Kyle Wickline

Work / U.S. Chamber of Connection

U.S. Chamber of Connection

A national movement against loneliness had supporters but no way for anyone to join, learn, or stay involved. Over six months I designed and launched its first paid membership, three online courses, and the systems behind them.

Organization
U.S. Chamber of Connection, Seattle
Role
Program & Experience Designer (contract)
Timeline
March to September 2025
Result
80 paying members in the first two weeks, and new recurring revenue

The situation

The Chamber of Connection is a national effort to rebuild human connection where people live. When I joined, it had an audience and a founder with a clear plan, but no membership model, no courses, and email that went out by hand to volunteers, donors, and members alike.

What I was responsible for

  • MembershipThe infrastructure for the Chamber’s first paid membership: the onboarding sequence, member dashboards, assessments, and certification tracking.
  • CoursesThree digital courses in Kajabi, including the weekly challenges, live-session content, and peer-led activities inside them.
  • GrowthPromotional funnels, landing pages, and onboarding content to drive enrollment.
  • CommunicationsSegmented, automated email flows for volunteers, donors, and members, with modular templates the team could reuse.
  • IntegrationConnecting Heylo, Mailchimp, and Squarespace so operations and outreach ran from one member record.
  • AlignmentWorking with leadership so the user experience, the curriculum, and the community strategy matched across platforms.

How it fit together

The design problem was the handoffs between systems. Someone should be able to find the Chamber, join on a Tuesday, know what to do by Wednesday, and never get an email meant for a donor. That meant deciding what each platform owned and wiring them together.

Chamber of Connection systems map and member journeySquarespacesite, landing pages,promotional funnelsKajabimembership, 3 courses,dashboards, certificationMailchimpsegmented flows:volunteers, donors, membersHeylocommunity andevent operationsConnected so the member record, course progress, and email segments came from one source instead of someone keeping them by hand.The member journey I designedDiscoverlanding pageJoinpaid membershipOnboardsequence + dashboardLearnweekly challenges,live sessionsCertifytracked automaticallyChamber of Connection systems map and member journeySquarespacesite, landing pages,promotional funnelsKajabimembership, 3courses, dashboards,certificationMailchimpsegmented flows:volunteers, donors,membersHeylocommunity and eventoperationsConnected so the member record, course progress, and emailsegments came from one source instead of someone keepingthem by hand.The member journey I designedDiscoverlanding pageJoinpaid membershipOnboardsequence + dashboardLearnweekly challenges, live sessionsCertifytracked automatically
The four platforms I connected, and the member journey that runs across them.

What came of it

Eighty people paid for membership in the first two weeks, and the Chamber had new recurring revenue. I built the flows and templates so the team could run them without me, which is the part I’m proudest of.

The research and communication habits I brought to this came from graduate school; the operations habits came from five years behind a counter. This was the first project where both mattered at once, and it’s the one that convinced me this is the kind of work I want to keep doing.

Visit the U.S. Chamber of Connection