Squared Away

Director of People

Squared Away

full-time

Posted on:

Location Type: Remote

Location: Alaska • Arizona • United States

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Salary

💰 $50,000 per year

Job Level

Lead

About the role

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

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
  • 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
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Applicant Tracking System Keywords

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Hard Skills & Tools
Airtableonboardingretention strategyprocess improvementdata managementemployee relationscompliancedocumentationworkflowsperformance management
Soft Skills
leadershipcommunicationempathyorganizationadaptabilityresiliencediscretioncoachingcollaborationproblem-solving