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Expensify's David Barrett | Unconventional process

Patrick Campbell Aug 16 2022

One size fits all. At least that's what mass commercialization after the 1950s wanted us to believe. But, is is really true? Whether you’re at Target, Walmart, or your local boutique, we’ve all been clothes shopping. If you see something that fits your style you’ve got to check and see if it actually fits your body. XL in one place is a double XL in another. And a small in one place is an extra small in another place. The changing room can be a humbling experience. If you're like me or you're in that a post-holiday exercise hiatus, it'll reveal that large is probably now a bit of a medium. And even if you do find an item in your size, after a period of time it might not really fit in stylistically.

This isn’t a metaphor for B2B SaaS swag, this is a metaphor for business operations. While Facebook ads might bring in 10% more leads for company X, company Y might try that and see an even smaller return than they had before. Additionally, that channel can wane if not tended to properly, and pretty soon Facebook ads aren’t a viable option anymore. But it doesn’t hurt to try.

Today’s guest, David Barrett the Founder and CEO of Expensify, knows this better than most. He exemplifies this concept of challenging existing principles, and also, trying out new ways of thinking. Over his decade-plus tenure leading Expensify, he has learned what attracts not only the best customers and where to focus on getting them, but he’s one of the deepest thinkers I’ve ever talked to when it comes to wisdom and advice on how to build an actual business..


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You have to have an appreciation and an excitement for other people's ideas, and like, an enthusiasm to be wrong.”

– David Barrett





Key term:


Unconventional refers to the opposite of conforming to what is generally done or believed. And when it comes to SaaS, standing out among the noise is key. Those unafraid of going against the grain are typically who succeed and change the world.


What to do today: 
  • Follow David Barrett.
  • Schedule a time to meet with your leadership team to discuss and evaluate your current processes (marketing, sales, product, etc.) across all departments.

What to do next quarter:

Experiment with your processes.

Every company is different and there’s no one way to do it — whether you’re looking to scale, acquire more customers, grow your teams, develop your product, etc. If you want different results, then you must be willing to try different things. 

And a great example of this statement, if not the example, is our guest David Barrett. In fact, he’s successfully built his company through unconventional processes. His trust in following his gut and not what everyone else is doing, or telling him to do, is what has led to Expensify’s wild growth and high retention rate — both with customers and employees. 

If you’re at a point where you’re ready to think outside the box, here are some key practices that have led to David’s success. Some of which may seem a little far-fetched, but be open. It may just be what you need.

One team:

Align and focus your entire company on building your product for the end user, and create role fluidity, inclusivity, and ownership in the workplace.


  • Give employees the freedom to decide what to work on. Encourage them to take on tasks or projects that feel relevant to them. This fosters trust and ownership.

  • Design a process that everyone in your company must follow. A process that allows everyone to share their ideas, problems to solve for, or projects with everyone in the company (e.g., a Slack channel). Allow time to gather well-rounded perspectives and input from colleagues to ensure it makes sense to work on the proposed problems or projects.

  • Set realistic expectations about the process that you’re changing or implementing.
    • A slow but intentional pace actually gets things done faster and more efficiently. The slower pace allows you to address and rectify issues that come to light before getting too deep into the process.

  • Hit growth by shrinking your targets. Don’t underestimate the power of small but precise steps.

  • Be patient and trust the process.


What to do within the next year:

Apply any or all of the above practices. Monitor and evaluate the output — whether the output was to inspire creativity and ownership, increase efficiency, or obtain better results, etc. 

And as stated, be patient and trust the process.


Who should own this? 

Depending on the structure of your organization, ownership may initially fall on your leadership team to help communicate and implement any changes. But, if you're working toward a more inclusive and collective process, each team member will eventually be responsible.


Who's up next week?

Next week, Vanta's Christina Cacioppo talks to us about automating security & compliance.

Do us a favor?

Part of the way we measure success is by seeing if our content is shareable. If you got value from this episode and write up, we'd appreciate a share on Twitter or LinkedIn.


This is a Paddle Recur production—the first media network dedicated entirely to the SaaS and subscription space.




By Patrick Campbell

Founder & CEO of ProfitWell, the software for helping subscription companies with their monetization and retention strategies, as well as providing free turnkey subscription financial metrics for over 20,000 companies. Prior to ProfitWell Patrick led Strategic Initiatives for Boston-based Gemvara and was an Economist at Google and the US Intelligence community.

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