Creative Product Designer
Find the moment before anyone else, prove it will sell, and turn it into a design that ships on time — plus the bench, the Shopify uploads, and the ad builds behind every drop.
19 tasks · 3 videos · 20-question quiz · pass at 90%
Moments: Research & the Pitch Gate
4The job starts before the design does. Find what the internet is already paying attention to, prove someone is already selling it, then pitch it — before you open Photoshop.
1The Morning Research RoutineRun the same sweep every morning: multi-model AI, Google Trends at 48 hours, then the competitor shelf.
- Run the trend prompt from the AI Prompt Library across multiple models — Grok, ChatGPT, Claude, Gemini. Each surfaces things the others miss; don't rely on one.
- Google Trends, sorted to the last 48 hours. Scan for anything with an Italian spin available.
- Check the competitor shelf — the "new" section on Barstool Sports, RotoWear, GoodShirts, ThreadHeads, Baseball Lifestyle 101, Baseballism, Grunt Style, Combat Iron, Tipsy Elves, Harebrained, Soda Sports, Eurooutfit.
- Italian-American pages — Paisano Prints, Dolce Society and similar: sort by best-selling. If it works on their site it will likely work on ours. Inspiration only, never a direct copy — the Italian-American community is small and direct copies get noticed and resented.
- What each source is for: Barstool/RotoWear/GoodShirts/BL101 = viral moments. Tipsy Elves = holiday. Baseballism/BL101 = clean sports looks to spin Italian. Grunt Style/Combat Iron = American-pride energy to convert into Italian-American pride.
- Funny outsells celebratory. Clean and celebratory works when the win is genuinely big.
Video coming soon
Moments — Research, Proof of Concept & the Pitch Gate
Links you'll need
2Proof of Concept — the Rule That Matters MostAn AI idea is a lead, not inspiration. Go find the #1 seller on that topic and build near it.
- AI giving you "Jack Caglione t-shirt" is an idea, not the inspiration. The next step is mandatory: search that term on Google, Etsy, Amazon, and TeePublic and find the single best-selling shirt on that topic anywhere on the internet. That is the inspiration.
- The logic: Barstool will not put up something that doesn't sell. Neither will the other established moment brands. If it's selling somewhere else, it will likely sell here.
- For Shirt Club and Italian phrase designs: go to Etsy or Amazon, sort by best-selling, and find which phrase people actually buy — right now, or evergreen.
- Always fill in the Will-It-Sell research-validation line on the Product Sheet. A design does not move toward ads without it. That line is the gate.
- Cite your source when you submit — it's noticed and valued.
Links you'll need
3Pitch Before You Design — ALL IN / TEST IT / PASSNo design work starts on a moment until the CEO has called it.
- Pitch the moment to the CEO first, with three things: what it is, when it hits, why it will work. No mockups yet.
- Three possible calls: ALL IN — build it, the Head of Product approves the art. TEST IT — the Social Media Operations Specialist posts it to social first; if it pops (the stated bar: ~5k likes), make the shirt. PASS — drop it, move on.
- The filter applied: is it actually circulating in the news right now? Spider-Man isn't Italian, but it was making millions at the box office and everyone was talking about it — spin it Italian and it sells. A good idea nobody is talking about is a PASS.
- The moment does not have to be Italian. The Knicks aren't Italian; the Knicks drop did roughly $93K in June 2026. Giving a huge cultural moment our Italian-American voice is the play. A small Italian moment nobody cares about is not.
- The "smack you in the face" test: if the concept isn't obvious within two seconds, it isn't ready. Same for the ad image — readable at thumbnail size, no guessing. If you're internally debating whether it works, that's the signal it won't.
- Check the sourcing and dates calendar before pitching around a date. Use Google Calendar as the live view, not the email notifications — the emails go stale.
4Tributes, Timing and TrademarksFunny is fine. Same-day is not. And never put a real person's face on a product without clearing it.
- Tribute rule: funny is acceptable, but it must be tasteful and it needs a little time. A shirt up two hours after someone dies reads as cashing in — on Vincent Pastore, the call was to wait a few days and frame it as tribute.
- Late is dead. If the design won't be out before the moment peaks, skip it. The Kentucky Derby tees released the day of the race and the Italy World Cup exit tee both missed.
- No trademarked league names, logos or official tournament branding. Keep it cultural, not licensed — FIFA is the standing example.
- No news-wire or photographer images in branded creative — a standing rule created by two simultaneous copyright claims in 2026.
- Be very careful with real people's likenesses — we got into trouble using Dean Martin's face.
- Check trademark exposure before pitching anything built on a brand, league or IP.
Design Standards & Submission
4Everything goes on the Product Sheet. The Head of Product approves. Numbered options when you're unsure, revisions turned around fast.
1The Product Sheet WorkflowOne sheet, every concept, research line filled, then the Head of Product's call.
- Every concept goes on the Product Sheet — keep everything in one place, don't spin up new sheets.
- You can list ideas as text before mocking them up — the concept gets approved first, which saves building something that gets denied.
- Multiple directions for the same shirt: submit as numbered options. Don't pick for them — let the Head of Product or the CEO choose.
- Volume is fine. Submit as many as you want, knowing only a portion get approved. Do not hold a batch back because the queue looks long.
- Approved and utilized is the only status that triggers additional compensation — "utilized" means HCI actually uses it for production, publication, sale, marketing, advertising or another official initiative.
- Mark approved items in the sheet yourself once you get the green check.
Links you'll need
2Design Specs — Blanks, Placement, Price TiersLightweight is the default. Comfort Colors is reserved. Shirt Club is front-only, always.
- Default blank: lightweight (Gildan soft-style / Bella Canvas 3001) unless told otherwise.
- Comfort Colors 1717 is reserved for big cultural moments and celebratory drops — heavier blank, roughly $13/unit vs $9.
- Shirt Club: front print only, never a back. A back print adds ~$5/unit and Club sells at $20. Three colors is the target, four is borderline, five is the absolute maximum.
- Shirt Club designs must be broad, not region-specific — the subscriber base is a mix of every Italian background.
- Price tiers on the site: lightweight front-only ~$32; heavyweight front-only ~$35; heavyweight front+back ~$38; celebratory/high-demand front-only $38.
- Limit a moment drop to 2–5 designs — three to four is the sweet spot. Test versions, kill losers fast, ride the winner.
- Files: 300 DPI, transparent PNG, 2–5 colors, no clipart. Include "Hardcore Italians" on the shirt.
- Ask before you prompt if you're unsure about Italian wording or spelling (Madone vs Madonne vs Maddone — the CEO made the call).
Video coming soon
Design Standards, Blanks & Mockups
3The Revision LoopFeedback comes fast and specific. Turn it fast and say when it's ready.
- The Head of Product leaves feedback directly on the sheet and in #design-product, often with inspo images attached.
- Common notes to pre-empt: too much detail in a face; duplicates of last year's design; quality/resolution needs tuning; a color reads better in a different shade; a design sits crooked.
- Post in the channel when revisions are done and the sheet is ready for review again. Don't leave it silent.
- Cohesion matters: when a set is meant to be one drop, keep a single design language across all of it (the slang tees — Mannaggia, Statazit, Fanabla, Maddone, Minchia — all black tees, white text, Italian flag beneath, matching the Gabagool tee).
- Concepts that don't make the drop get moved to the bench, not deleted.
4MockupsOur format, our blanks, back-first when the back is the story.
- Use S&S Activewear product imagery (ssactivewear.com) as the reference for blank colors and fit.
- When the back is the focal point, the back mockup shows first.
- Comfort Colors: leave the inside tag on mockups. All other brands: remove it — in Photoshop use the AI "remove, match to background" so it blends.
- Colors: Comfort Colors has no "Natural" — the equivalent is Ivory. Check the actual blank's color list before naming a color.
- Stay on the established Pinterest photo format. Talk to the CEO before changing anything about the format.
- Enlarge crewneck/hoodie designs to match tee proportions — undersized art on crewnecks was a repeat note.
Video coming soon
Shirt Club Design Rules
The Bench
2This is the company's #1 standing priority for this role. Every theme on the calendar carries a bench behind it so a weak drop gets a next-man-up instead of a lost month.
1What the Bench IsEvery planned drop: 5 launch designs plus 10–20 finished designs sitting ready. Art only.1 video
- Think of a drop as a starting lineup. The launch designs start; the bench subs in. If the drop underperforms, the swap happens that same week. If it wins, the bench becomes next year's plan.
- Every theme on the calendar gets a planned drop of 5 plus a bench of 10–20 finished designs.
- Art only — no mockups, no uploads until a bench design gets called up.
- The bench is not a dumping ground for rejects. Every bench design has to be a top-tier concept in its own right.
- Build it from what's proven: last year's best sellers for that drop plus AI research on the theme. Halloween's winning pattern was Italian wordplay — Franken-Stunad, Bada Boo, Boo-schetta, Grim Mercada. Iterate on what worked.
- Make secondary versions of promising concepts when you can't tell which will win.
- Bench designs can also sub into Shirt Club when a month's design underperforms.
- The Shirt Club bench stays stocked at all times, organized by month. Keep 2+ months of Club designs banked; below that gets flagged.
- Origin: last year's Halloween drop underperformed and the month was written off. The bench exists so that doesn't happen again — the Halloween folder with 14 benched designs is the model.
▶ Watch: The Bench — Backup Designs Per Drop
2Reading the Calendar for Bench WorkBold entries are planned drops. Every one needs its bench built ahead of time.
- Watch the marketing calendar — bold entries are planned drops. Each one needs a bench before it lands.
- Themes carrying benches as of August 2026: fall/hoodie collection, Vaffanculo Cancer, Italian Heritage Month, Christmas Wave 1, 12 Days of Christmas, the Humor/Slang Tee Drop, and Shirt Club (rolling, by month).
- In slow moment periods, bench work and the Product Drop Tracker are the priority — that's the standing instruction for when nothing big is circulating.
- Backup designs do not get mocked up or uploaded to the site unless they're called up.
Shopify & Printful Uploads
3Wrong descriptions become the Ops Coordinator's customer service emails. Get the fields right the first time.
1Listing StandardThe description has to match the actual blank. Every time.
- Description must match the blank. Lightweight says lightweight, heavyweight says heavyweight, Comfort Colors says Comfort Colors. Copy from the templates — don't freehand it.
- Embroidered items must say embroidered. When this is wrong, the Ops Coordinator eats the customer service emails.
- Tag every t-shirt #YGroup_tshirts so the Yotpo reviews link correctly. Wrong tags pull jewelry reviews onto t-shirt pages.
- When duplicating a listing, re-read every copied field. Duplicated text carrying over from the source product is the most common error.
- Upload as Draft unless told otherwise. The Head of Product or the CEO sets things live.
- AI-written descriptions get reviewed before they save — they've produced junk that had to be deleted.
Video coming soon
Product Templates & Shopify Upload Standards
2Printful BuildVariants, print areas, and what the platform physically can't do.
- Multiple colors go under one product box — select additional variants when uploading. Split a variant out only when the artwork itself differs (white boot on every hoodie color except beige, which takes the black boot; beige gets its own product, recombined later).
- Design files for existing products live in Printful under the original product — pull from there rather than rebuilding.
- Know the print areas. Sleeve prints are constrained by Printful's fixed sleeve print area; a design that doesn't fit won't work. Say so and propose the alternative — a back placement often solves it.
- Embroidery placement carries its own spec — e.g. the Italia boot at 1.5" × 1.6", small chest placement.
- Confirm the design reads 300 DPI after upload.
Video coming soon
Printful Variants & Print Areas
3Ongoing Listing CleanupA standing background task whenever there's slack in the queue.
- Run through all products and confirm description matches blank, embroidery is stated, and Yotpo tags are correct.
- Log corrections as you go so the same product isn't audited twice.
- This is explicitly a fill-the-gaps task for slow periods — alongside bench work and the tracker.
Facebook Ads
3Everything gets built and left OFF — the CEO reviews and sets live. Accuracy over speed: a live ad linked to the New York shirt with Philadelphia copy on it is pure wasted spend, and it's the reason this section exists.
1Build by DuplicationNever build an ad set from scratch. Duplicate one that already works.2 videos
- Everything lives in the Sales campaign.
- Duplicate an existing ad set — that's how the $30/day minimum, the customer exclusions and the Triple Whale URL parameters carry over. Building from scratch loses all of it.
- One ad set per design. Four shirts = four individual ad sets, not one ad set with four shirts in it.
- Naming convention: Shirt Name | Image or Video | creative description | v1 — append "AI" if it's an AI creative.
- Ad Studio generates the ad designs, works on mobile, and carries all product colors. It's in beta — report anything broken to the CEO rather than working around it.
▶ Watch: Facebook Ads — Full Walkthrough
▶ Watch: Ads Overview (older, for general gist)
Links you'll need
2The Settings ChecklistFacebook re-enables things behind you. Check every one, every time.
- Link to the product URL, not the collection URL. Collection links break the moment a product leaves that collection.
- Turn OFF: site links, products, summaries, the left-side carousel, and product browsing. Facebook silently re-enables these and pushes unrelated products — verify on every single ad.
- Confirm the Triple Whale URL parameter is at the bottom of every ad before publishing. This is what keeps attribution honest between Facebook and Google.
- Ad copy comes from the Marketing tab of the AI Prompt Library. Feed it the product name, the image and the moment context. Always generate 5 options — more context in, better copy out. Short, punchy, impulse-buy tone.
- Leave every ad toggled OFF. The CEO reviews and sets live, or tells you to.
- The CEO can't see drafts. To get something reviewed: toggle the ad off on the left, then publish — that makes it visible while staying inactive.
Links you'll need
3AI CreativesHand-pick every generation. Publish a clean version first.
- Publish the plain, non-AI version first, then duplicate it and add AI creatives. The AI toggle wipes the ad text — the clean duplicate is your insurance.
- Hand-pick every AI generation. Skip anything with missing arms, warped hands, wrong props or obvious AI slop — customers comment on it publicly.
- If the AI function is behaving and text survives, you don't need the separate AI/non-AI duplicate — check current behavior before duplicating.
Tracking, Reporting & Communication
31The Product Drop TrackerLog every drop so picks get smarter instead of staying guesses.
- Log every new drop: launch date, units sold, category.
- Wait a couple of weeks before recording numbers — a launch-day figure tells you nothing. Update after a few weeks or monthly.
- Pull figures from Shopify's 90-day product sales view.
- Category tagging is the point: it's how we see whether sports, viral memes, holidays or humor actually drive revenue, and double down on the pattern.
- After every drop and every moment, log what sold and why. This is the data that sets drop strategy.
- Loading the sheet with all new products and sales data is a named high priority for slow periods — it's what lets AI surface good picks daily without guessing.
Video coming soon
EOD Reporting & the Product Drop Tracker
2The EOD ReportEvery working day in #design-product. Four sections, no exceptions.
- Moments Reviewed & Opportunities Submitted — what you looked at and what you put up.
- High-Priority Opportunities — anything decaying that needs a call today. Say "nothing urgent" if that's true.
- Questions / Blockers — raise them here rather than sitting on them.
- Next Focus — what tomorrow looks like.
- The report is the record of the 15-concepts-per-week KPI. Keep it accurate.
3Slack, Approvals and the Weekly ReviewFast, visible, proactive. Raise problems early.
- Slack is the primary channel. Design work in #design-product so the Head of Product and the CEO both see it.
- Green check or thumbs-up from the CEO = approved, go. On moments he moves fast in Slack rather than waiting on the sheet.
- The Head of Product approves art. The CEO gut-checks moments and does one batch review a month.
- Raise blockers, delays and questions proactively and early — anticipated misses get communicated as early as reasonably possible.
- Design Feedback & Review — weekly Thursday 11:00–11:30 CT on Zoom. Come with the sheet ready for review.
- Use Google Calendar as the live view — calendar emails go stale.
Checks for success
Before anything ships, run through this list.
- Did the moment get pitched — what, when, why — before any design work started?
- Does every concept on the Product Sheet have its Will-It-Sell research line filled in?
- Did you find the actual best-selling shirt on that topic, not just take the AI's idea?
- Is every theme on the calendar carrying 5 launch designs plus a bench of 10–20?
- Is the Shirt Club bench stocked at least 2 months deep, organized by month?
- Does every listing description match the actual blank — and is every t-shirt tagged #YGroup_tshirts?
- Is each ad in its own ad set, duplicated from an existing one, linked to the product URL?
- Are site links, products, summaries, carousel and product browsing all off — checked this time, not last time?
- Is the Triple Whale parameter on every ad, and is every ad left toggled off for review?
- Is the Product Drop Tracker current, and did the EOD report go up with all four sections?
Ready to check your understanding?
20 questions on everything above. You need 90% to pass — screenshot your result and send it to your manager.
Take the quiz