Technical Operations & Compliance Lead

Flex Travels Solutions Inc.; Montreal (administrative region); Hybrid; CAD 110,000 - 150,000; Full time

Benefits offered by this job

Hybrid work model

Job summary

Flex Travel Solutions in Montreal, QC, is seeking a Technical Operations & Compliance Lead to own the operational engine of the engineering team. You will manage end-to-end delivery processes, production operations, and security/compliance efforts, working closely with the Senior Architect to scale velocity, cost efficiency and risk management in a hybrid work setting.

This role requires hands-on leadership, strong communication, and practical experience with AWS, React and Python stack, plus

Qualifications

• 5+ years of experience in technical project delivery or operations.
• Proven track record in a startup or small agency environment.
• Thrive in ambiguity; move fast and communicate clearly.
• Able to partner with engineers and founders; translate technical needs to execs.

Responsibilities

• Own end-to-end delivery process: sprint ceremonies, planning, retrospectives.
• Own Jira architecture, sprint tracking, and capacity models.
• Provide data-driven insights on team delivery across software and cloud stack.
• Manage production support and incident management from triage to resolution.
• Coordinate with Senior Architect on remediation while owning process and timelines.
• Track internal hours and monitor AWS costs and SaaS spend.
• Own SOC 2 Type 2 compliance and security controls; liaise with auditors.
• Manage vendor contracts, renewals, and relationships with tech partners.

Skills

Technical leadership

Jira

Delivery tooling

Incident management

AWS

React

Python

SOC 2 compliance

Vendor management

Tools

Jira workflows

Capacity planning

Incident management process

Postmortems

AWS architecture

Job description

# Technical Operations & Compliance LeadMontreal, QC (Hybrid)Full-timeAt Flex Travel Solutions, we foster an environment of passion, innovation and collaboration. We believe in a dynamic work culture that empowers employees to grow and expand their knowledge. If our ethos resonates with you, we'd love for you to join us!As a technology first company, we're currently looking for a Technical Operations & Compliance Lead to join our team.The Role: Flex Travel Solutions is a fast-growing B2B travel technology company specializing in airline commission payment processing. We are a lean, high-impact team of approximately 20 people, and we are looking for a hyper-organized, technically fluent operator to run the operational engine of our engineering team. You will work alongside our Senior Architect, who owns technical direction, architecture, and delivery, while you own the process, operational, and administrative layer that keeps the team running day to day, including production support and incident management. This is not a theoretical management role. We need someone who is excited to build structure out of complexity, get hands-on where it matters, and directly impact our engineering velocity, cost efficiency, and security posture.Responsibilities:Team Process and Delivery Ownership* Own our end-to-end delivery process: sprint ceremonies, planning, retrospectives, and how the team runs day to day.* Own our Jira architecture, sprint tracking, and resource capacity models.* Provide data-driven insights on team delivery across our software and cloud technology stack.* Build and maintain capacity planning tooling so priorities are visible and workload is balanced.* Flag risks and blockers before they become delivery issues, not after.Production Operations and Incident Management* Own our production support and operational process end to end, including monitoring, triage, escalation, coordination of remediation, and follow-through to resolution.* Build and evolve an incident management process the team actually follows, including severity levels, escalation paths, and postmortems.* Coordinate with the Senior Architect on technical remediation while you own the process, timeline, and communication.Financial Oversight and Project Costing* Track internal developer hours and external resource allocations against project budgets.* Monitor and help optimize AWS infrastructure costs and SaaS license spend.* Own the tech budget tracker and provide founders with regular visibility on spend versus plan.* Flag any budget variances proactively and propose corrective actions.Team Leadership and People Operations* Own a consistent, fair, and documented performance management framework, and run the formal annual performance review process for the technical team.* Own career pathing and individual development plans, partnering with the Senior Architect who provides the technical assessment and feedback.* Handle onboarding and offboarding processes for all technical team members.Security and Compliance (SOC 2 and CISO Path)* Take ownership of our SOC 2 Type 2 compliance framework.* Ensure internal controls, access management across Bitbucket and AWS, and all compliance documentation are strictly maintained.* Act as primary liaison with compliance auditors and security partners.* Deep hands-on experience in this area is a fast track to becoming our designated CISO.Vendor and Stakeholder Management* Act as primary point of contact for external tech partners, software vendors, and compliance auditors.* Manage vendor contracts, renewals, and relationships on behalf of the tech team.* Ensure vendor commitments align with business priorities and budget.Experience/Skills Required:The Startup Mindset* 5 or more years of experience in technical project delivery or operations.* Proven track record in a startup or small agency environment where you built structure from scratch.* You thrive in ambiguity and do not say that is not my job.* You move fast, communicate clearly, and close things properly.Technical Literacy* You speak the same language as engineers without being the one writing the code.* You understand the deployment lifecycle of full-stack applications including React, Python, and cloud infrastructure on AWS.* You can challenge estimates, spot bottlenecks, and ask the right questions to surface risk early.Jira, Delivery Tooling, and Incident Process* Advanced experience setting up Jira workflows, dashboards, and capacity planning tools.* Experience standing up or running an incident management process, including postmortems.* You track delivery against commitments and present data in a way founders and stakeholders can act on.* You do not just check boxes. You build systems that actually improve team velocity.People Leadership* Experience managing or matrix-managing engineers.* You run performance reviews with fairness, consistency, and documentation.* You navigate interpersonal dynamics with high emotional intelligence and low drama.Security and Compliance* Prior hands-on exposure to SOC 2 compliance, security auditing, or identity and access management frameworks.* Comfortable owning the compliance calendar, managing audit requests, and keeping controls current.* Bonus: experience as a designated CISO or in a formal security leadership role.What you can expect from us:* Real ownership from day one. You will not be a coordinator, you will be the operational backbone of the tech team.* A high-visibility role with direct access to founders and the Senior Architect on a daily basis.* A clear growth path. Strong performance in this role creates a direct path to formal CISO designation.* Lean team, real impact. Every process you build and every inefficiency you remove shows up directly in what the team ships.* Travel tech at a pivotal moment. We are expanding into new markets and the operational foundation you build will scale with us.* Hybrid work flexibility (minimum 3 days in office, based in Montreal, Quebec)