VP, Technology

Rewind is a service that protects the critical data that powers businesses of all sizes. Our focus is on backing up data that lives in the cloud— in apps like Jira, GitHub, Confluence, and Shopify. We are backed by Insight Partners, Inovia, Bessemer, and Atlassian Ventures and are proud to be recognized as one of Canada’s 50 fastest‑growing technology companies (2023 Deloitte Fast 50).

About the Role

As VP of Technology you will own the full technology function: engineering, cloud infrastructure, trust and security, and customer support. You will report to the CEO and set the bar for how we build, scale, and operate while maintaining a direct line to what customers actually experience. This is a hands‑on executive role for someone who leads through clarity and conviction, not hierarchy.

What You’ll Do

• Define and execute Rewind’s engineering, infrastructure, and technology vision—identifying architecture, scale, reliability, and market positioning.
• Collaborate with the executive team to align technology initiatives with company goals, ensuring revenue growth, profitability, and customer satisfaction.
• Unify engineering, cloud ops, trust & security, and support under a single approach that balances speed, quality, and cost efficiency.
• Own the technology budget and make ROI‑based decisions on tooling, vendors, and infrastructure investment.
• Lead and grow a multidisciplinary team of engineers, cloud operations specialists, and support professionals.
• Establish a culture of high accountability, continuous learning, direct feedback, and genuine collaboration across functions.
• Recruit and retain top technical talent and create conditions that make people want to stay.
• Champion the use of AI across the engineering organization to improve code quality, architecture review, debugging, and toil reduction.
• Maintain and strengthen Rewind’s SOC 2, GDPR, and CCPA posture and build a proactive security and data governance culture.
• Oversee the customer support organization, monitoring quality standards and metrics (CSAT, first response time, resolution rate).
• Partner with Sales, Product, and Customer Success to align engineering and support with real customer needs and close the feedback loop between user issues and product improvements.

What You’ll Bring

• 15+ years in technology leadership, with at least 8 years at a senior level owning engineering and/or technical operations.
• Proven track record scaling engineering and support teams in a high‑growth SaaS environment.
• Deep fluency in modern software development, cloud infrastructure, and SaaS business models.
• Strong security and compliance experience—understanding what it takes to protect customer data at scale.
• Confident, direct communication skills that align technical and non‑technical stakeholders.
• Active AI tool usage in your own work and a history of driving agency in AI adoption within teams.
• High agency—proactive, decisive, and accountable for yourself and your teams.

Nice to Have

• Experience in data protection, backup/recovery, or cybersecurity SaaS.
• Familiarity with ITIL or support operations frameworks.
• Experience with agile at scale across distributed teams.

Location

Preference for Ontario‑based candidates to facilitate occasional in‑person collaboration at the Ottawa HQ.

Compensation Philosophy

Base salary varies by market and individual qualifications. The described range serves only as a guideline and may be adjusted. Salary and benefits are determined competitively and fairly based on performance, experience, and level.

Benefits

• Flexible work hours
• Employee stock options
• Health benefits
• 3 weeks vacation
• 7 life leave days
• 2 Level‑Up days for professional development
• 1 volunteer day
• Summer Fridays and office closed during the holiday break in December
• Paid parental leave
• $2,000/year wellness/home office allowance
• $5,000/year professional development allowance

Why Join Rewind

At Rewind, you will shape the future of data protection for thousands of businesses. The company values trust, accountability, respect for people’s time, and encourages experimentation, critical thinking, and growth.

Inclusion Commitment

Rewind is committed to building an inclusive, supportive workplace where every employee can do their best work. The company welcomes candidates from all backgrounds and encourages diversity.

AI Usage Notice

The recruitment process may include AI‑enabled tools for managing and reviewing applications. Hiring decisions are ultimately made by human reviewers.