Director of People

About Squared Away

Squared Away exists to give people their most valuable resource back: time. We support high-performing executives, founders, and teams through exceptional executive-level support, while creating meaningful, flexible careers for a predominantly military-connected workforce. We operate in a fully remote environment with a hybrid model of W2 employees and independent contractors, and we take compliance, clarity, and culture seriously.

This role sits at the heart of how Squared Away works.

Reports to: Chief People Officer
Scope: Internal Experience, Policy & Culture

Role Summary

The Director of People is a senior People leader responsible for keeping Squared Away’s People systems running smoothly while continuously improving how we support, onboard, and retain our team. Reporting to the Chief People Officer (CPO), this role owns the operational backbone of the People department and works in close partnership with the Director of Teams to support retention and growth.

This role is deeply hands-on and systems-oriented. The Director of People is responsible for maintaining and evolving Airtable-based workflows, documentation, and processes that support onboarding, People operations, and cross-department coordination. They work very closely with the Chief People Officer, the Director of Teams, and other department Directors to ensure People systems scale cleanly and sustainably.

Onboarding and the early teammate experience are a core focus. The Director of People owns the structure, content, and systems behind onboarding and the first several weeks at Squared Away, ensuring clarity, consistency, and a strong foundation for long-term success.

This role requires consistent availability during core business hours, 9:00 am–5:00pm Eastern Time, with flexibility to support urgent People matters outside of standard hours when needed.

Application & Interview Timeline

Application Window: January 28 – February 4, 2026
Applications will be reviewed on a rolling basis, and interviews may begin as early as January 29, 2026
This posting may close prior to February 4 if a strong pool of applicants is identified
Interviews may continue through February 10, 2026, depending on applicant volume and scheduling
Anticipated Start Date: February 13, 2026 (flexible based on candidate availability and transition needs)

Eligible Work Locations

This role is open to candidates who reside and are authorized to work in the following U.S. states:

Alaska
Arizona
California
Colorado
Florida
Georgia
Hawaii
Indiana
Iowa
Kentucky
Maryland
Missouri
Nevada
North Carolina
Ohio
Oklahoma
South Carolina
Texas
Virginia
Washington

Key Responsibilities

People Operations & Systems

Own and maintain Airtable systems that support People operations, onboarding, and reporting
Ensure People systems remain accurate, reliable, and actively maintained
Identify opportunities for system improvements, automation, and process simplification
Build and document new workflows as Squared Away evolves
Partner with other department Directors to ensure People systems support cross-functional needs

People Operations & Compliance

Own the execution and continuous improvement of People policies, handbooks, and processes across W2 employees and independent contractors in collaboration with the Director of Teams and CPO
Ensure compliance with federal and state employment and contractor regulations, partnering with the CPO on risk assessment and mitigation
Serve as a subject matter expert on Squared Away’s contractor model and People documentation
Maintain the accuracy and integrity of People data, documentation, and records

Leadership & Team Management

Directly manage members of the People Team, including setting priorities, coaching performance, and supporting professional growth
Act as a senior escalation point for People-related issues that do not fall under TL/TLM leadership oversight
Support the CPO in managing complex employee and contractor situations with consistency, clarity, and empathy

Team Lead & Pipeline Support

Partner with the Director of Teams on retention strategy, insights, and systemic improvements
Support People-side processes that impact Team Leads and Team Lead Managers without directly owning TL/TLM performance management
Identify patterns across onboarding, transitions, and exits that inform retention efforts

Onboarding, Transitions & Performance Support

Own and continuously improve the onboarding experience, systems, and documentation
Design and refine the first several weeks at Squared Away to set clear expectations and reduce early churn
Ensure onboarding reflects real role expectations, timelines, communication standards, and documentation requirements
Collaborate with the Director of Teams to align onboarding with long-term retention goals
Support role transitions, internal promotions, and exits through strong documentation and process ownership
Participate in performance conversations and improvement planning when needed, in partnership with the CPO

Communication & Culture

Model Squared Away’s leadership values: trust, clarity, professionalism, transparency and empathy
Draft and review sensitive internal communications to ensure tone and content align with company standards
Help reinforce a culture where feedback is welcomed, documentation is respected, and people feel supported

What Success Looks Like

Onboarding is clear, consistent, and sets teammates up for success within their first several weeks, with reduced early churn and fewer onboarding-related escalations
Airtable systems and People workflows are reliable, well-documented, and continuously improving, with minimal breakdowns or manual workarounds
Retention trends and onboarding feedback are regularly surfaced, analyzed, and used to inform process improvements in partnership with the CPO and Director of Teams
People documentation, handbooks, and processes are easy to find, easy to follow, and trusted as the source of truth across the company
Cross-functional partners experience the People function as organized, responsive, and proactive rather than reactive
The CPO has clear visibility into People operations, risks, and trends without needing to manage day-to-day execution

Performance & Goal Reviews

Quarterly Goal Review: Quarterly goal-setting and review tied to retention, onboarding quality, system reliability, and People KPIs. This meeting confirms priorities, removes roadblocks, and aligns cross-department efforts.
Annual Performance Review: A comprehensive yearly review evaluating results, leadership behaviors, and alignment with Squared Away values. This review informs salary evaluation, profit-sharing alignment, and development planning.

How We Will Support You in This Role

We recognize that this role is fast-paced, highly visible, and constantly evolving. Success here is not about having every answer on day one, it’s about judgment, adaptability, and growth.

In this role, you can expect:

Direct partnership and regular check-ins with the Chief People Officer, with clear prioritization and context around decisions
Thoughtful onboarding and transition support to help you build confidence in Squared Away’s systems, culture, and expectations
Ongoing coaching, feedback, and trust as you grow into the role and expand your scope
Space to learn and strengthen areas like employment law and contractor compliance with guidance and support
A collaborative leadership team that values transparency, curiosity, and continuous improvement

We are committed to setting you up for long-term success, not perfection on day one.

Requirements

Demonstrated leadership experience in People-focused, operational, or team leadership roles. Experience in leadership positions at Squared Away is highly valued.
Experience supporting retention, onboarding, and early-stage teammate development
Beginner to intermediate Airtable experience required, with a strong desire and demonstrated ability to rapidly improve skills
Exceptional written and verbal communication skills, with the ability to represent the People department clearly and confidently
Ability to navigate sensitive situations with professionalism, discretion, and empathy, even during periods of uncertainty or change
Highly organized, process-oriented, and comfortable working across multiple systems and tools
Demonstrated ability to adapt quickly in a fast-paced, evolving environment and remain effective when priorities shift on short notice
Proven resilience in the face of change, ambiguity, and competing demands
Strong ability to manage up by anticipating needs, surfacing risks early, and supporting executive decision-making

Preferred Experience

6+ years of experience in People Operations, HR, or People leadership roles
Strong working knowledge of U.S. employment law and independent contractor compliance (or the ability and willingness to learn quickly)
Advanced or expert-level Airtable experience, including building views, automations, and workflows
Experience supporting both W2 employees and 1099 contractors
Strong working familiarity with the culture, policies, and processes of Squared Away or other fully remote companies
Background in fast-growing or operationally complex organizations
Prior experience partnering closely with executive leadership
Working experience with collaboration and operations platforms such as Google Workspace, Harvest, and Front
Eagerness to learn, accept feedback, and continuously improve
Experience serving as a visible, trusted, and forward-facing representative of a People team

Benefits

Base Salary: $50,000 annually
Quarterly Profit Sharing: Directors receive an equal disbursement from a collective 0.5% profit share each quarter
Paid Time Off: 15 days annually, inclusive of sick time
Paid Family Leave: 6 weeks of paid family leave
Health Benefits: This role is eligible for health benefits through Squared Away
Salary Evaluations: Every 24 months, with a 3–5% increase based on meeting or exceeding expectations