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Season 3, Episode 4 - Learning by Association

From Content to Connection: Rethinking Member Engagement With Jackson Boyar

Bill Sheehan speaks with Jackson Boyar about how associations can use strive to create meaningful member engagement in an attention economy.

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topics

Highlights

0:00

Welcome

1:22

Jackson's introduction and founder journey

5:59

The membership engagement crisis explained

8:35

Helping members find people like them

11:57

Turning onboarding and learning into connection moments

15:08

Mentorship as a natural outcome of peer groups

19:53

What younger professionals really value

23:21

Measuring engagement beyond clicks and views

26:58

Competing against big tech in the attention economy

30:00

Why associations are built for trust and neutrality

33:00

Peer learning as a differentiator for the next generation

44:07

Peer groups, paid communities and new revenue models

54:26

Why connection must come before content

In this episode of Learning by Association, host Bill Sheehan welcomes Jackson Boyar, CEO and co-founder of RallyBoard, for a wide-ranging conversation on one of the most pressing challenges facing associations today: Meaningful member engagement in an attention economy.

Drawing on his background as the founder of Mentor Collective and his work with associations across industries, Jackson shares why connection—not content alone—is becoming the defining value proposition for associations, particularly for millennials and Gen Z professionals. Together, Bill and Jackson explore how cohort-based programs, peer learning and informal mentorship can help associations move beyond transactional engagement toward deeper, more authentic member experiences.

The discussion also examines how associations can leverage their unique social capital to differentiate themselves from big tech platforms, create year-round value beyond the annual meeting and rethink engagement, learning and community as strategic drivers of relevance and growth .

Key topics covered in this episode include:

  • Why traditional engagement metrics fall short and what real engagement looks like
  • The role of cohort-based learning and peer connection in attracting younger members
  • How associations can design intentional member experiences that foster trust and loyalty
  • The intersection of learning, mentorship and community as a competitive advantage
  • Opportunities to scale connection while supporting staff capacity and sustainability

Speakers

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