Shape Up: The Cheat Code That Transformed Our Year


As the end of 2024 approaches, it’s time to reflect on the incredible progress we’ve made as a team. For FindBob, this year wasn’t just about building new features—it was about transforming the way we work. And that transformation came from one surprising decision: adopting Shape Up.

If you’ve ever played video games, you’ll know the thrill of discovering a cheat code. Suddenly, what seemed impossible becomes possible. You unlock new levels, move faster, and achieve goals you didn’t think you could. For us, Shape Up was that cheat code—a way to unlock creativity, streamline our processes, and deliver meaningful work.

Here’s how Shape Up became the ultimate game-changer for us.


The Challenge: Leveling Up How We Work

As a founder, I grew up on agile principles. Stand-ups, sprints, and backlogs were second nature to me. But as a CEO, I began to see the cracks. While agile kept us delivering, it sometimes felt like we were running in circles—chasing backlog items instead of solving real problems. Creativity got squeezed between meetings, and ambitious ideas often died in the shadow of “what can we finish in two weeks?”

I knew we needed something more. Something that gave the team the space to dream big and focus deeply, while still shipping with intention. That’s when we discovered Shape Up.

The Cheat Code: How Shape Up Works

Shape Up is a methodology created by Basecamp, and it’s designed to balance structure and creativity. It’s like discovering a secret weapon in a game—a system that helps you prioritize what truly matters, protect your team’s time, and still keep the pace of delivery.

The principles that stood out to us included:

  • Betting Cycles: Instead of a never-ending backlog, we made deliberate bets on the projects that mattered most.
  • Pitch Writing: Every idea had to earn its place through a well-crafted pitch that defined the problem, solution, and appetite.
  • Protected Work Cycles: No interruptions, no surprise deadlines—just focused time for the team to do their best work.


It was a leap of faith, but one that quickly paid off.


The Impact: Unlocking New Levels of Productivity

20 cycles later, it’s clear that Shape Up wasn’t just a new way of working. It was a cheat code that fundamentally transformed how we approached our work. Here are the biggest changes:

#1. Strategic Focus

Betting cycles forced us to prioritize. With limited time and resources, we couldn’t chase every idea. Instead, we focused on what would make the biggest impact. This clarity freed us from the trap of trying to do everything and allowed us to excel at the things that mattered.

#2. Creative Freedom

Writing pitches felt like unlocking a hidden level of creativity. It wasn’t just about documenting an idea; it was about shaping a vision that inspired the team. And because the scope was clearly defined, the team had the freedom to innovate within those boundaries.

#3. Deep Work

By protecting the team’s time, Shape Up gave them the space to go deep. Interruptions and meetings were minimized, and the results were remarkable. Ideas that might have been rushed in a traditional sprint blossomed into thoughtful, impactful solutions.

#4. Liberating the Backlog

One of the boldest moves we made was purging our entire JIRA backlog. It felt risky, but it was also incredibly freeing. Instead of being weighed down by years of unfinished tasks, we started fresh. Every new project had to justify itself through a pitch, ensuring that we only worked on what truly mattered.

 

Combining Shape Up with Agile Roots


While Shape Up provided the framework, we didn’t abandon everything we’d learned from agile. Instead, we blended the best parts:

  • Tight Feedback Loops: Agile taught us to stay close to our stakeholders, and we kept that alive with regular check-ins and clear acceptance criteria.
  • Spike Solutions: In longer cycles, we used quick experiments to de-risk ideas early.
    Cool Down Cycles: These became invaluable for addressing technical debt and planning ahead.
  • Shape Up didn’t replace our old methods: it enhanced them, turning agile’s strengths into something even more powerful.

 

What We Shipped: Proof of the Cheat Code

The proof is in the shipping. Over the past year, we delivered some of the most impactful features in FindBob’s history:

  • Advisor Volatility Index (VIX): Real-time insights into advisor sentiment and retention risks.
  • Partial Sale Listings: Flexible tools for selling portions of a book of business.
  • Deal Structure Tool: A game-changer for evaluating deal feasibility for both buyers and sellers.
  • Student Profiles: Supporting the next generation of advisors.
  • AI-Assisted Profile Generators: Helping advisors tell their stories with ease.
  • Readiness Assessments: To determine how prepared advisors are for succession regardless of the stage in their career.


Each of these features came from a Shape Up pitch, built during a betting cycle, and delivered through focused work. Without Shape Up, it’s hard to imagine achieving this level of clarity and impact.


What’s Next: Leveling Up in 2025

As we look to 2025, we’re doubling down on Shape Up. It’s not just about shipping more—it’s about continuing to empower our team to do their best work. Here’s what’s on the horizon:

  • Bigger Bets: Tackling ambitious projects that push boundaries.
  • Enhanced Collaboration: Refining how we work together to unlock even greater creativity.
  • Continuous Learning: Experimenting with new ideas and improving our process.

Shape Up isn’t just a methodology for us anymore. It’s part of our DNA, and it’s setting us up for a transformational year ahead.

 

Final Thoughts: Why Shape Up Feels Like a Cheat Code

The best cheat codes don’t just make the game easier—they make it more fun. That’s exactly what Shape Up has done for us. It’s given us a way to work that feels exciting, empowering, and purposeful. By focusing on what truly matters, we’ve unlocked levels of creativity and productivity we didn’t think possible.

To other CEOs and founders: if you’re looking for a way to elevate your team and transform your work, I can’t recommend Shape Up enough. It’s not just a system; it’s a cheat code for doing your best work.

Here’s to an even bigger 2025. Let’s keep building!