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About Prosper

Founded in 2005, Prosper introduced U.S. consumers to an innovative new approach to personal finance called peer-to-peer lending. Almost 20 years later, Prosper has helped over 2 million customers achieve financial well-being through a comprehensive suite of products.

Stephen's Bio

Stephen Baker is an automation machine, leveraging past experience in the realm of data engineering, platform management, graphic design, email development, and all other things marketing, to drive broader team goals toward their target with the use of Iterable and big data.

Fun Facts

Tech geek on the weekdays, dirt bike enduro rider on the weekends.
Enjoys the outdoors, especially the high desert of northern AZ and southern UT.
Magnet for rattlesnakes; have almost stepped on several.

Interview

What brings you joy in your role?

My arch nemeses are manual tasks, which are prone to delays and user error (despite best intentions). The best feeling is implementing an automation that returns value to stakeholders, or frees them from hours of distracting busywork: empowering them to focus on things that matter (such as experimentation, new campaigns, and refreshing old templates).

 

What’s a mistake you’ve made at work, and how did you deal with it, or what did you learn from it?

Some time ago, at a slightly less wise age, I was brazen in trying to solve all problems, all the time. I think that kind of go-getter attitude can be good in measured doses, but attempting to solve all of a company’s problems can lead to burnout and a lack of focus (or both). It is a difficult skill in and of itself, but getting buy-in from the broader organization, and your team, can help alleviate some of those high stress and high tension situations that you cornered yourself into by trying to be the hero, while adding the extra benefit of steering by focus (fewer projects implemented with prowess can be more fruitful than several projects implemented haphazardly).

 

What tips, tricks, or pieces of advice would give a new Iterable user?

Iterable is best used in the event-driven paradigm that has taken over web development in the past decade. Attempting to use it as a hybrid do-all CRM/CMS/ESP will have major consequences as its use grows over time. Most mistakes are only prevented on the initial implementation: it’s best to borrow modern techniques from software engineering principles (centralization of functionality with the snippet system, separation of concerns with external audience connectors, automating repeat tasks via the modern API with local/shared tooling, etc.).

 

What led you to choose Iterable over others in the market?

Iterable is the best platform for modern integrations with external pipelines, while remaining lightweight but not barebones. This makes it very fast and reliable. The API not being a REST dinosaur is near the #1 slot on my list of must-haves versus older competitors.

 

Besides Iterable, what are the other tools in your marketing toolkit that you can’t live without?

Integrating with a platform is important in understanding how it works, and what automations are available. My current toolkit involves a local development environment powered Python, Polars, and gcloud, with bonus connections to Atlassian products such as Confluence, to be a powerhouse of true marketing solutions. I encourage all marketers to embrace the technology around them. It unlocks new abilities you didn’t know you wanted!

 

What would you like to see brands doing more of? Or less of?

I’d love to see an industry-wide shift toward a ‘less is more’ approach in marketing. Over time—especially in eCommerce—email has been cannibalized by the relentless drive for short-term gains. It’s a classic Tragedy of the Commons: each business increases send volume to chase returns, flooding inboxes with unwanted messages. As engagement drops, the instinct is to send even more, worsening the problem. Email providers tighten filters, and the cycle continues. In the end, everyone loses—including the senders. That’s why protecting and prioritizing a healthy, engaged user list is one of the smartest long-term investments a brand can make.

 

What’s the best advice you’ve ever been given?

“Sometimes no code is good code.” It’s easy to underestimate the amount of work generated when standing up a half-baked feature or service. All code must be maintained, as all code eventually rots under the weight of dynamic business environments. More importantly, implementing half-hazard solutions leads to a false constraint on what is possible in the future (the dreaded ‘temporary, short-term solution’ that sticks around for 10 years). I try to approach any new project with this mindset.

 

If you weren’t a marketer, what would you be?

Probably a stuntman. I would optimize danger instead of conversions.

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