Global Leadership Community: Membership + Events Automation

The Problem

This global leadership community brings together entrepreneurs, executives, and change-makers through annual memberships and high-end adventure experiences (think Kilimanjaro treks, Arctic expeditions, leadership retreats).

They had two separate business models running simultaneously:

• Memberships: Applicants go through human review, get assigned to tiers (Veteran vs Virgin Striver, with age-based discounts), sign up through Outseta, and pay recurring fees
• Events: Members and non-members apply for specific adventure experiences, pricing varies by tier and event, payment links generated via Stripe

Everything was manual. Applications came in via forms. Staff manually reviewed them. Payment links were generated by looking up pricing in spreadsheets. Billing contacts were handled via email threads. The team was drowning in admin work.

The Technical Challenges

1. No Native HubSpot ↔ Outseta Integration

Outseta is their membership portal where people sign up and pay. Once someone becomes a paying member in Outseta, that status needed to sync back to HubSpot automatically to trigger welcome emails and update contact records. There's no native connector. We had to build a custom API integration.

2. Membership Tiers With Human Review

Membership isn't open to everyone. Applicants go through a vetting process. The team manually reviews each application and assigns the correct tier (Veteran member, Virgin Striver, under-35 discount, etc.). Once assigned, all downstream communication and pricing must reflect that tier automatically.

3. Event Pricing Varies By Tier AND By Event

Members pay different rates than non-members. And those rates vary event by event. The system needed to identify the applicant's tier, match it to the specific event they applied for, generate the correct Stripe payment link, and send it automatically.

4. Billing Contacts (Third-Party Payers)

Event applicants could nominate someone else to receive the payment link and handle billing. The system needed to create a separate billing contact record, send them the payment link, and associate them back to the original applicant.

What We Built

Pipeline 1: Membership Applications

Flow:

1. Application submitted via HubSpot form → Creates contact and deal in "Membership Applications" pipeline
2. Team reviews applicant → Manually assigns membership tier (custom property)
3. Tier assignment triggers workflow → Sends personalized email with link to Outseta membership portal
4. Applicant signs up and pays in Outseta
5. Custom API syncs Outseta → HubSpot → Updates contact record with payment status
6. Payment confirmation triggers welcome email sequence in HubSpot

Pipeline 2: Event Applications

Flow:

1. Event application submitted → Creates contact and deal in "Event Applications" pipeline
2. Workflow checks eligibility (age, membership status, event capacity)
3. If billing contact specified → Creates separate contact record and associates it via contact-to-contact association
4. Workflow identifies applicant tier + specific event → Generates correct Stripe payment link via custom property logic
5. Payment link sent to billing contact (or applicant if no billing contact)
6. Payment confirmation syncs back → Triggers dual confirmation emails (applicant + billing contact)

Custom API Integration (Outseta ↔ HubSpot)

Built a custom API integration to sync membership payment status from Outseta back to HubSpot in real time:

• Reads account-level membership data from Outseta API
• Matches to correct HubSpot contact via email address
• Updates custom properties in HubSpot (membership status, tier, payment date)
• Triggers automated welcome sequence once payment confirmed

Tier-Based Pricing Logic

Created a matrix of custom properties to handle tier + event pricing:

• Each event has custom pricing fields for each tier (Veteran Member, Virgin Member, Under-35, Non-Member)
• Workflow reads applicant tier + selected event → Pulls correct price → Generates Stripe link
• New events are added by populating pricing fields once; workflow logic handles everything else

The Results

Full membership lifecycle automated: From application to tier assignment to Outseta signup to HubSpot sync to welcome email. The team only touches the approval decision.

Pricing errors eliminated: Tier-to-event pricing is handled by workflow logic, not by someone looking up a spreadsheet and manually creating payment links.

Billing contacts automated: Third-party payers are created as separate contact records, receive payment links automatically, and are associated back to the applicant for tracking.

Referral tracking built in: Contact-to-contact associations capture who referred whom, making referral data searchable and reportable.

Technical Stack

• HubSpot (Sales + Operations Hubs) - Dual pipelines, contact management, workflow automation
• Outseta - Membership portal and recurring billing
• Stripe - Event payment processing
• Custom API - Syncs Outseta membership status → HubSpot
• HubSpot Forms - Application intake for both memberships and events