Most of my career lives in enterprise B2B software: long sales cycles, technical buyers, six-figure deals. So when a friend asked me to help rebuild the brand and website for It's By Jenna, a small Pittsburgh-area business combining a lip gloss line with esthetics services, I said yes mostly because it sounded fun. It turned out to be one of the more useful marketing exercises I've done in years, precisely because it was nothing like my day job.
Small businesses can't hide behind budget
In enterprise marketing, a weak message can survive for a while on the strength of a big paid media budget or an established sales team papering over the gaps. A small business has none of that cushion. Every word on the homepage has to work, because there's no budget to compensate for confusion. Rebuilding It's By Jenna's site forced a level of message discipline I don't always get to practice at scale: if a sentence didn't earn its place, it came out.
Two brands under one roof is a positioning problem, not a design problem
The business combined two distinct offerings, lip gloss products and skincare services, under one name, and the instinct was to solve that with a nicer homepage layout. The actual fix was strategic, not visual: deciding how the two halves of the brand talk to each other, what unifies them beyond the founder's name, and where the customer journey actually splits. That's the exact same problem I've solved at a much larger scale during Simio's merger integration. The scale changes. The underlying question doesn't: what's the one thing tying this together, and does every page say it clearly?
Real customer voice beats a marketer's instincts every time
The best copy on that site didn't come from me. It came from getting Jenna's actual voice, how she talks to customers at her market booth, into the homepage instead of a polished, generic version of it. I've known this principle in theory for twenty years. Watching it play out on a project small enough that I could see every word land was a good reminder that authenticity isn't a nice-to-have. It's the whole game, at any size.
Why I keep doing projects like this
I don't take on side projects like this for the money. I take them on because they keep my instincts sharp in a way that only comes from working at a different scale, in a different category, with a different level of resource constraint. Every enterprise marketing problem I solve gets a little clearer after I've had to solve the same underlying problem with a fraction of the budget and none of the safety net.