Karen Brennan, Author at The Strategy Group LLC

Artificial Intelligence in Nonprofits: Early Adoption, Thoughtful Experimentation

Overview

To better understand how artificial intelligence is taking shape across the nonprofit sector, The Strategy Group conducted a brief survey of organizational leaders. The goal was straightforward: assess where Artificial Intelligence (AI) is currently being used, evaluate its impact on organizational effectiveness, understand the status of AI governance, and surface emerging opportunities and concerns. Our sample of respondents was small, 21 nonprofit leaders, but we learned a […]

Karen Brennan2026-02-23T13:51:59+00:00February 23, 2026|

Short-term, Scenario, or Strategic Planning?

NONPROFIT PLANNING 101: WHAT’S RIGHT FOR YOUR ORGANIZATION?

If you’re leading a nonprofit in 2026, you already know funding feels less predictable. Staff capacity is stretched. Boards want clarity. Communities need more. The question isn’t whether you should plan. The question is: what kind of planning do you need right now?

At The Strategy Group, we are seeing three distinct planning needs emerge. Confusing them can cost time, […]

Karen Brennan2026-02-24T14:33:57+00:00February 22, 2026|

Radical Reflection | Welcome 2026

A Time for Radical Reflection? A Reset for Leaders

The start of a new year often brings momentum—and pressure. New goals, new plans, and an unspoken expectation to move quickly.

But before accelerating forward, many leaders benefit from a pause. That pause is radical reflection.

Designed by Debra Hertz and originally shared in a HAYVN Halftime conversation recorded in the post-pandemic period, this […]

Karen Brennan2026-02-04T00:24:39+00:00February 2, 2026|

Culture is No Longer a Side Conversation

The workplace continues to evolve at a rapid pace. While the shifts we’re seeing are especially visible heading into 2026, they reflect deeper, long-term changes in how work is designed and how people experience it. Workplace culture is no longer defined by where we work, but by how we work together.

Employees are seeking more than just a paycheck—they want alignment with […]

Karen Brennan2026-01-19T15:59:03+00:00January 15, 2026|

Associate Director of Development & Communications | Earthplace

POSITION DESCRIPTION

OPPORTUNITY

Earthplace is seeking to fill the position of Associate Director of Development & Communications. This position is a key supporting partner to the Development Director and plays an essential role in advancing Earthplace’s mission through annual giving, donor communications, and stewardship systems. The role is designed to complement the Development Director’s leadership by owning the planning and execution of […]

Karen Brennan2026-01-27T15:19:04+00:00January 12, 2026|

Executive Director | Kids Helping Kids

POSITION CLOSED

POSITION DESCRIPTION

OPPORTUNITY

Kids Helping Kids (KHK) is seeking an entrepreneurial, mission-driven Executive Director to lead the organization into its next phase of growth. This dynamic leader will guide a small, dedicated team, drive fundraising and donor engagement, and strengthen its programs that empower youth to serve their communities. The Executive Director will expand volunteer […]

Karen Brennan2026-04-03T14:16:29+00:00December 12, 2025|

Resetting Your Organizational Values: A Strategic Must for Nonprofits in 2026

Nonprofit leaders today are navigating extraordinary complexity: workforce shortages, shifting community expectations, funding volatility, and the relentless pace of change. In this environment, one truth has become undeniable:

Organizational values are not a “nice-to-have.” They are a strategic imperative.

Your values shape how decisions get made, how teams collaborate, how conflict is handled, and how effectively your organization delivers on its mission. When values are unclear or […]

Karen Brennan2025-12-11T20:16:44+00:00December 11, 2025|

Senior Director of Philanthrophy | Person to Person

POSITION CLOSED

POSITION DESCRIPTION

OPPORTUNITY

Person to Person (P2P) seeks a Senior Director of Philanthropy – an exciting opportunity for a highly motivated, dynamic, and talented individual with experience in the field of philanthropy. Reporting directly to the Chief Philanthropy & Strategy Officer, and with the potential for internal promotion within 18-24 months, the Senior Director of Philanthropy provides high-level, strategic […]

Karen Brennan2026-02-13T13:37:05+00:00November 16, 2025|

Job Opportunities | Horizons at NCCS

POSITIONS CLOSED

POSITION DESCRIPTION

OPPORTUNITIES

Horizons at New Canaan Country School (NCCS) was founded in 1964 and is the flagship program for what has become a national movement. There are now over 70 Horizons programs across the United States and counting. Each year we serve close to 400 underserved students in Kindergarten through 12th grade, […]

Karen Brennan2026-02-13T13:39:19+00:00November 13, 2025|

Five Ways to Work With Nonprofit Consultants

If your nonprofit organization has ever considered looking for some help with any aspect of your operations, planning, or leadership, it’s crucial that you weigh all your options before getting started. Knowing exactly what you need from a nonprofit consultant prior to engaging them will go a long way to save time and resources in the long-run. Here are FIVE ways your organization might work with a nonprofit consultant.

Executive […]

Karen Brennan2025-11-03T18:11:26+00:00November 3, 2025|

About Karen Brennan

Overview

A Time for Radical Reflection? A Reset for Leaders

POSITION CLOSED

POSITION CLOSED

POSITIONS CLOSED