Event Planner Confessions

Modernizing an experienced event team does not mean starting over. It means knowing what to preserve, what to change, and who needs to be involved earlier.In this episode of Event Planner Confessions, Cara Pratt talks with Dawn Wesley, Senior Manager of Agency Operations, Agency Awards and Recognition at Allstate, about team modernization, attendee experience, AI, supplier strategy, procurement, and the capabilities future event leaders will need.Dawn has spent more than three decades at Allstate and 16 years in sales leadership. Before leading the company's event-planning team, she experienced its incentive programs as an attendee and award winner. That background gave her a direct view into how event policies, recognition programs, guest experiences, and family inclusion feel from the other side of the plan.When Dawn moved into event leadership, she inherited a team with roughly 100 years of collective experience inside Allstate. Her job was not to dismiss that history. It was to modernize the work while respecting the knowledge and relationships that had already made the programs successful.The conversation then turns to supplier strategy and procurement. Dawn explains why planners must help procurement understand the purpose behind event decisions and why procurement should be involved before scopes, suppliers, and contract positions are already locked. When both teams understand the same business outcome, procurement can become an extension of the event team rather than a final approval step.Finally, Dawn shares what she looks for in future event professionals and why grit, curiosity, energy, and the willingness to learn can matter more than a traditional event-planning background.In this episode, you will learn:How attendee experience can reshape event policies and family programmingHow to modernize a team without dismissing its institutional knowledgeWhy diverse professional backgrounds can strengthen an established event functionHow AI can improve standards, analysis, planning, and work-life balanceWhy new supplier relationships can unlock ideas an experienced team has not seen beforeWhen procurement should enter the event-planning processThe future event team is not built by replacing everything that came before. It is built by preserving what works, opening the door to better ideas, and aligning the right people earlier.

AI can generate content at extraordinary speed. It cannot recreate the trust, spontaneity, and shared memory of a live room.In Part 2 of this Event Planner Confessions conversation, Ashley Currin continues her discussion with Jimmy Knowles, Global Head of Experiential at Canva, about artificial intelligence, human connection, experiential marketing, and the future of live events.Jimmy explains why he is not afraid of AI and how his team uses it to reduce administrative work, improve planning, generate meeting agendas and recap emails, and create more time for creative thinking.His goal is not to make AI the center of the experience. When the technology is being used effectively, Jimmy believes it should almost disappear into the background.As AI becomes integrated into every tool and digital content becomes harder to verify, Jimmy believes live experiences may become one of the last trusted platforms available to audiences and brands. A physical event provides something generated content cannot: a moment people know happened directly in front of them.The conversation also explores Jimmy’s push for greater experiential recognition at Cannes Lions. Although experiential marketers create the environments and activations that power the festival, the discipline continues to receive limited recognition through its stages and awards program. Jimmy shares the progress being made and why formal recognition could help experiential teams become part of the strategy instead of another budget line.Ashley and Jimmy then discuss how Canva’s experiential team grew from a team of one into a group of ten marketers with complementary strengths across strategy, production, and agency work.Finally, Jimmy shares two unforgettable Event Planner Confessions. He recounts the crisis that unfolded during Airbnb Open when thousands of attendees were spread across Paris during the terror attacks and explains why event insurance and crisis communication are now among the first things he considers.He also takes listeners behind Canva’s polarizing Enterprise rap battle and explains how the criticism unexpectedly revealed the strength of Canva’s community and gave the company permission to become even more unapologetically itself.In this episode, you will learn:How Canva’s experiential team uses AI behind the scenesWhy effective AI should almost disappear into the backgroundWhy live experiences may become more valuable as digital trust declinesWhat “Less URL, more IRL” means for the future of eventsWhy Jimmy is advocating for experiential recognition at Cannes LionsHow experiential can move from a budget line into the strategyHow Jimmy built Canva’s experiential team from one person to tenWhy crisis communication and event insurance must be established earlyWhat Canva learned when its rap battle divided the internetThe more AI creates, the more valuable real presence, trust, and human connection become.

Canva is one of the world’s most recognizable digital platforms. Jimmy Knowles is responsible for making it something people can walk into, explore, and feel.In Part 1 of this Event Planner Confessions conversation, Ashley Currin sits down with Jimmy Knowles, Global Head of Experiential at Canva, to explore how creative careers are built and how digital-first brands can create meaningful real-world experiences.Jimmy shares the unconventional story of being offered his first events job from a commencement stage in front of approximately 11,000 people. That opportunity led him to the Macy’s Thanksgiving Day Parade, Fox, Civic Entertainment Group, Airbnb, and eventually Canva.He takes listeners behind the scenes of Airbnb Open, which grew from approximately 1,000 attendees into a 20,000-person experience spanning seven venues in downtown Los Angeles. Jimmy explains how that work shaped his approach to community building, audience connection, and designing experiences at scale.At Canva, the goal is not simply to place logos and brand colors inside a venue. Jimmy and his team want every physical experience to feel colorful, playful, inclusive, and unmistakably Canva.That philosophy helped shape Canva Create as an “un-conference conference” built around how audiences should feel, not only what the program needs to communicate. Jimmy explains why the strongest experiential marketing should create something audiences could not imagine coming from another brand.The conversation also explores how Jimmy’s theater background continues to influence his work. From collaboration and improvisation to reading the room and recovering in real time, he explains why the skills learned onstage remain essential to event planning and experiential leadership.Finally, Jimmy shares what is ahead for Canva’s experiential portfolio, including the continued evolution of Canva Create, Canva Originals, the Canva World Tour, and new opportunities to expand Canva’s creative ecosystem.In this episode, you will learn:How Jimmy Knowles built his career in experiential marketingWhat Airbnb Open taught him about community and scaleHow Canva transforms a digital-first brand into a physical experienceWhy Canva Create was built as an “un-conference conference”Why curiosity remains one of Jimmy’s most important creative toolsWhat Canva is building next through events, content, and communityPart 1 explores how Jimmy learned to build experiences people can feel. Part 2 continues with AI, trust, industry recognition, leadership, and his Event Planner Confessions.

More content is not always more valuable.In this episode of Event Planner Confessions, Cara Pratt talks with Tavar James, vice president of global events at Forrester, about why the company introduced shorter, more intimate Forums alongside its flagship Summits and shortened experiences across parts of the portfolio.Tavar shares how a listening tour with attendees, sponsors, clients, and internal teams exposed the real friction around event participation: higher travel costs, tighter budgets, too much time away from work and family, content overload, and sponsorship value that was not always obvious enough.He explains how Forrester responded with more accessible formats, bi-coastal options, shorter agendas, more flexible sponsorships, and a stronger focus on relevance. He also discusses how the team is measuring the change through satisfaction, content scores, NPS, ticket revenue, sponsorship revenue, and the ability to act quickly on yellow and red signals.The conversation then turns to leadership. Tavar breaks down how a clear point of view, commercial thinking, and transparency with both executives and the event team helped build buy-in before the strategy had a long results history.And in true Event Planner Confessions fashion, Tavar shares the emergency that changed how he thinks about empathy, executive communication, and having a plan before anyone believes they will need it.In this episode, you will learn:Why Forrester added shorter Forums without eliminating its flagship SummitsHow attendee and sponsor feedback shaped the new event formatsWhy accessibility includes cost, geography, time, and the option to self-fund attendanceHow shorter events change content, scheduling, team recovery, and sponsor valueWhich attendee and commercial signals Forrester is using to evaluate the strategyWhy event leaders need a point of view tied to commercial outcomesHow transparency can close the trust gap between leaders and their teamsThe best event size is not the biggest or the smallest. It is the one designed for the outcome the audience and the business actually need.

Anaheim is one of the most recognizable destinations in the country, but recognition does not always lead to consideration.Visit Anaheim’s research found that roughly nine out of ten people knew the city, yet there was a 64 percent drop between awareness and the number of people who would consider bringing a meeting or convention there. The challenge was not getting people to recognize Anaheim. It was helping them understand everything the destination offered beyond its most famous icons.In this episode of Event Planner Confessions, Ashley Currin and Sam Monroe sit down with Scott Oklin, Chief Marketing Officer of Visit Anaheim, to unpack the strategy behind the city’s new A-City unscripted positioning.Scott explains how Visit Anaheim used research, local partnerships, unexpected creative agencies, experiential campaigns, and Anaheim’s real community to build a more emotional and complete destination story. He also shares how local restaurants, breweries, entertainment venues, cultural communities, and unexpected spaces can become part of the event itself.In this episode, you will learn:Why Anaheim’s challenge was consideration rather than awarenessHow Visit Anaheim used research to guide its new destination positioningWhy emotional connection can influence destination decisionsHow iconic attractions can introduce attendees to a city’s broader cultureWhy local restaurants, venues, and communities should become part of the event experienceHow destination marketers and event planners can tell a more complete story togetherThe real opportunity is not simply getting people to recognize a destination, but helping them see, feel, and experience everything it can become.