Operations leadership, on call · Orlando, FL · remote-friendly

About Jenna

I lead the systems a business runs on: choosing them, building them, connecting them, and answering for whether they land. But most of all, I pride myself on giving you the confidence that your system will launch, and that it won't turn into one more thing you have to babysit.

Jenna, business operations lead and founder of Casually Digital

I've spent over a decade in software development, and the biggest lesson it has taught me is that good software comes down to two things: a team that understands what's being built, and a clear plan to execute it. Most of what I do is making sure both are in place before the work starts, and that they stay in place until it's done.

I've always loved problem solving. It's how I approach just about everything, at work, at home, and everywhere in between, always looking for the better way to do something. I'm naturally curious, and I'd rather be handed the complicated version of a problem than the tidy one. When a project hits a roadblock, I actually get a little excited, because the answer is always in there somewhere. It just takes digging back through what's really happening until you find the piece causing it.

That same instinct is why I love being organized. Not neat for the sake of neat, but work that runs smoothly, where everyone can see what's coming next without having to chase anyone for it. I run my home life the same way. It's just how I'm built, and it's a big part of what I bring to every project, whether I'm scoping a system on day one or stepping into one that's already off track.

Where it shows up most is integration work: making separate platforms behave like one. I've brought systems like Amilia, Daxko, Quattro, and TractionRec into WordPress, and every time, the first decision is how deep to go. Sometimes a clean embed is all the experience needs. Other times it takes a fully custom API integration to feel seamless. Getting that call right early saves months of overbuilding on one side and a frustrated set of users on the other.

At a glance

The shape of the work.

What I run
The systems a business operates on, and the processes around them
Off-the-shelf software through fully custom platforms, plus the integrations that make them behave like one system.
What I do on them
Assessment and scoping through rollout, adoption, and what comes after
I'm not the one writing the code. I'm the one who steers the team building it and answers for whether it ships.
How it runs
A fixed-fee project or a defined-term retainer
Which one depends on the work, not on which service you came in through. Either way you get a written scope and a price before anything starts.

What having me as your operations lead actually means.

Leading means I own the outcome, not just a slice of it. I steer the work, make the calls, and answer for whether it ships. It means translating between engineering and leadership without losing anyone. And it means I write my own proposals, pick up my own phone, and tell you when something's a bad idea, including if the bad idea is hiring me.

I won't scope your project on the spot. Our first call is for understanding what you're really trying to do, not quoting it off the cuff. After we talk, I take the time to sit with it, come back with any questions, and then build a proper scope and send it to you in writing. You get a considered plan you can read, share, and hold me to, never a number I pulled out of the air on a call.

I also keep my engagement load small on purpose: never more than three projects at a time. It's the only way to stay the person actually doing your work instead of managing it from a distance.

One call

What that looks like in practice.

01
The problem
An organization came to me stuck on a CMS their marketing team couldn't touch. Every copy change, every new landing page, every SEO fix went into a developer queue and sat there.
02
The obvious fix, and why I didn't take it
Hand them the most flexible system I could. But a wide-open page builder solves the ticket backlog and quietly creates a worse problem, because the same freedom that lets a marketer publish a landing page in ten minutes lets them break the template, the accessibility, and the SEO in the same ten minutes.
03
What we built instead
The narrow version. A small set of components the team can actually assemble, with the accessibility and SEO rules baked into the components themselves rather than left to whoever happens to be typing that day. They ship without a developer now, and nothing they ship breaks the site.

Want to talk?

Thirty minutes, no pitch, no slides. Tell me what you're trying to ship and I'll tell you honestly if I can help.

Book a 30-min intro

Book a 30-min intro

No pitch, no slides. Tell me what you're trying to ship and I'll tell you honestly if I can help.

✓

Thanks for reaching out.

I'll respond in 24–48 hours. Looking forward to chatting soon!