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Chief Administrative Officer



Job Summary

The Chief Administrative Officer is responsible for assuring that the operating activities of PENCIL are running smoothly and efficiently at all times so that staff and board can achieve their objectives. The goal of this position is to help assure all team members have the guidance and resources they need to be successful, and that the work environment supports both their productivity and individuality by creating easy to use systems and supports at all levels of the organization.  Proactively focusing on these elements in close partnership with the CEO will assure that the full team has significant capacity for relationship building and expanding the impact of PENCIL’s work.

Job Responsibilities

  1. Guide all aspects of our human resource management to provide staff and volunteers with a welcoming and inclusive environment with many opportunities for professional and personal growth
  • Benefits, staff transitions, policy implementation and evolution, recognition and professional development
  1. Champion and lead our Diversity, Equity, and Inclusion work to assure we are actively evolving how we live out our vision and core commitments
  1. Support the meaningful engagement of PENCIL’s board members to maximize their impact and PENCIL’s impact
  • Oversee all board activities for both the Governing Board and the Emerging Leaders Board
  • Establish agendas and workplans in tandem with the CEO and other executive leadership; lead the annual meeting calendar development process to support those workplans; facilitate communication; assist the CEO and Board Engagement Committee with recruitment, onboarding and engagement
  1. Provide oversight and partnership in all financial management and activities to assure customer needs are met in a timely and efficient manner and best practices are implemented
  • Work very closely with our CFO and Business Manager to successfully manage all financial transactions in a timely manner while assuring strong internal controls are in place
  • Bi-weekly payroll, accounts payable and receivable, monthly financial reports/forecasting, annual budget process, annual audit, etc.
  1. Provide effective and inspiring leadership, internally and externally; manage key business relationships successfully
  1. Oversee the daily operations of all aspects of the business to assure all team members have the tools and resources they need to focus the majority of their time on their key targets
  • Key systems include facility management, technology infrastructure and devices, tracking of key deadlines, office equipment and supplies, contract review support, risk management thought leadership, etc.
  1. Assure systems documentation is in place for all critical business components and regularly audit our practices against our plans; review and update documentation regularly in partnership with the executive leadership team
  1. Assist in the development of current and long-term organizational goals through the evolution and use of our strategic plan, including being a key driver of expansion opportunities
  1. Document all activities in the designated customer relationship management tool (Salesforce) in a timely, accurate and complete manner to assure a full picture of all partnerships, ensuring that data is kept current at all times
  1. Serve as a Project Manager when needed
  1. Perform other functions as assigned


EDUCATION – Minimum of a Bachelor’s Degree but a Master’s degree is a plus


  • Proven ability to quickly process data and make decisions
  • Outstanding organizational and leadership abilities
  • Has demonstrated the ability to thoroughly document workflows and timelines
  • Thorough understanding of core business functions such as HR, Finance, Development, Marketing and Technology
  • Working knowledge of data analysis and performance/operation metrics
  • Demonstrable competency in strategic planning and business development
  • Excellent interpersonal skills
  • Understanding of ways to support equity and inclusion within organizations


  • Minimum of ten years’ experience as an executive with strategic thinking and problem-solving responsibilities
  • Minimum of five years’ experience managing human resource functions for a similarly sized, or larger, team
  • Minimum of five years’ experience in creating, documenting, and managing key business functions so all stakeholders can operate at their highest capacity

CONFIDENTIALITY – Ability to manage sensitive information in a professional and confidential manner as outlined in PENCIL’s Confidentiality Policy

Additional Information


PENCIL is proud to offer a comprehensive benefits package including medical, dental and vision plus employer-paid group life insurace, accidental death & dismemberment and long term disbility; a 401K plan with a 3% employer match; cell phone stipend, 10 paid holidays as well as 2-3 weeks between Christmas and New Year’s; paid time off (PTO) as well as a suite of voluntary offerings.

How to Apply

  • All interested candidates should submit a cover letter, resume, and three professional references, as well as the supplemental materials below.
  • As the CAO you will be leading our work to recruit and retain top talent for our staff and board and supporting everyone in our commitment to living out our Vision and Core Commitments.  Please include with your application materials a proposed orientation plan for a new hire’s first week of work at PENCIL.  There is no right or wrong plan, so create one that is a reflection of what you think most important.
  • Please also include a document which outlines how PENCIL manages reimbursements to staff for mileage and incidental expenses, like a coffee meeting with a potential PENCIL Partner.  This document would be a policy/procedure that you would share as a part of orientation.
  • Please also include a 1-3 minute video of your analysis of our most recent audit, which is posted on our website.  Again, no right or wrong answer, but we want to hear what key points you would make if you were sharing our financial picture with a potential new board member.

Application packages will be accepted through 8am on Nov. 21.  Candidates will be notified no later than Nov. 30 if they are moving forward in our interview process.

Apply Here


  • Date Posted: November 7, 2022
  • Type: Full-Time
  • Job Function: Administrative
  • Service Area: Education
  • Salary Range: $90,000 - $100,000
  • Working Hours: This position works 40 hours each week, typically Monday – Friday 8 a.m. – 5 p.m., with occasional evening and weekend hours for special events.