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VP, Engineering

RewindOntarioR&D
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Salary
Not listed
Job type
Full-time
Work mode
Remote
Posted
12 Aug 2026
Status
Open · checked 7d ago

About this role

Role Overview

Rewind Backups for SaaS Apps is seeking a VP, Engineering to lead the entire R&D function remotely from Ontario. This executive role reports directly to the CEO and suits an experienced technology leader ready to guide a fast-growing SaaS company through its enterprise-readiness transition.

Key Responsibilities

Design and execute the organization's overarching technology vision, ensuring alignment with overall business growth and profitability goals.
Guide the enterprise-readiness roadmap by overseeing architecture, security postures, SSO, compliance certifications, and advanced permissions.
Direct a multidisciplinary department that combines engineering, cloud operations, trust and security, and customer support.
Drive the internal AI transformation by integrating AI-native workflows into code generation, debugging, and general development processes.
Represent the engineering division during board meetings, investor discussions, and annual strategic planning sessions.
Oversee customer support standards, key metrics, and feedback loops to minimize support volume through proactive product quality.

Requirements

Bring fifteen or more years of technology leadership experience, including at least eight years in a senior capacity managing engineering or technical operations.
Demonstrate past success scaling engineering and support functions within a high-growth SaaS organization.
Possess robust expertise in modern software development, cloud infrastructure, and security compliance.
Display proven experience leading a B2B SaaS company through the complexities of moving upmarket into enterprise readiness.
Exhibit active usage of AI tools in daily workflows with a track record of championing AI adoption across technical teams.
Maintain strong, direct communication skills capable of uniting both technical and non-technical stakeholders.

Nice to Have

Background in data protection, cybersecurity, or backup and recovery SaaS.
Familiarity with support operations frameworks or ITIL.
Prior experience applying agile methodologies at scale across distributed teams.

Skills and Tools

Cloud infrastructure management
SaaS business model strategy
Security and compliance frameworks
AI-powered engineering tools and workflows
Enterprise architecture and readiness standards

Salary and Benefits

Flexible working hours and a remote-friendly environment with preference for Ontario residents
Employee stock options and comprehensive health benefits
Three weeks of vacation plus seven life leave days
Two Level Up days for professional development and one annual volunteer day
Summer Fridays and an office closure during the December holiday break
Paid parental leave
Annual wellness or home office allowance of $2,000
Annual professional development allowance of $5,000

About the Company

Rewind protects critical cloud data for businesses utilizing applications such as Shopify, GitHub, Jira, and Confluence. Recognized as one of Canada's fastest-growing technology companies, the firm is backed by prominent investors including Insight Partners, Inovia, Bessemer, and Atlassian Ventures. The company culture values a team-first mentality, performance-driven mindsets, customer centricity, taking initiative, and maintaining a balanced approach to startup life.

How to Apply

Interested candidates should visit the official Rewind careers page to submit an application.

Questions candidates ask

What is the location requirement for this role?

The position is remote-friendly across Canada, with a strong preference for candidates based in Ontario for occasional in-person collaboration at the Ottawa headquarters.

Who does the VP, Engineering report to?

This role reports directly to the CEO with no intermediate management layers.

What level of experience is required?

Candidates must have 15+ years in technology leadership, with at least 8 years at a senior level overseeing engineering or technical operations.

What perks and allowances are provided?

Rewind offers a $2,000 yearly wellness and home office allowance, a $5,000 yearly professional development allowance, health benefits, stock options, and paid parental leave.

How does AI fit into this position?

The VP, Engineering is expected to champion AI adoption across the organization, pushing for AI-native workflows that improve output velocity and code quality.

Ready to apply?

The application is on the official Rewind careers page.

Apply on company site