Customer Experience Specialist — Afternoons, Evenings + Saturday (Remote)

Read this entire posting before applying. If any of it makes you flinch, close the tab. You'll be doing both of us a favor. The short version We're hiring a Customer Experience Specialist to own the back half of the day at a growing DTC menswear brand — quiet luxury at accessible prices. You'll work 3pm–10pm ET Monday through Friday, plus a short 1–2 hour block on Saturday evening to clear the inbox before Sunday. Remote, open to anyone in the Americas, Oceania, or Europe who can hold the shift. $16–24/hr to start. You'd be the second person on a two-person customer experience team. A colleague owns mornings, 9am–3pm ET. From 3pm on, the inbox is yours. You report directly to the founder. This is an hourly contract role. It is not a salaried position today, and I'm not going to pretend otherwise. It's structured so that it can become one — see Compensation below for exactly what that means and what it doesn't. Most people who apply to this job aren't going to get it. Not because we care where you went to school or how many years you've done CS. We don't. We care about three things: instinct, judgment, and writing ability. You either have them or you don't. Why this is a good role You report directly to the founder. No middle manager. No skip-level. No layers. If you have an idea, you pitch it Monday and we try it Tuesday. From 3pm, the inbox is yours. Not a queue someone else is triaging. Not a shift where you escalate anything hard. Every email that lands in your window, every judgment call inside it — that's you. The back half of the day is where the hard stuff lives. Afternoon and evening is when the day's shipping problems surface, when West Coast customers are still at their desks, and when Australia and the UK start waking up. You're not covering a quiet stretch. You're covering the part of the day that decides whether a customer stays a customer. You're not typing refund templates. See the section below on how the AI works — it matters enough that it gets its own heading. The customers are worth caring about. Our average order is $100–300. These are grown men who paid real money for something they're excited about. When you write them a great email, they write back to say thanks. That's rare in this business. Where it goes is up to you. I'm not going to dangle a title. What I'll say honestly: this is a small team that will get bigger, and the person who consistently does more than the shift requires is the person who ends up running things. That might mean training the next hire. It might mean owning our CS philosophy outright. It might mean something neither of us has thought of yet. I'm looking for someone who treats the job as bigger than the hours, and I'll notice if you do. How the AI actually works here Be clear on this before you apply, because it's most of the job. We use Claude to draft customer emails in our brand voice. For a large share of the inbox, the first draft is already sitting there when you open the thread. Your job is not to write from scratch. Your job is to be the judgment the AI doesn't have. That means: reading the full thread and the order history and knowing what the draft got wrong. Catching that the customer already emailed twice and is angrier than the draft assumes. Knowing when the policy answer is correct but the human answer is to just refund it. Rewriting the two sentences that sound like a machine wrote them. Deciding this one shouldn't be sent at all and needs to come to me instead. Two ways to fail at this. The first is treating the draft as finished and hitting send — that's how a brand ends up sounding like every other DTC store. The second is ignoring the draft and slowly retyping everything by hand, which means you'll never keep up with the volume. The people who are great at this are fast, ruthless editors with strong instincts about people. If the AI part sounds like a downgrade from "real" CS work to you, this isn't your job. If it sounds like leverage, keep reading. Why you probably can't do this job Being honest with you: The writing bar is punishing. You're writing on behalf of a premium brand to customers in the US, UK, Canada, Australia, and Europe. If what you send reads like a support ticket or an unedited AI export, you won't last a week. Every email needs to sound like a real, warm, thoughtful human wrote it — because one did. There's no cushion. We're small. There's no brand equity yet. One badly handled email can cost us a customer for life, or a one-star review that sits on our storefront for years. Every interaction matters. If that pressure makes you sloppy or anxious, this isn't for you. The founder is demanding and blunt. Feedback is fast, honest, and unfiltered. If you need cushioning, you'll hate it here. If you thrive on it, you'll grow faster than in any job you've had. There is no script. Half the situations you'll handle don't fit a category. You'll be making judgment calls with no rulebook. If you need a manager to tell you what to do, you're going to freeze. Nobody is online with you. You have a teammate, but they're done at 3pm. During your shift it's you and the inbox. No queue to hide in, no one to tap for a second opinion in the moment. Some people thrive in that. Most don't. The hours are the hours. 3pm–10pm ET Monday through Friday, plus Saturday evening. Depending on where you live, that's your evening, your early morning, or your overnight. Work out what it actually means in your timezone before you apply. If you're going to resent it in month three, don't start. Don't apply if... You've only done CS at a big company with macros, playbooks, and a supervisor to escalate to. Your writing is "good." We need exceptional. If you're not sure which you are, you're the former. You're applying because you need a job, not because this specific job speaks to you. You need salaried employment, benefits, or PTO to make this work financially. Saturday evening is untouchable for you. You won't do a paid trial. You can't be reliably online 3pm–10pm ET, Monday through Friday, whatever that translates to where you live. You can't write English at a native or near-native level. This is the one hard requirement. What the week actually looks like Monday to Friday, 3pm–10pm ET. You start by picking up the handoff from the morning shift — anything still open, anything escalated to you. Then you own the inbox until close. Every customer email that lands in your window gets a real reply within 3 hours, no exceptions. We see 150–200 emails a day across both shifts. Some take 30 seconds. Some take 5 minutes. Inside your window, you handle all of them. For each one: read the full thread, check the order in Shopify, decide the right approach, work the AI draft into something worth sending, send it. Saturday evening, 1–2 hours. A focused pass to clear whatever came in over the weekend so nothing sits unanswered until Monday. Most Saturdays this is genuinely quick. Occasionally something real lands and you handle it. You pick the window that works for you as long as it's Saturday evening ET. You also: Escalate the hard ones to the founder with a one-line reason why. Notice patterns and flag them ("three people this week complained about X"). Leave a short end-of-shift note on anything still open, so the morning shift picks up clean. Refine our CS philosophy doc as new situations come up. That's the job. No phones. No live chat. No social. Just email, done at a level almost nobody else in DTC is doing it. Compensation $16–22 USD/hr to start, depending on experience and how fast you prove out. Up to $28/hr once you're running your shift without me in it. Roughly 36 hours a week — 35 across the weekdays plus the Saturday block. On salary: I'd rather under-promise here. This is hourly contract work now. As the business grows, I expect to move core team members onto salaried arrangements, and I'd want the person in this seat to be one of them. I'm not putting a date on that, because I'd be making it up. What I'll commit to is a compensation conversation at 90 days and every six months after, and complete honesty about where the business actually is. If you need a salary today, this isn't the job. If you want to be early in something and be paid properly as it grows, it might be. Timezone and location: you can be anywhere in the Americas, Oceania, or Europe. Be honest with yourself about what 3pm–10pm ET means locally — it's a normal workday in Australia and New Zealand, an afternoon-into-evening in the Americas, and a genuine overnight shift in most of Europe. I'll happily take a European applicant who's clear-eyed about that. I won't take one who discovers it in week three. The screening Two scenarios below. Answer both in 4–6 sentences each. We're looking at how you think, not how much you write. Overwriting is a red flag. Scenario 1. A customer bought a pair of our loafers 6 weeks ago for $180. She's emailed a dozen photos showing them clearly worn — creased leather, scuffed soles. She's now demanding a full refund because they "gave her husband blisters." She's cc'd her credit card company and threatened to file a chargeback and leave one-star reviews on Trustpilot, Google, and Instagram unless she gets refunded within 24 hours. How do you respond, and what do you actually say? Scenario 2. It's 9:15pm and a customer emails to say she ordered a pair of loafers as a Father's Day gift for her dad. The tracking shows delivered 4 days ago, but her dad says he never got them. It's a $150 order, no signature confirmation, delivered to a house in a nice neighborhood. She's polite in the email but you can tell she's upset — she mentions her dad had been going through a rough patch and this was meant to cheer him up. You have 45 minutes left in your shift. What do you do, and what's the email you send her? The final gate If your application is strong, we'll invite you to a 1-month paid trial. You'll handle real customer emails alongside the founder, get direct feedback, and prove out whether the instincts you showed on paper translate to real work. At the end of the month, we either move you onto the ongoing contract at your full rate or part ways cleanly. How to apply Send: Your answers to both scenarios above. One paragraph — no more — about the most relevant thing you've done. Not a resume dump. The one thing you're proudest of, and why. Any writing sample you're proud of. A CS email you wrote, a blog post, a Substack, a tweet thread — anything. We want to see your voice when nobody's grading you. Do not send a cover letter that starts with "I am writing to apply for..." It goes straight to the trash. We reply to promising applicants within 48 hours.