VP, Technology

This is a fully remote position, open to applicants in Canada.

📋 Description

• Establish the engineering and infrastructure vision and strategy for Rewind, outlining our architectural direction, scalability, and reliability, while keeping us ahead in the market.

• Create and implement a cohesive technology vision that positions Rewind as the leading provider in SaaS backup and recovery solutions.

• Collaborate with the executive leadership to synchronize technology initiatives with corporate objectives, ensuring revenue growth, profitability, and customer satisfaction.

• Integrate engineering, cloud operations, trust and security, and support functions under a unified strategy that balances speed, quality, and cost efficiency.

• Manage the technology budget, making decisions based on ROI regarding tooling, vendors, and infrastructure investments.

• Lead and develop a multidisciplinary team of engineers, cloud operations experts, and support staff.

• Foster a culture of high accountability, continuous learning, direct feedback, and authentic collaboration across all functions.

• Attract and retain exceptional technical talent, creating an environment that encourages team members to stay.

• Advocate for the integration of AI within the engineering organization.

• Uphold and enhance Rewind's compliance with SOC 2, GDPR, and CCPA standards, as this is essential to our operations.

• Cultivate a proactive culture of security and data governance.

• Supervise the customer support team, monitoring quality standards, metrics (CSAT, first response time, resolution rate), and ensuring prompt and effective issue resolution for customers.

• Collaborate with Sales, Product, and Customer Success to ensure that our developments align with genuine customer needs.

• Ensure that engineering/support, sales, and product teams effectively close the feedback loop between customer-reported issues and product enhancements, minimizing support burdens through proactive quality measures and self-service tools.

⛳️ Requirements

• Over 15 years of experience in technology leadership, including a minimum of 8 years in senior roles with ownership of engineering and/or technical operations.

• Demonstrated success in scaling engineering and support teams within a rapidly growing SaaS environment.

• Comprehensive expertise in modern software development, cloud infrastructure, and SaaS business models.

• Strong background in security and compliance — you understand the requirements for protecting customer data at scale.

• A confident and direct communicator capable of aligning technical and non-technical stakeholders without sacrificing clarity.

• Actively utilize AI tools in your work and have a history of encouraging your teams to do the same — AI fluency is a part of your operational approach.

• High sense of agency: you take initiative, act with conviction, and hold yourself and your teams accountable.

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

🏝️ Benefits

• Flexible work hours

• Employee stock options

• Health benefits

• 3 weeks of vacation

• 7 days of life leave

• 2 Level Up days for professional development

• 1 volunteer day

• Summer Fridays and office closure during the holiday break in December

• Paid parental leave

• $2000/year wellness/home office allowance

• $5000/year professional development allowance