Director of People

About Orchestry
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.

The Opportunity
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.

What You'll Be Doing
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

What You Bring

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…