Remote jobs in Canada

Orchestry is a rapidly growing SaaS company in the Microsoft 365 ecosystem, helping organizations simplify, govern, and automate their digital workplace. We work globally with partners and enterprise customers and operate as a fully remote company by design.

As we scale, we are intentionally building the foundation for the future of the company including our people, leadership capability, and culture. This role is critical to ensuring Orchestry grows with focus, agility, and strong execution.

The Director of People is a core leadership role at Orchestry, reporting to the COO and Co-Founder. This role partners closely with leadership to translate the company’s vision into a people and talent strategy that enables long term growth, adaptability, and performance.

We are looking for a leader who can define strategy and execute it. Someone who can think ahead about what the company will need as it grows and changes, while also operating hands on in a lean and fast-moving environment.

This is not a siloed or purely advisory role. You will work closely with leaders, managers, and employees across the company to build the talent pipeline, leadership capability, and culture that support Orchestry’s future.

Because Orchestry is fully remote, success in this role depends on the ability to intentionally build alignment, engagement, productivity, and strong working relationships without relying on proximity.

The ultimate measure of success is highly efficient, innovative, and adaptable teams.

People and Talent Strategy

• Partner with leadership on the long-term vision for the company and develop a people strategy that supports where Orchestry is going, not just where it is today
• Define and evolve a clear strategy for talent, leadership development, and culture as the company grows and changes
• Stay current on industry and talent trends, particularly in SaaS and remote work, and proactively bring insights, recommendations, and ideas to leadership
• Balance long term strategy with near term execution in a fast paced, high growth environment

Talent Acquisition and Retention Strategy

• Design and own a talent acquisition strategy, including where and how Orchestry sources talent in a competitive market
• Partner with hiring managers to define role clarity, success criteria, and capability needs
• Actively participate in hiring, including conducting interviews
• Design and advise on compensation structures aligned with company stage, market realities, and retention goals
• Develop strategies to retain and engage talent in a remote environment, driving productivity and long-term commitment

Culture, Leadership, and Performance

• Provide leadership and advisory on building and evolving a culture that fosters innovation, pace, productivity, and agility
• Ensure culture scales intentionally in a fully remote organization
• Design and evolve performance and feedback frameworks that emphasize accountability, collaboration, and outcomes
• Coach and support leaders on people leadership, decision making, and managing through ambiguity
• Help develop leadership capability across the organization as teams grow

Strategy, Operations, and Hands-On Execution

• Execute people initiatives personally in a lean, builder stage environment, wearing multiple hats as needed
• Oversee core HR operations including policies, compensation programs, benefits, payroll coordination, and compliance
• Research, interpret, and execute against employment standards across multiple jurisdictions as the company grows
• Ensure strong understanding and application of Canadian employment standards, with experience in United States employment standards considered a strong bonus
• Continuously assess where effort will have the highest impact and adjust priorities as the business evolves

• Eight or more years of progressive People or HR leadership experience, including senior level ownership
• Proven experience in high growth SaaS or technology environments
• Demonstrated ability to set strategy and execute, often at the same time
• A strong builder mindset with comfort operating lean, wearing multiple hats, and working through ambiguity
• Experience creating talent acquisition and retention strategies in competitive markets
• Proven success building culture, engagement, and productivity in fully remote teams
• Curiosity and discipline to stay current on talent, workforce, and industry trends
• Strong judgment, adaptability, and ability to think on your feet
• A low ego, highly collaborative leadership style focused on impact and contribution
• Deep understanding of North American employment practices, with multi jurisdiction experience preferred

How We’ll Measure Success

• A clear people and talent strategy that supports Orchestry’s long term vision
• Demonstrated ability to both define strategy and execute it effectively in a fast moving and ambiguous environment
• Strong hiring outcomes with faster ramp up and better role fit
• Leaders who are confident and capable people managers in a remote and fast moving organization
• A culture that fosters innovation, pace, productivity, and agility as the company scales
• The People function is viewed across the organization as a trusted partner and a practical tool that helps teams achieve great things and enables Orchestry to grow and adapt
• Highly efficient teams that collaborate well and deliver consistently

• A chance to build and shape the people function at a pivotal growth stage
• Direct partnership with the COO and leadership team
• Fully remote environment built intentionally for trust and outcomes
• Competitive salary and stock options
• Extended health benefits package
• Real ownership, real impact, and an opportunity to help define the future of the company

We offer a competitive total compensation package aligned to our location & phase of growth, including:

• 140,000 - 160,000 annual salary
• 100% remote work setup with schedule flexibility
• Comprehensive Benefits package including additional mental health, HSA and more.
• Professional development programs and home office allowance
• Regular team retreats and swag, opportunities to connect both in person and via remote events