VP, Engineering

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). We invite you to read our startup story to learn where we came from and where we’re going.

Read about our mission, story and values here.
To find out more about our perks, click here.
Some of our Blogs might help you get a better understanding of what we do here. You can find them all here.

We embrace the fast-paced, ever-changing nature of startup life. If you love working with speed, agility, and creativity, you’ll feel right at home here. Here's what it takes to succeed with us:

• Define Rewind's engineering and infrastructure vision and strategy — where we're going architecturally, how we build for scale and reliability, and how we stay ahead of the market

• Develop and execute a unified technology vision that positions Rewind as the market leader in SaaS backup and recovery

• Collaborate with the executive team to align technology initiatives with company goals, ensuring revenue growth, profitability, and customer satisfaction

• Bring together engineering, cloud ops, trust and security, and support under a unified approach that balances speed with quality and cost efficiency

• Own the technology budget, making ROI-based decisions on tooling, vendors, and infrastructure investment

• Represent engineering in board and investor conversations, contributing to annual planning, budgeting, and strategic prioritization

• Own Rewind's enterprise-readiness roadmap — SSO, advanced permissions, audit logging, compliance certifications, enterprise SLAs, and the operational maturity that comes with serving larger customers at higher stakes

• Define what "enterprise-grade" means at every layer of the product and the business, working cross-functionally with Sales, Product, and Customer Success to deliver against it

• Build the architecture, security posture, and processes that earn and sustain enterprise trust at scale — and evolve them as customer requirements grow

• Lead and grow a multidisciplinary team of engineers, cloud operations specialists, and support professionals

• Set the culture: high accountability, continuous learning, direct feedback, and genuine collaboration across functions

• You've inherited teams that needed a reset — you know how to rebuild trust, restore momentum, and create the conditions where great engineering happens

• Recruit and retain top technical talent, and build an environment where high performers want to stay and grow

• Champion the adoption of AI across the engineering org — in how your teams write code, review architecture, debug faster, and reduce toil

• Lead Rewind's internal AI transformation: you've done this before with a dev team, you have a point of view on how to do it well, and you set the example from the top

• Push for AI-native workflows that meaningfully lift output quality and velocity

• Oversee the customer support organization: monitoring quality standards, metrics (CSAT, first response time, resolution rate), and ensuring customers have timely, effective resolution of issues

• Partner with Sales, Product, and Customer Success to ensure what we build maps to real customer needs

• Ensure that engineering, support, sales, and product teams close the feedback loop between customer-reported issues and product improvements, reducing support burden through proactive quality and self-serve tooling

• 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 — you understand what it takes to protect customer data at scale

• You're a confident, direct communicator who can align technical and non-technical stakeholders without losing precision

• You actively use AI tools in your own work and have a track record of pushing your teams to do the same — AI fluency isn't something you're working toward, it's already how you operate

• High agency: you don't wait to be asked, you move with conviction, and you hold yourself and your teams to account

• Demonstrated experience leading a B2B SaaS company through an enterprise-readiness transition — you've navigated the technical, operational, and organizational complexity of moving upmarket, and you've done it in a product where trust and compliance are core to the value proposition, not afterthoughts

• Proven ability to lead and rebuild technical teams through change — you raise the performance bar while earning trust, and you know that culture and engineering quality are inseparable

• Experience participating in board and investor meetings, annual planning, and executive-level budgeting and prioritization

• Experience in data protection, backup/recovery, or cybersecurity SaaS

• Familiarity with ITIL or support operations frameworks

• Experience with agile at scale across distributed teams

Remote-friendly (Canada), with a strong preference for candidates based in Ontario for easier collaboration and occasional in-person meetings at our Ottawa HQ.

At Rewind, you’ll help shape the future of data protection for thousands of businesses. We’re performance-driven, innovative, and not afraid to challenge what’s possible. You’ll join a team that values trust, accountability, and respect for people’s time — and encourages every employee to experiment, think critically, and grow.

We support innovation through experimentation — including smart use of AI tools — and believe the best ideas come from those who aren’t afraid to push boundaries.