Head of Sales

Head of Sales

About Portless

Portless is redefining global eCommerce fulfillment by enabling brands to ship directly from China to the U.S. and other markets faster than local 3PLs, at lower costs, and with full branding control. Our innovative logistics model eliminates the need for U.S. warehouses, allowing brands to increase margins, reduce inventory risks, and accelerate delivery speeds.

We work with some of the fastest-growing eCommerce brands and are backed by leading investors who believe in our mission to revolutionize international fulfillment. As we scale, we’re looking for a Head of Sales to drive customer acquisition, build and lead a high-performance sales team, and directly impact revenue growth.

Role Overview

This is a hands-on role, perfect for someone who enjoys closing deals, optimizing sales execution, and leading a growing team.

You’ll be responsible for building pipeline, driving revenue, and refining our outbound and inbound strategies—all while working closely with marketing, operations, and customer success to ensure seamless onboarding and retention.

Key Responsibilities

Own & Execute Sales Strategy

• Develop and implement a structured sales process to drive customer acquisition and revenue growth.
• Define clear KPIs, quotas, and performance metrics to track and improve team success.
• Own the sales pipeline, ensuring accurate forecasting and proactive deal management.
• Experiment with outbound prospecting strategies to expand our reach within the eCommerce ecosystem.

Pipeline & Deal Execution

• Take a hands-on approach to closing deals—you’ll be actively selling while scaling the team.
• Build and refine sales scripts, objection-handling strategies, and pricing frameworks.
• Work closely with potential customers to understand their fulfillment challenges and position Portless as the best solution.
• Develop relationships with founders, operators, and supply chain leaders at fast-scaling eCommerce brands.

Team Leadership & Coaching

• Hire, train, and manage a growing team of Account Executives and SDRs overseeing Mid-Market.
• Provide ongoing coaching, deal support, and process optimization to improve performance.
• Establish a high-accountability sales culture focused on pipeline generation and closing deals.
• Act as a player-coach, leading by example in outbound outreach and deal execution.

Cross-Functional Collaboration

• Partner with marketing to align demand generation efforts with sales outreach.
• Work with operations and customer success to ensure a smooth onboarding process for new clients.
• Provide market insights and customer feedback to improve messaging, positioning, and product offerings.

What We're Looking For

Experience & Skills

• 7+ years in B2B sales, with 3+ years in a leadership role managing quota-carrying teams.
• Proven track record of closing deals and scaling revenue in a fast-paced environment.
• Experience selling into eCommerce brands, supply chain, or logistics is highly preferred.
• Strong understanding of B2B sales processes, including outbound prospecting, consultative selling, and deal negotiation.
• Hands-on leader who can both strategize and execute—this is not just a management role.
• Excellent communicator with a hunter mentality and a drive to win.
• Experience with CRM tools (HubSpot, Salesforce, or similar) and sales automation platforms.

Mindset & Approach

• Ownership mentality – you take full responsibility for sales results.
• Data-driven and metrics-focused, with a clear approach to analyzing and improving performance.
• Comfortable working in fast-changing environments where playbooks are still being built.
• Passionate about developing talent and creating a winning sales culture.

• Private Health Insurance
• Paid Time Off
• Work From Home
• Training & Development