Sr. Account Executive

Overview

Free trade as we know it is over, and the tools built for that era can’t keep up with the pace of change. U.S. tariff spend has grown roughly 10x in a decade – from about $30B a year to more than $300B. In fiscal year 2025, Customs and Border Protection collected a record $200B+ in duties, more than double the prior year, and 2026 is on pace to exceed it.

More than half a million companies move $5.5T across the U.S. border every year, yet fewer than 10% have in-house trade-compliance expertise – and the licensed-broker labor pool that exists to help them isn’t growing fast enough. An exploding cost-and-compliance burden is colliding with a constrained labor market. AI is the only way supply meets this new era of demand.

Caspian exists to close that gap. Our mission is to reduce the burden of trade and compliance so importers can focus on what they love: building and selling products. We’re building the AI trade advisor for the modern era.

What we’re building

Our journey began with duty drawback – a tax-recovery process that puts cash back into companies’ hands. It’s cumbersome and specialized, requiring an immaculate record of trade documents and deep expertise, which is why 70–80% of the estimated $10B in eligible refunds go unclaimed every year. As a result of our AI drawback service, Caspian built a data model and intuitive interface that lets customers view, analyze, and action their trade volume; we connect data sources across the supply chain into a centralized repository of their trade network, and use it to recover tariff spend compliantly and efficiently.

The hard part is the data: trade data is notoriously fragmented and messy – raw documents, Excel, CSVs, SFTP/EDI/API feeds. We pull it into one system and connect it together, and every action deepens our data graph. The same foundation powers each new trade compliance product we ship (your data model is your destiny). We’re a licensed customs organization – which lets us deliver both software and expert services – and we’re a seed-stage company with $11M raised, led by Primary Venture Partners. Roughly a year after launch, we have 80+ customers in production, from premium apparel brands to global industrial manufacturers, with revenue up 4x+ in the last six months and channel partnerships with recognizable industry players. These customers use Caspian as their outsourced trade compliance team supporting all of their global tariff needs.

About the Role

Reporting to the Head of Growth, we’re hiring an experienced Account Executive (open to a Sr. AE for the right profile) to join our growing sales team as a founding seller. You’ll own the entire deal cycle – generating pipeline, closing target customers, and expanding those relationships over time. This is a high-autonomy, high-creativity seat for someone who’s energized by building the sales motion at an early-stage company rather than inheriting a finished playbook. You’ll sell an AI-first product in a category that’s exploding, into a market that urgently needs what we’ve built.

What success looks like: in your first year you’ll ramp quickly to full productivity, self-source the majority of your pipeline through warm, network-based outreach, and help turn what works into a repeatable engine for the sellers who come after you.

What You’ll Do

• Sell into Caspian’s market of companies shipping physical goods – especially via warm leads, network-based outreach, and multi-step paths to decision-makers.
• Own our land-and-expand deal cycle end to end, from first conversation to close, with critical stakeholders at mid-market and enterprise importers.
• Run a consultative, value-led process: discovery, tailored demos of the platform, business cases, and clear ROI for supply-chain, trade-compliance, and finance buyers.
• Partner with GTM leaders – Head of Growth, VP of Trade Advisory, and the CEO/Founder – on closing and account growth.
• Use AI and automation to research accounts, personalize outreach, and multiply your own output – and bring what you learn back to the team.
• Represent Caspian in the field: industry events, small-group dinners, and conferences that warm up target buyers.
• Shape sales strategy, enablement, and the tooling stack (CRM, forecasting, lead-gen, pipeline management, outreach automation) as we scale.

About You

• 7–12+ years in B2B / technology sales (toward the higher end for the Sr. profile), with a track record of new-logo acquisition in fast-paced, early-stage environments.
• Demonstrated ability to build your own pipeline and drive complex deals to close.
• Skilled at prospecting and engaging customers to understand operational challenges and translate them into business impact.
• Comfortable selling to mid-level through executive personas – VP/Director Supply Chain, Director Trade Compliance, Director Logistics, CFO/VP Finance.
• An elite communicator who can distill complex ideas and build trust quickly.
• AI-native and resourceful – you reach for the AI-powered workflow that 10x’s your output before anyone asks.
• Genuinely excited to build the sales machine at an early-stage company.

We’re Also Looking For (‘Nice to Have’)

• Supply chain, freight forwarding, logistics, or trade-compliance experience – a licensed customs broker (LCB) or deep customs/drawback knowledge is a strong differentiator (not required).
• Experience selling a technical or data-heavy product, or selling into operations and finance buyers.
• A founding-seller or early-stage background where you built pipeline and process from scratch.
• An existing network among importers and trade-compliance, supply-chain, or finance leaders.
• Fluency building AI-powered sales workflows.

Location

Remote (U.S.-based), with monthly travel to meet customers and prospects, attend industry events, and spend focused time with the team at our San Francisco office. 

Compensation

On-target earnings of $250K–$350K depending on level and experience, on a standard 50/50 plan – half base salary, half variable earned against an assigned sales quota – plus the opportunity to receive meaningful early-stage equity in Caspian.