Vice President, People

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's mission is to help businesses protect their most valuable digital assets. As we

continue to scale, we are building the systems, leadership capabilities, and operating practices

that enable us to grow intentionally while maintaining our culture and values.

The Vice President, People, leads the design and execution of people strategies and systems that scale with the business. This role ensures our people practices, leadership capabilities, and operating model enable high performance, clear accountability, and sustained growth.

You are accountable for translating Rewind's values into durable systems, meaningful people

metrics, and a consistent operating cadence that supports how the company attracts, develops, and retains exceptional talent. This is a hands-on leadership role for someone who enjoys building structure where it matters, challenging assumptions, and building culture.

What You'll Do

People Strategy & Culture Stewardship

• Set and evolve Rewind's people strategy in support of company goals, growth plans, and long-term sustainability.

• Act as a trusted advisor to the CEO and executive team on organizational health, talent risks, leadership effectiveness, and culture decisions.

• Translate Rewind's values into operating principles, decision frameworks, and leader expectations.

• Partner with leaders to maximize the effectiveness of distributed teams and leverage the benefits of hybrid work.

• Develop and implement organizational health assessments and action plans that strengthen leadership effectiveness, employee engagement, and business performance.

People Operations & Execution

• Own the operating model of the People team, including structure, capacity,prioritization, and delivery standards.

• Design and implement people processes and operating rhythms that support effective planning, decision-making, and execution across the organization.

• Align People team priorities with company objectives and business needs.

• Establish clear forums and cadences, including talent reviews, leadership reviews, and retrospectives that connect people insights to business decisions.

• Ensure leaders across the company have clarity on expectations, accountability, and follow-through as the company scales.

People Metrics & Organizational Insights

• Define, track, and continuously improve People team KPIs, including engagement, retention, hiring effectiveness, and performance outcomes.

• Develop and maintain dashboards and reporting that connect people metrics to business outcomes and provide actionable insights to leaders and the executive team.

• Use people data and operational insights to inform discussions regarding organizational capacity, productivity, workforce planning, and organizational health.

• Provide strategic recommendations and action plans based on trends and emerging risks.

Remote-First & Distributed Work

• Own and evolve Rewind's remote and hybrid work strategy to ensure clarity, equity, and consistency across teams.

• Design systems and norms that support strong performance, collaboration, and connection in a distributed environment.

• Regularly assess what is working, what is not, and where adjustments are needed as the company grows.

Talent, Performance & Leadership

• Oversee talent acquisition, onboarding, performance management, learning and development, and succession planning.

• Coach leaders to be strong people managers who set clear goals, provide meaningful feedback, and hold themselves accountable.

• Support leadership development with a focus on execution, trust, and growth.

• Ensure performance management practices are consistently applied, including timely feedback, development plans, and decisive action when expectations are not met.

Mergers, Acquisitions & Organizational Change

• Lead HR due diligence activities for mergers, acquisitions, and strategic transactions.

• Develop and execute people integration strategies, including organization design, change management, communications, and talent retention plans.

• Partner with business leaders to ensure seamless organizational transitions and achievement of business objectives.

Employee Communications & Change Management

• Develop and execute the company's employee communications strategy and annual communications plan.

• Draft and oversee executive and organizational communications that support change initiatives, reinforce company values, and strengthen employee engagement.

• Ensure consistent, transparent, and timely communication during periods of growth and transformation.

This role is open for candidate located in Ontario.

What You'll Bring

• Proven experience in a senior people leadership role (VP or Senior Director level) in a scaling technology or SaaS organization that is PE or VC backed.

• Demonstrated success building and scaling people functions and operating models.

• Have built the People function, rather than inheriting a mature one

• Experience in a Canadian or cross-border (Canada and US) workforce

• Strong business acumen with the ability to connect people strategies to business outcomes.

• Demonstrated expertise in organizational design, change management, and organizational effectiveness.

• Experience leading M&A due diligence and post-acquisition integration.

• Experience supporting remote and distributed teams.

• Exceptional communication, influencing, and relationship-building skills.

• Sound judgment and the ability to navigate complex people and organizational situations.

• A pragmatic, hands-on approach and the ability to balance strategic thinking with operational execution.

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.