VP, Technology

Rewind AI, Inc.

Job Overview

Location

Ontario

Job Type

Full-time

Full Job Description

📋 Description

• Lead the full technology function including engineering, cloud infrastructure, trust and security, and customer support at Rewind AI, Inc.
• Define and execute the company’s engineering and infrastructure vision, ensuring architectural scalability, reliability, and market leadership in SaaS backup and recovery.
• Align technology strategy with company goals to drive revenue growth, profitability, and customer satisfaction in collaboration with the executive team.
• Unify engineering, cloud operations, trust and security, and support teams under a single approach that balances speed, quality, and cost efficiency.
• Own and manage the technology budget, making ROI-driven decisions on tooling, vendors, and infrastructure investments.
• Build, lead, and grow multidisciplinary teams of engineers, cloud operations specialists, and support professionals with a culture of high accountability, continuous learning, and direct feedback.
• Recruit and retain top technical talent by creating an environment that fosters long-term retention and high performance.
• Champion AI-native workflows across the engineering organization, embedding AI tools into code writing, architecture reviews, debugging, and toil reduction.
• Set the example by actively using AI tools in daily work and driving team adoption to improve output quality and velocity.
• Maintain and strengthen Rewind’s SOC 2, GDPR, and CCPA compliance posture, ensuring non-negotiable data protection standards are met.
• Cultivate a proactive security and data governance culture across all technical teams.
• Oversee the customer support organization, monitoring key metrics including CSAT, first response time, and resolution rate to ensure timely and effective issue resolution.
• Partner with Sales, Product, and Customer Success to ensure engineering efforts directly address real customer needs and reduce support burden through proactive quality and self-serve tooling.
• Close the feedback loop between customer-reported issues and product improvements to enhance product reliability and reduce recurring support requests.
• Operate as a hands-on executive who leads through clarity and conviction, not hierarchy, with direct visibility into customer experience and technical execution.
• Embrace a startup environment characterized by speed, agility, and creativity, while maintaining a team-first mentality and performance-driven mindset.
• Encourage work-life balance through flexible scheduling, recognizing the need to recharge while remaining responsive to urgent business needs.
• Foster a culture of taking initiative, ownership, and creative problem-solving where team members are empowered to lead improvements.
• Promote a fun, rewarding work environment where milestones are celebrated and team bonding is prioritized.

🎯 Requirements

• 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 of protecting customer data at scale, including SOC 2, GDPR, and CCPA
• Confident, direct communication skills to align technical and non-technical stakeholders without losing precision
• Active, established use of AI tools in daily work and a track record of driving AI adoption across teams

🏖️ 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
• $2000/year wellness/home office allowance
• $5000/year professional development allowance

Skills & Technologies

GitHub

Onsite

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Rewind AI, Inc.

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About Rewind AI, Inc.

Rewind AI, Inc. provides desktop software that records and indexes everything a user sees, hears, or types, creating a searchable memory of their digital activity. The application runs locally, encrypts data, and enables users to retrieve past meetings, documents, websites, and conversations through natural-language queries. It integrates with macOS and iOS, supports optical character recognition and audio transcription, and offers AI-generated summaries and action items. Targeted at professionals and teams, the tool aims to enhance productivity, reduce note-taking, and minimize context switching by preserving and surfacing relevant past information on demand.

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