VP, People

Rewind

16h

About The Position

Rewind’s VP, People leads the design and execution of people strategies and systems that scale with the business. The role ensures that people practices, leadership capabilities, and the operating model support high performance, clear accountability, and sustained growth. The VP translates company values into durable systems, meaningful people metrics, and a consistent operating cadence for attracting, developing, and retaining talent. This is a hands-on leadership role focused on building structure and culture. The VP sets people strategy, advises the CEO and executive team, and develops organizational health and leadership effectiveness. They own the People team’s operating model, processes, priorities, and business-aligned rhythms; define people KPIs and reporting; and use insights to inform workforce planning and organizational decisions. The role also owns remote and hybrid work strategy, oversees talent and performance programs, leads HR due diligence and people integration for transactions, and manages employee communications and change initiatives. Rewind is a service that backs up cloud-based business data. The company describes its culture as fast-paced and team-oriented, with a performance-driven, customer-centric, flexible, and initiative-taking approach. It supports experimentation, including the use of AI tools, and is committed to an inclusive workplace.

Requirements

Proven experience in a senior people leadership role at VP or Senior Director level in a scaling, PE- or VC-backed technology or SaaS organization.
Demonstrated success building and scaling people functions and operating models; experience building the People function rather than inheriting a mature one.
Experience supporting a Canadian or cross-border Canada-and-US workforce.
Strong business acumen and ability to connect people strategies to business outcomes.
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 ability to navigate complex people and organizational situations.
Pragmatic, hands-on approach and ability to balance strategic thinking with operational execution.

Responsibilities

Set and evolve Rewind’s people strategy in support of company goals, growth plans, and long-term sustainability.
Advise the CEO and executive team on organizational health, talent risks, leadership effectiveness, and culture decisions.
Translate company values into operating principles, decision frameworks, and leader expectations.
Partner with leaders to improve distributed team effectiveness and leverage hybrid work.
Develop organizational health assessments and action plans to strengthen leadership effectiveness, employee engagement, and business performance.
Own the People team operating model, including structure, capacity, prioritization, and delivery standards.
Design and implement people processes and operating rhythms that support planning, decision-making, and execution.
Align People team priorities with company objectives and business needs.
Establish talent reviews, leadership reviews, retrospectives, and other forums that connect people insights to business decisions.
Ensure leaders have clarity on expectations, accountability, and follow-through.
Define, track, and 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.
Use people data and operational insights to inform organizational capacity, productivity, workforce planning, and organizational health.
Provide strategic recommendations and action plans based on trends and emerging risks.
Own and evolve Rewind’s remote and hybrid work strategy to promote clarity, equity, and consistency.
Design systems and norms that support performance, collaboration, and connection in a distributed environment; assess and adjust them as the company grows.
Oversee talent acquisition, onboarding, performance management, learning and development, and succession planning.
Coach leaders to set clear goals, provide meaningful feedback, and hold themselves accountable.
Support leadership development focused on execution, trust, and growth.
Ensure consistent performance management, including timely feedback, development plans, and decisive action when expectations are not met.
Lead HR due diligence 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 on organizational transitions and business objectives.
Develop and execute the employee communications strategy and annual communications plan.
Draft and oversee executive and organizational communications that support change, reinforce values, and strengthen engagement.
Ensure communications are consistent, transparent, and timely during growth and transformation.