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 organized, detail-oriented, and proactive Executive Administrative Assistant to provide comprehensive support to both the CEO and CFO of a fast-growing, high-impact company. This individual will play a critical role in enabling executive effectiveness, supporting board and investor communications, and ensuring operational follow-through.

This candidate will manage calendars, email, travel, coordinate communications, prepare and enhance presentation materials (including Board decks), attend key meetings, and track follow-ups to ensure strategic priorities stay on track. The ideal candidate is a confident communicator, skilled in PowerPoint, Excel and Word, and thrives in a fast-paced, dynamic environment.

In addition, this role requires balancing competing priorities across two executives, anticipating needs before they arise, and exercising sound judgment in sensitive situations. The successful candidate will bring high emotional intelligence, strong discretion, and the ability to represent senior leadership with professionalism to both internal and external stakeholders.

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 Support

• Manage complex and dynamic calendars, email, travel and administration for CEO and CFO.
• Schedule and coordinate meetings across internal teams, investors, brokers, and external partners.
• Serve as primary point-of-contact for select communications and meeting logistics.
• Develop a deep understanding of the business to proactively solve problems; draft responses and represent the CFO/CEO when appropriate. 
• Maintain strict confidentiality and discretion across sensitive business communications and initiatives.
• Draft, proof, and refine executive-level communications (emails, memos, investor correspondence).
• Manage expense reporting, reimbursements, and travel systems (e.g., Concur).

Presentation & Board Deck Preparation

• Coordinate the preparation of high-quality Board decks and executive presentations.
• Own formatting, visual storytelling, and version control of PowerPoint materials.
• Enhance clarity, design, and impact of business presentations with a strong eye for detail.
• Support the CFO with financial decks, investor updates, and internal reporting visuals.

Meeting & Project Accountability

• Attend executive meetings and take clear, actionable notes.
• Track key action items, decisions, and next steps using Trello, Excel, or other preferred systems.
• Proactively follow up with stakeholders to ensure timely completion of deliverables.
• Maintain project trackers and prepare concise, executive-level status updates.
• Act as a liaison with key stakeholders, representing executives with professionalism and discretion.

Operational Coordination

• Coordinate planning and logistics for offsites, leadership meetings, and key company events.
• Maintain internal documentation, SOPs, and strategic planning materials.
• Support special projects and cross-functional initiatives as directed by CEO/CFO.

Minimum Qualifications (Knowledge, Skills, And Abilities)

• 3+ years supporting C-level executives in a fast-paced environment.
• Advanced PowerPoint skills (visual storytelling, layout design, formatting finesse).
• Strong writing and verbal communication skills.
• Proven experience managing calendars, meetings, and sensitive communications.
• Detail-oriented with exceptional organizational and follow-through abilities.
• Proficiency in Outlook, Teams, PPT, Excel, Word and productivity tools (e.g. SharePoint, Loom); comfortable learning and adapting to new technology stacks.
• Ability to thrive in ambiguity and take initiative to solve problems independently.
• Experience attending and documenting executive-level meetings (e.g. ELT, Board, Investor).
• Familiarity with project management tools (e.g. Trello).
• Exceptional time management skills with the ability to triage and prioritize across multiple high-stakes projects.
• High emotional intelligence, sound judgment, and discretion when handling sensitive matters.

Cultural Fit

• Growth-oriented, high-integrity, and dependable.
• Thrives under pressure and tight deadlines.
• Comfortable engaging directly with senior leadership and external stakeholders.
• Enjoys building structure, creating clarity, and driving execution.
• Proactive and resourceful, with the goal of making the CEO, CFO, and company more productive.  

Why Join Us?

• Be part of an innovative and growth-oriented company in the PEO industry.
• Opportunity to drive meaningful impact and be a part of a high-performing team.
• Competitive salary and benefits package.

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 highlighting relevant experience.
• Your Resume.
• A brief writing sample (e.g., an executive memo, meeting summary, or communication you’ve authored).
• An example of a presentation or board deck you've improved or owned
• Optional: A Loom or short video introducing yourself (1 minute or less).