Inside Trolley – A conversation with Myles F, Product Manager (Tax)

Our goal at Trolley is to build the payouts platform for the internet economy: a payouts ecosystem that allows businesses to send payments around the world as fast and effortlessly as email. Trolley’s payment and software pros take great pride in how we equip our users and their recipient partners with a seamless contractor payout experience. Whether we’re developing new customer-facing features, improving our banking collaborations, enhancing customer documentation, or optimizing our communications, we’re always striving to build a bigger and better Trolley for you: our users and customers.

This series of blogs sheds light on our exceptional team members and the work they do to make Trolley what it is today.

In the product development marathon, the long-distance race is actually run in many short, continual sprints. Always aiming to improve our product offerings in ways that better meet your needs, Trolley’s product managers are responsible for crafting the roadmap for all new products and coordinating their development and releases. After thorough research, they set the goals and rally our team to spin straw into gold — or at least code into features. 

Myles Foster, the product manager responsible for our Tax product, has worn many hats at Trolley over the years. He has gained valuable and varied perspectives by working in sales, support, and marketing, experiences that he leverages today in our product team. As one of the first members of the Trolley team over half a decade ago, Myles profoundly understands the needs of you, our customers, the markets you serve, and how we can help you with intuitive products that minimize the burden of an unoptimized end-of-year tax workflow.

Today, Myles will walk us through his journey at Trolley, from new joiner to product manager, and discuss how he’s working to solve the problems many companies like yours are facing when it comes to contractor taxes.


  • Name: Myles Foster
  • Title: Product Manager
  • Years with Trolley:
  • Years as a product manager: 1.5 years
  • Superpower: Building bridges between the business and technical sides of a company

Q&A with Myles

Explain your current role & responsibilities as owner of the tax product

As the Tax Product manager, I’m essentially a mini-CEO of the Tax product at Trolley. I have the autonomy to set the vision and priorities of the Tax product, and I am ultimately accountable if the Tax product is a success or failure.

I’m responsible for making sure our product is rock-solid for our customers, exploring opportunities to expand into other tax compliance products, and ensuring that we are accessible to anyone trying to solve a tax compliance problem.

This image has an empty alt attribute; its file name is Tax-Tour-CTA.gif

Tell me about how you started at Trolley and why you like working in FinTech

I find the Fintech space to be an exciting space globally. Growing up, I saw the rise of the internet and the emergence of all new business models. The unprecedented access to data and information through the internet created “blank canvas” opportunities everywhere. Now, we’re in the midst of a financial revolution where millions are shifting to remote and online work, which creates the demand for easy, instant online payments. Whether it’s faster payments of fiat currency into bank accounts or new digital currencies that offer an alternative to the centrally-controlled currencies of local governments – people are pushing for change, and the companies employing them are no longer satisfied with the status quo.

At Trolley, and in the Fintech industry in general, we are right at the center of that! Our team works to anticipate the problems associated with these changes and create suitable solutions.

Leaving my mark on this and contributing to this financial revolution has been extremely rewarding for me. I’m very excited to see what’s next!

– Can you explain what Trolley (as a company & as a product) looked like 5 years ago vs where it is now? 

Trolley was a product with a hypothesis; we were in the early days of the creator economy. Video streaming was becoming more popular, and brands were beginning to work directly with individuals on Influencer marketing deals. People were just starting to get paid for creative on-line work.

We thought this was an exciting space which had enormous growth potential. Our job was to figure out how close our beta product was to become the right solution for the companies in this space. Through hundreds of calls with potential customers, we were able to bring feedback internally. We learned to put ourselves in our partners’ shoes and feel their pain points. 

Today we have become heavily involved in the Creator Economy: Whether it’s Translators in Jordan, Influencers in LA, or Twitch Streamers in Sweden, we help them get paid timely and efficiently. Today, we are a critical part of establishing a healthy, trusting relationship between creators and the platforms or companies they collaborate with.

– What makes a product manager successful, in your opinion? 

Great product managers are market-problem obsessed. They are focused on solving problems they hear from customers. There are always different ways to address a problem, and a great product manager keeps the team focused on the importance of solving the problem rather than how they get there. This allows the team to bring in their unique input without being confined to traditional paths. A successful product manager empowers their team to explore and create new solutions.

Internally, successful product managers are able to take a vision and a goal and turn them into major product initiatives that move the company in the right direction while simultaneously getting everyone’s buy-in.

– What motivates you in your role? 

My role here at Trolley allows me to provide opportunities for all new ways of work—it has an impact on real people’s lives. It is really empowering that we help people all over the world earn a living wage by helping secure collaborations and realizing the potential of the internet economy. 

We are helping create opportunities that otherwise would be too costly and inconvenient to create. With the help of Trolley, companies can now pay independent contractors, creators, and artists worldwide. This allows people to pursue the careers they want from the comfort of their homes without the restrictions or commitments of employment. 

Think about it, a company in North America can pay an aspiring singer who is a full-time student on the other side of the world. How amazing is the power of the internet economy? On top of that, we help the people working at the organizations that sign up with us by saving their resources, expanding their pool of talent, and handling their tedious documentation. It is truly a win for everyone involved!

– What upcoming projects are you most excited about? 

I am particularly excited about the tax products that I manage. Governments and regulators are starting to catch up to modern times, as much of the tax code was written in a pre-internet economy era. 

The relatively new tax regulations create an extra layer of business complexity that many companies and individuals aren’t equipped to handle. Without the right expertise and an efficient reporting system, these tax regulations can impede partnerships, slow down internal processes, and significantly increase the workload. 

This is where Trolley can step in. We offer scalability and automation to lift the weight off their shoulders. We don’t want tax regulations to hinder fruitful collaborations. We are working on creating some exciting products that will tackle these problems!

Connect with Myles F on Linkedin to learn more about how he manages our tax products and brings continuous growth to Trolley. 

Share this article:

Join The Payouts Pulse

Sign up to have vital insights, industry news, and all things payouts delivered to your inbox monthly.

More to explore

Print Music Royalties: A Guide for Music Business Professionals

Print Music Royalties: A Guide for Music Business Professionals

This guide aims to help music business professionals looking to better understand…
Mastering the Art of Licensing Samples: A How-to Guide

Mastering the Art of Licensing Samples: A How-to Guide

Read to understand the complexities of managing the copyright, licensing, and royalty…
Sync Royalties: A Guide for the Streaming & Social Media Era

Sync Royalties: A Guide for the Streaming & Social Media Era

A guide to sync royalties—what they are, how they’re calculated, how they’re…
Understanding Payouts: How Are Performance Royalties Calculated and Reported?

Understanding Payouts: How Are Performance Royalties Calculated and Reported?

This guide serves as an entry point for those looking to understand…

Ready to get started?

To learn more about Trolley, schedule a demo with one of our team members or start a chat with a product expert by selecting the box on the bottom of your screen.