B2B Sales and Account Manager

We have a premium headwear brand based in New York City. We make unbranded, better-fitting caps in three real sizes and sell them direct to consumers and to businesses that want custom embroidered caps for their teams, events, and merch. More than 500 companies have ordered from us, including Google, Shopify, The Ritz-Carlton, and Stanford University.

Our wholesale side is growing fast. We now handle around 125 wholesale and custom orders every month, and we need someone whose full-time job is making sure those customers feel looked after and come back.

The role

This is a customer relationship role with two halves.

1. Wholesale customer success

• Reach out to every new wholesale customer after their order ships to make sure it arrived and they are happy with it
• Check in with existing accounts on a regular schedule (30, 60, 90 days and beyond) to see how the caps are being used, whether they need a reorder, and whether anything went wrong that we should fix
• Keep our CRM accurate and up to date for every wholesale account, including contact details, order history, notes from each conversation, and next follow-up dates
• Spot reorder opportunities (events coming up, new hires, seasonal needs) and bring them to the team
• Flag any issue, complaint, or at-risk account to the founders right away
• Work closely with the Lift Down team to learn our communication style and upsell tactics, and build a deep understanding of who our clients are and what they need

2. Instagram B2B outreach: Many businesses follow our Instagram after seeing one of our B2B ads. They are interested but not ready to order yet, or they mean to come back to our custom cap configurator and forget. Your job is to catch them before they go cold.

• Monitor new followers, likes, comments, saves, and DMs every day and identify which ones are business accounts, brands, agencies, or companies
• Assess whether an account is a legitimate business worth pursuing (real website, real team, real activity) versus a fake, spam, or irrelevant account
• Reach out to qualified accounts by DM or email , introduce Lift Down, and offer a blank sample cap so they can feel the quality
• Point them to our self-serve custom cap configurator and help them get started
• Log every lead in the CRM with a status and a follow-up date, and follow up on schedule until they order or clearly decline
• Report weekly on how many accounts you reached out to, how many replied, how many requested samples, and how many placed an order

What we are looking for

• At least 2 to 3 years of experience in customer success, account management, or B2B sales, ideally for an ecommerce or product brand
• Sales experience is important. A big part of this role is turning interested followers into customers and existing customers into repeat customers, so you need to be comfortable asking for the order
• Excellent written English. You will be writing to US business owners, marketing managers, and procurement teams every day, and your messages need to read as clear, warm, and professional
• Able to write without relying on AI. Our customers should never feel like they are talking to a bot, so you need to be able to write messages in your own voice and style, without running everything through ChatGPT first. AI tools are welcome for working through complex problems or tightening up a sentence now and then, but your English has to be strong enough to stand on its own
• Hands-on experience keeping a CRM organized (any CRM is fine as long as you are disciplined about it)
• Comfortable doing outreach on Instagram and by email , and comfortable with polite persistence
• Good judgment about people. You can tell the difference between a real company and a time-waster, and you know when to push and when to back off
• Organized and self-directed. You will own your own follow-up calendar and nobody will chase you on it
• A real understanding of how different kinds of businesses work and buy. A 10-person startup, a marketing agency ordering for a client, a hotel, a university, and a Fortune 500 procurement team all have different needs, timelines, and decision makers, and you should be able to adjust how you talk to each one
• Comfortable dealing with large companies. Some of our customers are S&P 500 companies, and you need to be able to hold a professional conversation with them without being intimidated or overly casual
• Familiarity with Shopify is a plus
• Full alignment with the US Eastern schedule. You need to be online and available from at least 8am to 4pm Eastern Time, Monday through Friday

Who you are

• Communication is the most important trait for this role. You write clearly, you listen well, and people enjoy hearing from you
• You understand how business relationships actually work. Trust is built over time, not in one message, and a customer who feels remembered is a customer who reorders
• Adaptable and a quick learner. We are a fast-growing company and things change often. You pick up new tools and processes quickly and you are not thrown off when priorities shift
• Comfortable with ambiguity. You will not always have a script, and you are fine figuring things out and asking good questions

What you get

• A long-term, full-time role with a small team where your work is visible and directly affects the business
• Direct access to the founders. No layers of management
• A clear playbook for the customer journey, plus the freedom to improve it

How to apply

We would rather read a few strong applications than a hundred generic ones, so please do the following.

(1) Put the words CLASSIC CAP at the start of your application subject line so we know you read this far.

Then, in your application, answer this question in a few sentences. Do not send a template or a copied cover letter.

(1) Tell us about a time you re-engaged a customer or client who had gone quiet. What did you say and what happened?

Applications that skip these steps will not be reviewed.