Squared Away

People Operations

• 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

Director of People

Executive Assistant

• Manage and optimize complex executive calendars across time zones
• Anticipate conflicts and proactively resolve scheduling issues
• Protect executive focus by enforcing priorities and boundaries
• Manage executive inboxes with discretion and sound judgment
• Draft, respond to, and triage correspondence on behalf of executives
• Ensure urgent matters are surfaced promptly and appropriately
• Coordinate domestic and international travel end-to-end
• Prepare detailed itineraries and anticipate changes or disruptions
• Prepare meeting materials, agendas, presentations, and reports
• Track action items, deadlines, and follow-through across initiatives
• Create, document, and refine workflows to improve efficiency
• Identify tools and processes that reduce friction and increase clarity
• Conduct research on competitors, tools, vendors, and market trends
• Provide concise summaries to support executive decision-making
• Handle sensitive and confidential information with absolute integrity

Director of People

Chief Executive Assistant