Building a Training-Based Design Business: An Interview with Jen Maher

We interviewed a handful of professional Squarespace designers to learn their secrets to running a successful web design business, with a particular focus on recurring revenue. Our takeaway: there’s no “one size fits all” approach in the web design ecosystem. This is good news because it means that, whatever your passions, strengths, and experience, there are an exciting variety of approaches for generating sustainable revenue, growing your client base, and loving what you do as a designer! Some of these designers have a single specialty focus, such as workshops, whereas others offer a range of services to suit their lifestyle. In this interview, we chat about training-based income with Jen Maher. Read to the end for Jen’s wisdom on tailoring your offerings to work for you and your clients!

Tell us about yourself and your business

I’m a Squarespace Expert, Squarespace Authorized Trainer, Squarespace Employee Educator and 99 Designs Top Level Designer. I’m also the founder of Nerdville - a Designer Training Program based in Omaha, Nebraska. While I’ve launched over 350 Squarespace sites, I’m passionate about sharing what I’ve learned and helping others fine tune their skills. I have always made training a priority when working with clients so that they have the knowledge and confidence they need to manage their online presence.

What is your rough split between one-time project income vs. recurring income?

This is a tricky answer for me - haha - so I’ll describe how my business works. I have a lot of recurring income but it’s not necessarily regular. If I had to put a number on the split, I would say 50/50.

I try to do everything that I can as “one offs” because it is so much better for my ADHD management not to have open website projects just hanging around in my head. So, I have been pushing clients to think about the design process differently. This is normally a win-win for both of us, because many Squarespace users are DIYers and just need a little help getting over some sort of hiccup. I get 99% of my clients from 99 Designs and then those clients become repeat clients.

I stopped offering “packages” quite awhile ago and have broken everything down into bite-sized sessions. I found that a lot of clients got overwhelmed, both by the amount that they have to learn and also by the monetary side of things. So, I offer a single session where they get to pick the topic. Then, during the session, I “plant seeds” about other topics and give them the coupon code and link to schedule a follow up session when they are ready to keep learning/working.

Jen’s Sessions

I have different sessions that are suitable for different clients, depending on the size of the project, their experience, and their budget.

• Design Audit and Fine Tuning Session - 90 Minutes - $350

• Coaching/Help Sessions - 90 minutes - $350

• QuickStarts - 90 minutes plus a little pre/post work - $500. Basically these are custom Squarespace templates that I build and design for the client over Zoom, while they watch and provide immediate feedback.

• Jen for a Day Session - $1200. This is a deeper version of the QuickStarts session. With this option, I will actually add in their content, do the back end SEO, etc.

• “Talk Nerdy to Me” - a video library.

All clients get 50% off any session after we have worked together once. I create a hidden page on their site in the Not Linked area where I add the link to my Acuity Scheduling and a coupon code for 50% off future sessions. That way, they can easily find me and book me in the future.

The QuickStarts and the Jen for a Day sessions also get one free 30 minute follow up session with me and I also make them a library of six or so short, easy to follow training videos using their site and content, showing them how to manage the basics on their own.

What do these sessions look like?

If a client comes through the Squarespace Marketplace looking for a traditional website design package, I will look through their brief and decide which option above would be good for them. If it is a photography client for instance, I will ask them if they would like to save money by learning how to upload their own content. I tell them about the 90 minute session and let them know that I can get the whole structure and basic design of the site done in 90 minutes and give them a video showing them how to upload their own galleries. We do the session and then I tell them that if they would like help with the actual launch process, they can book a second session whenever they are ready.

If the client is more like a landscape designer or an author with less experience, I will suggest the QuickStarts version where it’s still more of a “DIY with Expert Help” thing. If they really want me to do all of it, I have them book a day with Jen.

I will no longer do any projects that are so big that I can’t get them done in a day (5-10 page sites are usually fine).

What recurring income streams have you built into your business?

I offer a private member area called “Talk Nerdy to Me” that features videos of me working directly with clients, giving page-by-page website overviews of how I built websites and answering questions that members submit.

I have also just begun to partner with a couple of schools and organizations by offering regular training sessions to their students or members.

Schools: I offer group classes to a Cosmetology School and I’m hoping to repeat this process to one in all five regions of the US. Essentially, I create a generic template and duplicate it for all of their graduating students (they have four classes graduate per year). All of the students hop on a 90 minute session with me and I walk them though how to change their colors, fonts, add images, etc. I currently do not charge for this service because I am getting my referral fee from Squarespace so with 15 students in a class, I am making plenty off of that. I will be charging $25 per person in the future though. I am offering this same experience for a Canadian actors organization starting this fall and we are thinking that will be a quarterly class of 25 attendees.

How often do your clients come back for additional support beyond their initial training session?

I would say that 75% of my clients come back for at least one additional session. 50% come back for 3-5 total and about 25% use me on a regular basis.

What tools do you rely on for your recurring revenue streams?

Zoom for one-on-one collaborative sessions, Vimeo to record short training videos for clients as well as the videos that I add to my Talk Nerdy to Me library, Acuity Scheduling so that clients can book sessions, and then obviously the tools that I actually design with — Squarespace, SquareKicker, Illustrator, Canva.

What advice would you give to someone who is thinking about offering client training as a form of income?

The best thing that I ever did was to think about what topics need to be completely individualized and which ones can apply more broadly, and then adjust my offerings accordingly. For instance, a design and fine-tuning audit is very specific to that one client so they should have a one-on-one custom session. But, walking through the Groundwork SEO Checklist or Email Campaigns or a basic Social Media Marketing plan can be generalized to fit multiple industries, brands, etc. So, I can scale my business by turning those into a pre-recorded video series and also “Bring a Buddy” sessions. 

If a client is interested in learning about SEO and Voice Search Optimization, they can pay $350 for a 90 minute session on their own or if they find a friend to tag along, I will do it for $250 each - they both save $100 and I earn $150 more for doing the same amount of work. If they do a small group session of 5, it’s just $150 per person and now I am making $750 instead of $350.

And, most importantly, don’t forget that a lot of clients get overwhelmed easily. Finding ways to let them go at their own pace can be a total game changer. When I was offering more of a package option - a series of 5 sessions for example - I always let the clients schedule their own training sessions at their own pace. Some clients would do all 5 sessions in a week and others took a couple of months.

“Most importantly, don’t forget that a lot of clients get overwhelmed easily. Finding ways to let them go at their own pace can be a total game changer. ”

Connect with Jen:

Website: jenmaher.expert
Instagram: @jenmaher_squarespaceexpert
YouTube Channel: Jen Maher
Squarespace Templates: store.squarekicker.com/creators/jen-maher-consulting

Want to build websites that feel elevated, intentional, and client-ready? Explore the SquareKicker Template Store and browse Jen’s expertly designed Squarespace templates—crafted to help you deliver standout work with less effort.