Questathon | A Customer Success Journey
Winning a customer is one thing.
Understanding them, keeping them happy, and getting them to renew? That's a different game.
What happens when your customer says everything is going well, but the people making the decisions tell a different story?
That's the challenge.
We're bringing together customer success professionals, account managers, salespeople, business enthusiasts, and curious problem-solvers for a full day to tackle one question:
Can you understand what's really happening inside a customer account, uncover the risks nobody is talking about, and build a plan that actually works?
This is not a traditional hackathon.
You won't spend the morning writing code. You'll spend it playing a game, talking to customers, making decisions, and discovering that what people say isn't always what they mean.
And every decision you make could change what happens next.
The Challenge
You're a newly appointed Customer Success Manager (CSM), and two accounts have just landed on your desk.
Both customers have purchased your product. Both say things are going well. Both have renewals approaching that nobody has properly looked into.
The previous CSM left behind a note.
It ends with two words: "Good luck."
Your challenge unfolds in two parts.
L1: Play the Game. Understand the Customer.
Step into an interactive world where you'll navigate customer accounts, meet different stakeholders, and choose how to approach conversations.
The people you meet have their own priorities, opinions, and concerns. They'll remember what you say and how you treat them.
Your job is to figure out:
Who actually makes the decisions?
Who controls the budget?
What does the customer really think about your product?
What risks and opportunities are hiding beneath the surface?
What information is still missing?
By 2 PM, you'll need to piece together what you've learned and decide what you can actually trust.
L2: Build the Plan. Prove It Works.
Now turn your findings into an actionable account plan.
Use any tools you like, including AI, to organize your findings, identify renewal risks, prioritize opportunities, and decide your next moves.
But there's a twist.
Two new customer accounts will land on your desk.
Your approach needs to work on those too, not just the customers you've already met.
What Makes This Hard
Real customers don't come with a complete instruction manual.
The person who uses your product might not be the person paying for it. The person who loves your product might have no say in the renewal. And the person who says everything is fine might be the one you should be most worried about.
Different stakeholders have different motivations. Information can be incomplete, contradictory, or deliberately left unsaid.
You'll need to ask the right questions, recognize patterns, make decisions with limited information, and figure out what actually matters.
The challenge isn't just collecting information. It's knowing what to do with it.
What You'll Spend the Day Doing
The Morning: Play the Game
You'll start with a challenge walkthrough before stepping into an interactive customer success simulation.
Explore accounts, meet stakeholders, navigate conversations, and uncover what is really happening behind the scenes.
Every choice matters.
The Afternoon: Build the Plan
Take everything you've discovered and turn it into an account strategy you could confidently defend to your manager.
Use AI, spreadsheets, documents, or whatever tools help you think and work better.
Then test your approach against two completely new accounts.
The goal isn't to create the most polished presentation or build the fanciest application.
The goal is to make better decisions with incomplete information.
What You'll Get
An interactive, game-based Customer Success challenge with realistic business scenarios
Two customer accounts to investigate, with stakeholders, hidden risks, and decisions that affect your journey
A chance to practice customer discovery, stakeholder mapping, renewal planning, and account strategy
The freedom to use AI and any other tools to build your approach
Two unseen accounts to test how well your strategy generalizes
A full day of problem-solving, experimentation, and learning alongside other participants
Who Should Join?
This is for you if you're working in, learning about, or curious about:
Customer Success · Account Management · Sales · Business Strategy · Customer Experience · Stakeholder Management · AI for Business · Problem-Solving
Customer Success Managers, Account Executives, founders, business professionals, students, and anyone who enjoys solving complex people problems are welcome.
No coding experience required.
You don't need to know everything about Customer Success. You just need curiosity, good judgement, and the willingness to question your assumptions.
One important thing
If you're reading this description and thinking the challenge sounds a little vague, and you're not entirely sure what you're supposed to do...
Welcome to Customer Success.
Two accounts. Multiple stakeholders. One renewal on the line for each.
Can you figure out what's really going on before it's too late?
Come play, solve, and build with the AI Hackers Collective.