saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love brought to you by . I’m your host Anna Nadeina, Head of Growth for

In episode #14 we are talking with Ryan Singer, the member of the initial 3-people team at 37signals, now author of Shape Up: Stop Running in Circles and Ship Work that Matters, and the founder of Felt Presence, helping product teams stop running in circles and regain the thrill of building.


The Challenges of Traditional Software Development

Traditional software development methodologies, such as Agile and Scrum, often fall short when it comes to larger, more complex projects. While these approaches can be effective for managing small, iterative tasks, they struggle to provide the necessary clarity and strategic direction required for successful product development. Teams often find themselves lost in a sea of tickets, unable to see the bigger picture or make informed decisions about trade-offs and priorities.

Another common issue is the disconnect between the product vision and the technical feasibility of implementation. Designers may create beautiful, detailed mockups, but the engineering team may struggle to translate those designs into a functional, scalable solution. This disconnect can lead to wasted time, unexpected complexity, and a final product that doesn’t quite meet the initial vision.


The Shape Up Methodology: A Proven Approach

Ryan Singer and the team at Basecamp developed the Shape Up methodology as a solution to these challenges. The core premise of Shape Up is to shift the focus from estimating timelines to setting project time limits and shaping the work to fit within those constraints.


The Shaping Phase

The first step in the Shape Up process is the “shaping” phase. During this phase, a small team of product, design, and engineering representatives come together to define the problem, explore potential solutions, and shape the work into a cohesive, feasible project. This collaborative effort ensures that the technical factors and trade-offs are considered upfront before any actual development begins.

Rather than diving straight into detailed design or coding, the team focuses on creating rough sketches and architectural concepts. This allows them to quickly iterate on ideas, identify potential roadblocks, and arrive at a clear, shared understanding of what can be accomplished within the allotted time and budget.


The Betting Phase

Once the shaping phase is complete, the team “bets” on the project, committing to deliver a working solution within a fixed, time-boxed cycle (typically 6 weeks). This commitment forces the team to make tough decisions, prioritize the most important features, and avoid scope creep.

During the development cycle, the team works in a focused, uninterrupted manner, with no new tasks or features introduced. This helps maintain momentum and ensures that the team can deliver a tangible, functional product at the end of the cycle.


The Cooldown Phase

After the development cycle, the team enters a “cooldown” phase, where they take a step back, reflect on the process, and prepare for the next project. This break allows the team to recharge, address any technical debt or polish work, and set the stage for the next shaping session.


The Impact of Shape Up Across Business Types

While the Shape Up methodology was initially developed and refined at the bootstrapped company Basecamp, Ryan has found that its principles can be effectively applied to companies of all sizes and funding models, from VC-backed startups to established enterprises.

The key difference lies in the implementation details. Bootstrapped companies may have the luxury of longer project cycles and more parallel exploration, while VC-backed companies may need to be more targeted and focused on specific, high-impact initiatives that align with their business goals and investor expectations.

Regardless of the company type, the core benefits of Shape Up remain the same: improved decision-making, better alignment between the product vision and technical feasibility, and the ability to consistently deliver high-quality, customer-centric solutions within defined time and budget constraints.


Bridging the Gap Between Design and Engineering

One of the key challenges that Shape Up addresses is the disconnect between design and engineering. By bringing these disciplines together during the shaping phase, teams can identify and resolve technical constraints and trade-offs early on, before any code is written.

Instead of relying on detailed design mockups that may not accurately reflect the technical complexity, the team creates rough sketches and architectural concepts. This approach allows them to explore multiple options, understand the feasibility and cost of different approaches, and arrive at a solution that balances the desired user experience with the technical realities.

The result is a more cohesive, technically sound product that can be delivered within the allotted time and budget, without the need for costly rework or unexpected complexity.


Adopting Shape Up: A Scalable, Repeatable Process

Adopting the Shape Up methodology can be particularly beneficial for teams that are struggling with the limitations of traditional development approaches, such as endless project timelines, unexpected complexity, and a disconnect between the product vision and the final outcome.

While small, co-located teams may be able to navigate these challenges through sheer collaboration and experience, as organizations grow and scale, the need for a more structured, repeatable process becomes increasingly important.

By introducing the Shape Up framework, teams can establish a consistent way of shaping, betting on, and delivering projects, regardless of the team’s size or the complexity of the work. This not only improves the quality and timeliness of the final product but also helps to scale the product development process as the organization grows.


Head of Growth,