Senior Account Executive, Mid-Market & Enterprise (US) Remote (US Only) | | Sales

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Senior Account Executive, Mid-Market & Enterprise (US)

Employement type Full-time Experience Level Senior Location Type Remote (US Only) Department Sales Compensation $130,000-$180,000 Overview Application

Read this first.

We're hiring a closer. You'll sell to brands doing $20M to $500M+ a year, and half of them already have a cross-border provider. Your job is to take them.That means replacing an incumbent, getting Finance, Ops, and e-commerce to agree, and running a 60–120 day cycle without a sales engineer attached at the hip. If that sounds like a great Tuesday, keep reading. If it sounds exhausting, this isn't your job, and that's fine.

To be specific, don't apply if you:

• Have mostly worked inbound. Most of your pipeline here, you'll build yourself.
• Need a polished deck, an SDR team, and a deal desk before you'll run a deal.
• Talk about "trusted advisor" more than you talk about closed-won.
• Can't explain why your last three lost deals were lost.
• Want a big-company sales org with a territory plan handed to you on day one.

About Openborder

OpenBorder makes selling across borders as easy as selling at home. We handle the hard parts for e-commerce brands: landed-cost checkout, duties and tax, DDP shipping, local payments through our own entities, VAT filings, and compliance. Our founders built brands to a $100M run-rate with more than half of revenue outside the US, so we built what they wished they'd had.
Today 200+ merchants run on OpenBorder. The pitch writes its own business case. Tariff changes and the end of de minimus have made 2026 the year every brand rethinks cross-border. Incumbents who own the market charge sky-high fees.

The role

You'll own a quota and a book of mid-market and enterprise D2C brands in the US. You'll be judged on new ARR realized. Activity metrics are for you to manage, not for us to count.

What you'll actually do

• Build your own pipeline. Outbound to Heads of e-commerce, CFOs, and COOs at brands with real international revenue. Work the partner leads our 3PL, returns, and shipping partners send you.
• Sell the business case. Build the savings model with the brand's own numbers: payments, duties, shipping, conversion. Make the CFO the champion.
• Take out incumbents. Most brands you call already use someone. Know the alternatives cold, and know where they're weak.
• Run complex deals. Multi-threaded, with Finance, Ops, e-commerce, and IT, through security, legal, and procurement, to signature.
• Forecast like it's your money. Commit numbers you hit. Keep the CRM clean enough that leadership never has to ask.
• Shape the playbook. You're early. What works for you becomes how the next ten AEs sell.

Your first 90 days

• A pipeline (self-sourced plus marketing inbound) of at least 3x your quarterly quota.
• Your first deal closed, or in contract.
• A point of view, in writing, on which brand profiles win fastest and why.

You’ll love it here if you…” / “You’ll hate it here if you…

Get a rush from stealing a customer from an incumbent Prefer greenfield deals where nobody pushes back Can build a CFO-grade savings model in a spreadsheet, live, on the call Hand every number to a solutions engineer Want uncapped commission and a quota you can actually hit Want a high base and a soft number Like being early enough that your playbook becomes the company's Need enablement, battlecards, and a sales ops team on day one Find duties, payments, and DDP shipping interesting, because that's where the money is Want to sell features without understanding the plumbing Hold yourself to your forecast Treat "commit" as a mood Want equity in a company betting that cross-border gets rebuilt in 2026 Want the safety of a 5,000-person SaaS company

Both columns describe good sellers. Only one of them fits this job.

What we need from you

Non-negotiable

• 5–10 years of closing B2B deals, with at least 3 years as a full-cycle AE selling to mid-market or enterprise buyers.
• A quota record you can prove: name the number, your attainment, and your rank on the team for each of the last three years.
• Deals of $100K+ ARR closed, with three or more stakeholders including Finance.
• You've self-sourced a majority of your pipeline in at least one role.
• You sell into ecommerce: ecommerce SaaS, payments, logistics, or the Shopify Plus ecosystem.
• You’re comfortable building and defending an ROI model with a CFO.

Gets our attention

• You've sold payments, merchant-of-record, cross-border, tax, or logistics software.
• You've replaced an incumbent provider at a $50M+ GMV brand.
• You were an early AE at a startup and helped write the playbook.
• You already know Heads of Ecommerce at brands we'd want to win.

Doesn't matter to us

• Where you went to school, or whether you did.
• Your title. "Senior" is about what you've closed, not what LinkedIn says.
• Whether you've managed people. This is an individual contributor role.

The details

Title Senior Account Executive, Mid-Market & Enterprise Reports to Head of Commercial Location Remote (U.S.). Travel for key deals, events, and team offsites Compensation $130,000–$180,000 base (depending on experience), plus uncapped commission and equity Start date When you're ready

You'll love it if you…Both columns describe good sellers. Only one of them fits this job.

• 7+ years of experience in operations management, business operations, or a related field.
• Proven experience leading teams and managing complex operational processes.
• Strong analytical, problem-solving, and decision-making skills.
• Experience with process optimization, performance metrics, and operational reporting.
• Excellent communication and stakeholder management skills.
• Ability to manage multiple priorities in a fast-paced, growing environment.
• Proficiency in operational tools, reporting systems, and workflow management platforms.

What to include in your application

Please share the following three things:

• Your CV or LinkedIn, plus your quota and attainment for each of the last three years.
• The best deal you've ever closed: the brand or company, the ARR, who you beat, and the moment it almost died.
• One D2C brand you'd target first at OpenBorder, and the opening line of your email to them.

If sharing your numbers feels uncomfortable, this probably isn't the role for you. If you've already got a brand in mind, we want to talk.

What you will bring

Our process is structured, fast (about three weeks), and the same for every candidate. Here's every step:

• Application review. We read every answer to the three things above.
• Take-home exercise (60–90 min). You'll build a savings model for a sample brand and write a short outbound email. You have 48 hours, and we'll never use your work.
• Screening call (30 min). We'll talk about your goals and strengths, and ask for the names of your last few managers. We will call them.
• Career walkthrough (60–90 min). We go through your career role by role: your quota, your attainment, your best and worst deals, and why you left. Bring your numbers.
• Mock sales call (90 min). You'll run a discovery and pitch call with our team playing a skeptical brand that already has a provider. Expect hard objections.
• Founder conversation (30–45 min). We'll talk about how you work, a deal you lost, and what you want to build. You can ask us anything.
• References. We'll speak with at least three former managers. We take this seriously. Make sure they'd say what you've told us.

If a structured process with real exercises sounds like a hassle, that tells you what working here is like. If it sounds fair, it is: everyone gets the same questions and the same scorecard.