Fresh Books

About the Role

As the Director, Information Security, you will lead and elevate FreshBooks’ enterprise information security program. You’ll oversee key security teams (GRC, privacy, security engineering), and collaborate closely with leaders across engineering, data, and IT to ensure security is embedded into everything we build. You’ll guide the organization through audits, risk management, and incident response, while acting as a trusted advisor to senior leadership. This is a hands-on leadership role that requires both strategic thinking and practical execution.

Note: This role can be worked remotely from the US or Canada. Occasional travel to Toronto (up to 25%) is expected.

What You'll Do

• Lead and support high-performing GRC, privacy, and security engineering teams
• Oversee departmental security roadmaps, budgets, vendors, and contract management
• Act as Incident Commander during major security incidents and lead tabletop exercises
• Chair the Security Steering Committee and support the Risk Management Committee
• Manage third-party risk and ensure security terms in contracts align with business needs
• Drive audit readiness and compliance for SOC 2 Type II and PCI-DSS
• Track and report on departmental KPIs, KRIs, and communicate security risks to senior leaders

What You'll Bring

• 7+ years of experience in Information Security, IT Governance, Risk, or Compliance
• 3+ years in a leadership or management role within security teams
• Bachelor’s degree in Information Security, Computer Science, or related field
• Industry certification such as CISSP, CISM, or CRISC
• Strong understanding of cybersecurity concepts, compliance, and risk management
• Proven experience managing audits and regulatory frameworks (NIST CSF, NIST 800-53, RMF)
• Excellent communication, leadership, and cross-functional collaboration skills

You'll Stand Out If You Have

• Experience implementing DLP strategies and rolling out related tools
• Hands-on experience with SIEM solutions and managing critical alerts
• Expertise in security awareness programs, policy development, and contract review

About FreshBooks

You've probably learned a bit about FreshBooks before making it to this point, but let us take a moment to introduce ourselves: FreshBooks is a leading cloud-based SaaS accounting software platform built for small business owners and consistently ranks #1 easiest to use. With an emphasis on keeping things simple and stress-free wherever possible, FreshBooks makes the hard parts of running a business a little bit easier. With FreshBooks, our customers can get paid faster and spend less time on admin and paperwork, so they can focus on what they do best—growing their businesses.

We believe in human-centric connections that empower teams to do their best work. Headquartered in Toronto, Canada, our team operates in clusters across North America and Europe using a variety of working environments—remote, hybrid, and in-office—all based on what’s best for the team, collaboration, and mental well-being. We are committed to creating a supportive and flexible workplace where everyone can thrive, grow, and make an impact on the lives of small business owners and accountants worldwide.

Perks & Benefits

We understand that you'll weigh many factors when deciding if FreshBooks is the right next step in your career. Here are some of our offerings for our employees (we call ourselves ✨ FreshBookers✨) to support their growth:

• ???? Comprehensive health and wellness benefits. Including a retirement savings program or pension plan matched to your local office, stock options for every full-time employee, generous time off, parental leave and new parent support, annual healthy living credit, comprehensive medical and dental benefits, fertility and gender-affirming benefits dependent on your region, and more.
• ???? Perks that matter. Including a Peer Recognition Program, an Employee Assistance Program, headphone credit, meaningful in-person gatherings to bring onsite and remote employees together, and more perks matched to your local cluster.
• ???? Working environments to help you thrive. Beautiful office spaces welcome you in Toronto, Amsterdam, and San Luis Potosi. If you don't have access to a FreshBooks office, you receive a home office credit to set up your home office. We are committed to creating supportive and flexible environments to support the best interests of the team, collaboration, and mental well-being.
• ???? Supportive peer group, mentors, and leaders. We care about each other across the organization and have programs to support this so everyone feels a strong sense of belonging, and believes in collective impact.
• ???? Accelerated growth. Comprehensive company onboarding, career development through continuous coaching, training, and learning on the job.

Even if your experience doesn't meet every bullet on the above lists, we'd love to learn more about you and why you think FreshBooks is the next step in your career.

FreshBooks is an equal-opportunity employer. We do not discriminate based on gender, religion, race, mental disability, sexual orientation, age, or any other status. All applicants are considered based on their qualifications and merits. At FreshBooks, we inspire an environment of mutual respect and we believe diversity and inclusion are crucial to our success.

FreshBooks provides employment accommodation during the recruitment process. Should you require any accommodation, please indicate this on your application and we will work with you to meet your accessibility needs. For any questions, suggestions or required documents regarding accessibility in a different format, please contact us by phone at 1-416-780-2700 and/or email at accessibility@freshbooks.com.

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