My Professional Journey

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How I Got Here

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Divine Intervention

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Serendipity

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My Professional Journey ♥ How I Got Here ♥ Divine Intervention ♥ Serendipity ♥

Two women, smiling and hugging each other, in black and white photograph.

Me & My Sister getting ready to head out for the evening. In this era, I was positively reinforcing children by day… and surviving mosh pits by night… haha

Circa 1995

Child Development, Restaurants & Marketing… Oh My!

  • Around this time, I was in Kansas City working my way toward a Child Development Degree. and supplementing my income as a nanny. I was also a corporate trainer for a couple of restaurant groups - PB&J and Houston’s Restaurants.

    Before I knew it, I was a Catering and Marketing Manager for a lovely restaurant called Morton’s of Chicago and then I became a Marketing Manager for the The Westin Crown Center Hotel.

    I love to think back at this period of my life because I think the unique combination of fine tuning my positive reinforcement skills and people skills - plus, becoming obsessed with all things marketing have served me well throughout the years in this industry.

Group of 16 people in a bar or restaurant, some sitting on a bench, others standing behind, smiling at the camera. A yellow heart with the name 'Mel' and an arrow pointing to a woman seated in front, middle, wearing a gray top.

Me and my co-workers (basically like my own version of the “Friends” TV show) at Champions Run Golf & Country Club where I was the Membership Director.

Early 2000s

a move to omaha brings 3 pretty rapid career changes (including starting my first business) and a chance to build my first site!

  • I moved to Omaha to be the Marketing Manager for a local restaurant but was soon brought on as the Membership Director for Champions. This is where I met (and “grew up” with) some of my very best friends and also met my husband, Maurie!

    I was a Manager at the Club for almost three years but there was a real need for a nanny placement agency in our area so in 2004, I took out an SBA loan, leased a space and launched NannySource!

    At NannySource, I offered weekly training classes to my nannies (I had over 400!!!) and also did my own marketing. To my surprise, I was able to build my own website on the Network Solutions platform rather than hiring a Graphic Designer.

    I had so much fun doing it, that I turned it into a hobby and built sites for my friends and family over the next few years.

    This period of my life is professionally significant because I got first hand experience as a small business owner. This has really helped me know the excitement, challenges and successes that face the entrepreneurs that I work with now as a Squarespace Exoert!

Five women wearing headbands and casual clothes standing together in a hallway, smiling at the camera.

Me and my fellow “Specials” (PE, Library, Art, Music & Technology) Teachers on a retro sports dress up day at St. Patrick’s Catholic School in Elkhorn, NE.

2005-2017

Teaching, Technology, Training & Speaking

  • 18 months after opening NannySource, my daughter was officially starting school and I got offered a teaching position at her K-8th grade Catholic School.

    I couldn’t pass up the opportunity to work in the same building with her so I became the K-8th grade Computer & Technology Teacher. Another part of my position was to provide technology help and training to the teachers and staff in our building.

    Before I knew it, I was providing training to teachers and staff throughout the Omaha Archdiocese. I helped them navigate standard technology skills and programs but more importantly helped them find ways to incorporate technology into their classrooms.

    I became a Learning.com trainer (national educational software) and also a Mimio Certified Trainer (an international smart board technology company). These two certifications got me started with larger group training sessions and ultimately led to speaking engagements at workshops and conferences such at NETA.

    The 12 years that I spent at St. Patrick’s Catholic School fueled my love for technology and my passion for sharing the knowledge that I gained with others.

Collage of three black and white photos showing people using smartphones and working at desks, with text promoting social media marketing consulting.

Early Canva Days!
Before I started building websites on Squarespace, I offered Social Media Marketing Management and created content through Canva which was like the “bees knees” to me!

2017

Starting a Second Business & Discovering Squarespace

  • With our daughter getting closer to “leaving the nest”, my husband and I started thinking more about our future and made plans to build a second home in the Baja California Sur, MX.

    I knew that I would need a more flexible career to ensure the best work/life balance if we took this step so I went back to my entrepreneurial roots and started thinking of small business/freelance opportunities.

    My initial plan was to launch a business called T3 (T Cubed for Technology Training for Teachers) where I could continue my current teacher training but do it on my own schedule. I was a little nervous to just jump right in so I took a part time office position working for a Graphic Designer friend of mine at Trezenbold.

    I learned SOOOO much from my friend, Jeff - about running a business, graphic design and WordPress (which I hated, hahaha).

    I saw that most of our website clients needed Social Media Marketing help and there weren’t a lot of options locally.

    So, I took my past marketing knowledge and experience and coupled it with online Social Media classes and scrapped the T3 idea.

    Instead, I launched Jen Maher Consulting and began offering Social Media Marketing services and Content Creation.

    This was an absolutely PERFECT fit for my plans and I was loving it… EXCEPT so many of my clients had awful websites and I found myself building more and more websites on WordPress and other platforms that I loathed.

    One day, a client recommended Squarespace to me and I was intrigued. To be honest, I flipping hated it (if you ever worked with version 7.0, you understand that it was clunky to say the least). But, it bothered me that I couldn’t “figure it out” so I spent a weekend truly diving in. It finally clicked and I truly understood the platform and became a HUGE cheerleader. It was a truly powerful platform that was super easy to build on and maintain once you had the knowledge and skills.

A young girl appears excited or surprised, standing next to a table with a laptop and a sign, in front of a large screen displaying a webpage or presentation.

Getting ready for an In-Person Squarespace Workshop. As a Squarespace Authorized Trainer, I have always loved doing small group workshops helping users learn everything they need to know to build their first site.

2018

Getting Accepted into the Squarespace Authorized Training Program

  • I was so obsessed with Squarespace that I was literally just pounding the pavement offering to make websites for just about anyone. I think I built something like 50 in my first year!

    I really missed my days of teaching and training though so you can imagine how happy I was when I noticed that Squarespace offered an Authorized Training Program!

    I applied in the fall of 2018 and was SOOOO excited when I got the email that I had been chosen to participate in the program.

    I completed the training program, was given my official badge by Squarespace and they listed me on their website as one of their Authorized Trainers.

    As an Authorized Trainer, I preferred to do small group classes (which I did in the conference room at a local co-working space). In these classes, I walked the attendees through all of the first steps of building their first Squarespace site and gave them the knowledge they needed to complete the content upload on their own.

    I also did something called a Lunch and Launch which was basically the same thing but it was a one-on-one session so we could complete it in just two hours.

    These two “products” became the groundwork for my “Jen for a Day - aka Let’s Build a Template Together” packages.

Two women sitting on barstools at a kitchen counter, smiling at the camera with laptops in front of them. Behind them is a modern kitchen with hexagonal tiles on the wall, a range hood, and pendant lighting.

Shortly after I got my Expert Badge - working alongside Abby at my (then) office in Waterloo, NE. As my business grew, I handed off Social Media to Abby - who would also become the first “Nerd” in Nerdville, my Squarespace Designer Training Program.

2019

Getting My Squarespace Expert Badge and Training Other Experts

  • Squarespace announced their Squarespace Expert program and the Squarespace Marketplace and I got asked by Squarespace to be one of the first round of Designers to be brought into the program! (which pairs Designers and Users).

    Somehow or another, I slayed the program algorithm (which is run through 99 Designs) and I quickly found success.

    I was brought on by Squarespace to perform online training sessions for other Experts to help them navigate the Marketplace/99 Designs and find success too! I was lucky enough to be able to provide these Zoom training sessions to Squarespace Experts that were brought into the program in both the first and second rounds of acceptance and I got to build my Squarespace Community (SO many new nerdy friends!).

    My success with the program meant that it was time to restructure my business. I gave the Social Media Marketing side of my business to a friend, Abby, and she began learning more about Squarespace as we worked alongside one another at my office. This would be the birth of Nerdville by Jen Maher.

Office interior with glass walls displaying service categories, including office, branding, training, and design, with chairs, tables, and plants visible inside.

Nerdville technically started in 2019 when I brought Abby into the office but I went full force and launched the full squarespace designer training program in 2020. The picture above is my favorite of many Nerdville locations. In the early years, I was lucky enough to office out of a really cool building - a former middle school turned office/co-working space - so, I got to move the office around a lot as the team evolved.

2020

Launching Nerdville by Jen Maher

  • Becoming an Expert provided me with an opportunity to grow and scale my business. I knew that I needed to outsource elements of my business and bring new people on.

    I brainstormed and evaluated all of my options and ultimately decided to bring on inexperienced designers that had that perfect left brain/right brain balance and train them on my own.

    This became Nerdville - a Designer training program in Nebraska where I worked one-on-one with Squarespace website designers and helped them launch and grow their own Squarespace website design businesses.

    They helped me with projects through the Squarespace Hire an Expert program and were able to learn and fine tune their skills alongside me.

    I had 9 designers go through the full training program and several dozen others reach out for individual specific training through Zoom.

    The program was in full force through 2023 but has began to morph in 2024. Dreyah, Emma and I (and a few others from time to time) still continue to work alongside one another and collaborate on projects (sharing new knowledge, ideas and offering one another support).

    But, it is just Emma and I working projects through my own Squarespace Expert profile.

    Emma still builds custom websites and also offers Zoom Coaching & Help Sessions while I focus more on working one-on-one with DIY clients and providing small group classes known as my Rabbit Hole Sessions.

    Nerdville is no longer an actual training facility but instead has sort of morphed into a Community of Squarespace Gurus. You can meet a few of my favorites through my Instagram account and the Pour Me a Nerdy Martini episodes.

    But, keep an eye out because I feel like there might be some really exciting things being born through Nerdville in 2024!

A woman with short, blonde hair and a denim jacket holding a microphone, smiling, and giving a thumbs-up gesture.

Squarespace has trusted me to provide training to other Experts and Circle Members, and in 2021, they asked Becca Harpain (Inside the Square) and I to provide Onboarding Training to their own internal staff.

2021

Becoming a Squarespace Employee Educator

  • The Squarespace Learning Team provides onboarding training to all new Squarespace staff. The purpose is to familiarize their employees with the platform regardless of their position. So, whether you are in the Accounting Department, a Developer, Support Rep or any other position, you will have a foundational knowledge of the product that you are working for. ( I absolutely love that they do this, BTW).

    In 2021, the team reached out to myself and Becca from Inside the Square and asked if we would be interested in taking this program over for them so that their employees not only learned about the platform - they also got an industry level perspective,

    Becca and I excitedly created a 90 minute training course called “Getting Started with Squarespace” that walks the attendees though the basic steps of building and designing their first Squarespace website.

    Since 2021, Becca and I have alternated who teaches the Live Onboarding Sessions through Zoom.

    I literally get teary eyed every time I complete a session because I just love having the opportunity to do these sessions and get to know the people behind the scenes that make it possible for us to do what we do. ♥

Four women participating in a panel discussion on stage, holding microphones, with an audience in front; one woman speaking into a microphone.

Squarespace hosted the first Circle Day - a worldwide conference for Squarespace Circle Members in August of 2022. Jen and the Nerds were chosen to take the stage as the first Circle Day speakers ever.
Such a Ridiculously HUGE honor!

2022/3

Taking the Speaker Stage at Circle DaY

  • Squarespace hosted their first Circle Day at their Headquarters in NYC in August of 2022 and I was selected to be a speaker! I dragged my Nerdville Team - Emma, Noah and Dreyah - to NYC and we were the first to take the stage.

    We hosted a panel discussion on the various ways to grow and scale your Squarespace Design business since these guys had been alongside me on my own journey and had all started their own businesses as well.

    The event was truly life changing and we were BEYOND thrilled to attend the 2023 Circle Day too!

    In 2023, we co-hosted a Rooftop Happy Hour with our buddies from Squarekicker on Tuesday and got to know some really amazing new friends.

    The following day, we were invited to a private sit down with Anthony Casalena (founder & CEO of Squarespace) for a quick chat before attending a learning day where we dove deep into Squarespace Courses.

    The following day was the official Circle Day where we got to hang out with a couple hundred nerdy Squarespace folks in person and a couple thousand more online. It was a fantastic opportunity to learn, be inspired, feel supported and be surrounded by like minded humans.

2024

♥ Squarespace & Squarekicker go together like PB&J ♥

Announcing the Squarekicker Template Shop - where you can purchase a “leveled up” Squarespace template and have a KICK BUTT new website
JUST. LIKE. THAT.

and guess what? I’m a …

SquareKicker logo with black and lime green design, featuring the text 'sk' inside a lime green square and 'SquareKicker template creator' written beside it.
LEARN MORE

  • I closed out the year by being a guest on Squarespace Circle Live - a monthly, online talk show hosted by Squarespace for their Circle community, a program for web designers and developers. The show features interviews with Circle members, Squarespace product experts, and other industry experts, sharing insights, tips, and strategies for using Squarespace effectively.

    WATCH THE EPISODE HERE

2025

Becoming an Instructor for Squarespace’s “How to Become a Website Designer” Course!

  • OH MY GOSH YOU GUYS!

    2025 started off with a BANG! I got to fly to NYC and record a lesson titled “Designing a Luxury Client Site” for Squarespace’s How to Become a We Designer course!!! The course is free and features some amazing instructors so check it out by clicking HERE.

    emma and I returned to Squarespace Headquarters in September for Circle Day 2025 where I was chose to lead a small group discussion.

    check out all of my circle day highlights by clicking HERE!

  • Jen as an Instructor for Squarespace's "How to Be a Web Designer" Course

    Jen was chose to be an instructor for this free course offered by Squarespace.

    In her lesson, Jen demonstrates how to build a website for a luxury brand retreat client.

    View the Course Here

  • The Squarespace Entrepreneur Podcast

    Hosted by Omari Harebin from SQSP Themes. Our podcast episode featured a discussion on how to grow and scale your business, dealing with imposter syndrome and how i am adjusting my business model to fit my adhd - turning my adhd into my superpower as Omari puts it :)

  • Squarespace's "Ask the Expert Series"

    Jen was chosen as one of four designers to be featured on Squarespace’s YouTube channel to discuss how amazing the Squarespace Marketplace (AKA- Hire an Expert program) has been.

  • The Business Connection TV Show on KPAO Channel 22

    Jen was interviewed by BC Clark on The Business Connection TV Show - a program that offers resources, advice and support for small businesses in Nebraska and Iowa.

  • News Feature - Women's coworking space offers community for women who work from home

    News Story about small business owners, students, remote professionals flock to Trouvaille, a female co-working space

  • Digital Marketing Days Guest Speaker

    Teaching others everything I know about Voice Search Optimization and how to use it to get ahead of your competition.

  • Speaker - Nebraska Educational Technology Association

    For three years, Jen took the stage and offered advice and training on how to integrate technology into the classroom.

  • Small Business Development Podcast with Sarj

    Jen has been a guest on Sarah Boyce’s podcast a couple of times now talking about everything from imposter syndrome to websites and everything in between.

  • Now or Never Podcast by Tim Rexius

    Jen and Kath Derrison talked with Tim about how and why they founded the Fempreneur Fair and how important it is for small business owners to support one another.

  • Squarespace Designer Summit

    A community summit created to share design processes, top tips & inspiration on how to become a better designer, scale or pivot your web design business.

    This Summit is an independent initiative organized by Elizabeth Ellery for the benefit of Squarespace designers and enthusiasts.

  • Speaker - Squarespace Circle Day 2022

    Jen and the Nerdville team took the Main Stage at Squarespace’s inaugural Circle Day Event in NYC. We hosted a panel discussion on how to grow and scale your Squarespace design business.

  • GUEST - SQUARESPACE CIRCLE LIVE

    Squarespace Circle Live is a monthly, member-exclusive talk show hosted by Squarespace. It features interviews with Circle members, Squarespace product managers, and experts, providing valuable insights and community engagement.

  • Squarespace Circle Professional Learning Blog

    Jen's small group classes and one-on-one training sessions are one of ten learning opportunities listed on the Squarespace Circle's Professional Learning Blog - where learners can "Learn at your own pace with webinars and online workshops created by Circle members." - pros.squarespace.com/professional-learning