Switching to Dubsado as a Wedding Photographer: How Jordan Went from 2 Hours Per Booking to 5 Minutes

If you’re a wedding photographer still running your business out of your Gmail inbox, snoozed reminders, and a prayer — this one’s for you.

Jordan Craig had been delivering a very high touch, high level client experience for years. The problem? His backend was a mess — and he was the only one who knew it. Every proposal was written from scratch. Every reminder lived in his head. Invoicing happened in QuickBooks, which meant copying and pasting client info across multiple tools just to book one wedding.

Setting up Dubsado for his wedding photography business changed all of that. Within 30 days of joining Systems in Session, Jordan had his entire wedding workflow automated, 33 client emails written in his own voice, and his highest package ever booked — on Super Bowl Sunday.

But first, hi, I’m Colie. I help creative service providers grow and streamline their businesses using Dubsado, HoneyBook, and Airtable. If you’re ready to stop being the bottleneck in your own business, Systems in Session is the 60-day done-with-you program where we build your Dubsado workflow together — correctly, the first time.

What Jordan’s Wedding Photography Business Looked Like Before Dubsado

Jordan is a wedding and portrait photographer based in Lake Placid, New York — a local go-to for high-touch, fast-turnaround photography in a market where he says he doesn’t see others doing what he does. He also shoots commercial winter sports media for international events and covers real estate. The work was great. The backend was not.

People from outside his business who learned what his process looked like would ask: “How did you make it this far?”

He was using Pixieset’s studio manager, which technically keeps track of things, but has just about zero automations. Every wedding booking was taking him anywhere between an hour and a half to two hours just during the proposal phase — getting the initial questionnaire sent out, the contract, the invoice. All of it manual, all of it him.

When he walked me through his booking process on one of our early calls, I had to stop him. I’ve never told a client to just stop talking before — but I told Jordan: “You can stop. That’s way too much. Don’t worry, we are going to automate as much of that as possible.”

Wondering if Dubsado or HoneyBook is the right fit for your photography business? Read my full comparison here.

Why He Kept Putting Off Setting Up a CRM

Jordan had first become aware of me back in September, right in the middle of his busy season. The leaves change colors in the Adirondacks, weddings are stacking up, fall portraits are booked out, and world cups come through Lake Placid regularly — long days covering high-level international events. He kept telling me he was interested, just not ready.

He also knew he could have paid someone a five-figure investment to set up his Dubsado for him — but that wasn’t what he wanted either. As he put it: “I don’t want this software or this process to feel alien to me. As the manager, as the owner, I don’t have to be involved in the nitty gritty — but I need to understand how to do it and understand how it works.”

What he didn’t know existed was a done-with-you option. Someone who would teach him, sit shoulder to shoulder with him through the Dubsado setup, and answer questions like “why is this a public link versus a private link?” without making him feel dumb for asking.

He found me through a training I did with my friend Maddie Peschong called Charge More, Stress Less last summer. He joined the Systems in Session waitlist in August, waited out his busy season, and two months later signed up to start in January. Our shared goal: get his Dubsado wedding workflow fully built before Valentine’s Day, when inquiries traditionally start picking up for wedding photographers.

During his first week he added his new Dubsado contact form on his website — and woke up to four inquiries the next morning. Coincidence? Almost certainly. But we used it as motivation to move fast.

Setting Up Dubsado for Wedding Photography: What We Built Together

Jordan was not one of those clients who was scared of automation. He kept asking if there was anything else he could automate. What he needed was the confidence that he was setting it all up correctly the first time — because that’s exactly what had kept him stuck in his manual process for so long. He’d read the forums. He knew Dubsado could get complicated. He just didn’t want to create more problems for himself.

We got his full Dubsado wedding workflow built in 30 days. Proposals, questionnaires, contracts, automated touchpoints, add-on offers, review requests, offboarding — all of it mapped and loaded into Dubsado, then tested together before a single real proposal went out.

But the piece that surprised him most wasn’t the automations.

Jordan went through the Email Like You Mean It trainings inside Systems in Session and came out with 33 emails for his wedding workflow. Eleven of them were pure client education — no task attached, no link to click, just intentional communication during the long stretches of time where he previously would have gone completely silent.

Here’s what he said about realizing that: “I had been leaving my clients in the dark for long stretches of time. Just having that whole framework of the right communication at the right time — whether they respond to it or not — I know I’m delivering an experience that’s more dialed in, and that trust feedback loop continues to build.”

We also took a closer look at his offer suite while writing those emails. He offers videography, drone coverage, and second shooter add-ons — but couples often book him in a rush just to lock in their date, without thinking through everything they might want. So instead of only mentioning those add-ons on the booking call, we built Dubsado automations that introduced each option naturally throughout the client journey. By the time decisions needed to be made, the idea had already been planted. No pressure, no hard sell — just the right information at the right time.

Want to see how client emails are different from email marketing? Read this post.

Super Bowl Sunday: His Highest Package Ever Booked Through Dubsado

It was Super Bowl Sunday. Jordan had a discovery call booked with a couple — engagement clients who were thinking about their wedding. He’s not a big football person, so he booked the call because that’s what was convenient for them.

The call went well. They almost led it themselves. Jordan pulled up the Dubsado proposal right after and let the automations run. They viewed it that same day, signed the contract within a few days, and made their first payment within a week.

He sent me a support ticket — not a question, just an update. He’d booked his highest package ever and the process was so amazing. I was sitting next to my husband on the couch when it came through.

That’s the moment I work toward with every client inside Systems in Session — not just a Dubsado workflow that works, but actually getting to feel it working.

The Time He’s Getting Back

Jordan did some back-of-napkin math. Once his portrait and real estate service lines are also in Dubsado — not including corporate, which is a different kettle of fish — he’s projecting 180 hours back per year. Not just this year. Every year going forward.

The Dubsado proposal process alone dropped from 90–120 minutes per client down to five minutes.

But the hours were only part of it. Before, the business was leaching into other days and times of the week — and that’s not why he got into business.

He and his wife have a five-year-old and a three-year-old. Systems in Session reignited a backlog of things he’d wanted to do in his business but had let fall to the wayside — and during the 60 days, he even published his first blog posts in a long time. Not a task I assigned. Just what happens when you stop spending every spare hour on admin.

Now he checks Dubsado from his phone while he’s out with his family and sees things moving. Proposals being viewed. Questionnaires completed. Payments coming in. All without him having to be present for it.

Curious what other photographers have said about getting their time back with Dubsado? Read Kelly Bullock’s case study here.

His Favorite Part of the Dubsado Setup Process

I asked Jordan what his favorite part of Systems in Session was. He gave me two things.

The first was being a brand new Dubsado user and getting to build everything correctly from the start — with someone who’s been through the setup dozens of times there to catch mistakes and answer questions. That’s what had kept him stuck for so long. He knew he could get into Dubsado on his own, but the forums were full of warnings about setting it up wrong and creating more work for yourself. Having someone shoulder to shoulder with him made the difference.

The second was the custom GPTs inside the portal — which he genuinely didn’t realize he was getting.

He’d dabbled in ChatGPT before to help draft emails, but as he put it: “It wasn’t really in my voice. And there were always like five hyphens — you know, the long hyphens where you’re like, no one uses the long hyphen.” The custom GPTs, combined with the Email Like You Mean It framework, got him 90% of the way there in seconds — in his own voice, without the toiling.

What’s Next

His Dubsado wedding workflow is running. But family portraits, engagement sessions, and real estate are still manual — still the old way. His goal is to get those into Dubsado before his summer busy season hits around mid-May.

He’s also onboarding a virtual assistant — and because he built the Dubsado system himself, he can actually explain how it works. He handed her the workflows, recorded Loom videos walking her through everything, and gave her a starting point that made sense. That’s a completely different position than handing someone a system you don’t fully understand yourself.

As Jordan said: “The whole process is now fully built out and identified, and all the steps are contained in one place. I can walk away knowing there’s nothing undone — and if there are other things I want to do, business development or marketing, I can invest time in those. But I don’t have to do it at the expense of taking care of my clients.”

Ready to Set Up Dubsado for Your Wedding Photography Business?

Jordan came into Systems in Session as a first-time Dubsado user who had been putting off getting a CRM for years because he didn’t want to set it up wrong. He left with a fully automated wedding workflow, 33 client emails written in his own voice, and his highest package booked — all in 30 days.

If you’re a wedding photographer who is delivering a great client experience but personally responsible for every single step that makes it happen, Systems in Session was made for you. We’ll build your Dubsado workflow together — so it runs without you, and you can get back to the work (and the life) you actually love.