Staff Security Operations Specialist, LeapSec

Company Description

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: Workleap Agent, our newest solution built to make every manager more effective, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

Your role

You will own how Workleap detects, investigates and responds to threats across Workleap and ShareGate, and you will build the AI layer that runs it. Our security tooling generates more noise than a small team can work, and too many findings are ambiguous or wrong. This role exists now to turn detection and response into a system where agents triage, enrich and investigate, and people make the calls that genuinely need judgment. It is a hands on Staff individual contributor role with no direct reports.

Your impact: 

• Build the pipeline that runs security operations end to end: integrations that pull alerts and findings out of every source tool, an agentic system that triages, enriches, correlates and drafts the investigation, and a connection into Jira that routes each result to the owning team with evidence and a fix path, so no finding is ever copied by hand.
• Define the trust model for those agents, deciding what they close alone, what they recommend and what always goes to a human, backed by evals and secured against prompt injection and permission abuse.
• Drive false positives and misrated findings out of our security tooling, so every finding that reaches a person is real and correctly prioritized.
• Own detection engineering end to end, written as code and mapped to MITRE ATT&CK, so coverage survives any change of platform.
• Lead security incident response from triage to postmortem, with agents gathering the evidence, and hold our managed detection partner to a measurable standard.
• Make security a partner developers want to work with, delivering findings in their workflow with clear evidence and a fix path.

Your team

Over the next 12 months, LeapSec is delivering two strategic bets: putting security inside product squads, with agents carrying vulnerability and detection work, and automating SOC 2 evidence so nobody gathers it by hand. You will own the detection and response side of that work: cleaning up the tooling, building the agents, and proving how much they can be trusted to do alone.

LeapSec covers Security Operations and Compliance across Workleap and ShareGate. You will report to the Director of Infrastructure and Security and work daily with our Staff Application Security Specialist and security tooling team, and as needed with Infrastructure, ITX and product engineering. We are a small team with a wide mandate: we track work honestly in Jira, deliver on fixed dates, and expect people to own outcomes end to end.

Our environment is Azure first, with a cloud native SIEM and XDR stack, Zscaler, Cloudflare and a managed detection partner today. We choose tools on merit and expect to keep choosing.

What you'll bring

• 7+ years in security operations, incident response or detection engineering, with recent hands on time in a cloud SaaS environment;
• Deep experience working findings that are not clean: validating what tooling flags, tuning false positives out at the source, and deciding with incomplete evidence whether something is real;
• Years of working directly with developers, getting fixes shipped without authority and keeping the relationship intact when the answer is no;
• Built and shipped agent systems for security work that others depend on, such as MCP servers, Claude skills, subagents or custom tools, with evals that decide when the output is trusted;
• A working model of how agentic systems fail and get attacked, including prompt injection, tool permission scoping and credential handling;
• Detection engineering as a discipline: detections as code, a SIEM query language you write fluently, and false positive rates you actually measure;
• Strong grasp of identity and cloud attack paths, ideally in Azure and Entra ID;
• Bonus: experience directing a managed detection partner, threat hunting or forensics, and working proficiency in French.

Most of this sounds like you? Apply.

What the job comes with

• Base salary: $125 000 - $160 000. This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate's region to align with local market conditions.
• Annual bonus program.
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gatherings twice a year.
• Claude access, for everyone.

What drives us

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire 

Transparency is how we hire — for you as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

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