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.

Thriving at Rewind:

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:

• Team-First Mentality: We put teamwork at the core of everything we do, believing that we are better when we are together. Success is shared, and when the team wins, we all win.

• Performance-Driven Mindset: We are proactive, goal-oriented, and focused on delivering tangible, high-quality results. We go beyond meeting expectations - we aim to exceed them.

• Flexible Work-Life Approach: We encourage balance and understand the need to recharge. While we stay agile for urgent needs, we make sure there's time to recover and enjoy life.

• Customer Centricity: Our commitment to customers shapes everything we do. We listen, build relationships, and innovate - from our dedicated customer support team to our engineers, everyone at our company is focused on solving problems that matter most to our users.

• Taking Initiative: We value ownership and proactive problem-solving. We encourage team members to think creatively, take ownership, and lead improvements. Your ideas and actions drive our success.

• We Make Time for Fun: We work hard and make time to enjoy the journey. It’s not just about hitting milestones—it’s about making the experience rewarding along the way.

Rewind protects the data businesses run on - and technology is how we deliver on that promise. As VP, Engineering, you'll own the full R&D function: engineering, cloud infrastructure, security, and customer support - reporting directly to the CEO with no layers in between. You'll be the company's most senior technical voice, a genuine strategic partner to the executive team, and the person who sets the bar for how we build, scale, and operate.

The context matters: we're at a pivotal point in our growth, moving deeper into enterprise - and we need a leader who has done this transition before. You've taken a B2B SaaS product through the enterprise-readiness inflection: you know what that demands architecturally, operationally, and organizationally, and you know the difference between scaling for volume and scaling for trust. You've also led technical teams through real transformation - AI adoption, culture resets, periods of change - and you've left those teams with more momentum and capability than you found them.

We run lean, we move fast, and we expect our leaders to be close to the work. If you've built high-performing R&D functions in focused, high-growth environments and driven meaningful outcomes with compact teams, that's the experience that travels here.

What you'll do

Set and execute the technology vision

• 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

Lead the enterprise transition

• 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

Build and lead high-performing teams

• 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

Drive AI-powered engineering

• 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

Connect technology to the customer

• 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

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 — 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

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

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

Compensation Philosophy
The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process.

In some cases, we’re open to hiring at a higher level for the right person and are committed to paying competitively and fairly.

If your experience is closer to an earlier career stage, we may still consider your application. In that case, we would evaluate the role at a different level within our levelling framework.

Pay is just one part of the overall compensation at Rewind.

Why join Rewind

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.

How Rewind Will Support You
We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life which includes but is not limited to: 

• 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

Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply.

AI Usage

Our recruitment process may include the use of artificial intelligence–enabled tools to help manage and review applications efficiently. These tools assist our team, but hiring decisions are ultimately made by human reviewers.