Checkfront
Director of Security and Compliance
CheckfrontCanada3 hours ago
Full-timeOther, Information Technology +1
About Us

At Checkfront, we’re builders, doers, and difference-makers—driven by a shared mission to reshape the tours, activities, and experiences industry. Alongside our sister brands, Rezdy and Regiondo, we power more than 20,000 businesses and support over $10B in bookings globally. Our technology helps operators thrive while delivering unforgettable moments to travelers around the world.

We work in an industry built on adventure, energy, and human connection—and that same spirit fuels how we show up every day. Spanning North America, Europe, and APAC, our teams are united by bold goals, a bias for action, and an unwavering commitment to delivering for our customers.

But our success starts with people. Our teams are the engine behind everything we create. We value self-starters who take ownership, embrace challenges, and raise the bar—for themselves and those around them. We believe in creating space to grow, take risks, and make a real impact—and we celebrate those who lead with curiosity, grit, and drive.

If you’re passionate about performance, hungry to learn, and ready to help shape the future of travel—this is your kind of place. Let’s build, grow, and win together.

About The Role

We are seeking an experienced Director of Security and Compliance to lead our growing security and compliance team. This role will oversee a team of security and compliance specialists, drive our global security and compliance strategy, and ensure that our organizational security posture and practices meet international standards.

We are open to candidates based within Canada.

What you will do

  • Leadership & Strategy
    • Lead and mentor the security and compliance team
    • Develop and maintain the organization’s information security and compliance roadmap
    • Represent the security and compliance team in leadership meetings and cross-departmental initiatives
  • Governance, Risk, and Compliance (GRC)
    • Own compliance programs across multiple jurisdictions
    • Ensure ongoing compliance with data protection and security regulations, primarily for software deployed out of the US, but subject to global regulations (GDPR, PCI, CCPA, EU AI Act)
    • Oversee vendor risk management, security questionnaires, and contract reviews
  • Security Operations
    • Oversee monitoring, incident response, and vulnerability management practices
    • Partner with engineering and IT to ensure secure development and infrastructure practices
    • Manage internal audits, risk assessments, and penetration testing processes
  • Customer and External Engagement
    • Act as the security point of contact for enterprise customers
    • Lead responses to client due diligence requests and RFPs
    • Build trust through transparency and strong security posture
What we are looking for

  • 7+ years of experience in security, compliance, or risk management, with at least 3 years in a leadership role
  • Strong understanding of SaaS business models and regulatory environments
  • Hands-on experience with SOC 2, ISO 27001, GDPR, and other global frameworks
  • Proven track record of building and leading security and compliance teams
  • Excellent communication skills with both technical and non-technical stakeholders
  • Certifications such as CISSP, CISM, CISA, or ISO 27001 Lead Implementer/Auditor are an asset.

When you join our team, you’re stepping into a culture built on momentum, ownership, and connection.

We move fast, think big, and focus hard—without losing sight of the people behind the work. Across all our brands, we’re united by a belief that impact comes from empowered teams, clear priorities, and a shared commitment to our customers and each other.

Here’s what you can expect:

  • High trust, high impact: We give our people the autonomy to lead, innovate, and make decisions that matter
  • Curiosity is encouraged: We value learning, asking questions, and pushing boundaries—not just getting things done, but doing them better
  • Collaboration over ego: We work as one team across geographies and brands. Success is shared, and support is a given
  • Space to grow: Whether you're stepping into leadership, learning a new skill, or tackling your next big challenge—you’ll be backed to take risks and grow from them
  • Progress over perfection: We embrace change, move quickly, and are constantly iterating to improve how we work and what we deliver

You’ll be joining a global team that’s passionate about building something that matters—and having a good time while doing it.

We’d love for you to join us on this exciting journey. Together, let’s shape the future of the leisure and tourism industry!

Salary Range $140K-160K

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