Job Description

The Head of Sales, Promotional Products leads Outdoor Cap’s promotional products sales business unit. This executive-level leader is responsible for establishing sales vision and strategy, cultivating senior-level customer relationships, and driving growth through distributors, wholesalers, and decorators across the promotional products industry. The Head of Sales is accountable for developing and leading a high-performing sales organization, setting ambitious revenue and profitability goals, and ensuring flawless execution in partnership with cross-functional teams. The ideal candidate is a proven leader in the promotional products space with a track record of scaling revenue, building strategic customer plans, and elevating organizational performance. 

Essential Duties & Responsibilities 

• Upholds Outdoor Cap's Mission-Vision-Values and Founder’s Pillars by acting with integrity; working together as a team; treating each other with respect.
• Own revenue growth and profitability targets for the Promotional Products business unit
• Develop and execute annual sales strategies with clear revenue, margin, and customer acquisition goals
• Recruit, lead, and develop a high-performing sales team, holding them accountable to results through coaching, metrics, and performance reviews
• Build and manage senior-level relationships with top distributors, buying groups, and national accounts to expand market share
• Negotiate contracts, pricing, and programs that strengthen Outdoor Cap’s competitive position and profitability
• Direct accurate forecasting, pipeline management, and reporting to ensure reliable sales and inventory planning
• Collaborate with the Product team to design and deliver assortments tailored to customer needs, market demand, and channel opportunities
• Partner with Sourcing, Marketing, and Operations to ensure programs are executed on time, on budget, and with flawless quality
• Lead execution of promotional industry trade shows, customer meetings, and key events to maximize impact and ROI
• Monitor competitive activity and market trends, adjusting sales strategies quickly to maintain a winning edge
• Collaborate with stakeholders to align sales goals with company-wide objectives and long-term growth initiatives
• Ensure customer programs are executed flawlessly, resolving issues quickly and reinforcing trust in Outdoor Cap as the most reliable headwear partner

Skills & Competencies 

• Leadership and People Development: Proven ability to recruit, coach, and scale high-performing sales teams. Creates accountability through clear expectations, measurable goals, and a performance-driven culture.
• Teamwork and Collaboration: Builds trust and respect across the organization by engaging in clear, timely, and detail-oriented communication. Effectively sets priorities and manages timelines to drive results through others. 
• Strategic Capacity: Builds and executes long-term vision while staying agile in the face of market shifts. Connects customer insights and industry trends to actionable growth strategies.
• Financial Acumen: Strong command of P&L, forecasting, and sales analytics. Skilled at balancing top-line growth with profitability and cost-to-serve.
• Customer Focus: Deep understanding of the promotional products industry and distribution model. Builds senior-level relationships that translate into long-term strategic partnerships and revenue growth.
• Negotiation and Influence: Effective at structuring contracts, pricing, and programs that create win-win outcomes for customers and Outdoor Cap.
• Cross-Functional Collaboration: Works seamlessly with Product, Sourcing, Marketing, and Operations to ensure customer needs are met with speed, quality, and innovation.
• Communication and Presence: Strong executive presence with the ability to influence at all levels. Skilled at presenting strategy, results, and opportunities with clarity and impact.
• Market Awareness: Maintains a sharp pulse on competition, industry trends, and customer needs, using insights to anticipate challenges and capture opportunities.

Education & Qualifications 

• Bachelor’s degree in business, Marketing, or related field required; results-driven experience in sales leadership will carry equal weight in evaluation
• 10+ years of progressive sales leadership experience, with at least 5 years in the promotional products industry
• Demonstrated success managing P&L responsibility and delivering sustained revenue growth
• Strong knowledge of distributor, wholesaler, and decorator networks within the promotional products channel
• Proven track record of negotiating contracts, pricing, and programs that improve profitability and customer outcomes
• Visionary mindset with ability to anticipate shifts in customer behavior, industry trends, and technology adoption
• Tech-minded leader with experience leveraging CRM, ERP, and digital platforms to modernize sales processes; openness to applying AI and emerging tools to increase efficiency, insight, and customer value
• Strong analytical skills, with ability to leverage data for forecasting, performance management, and strategic decision-making

Physical/Mental Requirements  

• Must be able to remain in a stationary position (seated) 80% of the day and occasionally reach, bend, and move inside the office to access files and product.
• Domestic and/or international travel up to 25%
• Required to have close visual acuity to perform computer tasks and operate other office machinery.
• The person in this position frequently communicates with internal and external customers and must be able to exchange accurate information in a clear manner.
• Ability to move 10-20 lbs. occasionally throughout day.
• Able to hear a telephone ring.
• Color vision (ability to identify and distinguish colors)

Nothing in this job description restricts management’s right to assign or reassign duties and responsibilities to this job at any time.