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IL Squarespace Web Designer (remote)

Bitter Jester Foundation for the Arts, NFP
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We are a small 501(c)(3) public charity - an Arts nonprofit based in Chicagoland - that has a functional but tired website with a not-great UI or UX. Our main program (and the bulk of the website) is a seasonal 20 year-old Music Festival that features young, up-and-coming bands from around the country before they break out. We also produce “The Comic Thread” sketch comedy troupe and “The Purple Shirts” performance ensemble.

We're looking for two part-time students who will be available roughly 20 hours per week (give or take) beginning on Aug. 1st and concluding their work by Sept. 1st. They will work together (not necessarily at the same time, but as a team overall). We have a set budget and can pay hourly for work. It is important to note that this is a youth-employment-grant-funded opportunity with specific grant requirements; as such. we can only accept applicants as follows:

ESSENTIAL SKILLS: Candidates MUST be:

  • Living in or currently enrolled in a college or University in Illinois;
  • Upperclassmen (i.e. not younger than 19 and not older than 22);
  • Very familiar with Squarespace design and UI;
  • Experienced in migrating a Squarespace 7.0 website to Squarespace 7.1;
  • Someone with a User-Experience Design Background;
  • Someone who knows how to think about Information Architecture;
  • Extremely familiar with improving organic SEO;
  • Able to work on a team, take direction, and REGULARLY COMMUNICATE;
  • Someone with an excellent work ethic and good with tight deadlines;
  • A very detail-oriented person very good with executing repetitive tasks flawlessly;
  • Able to complete their work by Labor Day, 2025;
  • Able to submit the requested materials (listed below) and not a generic response.

ADDITIONAL SKILLS: The ideal candidate will also be:

  • A creative thinker;
  • A good writer;
  • Experienced with Graphic Design;
  • Experienced with Marketing;
  • Experienced with building online stores (we have a few things we would like to make available in a store, but that aspect is less important to the main tasks below).

THE JOB: We have two primary tasks:

THE FIRST TASK is to redesign and refresh the look and feel of the current website. We need a modern, photo/graphic focused, user-friendly site and we must improve the overall UI and UX. We need to create Marketing Funnels that make complex information concise and understandable with trackable conversions. Basically, we're looking to overhaul the entire look and feel of the site to be more modern, more user-friendly, and yield better end results with dedicated pipelines of info and conversions. – NOTE: We do not necessarily need a complete redesign of every single page in this phase of the work. Depending on workload and timing, you might just be getting things started for us and doing “big picture” UI and flow. We do need to get our main landing pages (plural) redesigned and published AND, at a minimum, you will templates for other pages/page types that our team can later implement / continue your work. So… to recap: this will be a general “vibe and design layout” job with multiple page TEMPLATES being built in SS 7.1 That is the initial goal. Then, if time and budget permit, implementing those design templates and creating / transferring the content from our old site would be ideal, but that's not a requirement for this job.

THE SECOND TASK is closely linked to the first. It's to migrate our current Squarespace 7.0 site into their updated 7.1 ecosystem. This is a large undertaking in and of itself as our site currently has 250+ pages and Squarespace's auto-migration feature from 7.0 to 7.1 caps sites at 100 pages. This potentially means that well over 100 pages will need to be rebuilt from scratch WHILE maintaining / improving our existing organic SEO. - NOTE: As with the first task, getting the first 100 pages transferred and making sure our existing SEO and other info is maintained is a must. Then, adapting those pages to meet the new design would be the second step. Beyond that, manually copying the remaining 100+ pages would be great (and you might be able to get started on that), but that may also get pushed off to another job at a another time. We can hammer out those details and agree upon an efficient way to minimize / streamline this work once we select our candidates.

THE PROCESS: Our currently thinking is that one hire will primarily be responsible for the new design (including IA, and creating new pages) while the other hire will be primarily responsible for migrating the existing pages (100 automatically + rebuilding X-number of additional pages). Note: Rebuilding of pages / re-working migrated pages will ideally be in accordance with the new design (again, open for discussion). That said, both hires will collaborate on design concepts and both should be able to assist the other, especially curing crunch time.

We have identified THREE PRIMARY User Personas and their Goals (i.e. multiple Funnels):

  1. Prospective Musicians (i.e. “Join the Festival!”)
    • Young performers looking to perform/compete at the Bitter Jester Music Fest via our online application
    • Young performers looking to network with other musicians
    • Young performers looking to discover new music themselves (and, ideally, buy our vinyls or listen online)
  2. Prospective Concertgoers (i.e. “Attend the Festival!”
    • People living in Chicagoland interested in attending our concerts
    • People who will be traveling to Chicagoland in the summer interested in attending our concerts
    • People from anywhere in the world interested in discovering new music (i.e. purchasing our vinyls or listening online)
  3. Prospective Sponsors/Donors (i.e. “Support or Nonprofit”)
    • Corporate Sponsors
    • Individual Donors
    • Volunteers

We have identified TWO SECONDARY User Personas and their Goals (i.e. multiple Funnels):

  1. Prospective Mobile Stage Renters (i.e. “Need to Rent a Mobile Stage?”
    • Orgs / Cities / Park Districts looking to rent a mobile stage
  2. Those Looking to Book Live Entertainment (i.e. "Need Live Entertainment?")
    • People who wish to hire solo musicians or bands for events
    • People who wish to hire The Purple Shirts for private parties

WHAT TO SUBMIT: We need to see: 

  1. A Cover Letter - please explain why you're interested in this position, how you know you will accomplish the tasks above, and why you think you're the best fit. If you have a desire to work for nonprofits in the future or music festivals, specifically, please share those desires or past experiences.
  2. A Portfolio - please include either some images (screengrabs) or, ideally, links to various websites you've designed (Squarespace 7.1 much preferred but not required) or played a major role in re-designing/re-building along with some notes to us about what you are most proud of for each and any problems you faced and how you solved them.

ADDITIONAL THINGS TO SUBMIT: not required, but feel free to also include:

  1. Your Resume (if not web design related, don't waste your time updating and submitting)
  2. A Letter of Recommendation (again, if not web design related, don't worry about this and don't spend a lot of time to collect a new one as we are on a tight deadline)

FINAL EXPECTATIONS: We are looking to make a decision on these hires within the next two weeks (i.e. by 8/1 ideally). If you have a qualified friend with whom you've partnered, please encourage them to apply as well (and make sure you mention each other in your cover letters!). –– We need motivated self-starters on this project who are comfortable with phone calls, zoom meetings, and REGULAR COMMUNICATION AND WORK UPDATES. Ghosting will not be tolerated and lack of progress will result in termination (again, we are on a tight deadline). –– You can expect very detailed notes and feedback from our team and should plan on having at least one (probably 2-3) check-in meetings each week. –– As stated, we have a fixed budget for this project so you will be expected to keep a very detailed and accurate log of your hours and what you accomplished for each work session. We will discuss those specifics with our final candidates. –– In order to qualify, candidates MUST be 22 years old or younger and either living in or attending a college or university in Illinois (sorry, no exceptions). –– All work must be completed by Labor Day, 2026. THAT SAID: because of our limited budget and the tight timing, we are anticipating that this may need to be a multi-phase project where not all work gets completed. As such, when we hire you, we will (as a team) clearly identify realistic goals and timelines so that, by Sept 1, 2025, BJFA has a functional updated website even if it is not the fully-realized “Version 2.0" that it will ultimately become.  –– Bitter Jester (as you might imagine from the name) is a fun group of people and we like to think we're fun to work with! This project will likely get stressful at times but we value open communication and are always willing to work around unforeseen circumstances and personal conflicts, within reason. Any questions, just include those in your cover letter (or reach out to us prior to applying) and we'll get back to you asap! Thank you and good luck!!