tools to enhance security operations and productivity.

Nice To Haves

Experience defining application security strategy and maturity roadmaps for a high-growth, product-driven company.
A background in building AI-powered security tools or detection systems.
Speaking experience at security conferences, meetups, or community events.
Experience with threat modeling frameworks adapted for AI/ML systems.

Responsibilities

Define and execute Homebase’s multi-quarter Application Security roadmap, aligning security initiatives with business objectives and company OKRs.
Architect secure-by-default patterns, frameworks, and paved roads that developers adopt naturally, removing entire classes of vulnerabilities before they reach production.
Evaluate emerging security technologies and make build-versus-buy decisions that shape the security platform.
Drive security and product trade-off decisions at the architectural level, balancing protection with velocity.
Influence company-wide engineering practices and security investments through data-driven recommendations.
Lead threat modeling and security architecture reviews for AI-powered features, model training pipelines, and LLM integrations.
Design and implement security controls specific to AI/ML systems, including prompt injection defenses, model input validation, output filtering, and data pipeline integrity.
Create AI-powered vulnerability detection and security automation that multiplies the team’s effectiveness.
Partner with AI engineering teams to establish secure development patterns for model deployment and inference infrastructure.
Stay ahead of the evolving AI threat landscape and translate emerging risks into practical engineering guidance.
Build and maintain security tooling and automation that integrates seamlessly into CI/CD pipelines, enabling continuous security validation at scale.
Own the vulnerability management program: design modern systems for detection, prioritization, tracking, and remediation of security debt across the product portfolio.
Own the bug bounty and responsible disclosure program, turning external researcher findings into systemic improvements.
Embed security into the full software development lifecycle through scalable guardrails, automated testing frameworks, and developer-facing documentation.
Partner with senior leaders across Engineering, Product, and Infrastructure to improve Homebase’s overall security posture.
Pioneer a security partnership program, mentoring engineers across the organization, and driving a culture of shared security ownership.
Provide expert guidance during security incidents and lead post-incident analysis to drive systemic improvements.
Curate and author security guidance, patterns, and training content that raises the security bar organization-wide.
Influence security decisions at the department and company level; shape how Homebase invests in security capabilities.