Guest to
Giver Journey
The annual Charity Wine Auction, hosted by Willow Park Wines & Spirits, returned for its milestone anniversary as "Wonderland." An immersive philanthropic experience where every design choice was crafted to move people from guests to givers.
The Purpose
Meet Claire. A longtime Willow Park Wines & Spirits customer who always figured the auction "wasn't for her." Move someone like Claire and see what can happen.
The Journey
Claire went on five-stage journey from a curious regular, to first-time guest, to proud giver. Each step maps what she does, how she feels, and where she hesitates.
The Challenge
How do you move someone like Claire from guest to giver ?
After thirty years, the Charity Wine Auction had a reputation it could coast on. Filling the room was never the hard part. The real challenge was turning a hesitant first-timer into someone who not only gives, but keeps giving.
The Approach
Along with my team, I led the 30th Charity Wine Auction start to finish, from first concept to closing night and everything in-between. With four years running the event, I already knew this milestone needed more than a bigger version of the usual: it called for a redesign of the guest experience.
We first mapped who the auction touches from core, direct, and indirect stakeholders. Then shaped what Claire's journey would look like by testing ideas, sketching campaign flows, and questioning every assumption. The campaign was heavily framed around thirty years of community impact and our community partners: essentially our why for people to rally behind the event.
Widening the circle
The biggest shift was widening who the night was for. We welcomed the Calgary Co-op Community Foundation as a new partner: acting as another pillar for shared community-strengthening and new donors.
Defining success
Understanding who, what, and why
Ambition then needed targets. We set goals we could measure: raise $160,000 across the live and silent auctions, sell out every ticket and sponsorship package, and build partnerships that would outlast the evening.
Visual storytelling
We wanted to build a world, not a room. Guests fell through a rabbit-hole entrance into the Mad Hatter's Garden, moved through the silent auction, then descended to the Queen's Court live auction in the basement. Live entertainment, fine wine, and gourmet food filled every space — each one designed to spark curiosity and create an environment for giving.
The Experience
What does Claire really think?
“When I walked through the rabbit hole, I knew this was something else.”
“Chef-catered dinner from my favourite restaurant? Bid placed!”
“Over five million dollars has been raised from this event? I had no idea.”
Every room is so immersive I forgot I was hesitant about coming.
Does a bid from someone like me really make a difference?
I thought this wasn’t for people like me — turns out, I fit in!
Wanders spaces, cheers with friends, and places a bid.
Raises her paddle, a strong public moment of commitment.
Posts the night to social media, drawing her friends in.
Wonderland rooms, live performers, fine wine, and gourmet food.
Auction items offering experiences she couldn’t find anywhere else.
People around her openly bidding — here, giving is just what you do.