What if your photography business could keep booking clients, serving couples beautifully, and generating revenue—even when you’re going through the hardest season of your life?
Most photographers think scaling means raising prices or shooting more weddings. But what if I told you that true scaling means your business runs smoothly whether you’re on vacation, navigating a personal crisis, or simply choosing to step back for a season?
In this episode, I’m sitting down with Jess, one of my Scale It graduates who transformed her thriving-but-exhausting photography business into a sustainable model with an associate team, a full outsourcing crew, and systems that gave her freedom when she needed it most. Jess specializes in intimate weddings with 30 guests or less, and she’s not just a photographer—she’s also a planner and day-of coordinator for her couples. Her story is a perfect example of what it looks like to build a business that truly runs without you.
When Jess joined Scale It in January 2025, she was in her fourth year of business. She was financially successful, but stuck in what she calls “creative robot mode” every busy season. She loved what she was building, but she knew it wasn’t sustainable. She wanted to create a business that could run on autopilot, give her more balance, and create freedom outside of work.
Fast forward to August 2025, and Jess has built and booked her associate team, generating revenue without trading all her time. She’s fully outsourced key areas of her business with a VA, blog and Pinterest manager, and social media manager. She’s created systems and workflows that give her peace of mind, allowing her to serve clients seamlessly without being hands-on. And perhaps most importantly, Jess walked through a really hard personal season while in the program, and because of everything she had implemented, her business kept running smoothly in the background—even booking multiple weddings for 2026 in one week while she was going through something difficult.
Listen to the episode below, or keep reading for a summary of what’s covered.
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Meeting Jess: The Mountain Town Photographer Who Does It All
Jess isn’t your typical wedding photographer. She specializes in intimate weddings with 30 guests or less—elopements are her jam. But what makes her business model so unique is that she’s not just the photographer. She’s also the planner, the day-of coordinator, the right-hand gal who becomes best friends with her couples.
“We’re not just your photographers. We’re also your planners. We’re your day of coordinators. We’re your right hand gals,” Jess shared. “And I know you hear that a lot in the industry, but we truthfully do become best friends because we not only sit with you while we’re planning for hours on hours, but then we’re also with you on your day all day and then beyond that as well with album creation.”
Jess lives in Breckenridge now (she’s a mountain town girly through and through), and she specializes in Breck, Crested Butte, Telluride, Jackson Hole, and Moab, Utah. Outside of photography, she’s a big outdoors person—hiking, skiing in the winter, backpacking, camping. She recently found running this season, which has become her way to relax and find solitude in nature.
I have to share this quick story: Jess is actually “the one that got away” from me. She used to second shoot for me back in the day, and we worked so well together. Our personalities just clicked, my clients loved her, and when I was looking to add another associate photographer to my team, Jess was the ONE. But she said no! And honestly, I’m so glad she did because she was ready to build her own team instead of shooting for someone else. She already had a super successful business—she just needed to learn how to scale it.
Why Jess Needed to Scale (Even Though Her Business Was Already Successful)
Here’s the thing that I think is so important for photographers to understand: you don’t have to be burned out or hate your business to need to scale. Jess was financially successful. She had a system for booking clients, serving them, delivering galleries. Everything was great on paper.
But she was in “creative robot mode” every busy season. She was stretched thin. And even though she loved what she was doing, it wasn’t sustainable.
“I felt like I had this amazing system of booking clients, serving clients, delivering galleries,” Jess explained. “But I was like, oh my gosh, what if I could do what I’m doing, but also run it on autopilot and step away from my business and allow more work life balance, especially being a one woman show and doing all things that I was doing completely alone. It was starting to really wear on me.”
That’s when she decided to join Scale It. She had followed me for a long time, and she loved how the program was all about figuring out how to get your business to work on its own so you can step out and feel like everything is running itself—not taking away from the personal aspect of business, but having systems, outsourcing, and an associate team in place.
What Was Holding Jess Back Before Scale It
Jess is a big dreamer. She comes up with ideas and thinks, “Oh my gosh, how amazing would it be if we did this?” But getting from point A to point B? That’s where she struggled.
“If you’re here and you’re needing to get or wanting to get here, it’s so hard to come up with how to get there—like the step-by-step track,” Jess said. “I just really loved that Scale It was like, okay, these are your goals. This is how to get you there. Because I just felt like I had all these big dreams. I just didn’t know how to break it down to things that were valuable and digestible.”
And it was off-season when she joined, so she had the time to dive in. Having me there to tell it to her straight while also providing guidance, audits, and mentorship made everything feel so manageable.
This is something I see with so many photographers. They have the vision. They have the drive. They just don’t have the roadmap to get from where they are to where they want to be without burning themselves out in the process.
Jess’s Biggest Wins: Building a Team That Supports Her Business
Full Outsourcing: A Team of Women Behind the Scenes
Before Scale It, Jess had outsourced small tasks here and there—Pinterest, blogging, things like that. But she didn’t have anyone on consistently, so she never really saw the consistent return on investment from outsourcing.
Now? She has an entire team of women behind her.
She has a VA who handles all her wild ideas. Jess brain dumps into Notion, and her VA organizes her thoughts and plans out how to get her there. She has a Pinterest and blog manager who takes her beautiful galleries and the brain behind how she planned those days and puts them in blog form. She has a social media manager who handles the strategy (Jess still loves doing social media herself because it’s fun for her and shows her personality, but having someone behind the strategy is huge).
“Having someone behind the strategy of social media is huge for us because I’m a dreamer, so I’m like, well, let’s just post this, and she’s like, well, that doesn’t really make sense,” Jess laughed. “So she’s constantly reeling me in as well.”
The goal of outsourcing isn’t just to have tasks off your plate. It’s about having 80% done so you can focus on the 20% that needs your refinement. When you train someone well and set up your systems properly (which we dive deep into in Scale It), it truly feels like having partners in your business who see you and get you.
Building and Booking an Associate Team
Beyond outsourcing, Jess also built her associate team—a team of photographers who can be an extension of her on wedding days.
Now, here’s what’s unique about Jess’s business model: because she offers planning services along with photography, she structured her associate team a little differently than a traditional photography business might.
For elopements (typically 10 guests or less), she feels comfortable sending an associate who knows exactly where to go and how to serve couples just like Jess would. But for larger intimate weddings (10 to 30 guests), they might need an entire team there to day-of coordinate and photograph—making sure everything is happening on site the way it’s supposed to.
And here’s the game-changer: Jess created what she calls a “planning portal”—an updating link that clients receive once they’re booked. All the day’s details live there. All vendors have access. It’s their biggest selling point, and it’s also the tool that allows her to send an associate without needing to be there herself. If anyone has questions on the wedding day, they go to the planning portal. Everything is right there.
This is what I mean when I talk about systems that set everyone up for success. Jess didn’t just hire team photographers and hope for the best. She built the infrastructure that allows her business to run beautifully without her being hands-on every single time.
The Freedom That Changed Everything
Jess told me that the biggest win of all—the one that encompasses everything she accomplished—was the freedom she got back in her business.
“I’d say the biggest one is the freedom that I got back in my business, knowing and feeling that everything was running and serving my clients with the best client experience with me not being hands on,” she shared.
And friend, this freedom became more important than she ever could have anticipated.
Scaling Isn’t Just for Vacations—It’s for Life’s Hardest Seasons Too
Here’s where Jess’s story becomes so powerful, and honestly, it’s a perspective on scaling that I don’t think gets talked about enough.
Most photographers think about scaling in terms of vacations. “I want to go on vacation without my laptop.” “I want to take a week off and not worry about my business.” And those are absolutely valid goals.
But about halfway through the Scale It program, Jess went through a really hard personal season. She went through a pivot in her relationship—a breakup from a relationship she’d been in for many years. She was finding herself again, moving, literally uprooting her life to choose herself and to be completely alone.
And here’s what she told me: “Knowing that my business was still running itself and showing up for my clients, and there wasn’t a ball dropped across marketing, across communication, across planning—everything was still on autopilot and working so well. That was something that allowed me to step back and really get into therapy and do what I needed to do personally to be able to show up this year in wedding season the best that I possibly could.”
This is such an important conversation, especially in the wedding industry. We’re showing up on people’s best days. We’re capturing love stories. And behind closed doors, you don’t really know what other people are going through.
Jess never had to post a disclaimer on her Instagram Stories saying that gallery delivery times would be delayed or that she was going through something hard. Her clients didn’t need to know the nitty-gritty details of her personal life while she was processing. Her business ran without her needing to “air out her dirty laundry,” as she put it.
“Your clients do not want to see this. It’s not professional,” Jess said. “Your business is not personal, although you are your business. It’s this beautiful line that we’re dancing. And it was just such an awesome season to be able to step back and say, okay, my team has got it. They know what I need. They know what we need to succeed.”
And here’s the kicker: This season has been Jess’s most exponential ever. She just booked four 2026 weddings in one week. FOUR. In one week. Because her systems are in place. Because her team is supporting her while she’s in busy season. Everything is great.
She’s also booked weddings for her associate team, which she literally just launched. That’s income coming in without her needing to trade her time for it.
Why Scale It Worked for Jess’s Unique Business Model
I want to address something that I know holds a lot of photographers back from investing in education: the fear that a program won’t work for their specific business model.
Jess’s business is SO unique. She’s not just a wedding photographer. She’s not just a wedding planner. She’s both, and she offers something completely different from what most people in this industry offer.
When I asked her what specifically helped her in Scale It, she said: “My business model is so unique. It’s not just a wedding photography business. We’re not just wedding planners either. And we also offer something that is so different from everything else out there. So I had to take Scale It and really meld it and mold it to fit what I was looking for. And the fact that it was able to do that is huge.”
This is exactly why I don’t teach a “do what I did and replicate my business exactly” approach. Yes, I share everything I do—I don’t gatekeep. But the mentorship piece is about helping you customize the strategies to YOUR business.
On our hot seat calls in Scale It, we were always diving deep into Jess’s specific business—talking through how she could communicate her unique offering more clearly, what verbiage would work best, how to structure her associate team differently because of her planning services. It wasn’t about making her business look like mine. It was about giving her the foundational strategies and then helping her apply them in a way that made sense for her.
The Scale It Approach: Slow, Intentional, and Side-by-Side
When I asked Jess what made Scale It work so well for her, she emphasized a few key things:
The modules being a month long gave her time to actually dive into each topic instead of feeling overwhelmed by too much information at once.
The slow intentionality of the program itself meant she could implement as she learned, not just consume content and hope she’d remember it later.
The side-by-side mentoring—whether that was DMing me in our private community with questions or collaborating with the other women in Scale It—meant she never felt alone in the process.
“I definitely say the step-by-step,” Jess shared. “I’m a big dreamer, so I come up with ideas, but having you Claire there, essentially holding our hands and being such an amazing mentor that will just tell it to you straight but also give you guidance and the audits and all of that amazing stuff—it just felt so manageable.”
And here’s what I want you to hear: Yes, I gave Jess the education. Yes, I gave her the resources. Yes, I gave her mentorship. But Jess’s success is because she got in and got the stuff done. She trusted the process. She leaned into it. She did the work.
That’s what it takes, friend. Not just consuming education, but actually implementing it.
What’s Next for Jess
Right now, Jess is taking things day by day. She’s continuing to specialize in Breckenridge, Crested Butte, Telluride, Jackson Hole, and Moab, Utah. She’s working on expanding into Aspen and Vail to blanket Colorado. She’s getting a dog soon (a personal joy that’s going to bring so much love into her life). And most importantly, she’s focused on serving her clients to the best of her ability while also serving herself.
“I just want to serve my clients to the best of my ability and also serve myself, and I think that that’s exactly what Scale It allowed me to do,” Jess said.
That’s what scaling is really about. Not just making more money or booking more weddings. It’s about building a business that serves your life instead of consuming it.
Key Takeaways
- You don’t have to be burned out to need to scale—if you’re in “creative robot mode” every busy season, it’s time to create more sustainable systems
- Outsourcing works best when you have the right training and systems in place so team members can do 80% of the work without constant hand-holding
- Associate teams can be structured in unique ways depending on your business model and the services you offer
- Scaling isn’t just about vacations—it’s about having a business that runs when life gets hard, when you need to step back for personal reasons, or when you simply want more freedom
- Your clients don’t need to know every detail of your personal life when you have systems that allow your business to run professionally no matter what
- The right education is customizable to your unique business, not a one-size-fits-all “do what I did” roadmap
What’s Covered in This Episode
- How Jess built her unique photo + planning business model in mountain towns
- Why she joined Scale It even though her business was already financially successful
- The specific outsourcing team she built (VA, Pinterest/blog manager, social media manager)
- How she structured her associate team for intimate weddings and elopements
- The “planning portal” system that allows her business to run without her being on-site
- Going through a difficult personal season while her business continued thriving
- Booking four 2026 weddings in one week after implementing Scale It strategies
- How Scale It is customizable to unique business models beyond traditional wedding photography
Resources Mentioned in This Episode
- Apply for Scale It Mentorship Program—my five-month group mentorship focused on building associate teams, outsourcing effectively, and scaling your photography business for work-life balance
- Follow Jess on Instagram @jessicaluannphoto (changing this off-season, so keep your eye out!)
- Visit Jess’s website to see her planning portal and unique photo + planning services at jessicaluannphoto.com
Thank you so much for tuning into today’s episode. I’ll be back in your ears with more photography business education every two weeks, so be sure to subscribe to the show. If you’re loving these episodes, I’d be so grateful if you’d leave a five-star review on Apple or Spotify so the podcast can reach more listeners just like you.
While you’re at it, screenshot this episode, share it on Instagram, and tag me @itsclairehunt. I would love to know what resonated with you most so I can create more episodes that serve you right where you’re at.
And if you’re ready to dig deeper and build systems that allow your business to run without you—whether that’s for vacations, hard seasons, or simply more freedom in your everyday life—Scale It might be exactly what you need.
Until next time, friend.
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