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Early Traction, Rapid Iteration: What I Learned Building Upsteer

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Early Traction, Rapid Iteration: What I Learned Building Upsteer

For our final product pivot at Upsteer, we had a clear goal: help B2B e-commerce brands automate their order-to-cash workflows. After nearly a year of working closely with e-commerce operators, we kept hearing the same story—brands expanding into B2B to drive profitability but unable to capitalize on the opportunity due to manual processes, delayed payments, and spreadsheets flying between teams.

This case study is written in more of a blog-style / short form format, since Upsteer's journey wasn't defined by a single project or moment. It was shaped by 150+ interviews, fast iterations, technical experiments, and a lot of lessons learned along the way, many of which I think are worth surfacing beyond the usual case study structure.

The Problem

Coming from Fivetran, I had a strong curiosity about inefficiencies in e-commerce / retail. It's a space I knew well and one that was full of friction. After multiple pivots and 150+ interviews with e-commerce brands, a pattern emerged: the moment brands entered B2B/wholesale, everything got harder.

These companies were managing receivables for the first time, often with little to no systems in place. Anecdotally and through our own product data we found that over 50% of invoices were paid late. On top of that, these teams were shifting from a cash-based finance model to accrual-based accounting, introducing a new layer of complexity and compliance risk.

Automating this workflow with 100% accuracy wasn't just a nice-to-have—it was critical to growth and financial stability.

Iterating Toward Traction

We explored multiple directions throughout 2024. Some with promise, others with clear signals to move on. But one problem kept rising to the surface: brands couldn't get paid on time, lacked visibility into collections, and were manually stitching together data across systems.

That's when we honed in on order-to-cash automation.

We built and launched a platform to automate invoicing, payments, and reporting for B2B e-commerce.

What We Achieved

While we didn't fully reach product-market fit, our final pivot led to meaningful traction and strong early signals:

  • Onboarded 21 paying customers in under two months
  • Processed $3.5M+ in invoices
  • Generated $45K in ARR
  • Reduced Days Sales Outstanding (DSO) by an average of 32%
  • Saved customers 8+ hours per week

Key Product Improvements

  • Launched a Flask-based public API powering integrations with tools like myPocketCFO
  • Reduced onboarding time from 3 days to 20 minutes using AI-powered data mapping

What I Learned

This experience reinforced a few core product lessons:

  • Iterate fast and talk to customers early and often
  • Sell early (even before you have a working product)
  • Understand your customers' willingness to pay as soon as possible

There are so many more lessons I could share, but I'll save that for another post.