About Peoplease

Peoplease is a leading Professional Employer Organization (PEO) providing solutions to small and medium-sized businesses in the blue and gray-collar industries. We enable our clients and partners to achieve their aspirations by offering world-class service and administrative solutions in payroll, human resources, benefits, and risk management. At Peoplease, we foster a culture of inclusion and belonging, driven by our core values: Engagement, Integrity, Tenacity, Curiosity, Happiness, and a Service-obsessed mindset.

Position Summary

We are seeking a highly capable executive assistant who goes beyond traditional administrative support to act as an extension of the CEO and CFO. This role combines high-level executive assistance with operational problem-solving and technology-driven solutions to enhance efficiency, collaboration, and clarity across the organization.

The ideal candidate is resourceful, tech-savvy, and systems-minded, with demonstrated experience using the Microsoft 365 ecosystem (Teams, SharePoint, Planner, Lists) to streamline workflows, create visibility, and maximize executive effectiveness. Familiarity with EOS operating model (Traction) is highly valued, as this individual will support leadership rhythms, meeting structures, and cross-functional alignment.

This is a high-trust role that requires exceptional judgment, communication finesse, relentless attention to detail, and the ability to anticipate needs before they arise. You will play a critical part in enabling executive focus, enhancing organizational coordination, and ensuring that strategic priorities move forward on time.

Candidate must be a self-starter with the ability to function as a remote employee in a distributed work team.

Essential Duties and Responsibilities

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Executive Partnership & Administrative Excellence

• Provide comprehensive administrative support to the CEO and CFO, including calendar management, email coordination, travel planning, and communication oversight.
• Anticipate needs and proactively clear barriers to optimize executive time and focus.
• Act as a professional, reliable representative of the executive team in internal and external interactions.
• Draft, refine, and manage executive-level communications with clarity, accuracy, and sound judgment.
• Manage expense reporting, reimbursements, and travel systems.

Operational & Strategic Support

• Attend executive-level meetings (ELT, Board, investor, strategic sessions) and capture action-oriented notes.
• Create and maintain follow-up systems that ensure accountability across teams.
• Support the implementation of operating system tools, processes, meeting structures, and scorecard tracking.
• Help translate leadership priorities into structured plans, dashboards, and recurring communication cadences.
• Maintain project trackers and prepare concise communication on progress, blockers, and next steps.

Technology & Process Optimization

• Serve as an internal Microsoft 365 champion, driving effective adoption and use of Teams, SharePoint, Planner, and Lists.
• Seek continuous improvements to processes, workflows, and information flow across the organization.

• Serve as a Teams champion, positioning Teams as the forward-facing, user-friendly platform for communication and collaboration.
• Assist leaders in optimizing their Teams environments for task and project management by integrating Planner for task tracking and Lists for structured project oversight.
• Configure and maintain SharePoint-based Lists to surface pending items and ensure visibility of priorities.
• Demonstrate curiosity and a continuous improvement mindset by identifying challenges with tool adoption and usage.

Presentation & Communication Excellence

• Prepare high-quality Board decks, leadership presentations, and investor materials with strong visual storytelling.
• Lead formatting, design, and version control for all key executive presentation materials.
• Support the CFO/CEO with financial decks, investor updates, and internal reporting visuals.

Organizational Coordination

• Plan and execute offsites, leadership meetings, and key company events.
• Coordinate and support special cross-functional initiatives as directed by the CEO and CFO.
• Strengthen transparency, communication, and collaboration across teams.
• Manage documentation, SOPs, and knowledge systems to ensure clarity and continuity.
• Help build a high-accountability, high-trust culture that reflects our core values.

Minimum Qualifications (Knowledge, Skills, And Abilities)

• 3+ years supporting C-suite executives in a high-growth or fast-paced environment.
• Advanced proficiency in Microsoft 365 (Teams, SharePoint, Planner, Lists, PowerPoint, Excel, Word).
• Experience or familiarity with EOS/Traction strongly preferred.
• Excellent writing, communication, and interpersonal skills.
• Proven ability to manage complex calendars, competing priorities, and sensitive communication.
• Strong project management skills with a proactive, solution-oriented mindset.
• High emotional intelligence, sound judgment, and exceptional discretion.
• Ability to thrive in ambiguity and create clarity through structure and process.
• Detail-oriented with strong organizational and follow-through abilities.

Why Join Us?

• Partner directly with both the CEO and CFO on high-impact initiatives.
• Opportunity to shape processes and influence organizational effectiveness.
• Competitive compensation and benefits package.
• Opportunity to grow into expanded operational leadership over time.

Physical Demands and Work Environment

The role requires regular communication and occasional travel to support the distributed workforce. The role will primarily function indoors but may involve working in varying temperatures or outdoor environments as needed.

To Apply

Please submit:

• A short cover letter outlining your experience and impact.
• Your resume.
• A writing sample (executive memo, issue summary, or strategic communication).
• A sample Board or executive-level presentation you’ve prepared.
• Optional: a 1-minute Loom/video introduction