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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
What You Should Know About Head of Sales, Portless

Are you a sales visionary looking to take the reins of a dynamic and innovative company? Join Portless as the Head of Sales and become a key player in our mission to redefine global eCommerce fulfillment! At Portless, we're changing the game by allowing brands to ship directly from China to the U.S. and beyond, all while reducing costs and increasing delivery speeds. In this hands-on role, you'll not only lead a high-performance sales team but also directly engage in closing deals and driving significant revenue growth. You’ll develop our sales strategy, optimize execution, and create lasting relationships with fast-scaling eCommerce brands. Collaborating closely with marketing, operations, and customer success teams, you'll ensure a seamless onboarding process while refining our sales approach. If you have over 7 years of B2B sales experience and a proven track record of success in leadership roles, especially within eCommerce or logistics, we want to hear from you! This is your chance to lead by example, inspire your team, and cultivate a winning sales culture that thrives in a fast-paced environment. At Portless, your efforts will have a direct impact on our trajectory and success in the industry.

Frequently Asked Questions (FAQs) for Head of Sales Role at Portless
What are the primary responsibilities of the Head of Sales at Portless?

As the Head of Sales at Portless, you'll be tasked with developing and executing a structured sales strategy aimed at customer acquisition and revenue growth. You'll define KPIs and performance metrics, manage the sales pipeline, and play a key role in closing deals while leading a talented sales team.

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What qualifications are required for the Head of Sales position at Portless?

To qualify for the Head of Sales role at Portless, candidates should possess over 7 years of B2B sales experience, with at least 3 years in a leadership role. Experience in eCommerce, logistics, or supply chain is highly preferred, along with a hands-on approach and strong communication skills.

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How does the Head of Sales at Portless collaborate with other teams?

The Head of Sales at Portless works closely with marketing, operations, and customer success teams to align sales strategies with marketing outreach, ensure smooth onboarding for new clients, and leverage market insights to enhance product offerings.

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What skills are essential for succeeding as the Head of Sales at Portless?

Essential skills for succeeding as Head of Sales at Portless include a deep understanding of B2B sales processes, strong negotiation abilities, an ownership mentality, and a data-driven approach to performance improvement. Experience with CRM tools is also crucial.

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What benefits can the Head of Sales expect at Portless?

The Head of Sales at Portless will enjoy a competitive package that includes private health insurance, paid time off, flexible work-from-home options, and opportunities for training and professional development.

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Common Interview Questions for Head of Sales
Can you describe your experience in leading a sales team?

To answer this question effectively, share specific examples of your leadership style, the size and structure of the teams you managed, and notable successes achieved under your guidance.

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What strategies do you use for developing sales pipelines?

Discuss your approach to segmenting your target market, leveraging CRM tools, and employing outbound and inbound techniques to build a robust sales pipeline effectively.

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How do you handle objections from potential clients?

Provide detailed strategies for addressing objections, such as actively listening to customer concerns, empathizing with their situation, and responding with evidence-based solutions that align with their needs.

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What metrics do you focus on to measure sales team success?

Mention key metrics such as conversion rates, average deal size, sales cycle length, and customer acquisition cost to demonstrate your data-driven approach to evaluating sales performance.

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How do you integrate feedback from the sales team into the sales strategy?

Illustrate how you create open channels of communication for the sales team to share insights and feedback, and how you use this information to iteratively improve your sales strategies.

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What is your approach to training new sales team members?

Discuss the importance of structured onboarding processes, mentorship, hands-on coaching, and continual development initiatives to ensure success for new hires.

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How do you prioritize competing sales initiatives?

Explain your method for evaluating the potential ROI of various sales initiatives and how you align them with overall company goals to prioritize effectively.

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What experience do you have with sales automation tools?

Share specific examples of sales automation platforms you have used, how you implemented them, and the impact they had on your team's efficiency and performance.

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How do you foster a high-accountability sales culture?

Talk about the techniques you use to promote accountability, such as setting measurable goals, regular performance reviews, and recognizing achievements within the team.

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Can you provide an example of a successful sales campaign you led?

Offer a detailed narrative of a specific campaign, including your objectives, strategies employed, challenges faced, and the measurable success achieved, showcasing your skills in driving results.

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Full-time, remote
DATE POSTED
March 23, 2025

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