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Head of NA Sales - CastleGate Forwarding

CastleGate Forwarding (CGF) is a rapidly growing freight forwarding start-up within Wayfair, moving containers across the globe. We offer a full suite of shipping services (Asia consolidation, ocean freight, drayage, customs brokerage, cargo protect, etc.) that aims to provide Wayfair suppliers with predictable, reliable, and competitive Freight Forwarding solutions.

As part of CGF, you will play a key role in defining and executing Sales strategies across North America. You will collaborate with business unit leaders across the International Supply Chain and drive strategic decisions within and beyond your region. As you pursue strong relationships with Wayfair suppliers, success will be demonstrated by increasing supplier satisfaction and growing the volume shipped by CastleGate Forwarding. This is a highly visible and exciting leadership role and one that will offer the right candidate an opportunity to be part of a fast growing environment within the e-commerce industry.

What You'll Do 

  • Define targets and performance manage a large team to meet CGF’s volume and profitability goals in North America for each of our business lines.
  • Deliver on cross functional initiatives to maintain high supplier satisfaction across Wayfair’s supplier portfolio (ex NPS Targets)
  • Build team capabilities to allow for effective acquisition and supplier management of Wayfair suppliers (CGF customers) of all sizes and business models. 
  • Drive initiatives that improve volume, profitability, & supplier satisfaction. 
  • Hire and manage a team of Sales Managers and Associates, including launching and overseeing a Lead Generation Team
  • Support the professional growth of the team within CGF and overall Wayfair operations
  • Partner closely with other supplier-facing teams (e.g. Commercial, Inventory Management, Fulfillment) to share insights and feedback and drive increased volume
  • Identify and drive opportunities for service enhancements to further strengthen our value proposition through our Voice of the Customer Program
  • Optimize Sales Efficiencies in our CRM (Salesforce) and through inbound lead sourcing & pipeline management. 
  • Travel between 25%-50% of the time to Tradeshows, Supplier sites, and Industry Conferences

What You'll Need 

  • 5+ years of sales experience/business development in the ocean/freight forwarding or International Supply Chain industry
  • 5+ years of experience as a sales leader and/or at a premier operations consulting firm strongly preferred
  • Proven track record of building and scaling high performing sales teams managing multiple levels of experience and owning both strategy and organizational OKRs/KPIs
  • Honed leadership and project management skills, with the ability to lead cross-functional discussions and to effectively scope and deliver projects under tight deadlines using influence vs. a direct reporting approach, including across geographically dispersed teams.
  • Experience building capabilities and creating a Sales infrastructure through optimized  processes, enhanced tooling, and effective upskilling
  • Proven expertise using Google Suite & Salesforce to work with data and communicate ideas
  • Demonstrated proficiency in both written and verbal communication in the English language

About Wayfair Inc.

Wayfair is one of the world’s largest online destinations for the home. Whether you work in our global headquarters in Boston, or in our warehouses or offices throughout the world, we’re reinventing the way people shop for their homes. Through our commitment to industry-leading technology and creative problem-solving, we are confident that Wayfair will be home to the most rewarding work of your career. If you’re looking for rapid growth, constant learning, and dynamic challenges, then you’ll find that amazing career opportunities are knocking.

No matter who you are, Wayfair is a place you can call home. We’re a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success. We value and rely on the collective voices of our employees, customers, community, and suppliers to help guide us as we build a better Wayfair – and world – for all. Every voice, every perspective matters. That’s why we’re proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, genetic information, or any other legally protected characteristic.

Your personal data is processed in accordance with our Candidate Privacy Notice (https://www.wayfair.com/careers/privacy). If you have any questions or wish to exercise your rights under applicable privacy and data protection laws, please contact us at dataprotectionofficer@wayfair.com.

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Average salary estimate

$135000 / YEARLY (est.)
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$120000K
$150000K

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What You Should Know About Head of NA Sales - CastleGate Forwarding, Wayfair

As the Head of NA Sales at CastleGate Forwarding (CGF), based in the vibrant city of Boston, Massachusetts, you’ll find yourself at the forefront of an innovative freight-forwarding start-up that’s part of Wayfair. Your journey here will entail crafting and executing impactful sales strategies tailored for the North American market. Picture yourself collaborating with diverse business leaders, building powerful relationships with Wayfair suppliers, and ensuring their utmost satisfaction. In this integral role, you're not just leading a team; you're fostering a culture that prioritizes growth, innovation, and excellence across all business lines. You'll manage a talented team of Sales Managers and Associates, guiding them to amplify our services, optimize performance metrics, and drive profitability. From defining team targets to enhancing supplier management initiatives, your leadership will be vital in navigating this competitive industry. You’ll even get to hit the road, traveling approximately 25%-50% to engage with suppliers and industry peers at various events. With a solid background of over 5 years in sales or business development within the ocean or freight forwarding domain, you’re prepared to leverage your expertise and drive CGF’s success. If you are ready to take on a challenge in a fast-growing e-commerce environment while enjoying a fulfilling work culture, CastleGate Forwarding is where you belong.

Frequently Asked Questions (FAQs) for Head of NA Sales - CastleGate Forwarding Role at Wayfair
What are the primary responsibilities of the Head of NA Sales at CastleGate Forwarding?

The Head of NA Sales at CastleGate Forwarding is responsible for defining sales targets, managing a diverse team, and executing strategies to increase supplier satisfaction and profitability across North America. This includes collaborating with various departments to enhance supplier management, optimizing sales processes, and representing CGF at industry events.

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What qualifications are needed for the Head of NA Sales position at CastleGate Forwarding?

Ideal candidates for the Head of NA Sales position at CastleGate Forwarding should have a minimum of 5 years of sales experience in the ocean or freight forwarding industry, alongside proven leadership capabilities. Experience with strategic sales development and managing high-performing teams is crucial, as well as familiarity with tools such as Google Suite and Salesforce.

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How does CastleGate Forwarding support the professional growth of its Head of NA Sales?

CastleGate Forwarding fosters an environment conducive to professional growth through mentorship, skills development, and opportunities for team leadership. The Head of NA Sales will be tasked with supporting the growth of their team, ensuring that each member develops the requisite skills to excel in their roles within CGF and the broader Wayfair organization.

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What are the key performance indicators for the Head of NA Sales at CastleGate Forwarding?

The Head of NA Sales will be evaluated based on their ability to meet sales volume and profitability targets, enhance supplier satisfaction scores (NPS Targets), and effectively build and manage a high-performing sales team that can deliver superior results for CGF.

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What travel requirements are expected for the Head of NA Sales position at CastleGate Forwarding?

The role of Head of NA Sales at CastleGate Forwarding involves travel commitments of approximately 25%-50%. This travel is essential for attending tradeshows, meeting suppliers, and participating in industry conferences, enabling the leader to build relationships and drive strategic initiatives.

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Common Interview Questions for Head of NA Sales - CastleGate Forwarding
How do you approach building and managing a sales team in the freight forwarding industry?

Discuss your experience with recruitment, training, and fostering a collaborative culture within your sales team. Highlight specific strategies you've employed that resulted in improved performance and employee satisfaction.

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Can you share a successful sales strategy you implemented in your previous roles?

Provide an example of a sales strategy that had measurable results. Explain the planning process, execution, and how you measured success, especially focusing on specific metrics related to supplier engagement or revenue growth.

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What methods do you use to maintain supplier satisfaction?

Talk about your approach to communication, setting expectations, and follow-ups with suppliers. Share specific instances where you turned supplier feedback into actionable steps that enhanced their experience.

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Describe a time when you had to manage a cross-functional team project.

Elaborate on your leadership role in a cross-functional initiative. Describe how you navigated challenges, aligned diverse teams, and achieved the project objectives while maintaining stakeholder buy-in.

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How do you leverage technology like Salesforce to drive sales performance?

Discuss your proficiency with Salesforce, emphasizing tools you use for data analysis, reporting, and pipeline management. Mention how these insights led to strategic decisions that enhanced sales outcomes.

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What is your strategy for meeting challenging sales targets?

Options could include setting SMART goals, motivating your team, analyzing market trends, and adjusting your sales tactics in response to competitors or shifts in demand.

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How do you ensure alignment between sales and operational capabilities?

Describe your approach to collaborating with operational teams. Highlight methods you use to ensure sales strategies are matched by logistics capabilities, and how this alignment is crucial for customer satisfaction.

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How do you handle underperformance in your sales team?

Explain your process for identifying underperformance early, addressing it constructively through one-on-one discussions, offering additional training, and setting follow-up plans to support improvement.

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What role does market analysis play in your sales leadership?

Discuss how you conduct market analysis to identify opportunities for growth. Include examples of how you’ve made strategic pivots based on market trends and competitor analysis.

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How would you describe your leadership style?

Share your leadership philosophy, focusing on how it fosters team growth and engagement. Provide examples of how your leadership style has contributed to previous successes in sales team performance.

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April 2, 2025

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