E46 | Revolutionizing Fan Engagement with AI and Storytelling, with Bill Bailey
- Gail Montgomery
- Sep 26
- 4 min read
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“Give context and remove obstacles”
Bill dropped that leadership gem during our conversation and it set the tone for everything that followed.
Clear goals. Fewer blockers. Faster wins.
Yes please!
Bill Bailey is the Head of Sports and Entertainment at Satisfi Labs, a conversational experience platform used by major teams and venues.
He grew up in analytics, learned to tell data driven stories, and now helps organizations turn fan questions into instant answers across web, apps, Facebook, and WhatsApp. Satisfi has been at this for nine years and holds significant market share in sports and entertainment. The mission is simple. Protect the brand, help fans quickly, and route high value moments to humans right away.
Here are the three big themes we loved, each with a leadership tip and a way to make it fun.
1) Fan Conversations at Scale that Stay On Brand
Satisfi deploys brand trained chat across multiple channels so fans get answers when they actually plan their day. Bill shared two numbers that tell the story. Around 63 percent of conversations happen after hours. For a global ticketing partner, AI now resolves 85 percent plus of issues that once became problem tickets. Fans get instant clarity. Teams save time. Sales reps jump in when a suite or premium opportunity appears. Everyone wins!
Leadership Tip: List your top 25 repeat fan questions. Tag each one as Inform, Transact, or Escalate. Train AI on Inform and the straight line parts of Transact. Create crystal clear triggers for Escalate so a rep gets pinged the moment a high value intent shows up.
Make It Fun: Run a monthly “Fan/Customer Fire Drill.” Pick three real scenarios at random and time the response from question to complete answer. If you beat last month, celebrate with a scoreboard selfie. If you miss, choose one improvement and retest next week!
2) TELL the Story and SHOW the Story
It was obvious in our conversation that Bill’s superpower is turning complex into clear. And who doesn’t need more of that? In food industry analytics he learned to prove a narrative with numbers. In sports he learned to move people with that narrative. Different minds absorb information in different ways, so he layers formats. Say it out loud. Put a simple slide on screen. Draw the model. Repeat the three points and connect them as you go. Clarity creates action and trust.
Leadership Tip: Use a “1 3 1” rhythm for every update. One sentence on the goal. Three short bullets on what changed this week and why it matters. One sentence on what you need next. This pattern respects attention and builds momentum.
Make It Fun: Try “Whiteboard Karaoke.” One person draws the idea for 60 seconds while a partner explains it in real time. Switch roles. You will spot the fuzzy parts fast and you will laugh while you fix them!
3) Relationships Over Transactions and Leadership That Travels
Bill’s secret sauce is genuine curiosity. He asks how a business truly operates, waits for the answer, and earns credibility quickly. His favorite leadership advice came from mentor Hugh Weber. Give context and remove obstacles. Hire smart people, point the lantern at the path, clear the rocks, and let talent run.
Leadership Tip: Open one on ones with two questions. “What context do you need from me this week?” “What is in your way that I can move?” Capture answers in a shared doc and close the loop within 48 hours.
Make It Fun: Create an “Obstacle Wall.” Teammates add sticky notes for blockers. Spend five minutes each week claiming notes and sharing the removal plan. Ring a bell when a blocker disappears!
AI that respects the brand. Stories that land. Relationships that last longer than a quarter. That is Bill Bailey’s playbook. When things zig instead of zag, smile and take the next right shot. Onward! Yes, AND!!
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Bill Bailey is the Head of Sports and Entertainment at Satisfi Labs, where he leads partnerships with major leagues, teams, and venues. His focus is brand safe conversational AI that answers fan questions in real time and escalates high value opportunities to humans instantly.
Bill’s path runs through analytics leadership in the food industry managing margins for a multi-billion-dollar business, executive roles in the NBA ecosystem, stewardship of a family office, and a growth journey at SSB (where he was Bruce’s BOSS!) that scaled from two sports clients to 180 before a successful exit. He is known for translating complexity into action through clear storytelling, strong relationships, and a leadership philosophy anchored in one principle. Give context and remove obstacles.
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