"Jen’s role in my business feels way less like an assistant and way more like a partnership. She understands my business and my clients and really helps me serve my clients in a deeper way. We’ve been working together for years now and every time I throw something new at her, she learns it quickly and finds new ways to provide value for my business."
-kristin
jen madigan
ceo, online business manager
Jen is a photographer, mentor, and creative entrepreneur with over 15 years of experience navigating the ins and outs of running a thriving business. With expertise in a wide range of systems, tools, and workflows, she’s passionate about helping photographers transform their businesses into well-oiled machines that feel effortless to run. Known for her knack for spotting the most efficient path to any goal, Jen is your go-to guide for streamlining processes, embracing automation, and building systems that not only save you time but also create more freedom—so you can focus on what truly lights you up. Whether you’re drowning in to-dos or just ready to reclaim your time, Jen’s expertise will help you simplify and thrive.
Skylar Albritton-Hupy
lite assisting
Skylar's extensive background in the wedding industry has honed her skills in clear communication, exceptional customer service, and the ability to keep everything running smoothly—making her an invaluable asset to any team. With a sharp eye for detail, stellar organizational skills, and a talent for creating seamless workflows, Skylar is dedicated to supporting clients with efficiency and care. She’s the kind of person who brings calm to the chaos, ensuring every project is handled with precision and a touch of magic.
christina irvin
lite assisting / ala carte podcast editing
Christina brings her experience as a creative entrepreneur and business owner to the table, giving her a unique perspective on the needs of busy professionals. Her genuine passion for helping others thrive means she’s all about making your life easier so you can focus on doing the work you truly love. From content creation and social media scheduling to enthusiastically editing podcasts, Christina’s got the skills and drive to keep things running smoothly and efficiently.
Emmaline Hall
lite assisting
Emmaline combines her sharp eye for detail, stellar organizational skills, and creative flair with a background in teaching and content coordination. Her natural drive to help others has always been at the heart of everything she does. Whether it’s blogging, content creation, podcast editing, or tackling other tasks, Emmaline supports clients with precision, creativity, and care—making sure every project is completed seamlessly and with heart.
kallen prosterman
social media
Kallen is a social media pro who helps photographers tell their stories, grow their online presence, and attract dream clients with strategic content and engagement. She’s a wizard with Pinterest SEO, social algorithms, and staying ahead of trends to make sure her clients shine in a crowded digital world. With experience managing social media for Esther Perel Global Media (where she helped double the following!) and leading campaigns for youth voter registration and boutique brands, she knows how to craft content that resonates and drives results. As a filmmaker with an eye for aesthetics, Kallen blends strategy with artistry to create a cohesive, standout digital presence—so you can focus on what you do best while she handles the rest.
meet the team
real talk
We know outsourcing can be scary, but hear me out!
If you've got big goals for your business but find yourself
...spending large chunks of time doing "busy work"
...procrastinating large projects because you don't have "time"
...staying small even though you have big dreams
We can help!
Whether you're a photographer who runs multiple facets of business (coaching, associate programs, etc) or just starting to outsource, we offer several different ways to work with our team!
ready for some freedom with your time?
If you're nodding along with everything I'm saying, I'd love for you to reach out so we can chat more about your specific needs. We offer a complimentary 15 minute discovery call to figure out if virtual assistant services would benefit you and your business! Plus, business is way more fun with a team - just sayin'.
Ready to offload some tasks?
client reviews
Skylar has become an integral part of our team, and we could not be more thankful that she is sharing her talents with us. She has already provided our business with invaluable client and vendor support and helped us uplevel our marketing strategies through graphic design production and blog management. Her organizational skills are unmatched, and her natural ability to maximize systems and workflows is a life saver. She is truly a joy to work with throughout the week!
Kati J.
client reviews
“Jen was an absolute dream to work with - she came highly recommended to me at a point where I wanted to take my business to the next level. Her knowledge on working with the back end of creative businesses is game changing and her proactive ability to find solutions to any problem was transformative for my business.”
Matt R.
client reviews
"Jen’s role in my business feels way less like an assistant and way more like a partnership. She understands my business and my clients and really helps me serve my clients in a deeper way. We’ve been working together for years now and every time I throw something new at her, she learns it quickly and finds new ways to provide value for my business."
Kristin S.
client reviews
Working with Jen has been literally the best decision I’ve ever made, and the single most driving factor of growth in my business. The first week I started delegating tasks to her she helped me pull in $7000 in bookings and well, the rest is history. The first full calendar year I had Jen on my team was my single highest grossing year to date. Investing in Jen has also allowed me a level of wealth in the form of my time and freedom that is absolutely priceless."
Suzzane B.
client reviews
"Jen helped me design and transfer over my website from one platform to another seamlessly. She was extremely quick, efficient and answered all of my questions and even sent videos and screen grabs so I would know how to change things myself in the future! One thing I was worried about was my SEO and how it would be effected long-term. Happy to report she also did a great job on the back-end and my SEO has never been better!"
Jessica C.
client reviews
"Jen’s services have been such a tremendous help for me and my creative business. She has set up systems, streamlined my processes and saved me so much time. Jen is a perfect combination of organized and creative. She is able to utilize her analytic skills to effortlessly assist with all the tasks I need, while also having the capacity to create beautiful graphics, guides and marketing materials with ease. The time she has freed up for me to spend with my family is priceless. She is a caring professional that is also a great listener and concise communicator. Jen has helped me to not only refine processes, but often provides that little extra bit of motivation I need to turn ideas into reality."
Cassandra B.
client reviews
"I am so grateful I hired Jen to tackle switching my website from one platform to another! It felt like such an overwhelming task, and she made it so easy to not only move over the material but also to re-imagine it in a way that I wanted. Jen was patient and communicative throughout the process, and anytime we experienced a limitation of the new platform, she was persistent in exploring it from different angles and sharing ample solutions to ensure I loved the final product. Not only did she build the site of my dreams, but she also helped me in learning how to navigate the new platform, and because of that, updates to the website have been seamless and so much more enjoyable than figuring it out on my own."
Ashley T.
we'd love to hear all about your business and how we can help!
ready to chat?
Depending on your needs, we offer a variety of options to assist photographers with tasks like social media, content creation, workflows, and more.
Our full assisting packages are designed for business owners ready to take big strides forward—whether you’ve outsourced before or are diving in headfirst to scale your business faster. These packages offer comprehensive support to keep your business running smoothly.
Need a little less day-to-day help or just starting to outsource? Our lite packages are perfect for photographers easing into delegation, providing weekly support without feeling overwhelming. We also offer podcast editing packages for those looking to focus in on that area.
For the DIYers out there, our Outsourcing Intensives might be just what you need! In a single day, we’ll outline workflows, identify ways to streamline your business, and create an action plan to get you on track. Plus, we’ll implement up to a 10-step workflow for you and provide a Loom video tutorial to help you get started confidently.
Pricing starts at $775–$1,100 for our lite 8-hour/month package, depending on the team member. Full assisting starts at $1500 and our social media packages range from $1,800–$2,600, offering flexibility and tailored solutions to meet your unique needs.
Let’s chat about freeing up your time!
our mission
As a small female owned business, we strive to assist other female, female identifying, trans, or non-binary individuals find more freedom within their business. We seek to empower creatives of all races, religions, sexual orientations, physical abilities, or ethnicities, not just because it’s the right thing to do, but because we believe inclusion helps us all better connect, belong, and grow.
We believe black lives matter, trans lives matter, and inclusivity within our business and community are important. All are welcome here.
contact us
We'd love to hear from you! You can reach us via the contact form or via email at info@jenmadigan.com
Our business hours are 9-3 CST Monday - Thursday.
We will be in touch shortly. Meanwhile, feel free to browse our Instagram feed. via the link below.
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