I often get questions about working in nonprofit, so I decided to launch Career Conversations - a series of LinkedIn Live conversations with people currently in nonprofit L&D roles. We are talking all about their organizations, their teams, and their personal career journeys.

In this episode, I’m bringing two of these conversations to you. We’re hearing from Nadra Dennis, the learning and talent development director at the Center for Employment Opportunities, and Dr. Jaimie Hoffman, the senior director of learning and development at Big Brothers Big Sisters of America.

▶️ Curious about Working in Nonprofit? Get an Inside Look from These Nonprofit L&D Pros

▶️ Key Points:

02:22 The Career Conversations series

05:16 Introduction to Nadra Dennis and the Center for Employment Opportunities

09:03 L&D at the Center for Employment Opportunities

14:05 Adding capacity to your L&D team

15:56 Nadra’s career journey and interest in nonprofit

22:16 Advice from Nadra for people looking to transition into L&D or the nonprofit sector

30:05 Introduction to Dr. Jaimie Hoffman and Big Brothers Big Sisters of America

39:09 L&D at Big Brothers Big Sisters of America

44:40 Creating trainings with a lean L&D team

50:08 Jaimie’s career journey and interest in nonprofit

59:38 Advice from Jaimie for people looking to transition into L&D or the nonprofit sector

I absolutely loved talking with Nadra and Jaimie about their organizations, their L&D teams, and their career journeys into nonprofit.

I asked ChatGPT to help me identify themes from these two conversations, and I absolutely loved what came back.

Nonlinear, Mission-Driven Career Path to Nonprofit

Nadra and Jaimie didn’t start out in nonprofit. But, their curiosity, passion, and search for impact, led them there.

Nadra began in higher ed, initially aiming for a career in media, and found her passion through student programming and leadership development.
Jaimie also started in higher ed, with a music degree, pivoted to faculty roles, and then shifted into L&D because of her love for coaching and creating meaningful learning experiences.

Lessons: It’s not too late to transition to nonprofit or L&D. You don’t need a formal education in adult learning, but you do need curiosity and a love for learning. Nonprofit is a great place for those of us looking to make real-world impact.

Behavior Change is the Goal, Not Training

Nadra and Jaimie both talked about their approach to solving performance problems.

And it went far beyond training.

Nadra shared that her team reduced their internal offerings from 80+ to 34 to focus on impact, not volume.
Jaimie shared her focus on aligning learning initiatives with business strategy and behavior change, especially around volunteer retention.

Lessons: Nonprofit cares about performance. It’s a good fit if you love strategic, outcome-driven work.

Capacity Building with a Small L&D Team

Both Nadra and Jaimie shared that they have lean L&D teams - 3 members each - so they get creative to maximize their impact.

Nadra uses learning ambassadors (staff trained to deliver training) to expand reach and build internal capacity.
Jaimie is developing a peer training program and collaborates cross-functionally to scale learning in a federated system.

Lessons: Nonprofit L&D teams are creative problem solvers. They leverage internal champions and partnerships to scale learning.

Federated or Decentralized Learning

Nadra and Jaimie both shared that they work in national offices that support local or regional affiliates or agencies. This is fairly common in nonprofit and it adds a layer of complexity.

Nadra splits learning responsibilities between central staff and program staff.
Jaimie supports 230 agencies and must design learning experiences that are adaptable and scalable.

Lessons: Nonprofit L&D pros must think differently about scaling learning and be able to tailor learning across varied audiences.

L&D and Organizational Culture

Both leaders see L&D as a lever for shaping culture and belonging, not just skill-building.

Nadra talked about DEI trainings, onboarding buddies, book clubs, and performance coaching—all tied to belonging.
Jaimie spoke about the deeper why behind working in nonprofit: making a difference, modeling values, and enabling mentorship.

Lessons: If you are looking for connection and purpose, nonprofit might be for you. And also, as a nonprofit L&D pro, it’s your job to create connection and purpose for others.

Mentorship and Reinventing Careers

Both Nadra and Jaimie spoke of their path to nonprofit L&D. They both benefited from mentors and professional development. And they now advocate for mentorship and guidance in the field so others can make this transition too.

Nadra credited informal opportunities and certifications that helped her move toward L&D.
Jaimie, a certified coach herself, runs a podcast and wrote a workbook for educators pivoting careers.

Lessons: There is power in mentorship - both giving and receiving it.

To learn more about Nadra’s and Jaimie’s experiences in nonprofit L&D, tune into episode 130 of the Learning for Good podcast.

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