Job Details

Chief Executive Officer

  2023-03-15     Sunday Afternoons     340 A Street, Suite 1     Hybrid Remote  


Title: Chief Executive Officer

Location: Ashland, Oregon

Position: Full Time


Reporting to the Founders, the CEO will drive and oversee the creation, communication, and execution of business strategies to capture growth and profitability of this leading headwear brand. The individual will have an in-depth understanding of business and the outdoor industry, accountability for the organization’s positive evolution, and experience with the complexities of managing large retail partnerships while identifying new opportunities for expansion. The successful candidate will possess a high aptitude for navigating the intricacies of a family-owned business in a growth phase. The CEO will foster a healthy, inclusive, learning-oriented culture while maintaining the company’s passion and commitment to providing high-quality products to consumers globally.


  • Align organization vision and resources to strategy driving progress and adjusting as needed; ensure effective allocation of resources across company to achieve financial and brand priorities.
  • Create and oversee long-range planning, delivering financial results as aligned with the Board and leadership team; drive operating metrics and financial performance to consistently achieve revenue and profitability targets, using data and analysis for decision making.
  • Foster a high-performance culture with a sense of urgency and accountability among leaders, team members, and internal and external partners; mentor and guide team to drive results and maintain a culture of innovation, collaboration, transparency, and trust.
  • In partnership with the CFO, oversee P&L accountability; demonstrate exceptional financial acumen in all business decisions.
  • Identify and execute market opportunities to drive revenue and brand awareness.
  • Serve as a knowledgeable, respectful, authentic spokesperson for the brand.
  • Build key relationships with vendors, customers, and third-party partners.
  • Serve as an approachable, authentic leader who creates trust and encourages listening, learning, and continuous improvement.


Education and Background:

  • 10+ years’ experience leading an outdoor or apparel company, successfully delivering full P&L results.
  • Mid-size company experience leading an organization through rapid growth.
  • Demonstrated success leading cross-functional teams to achieve collaborative results, including financial and operational excellence.
  • Outstanding leadership skills: inspire, empower, and develop leaders and teams to achieve organization’s goals while fostering a respectful, accountable, fun culture.
  • Ability to quickly assimilate market, financial, and business economics.
  • Excellent written and verbal communication skills.
  • Desire to live in Southern Oregon.
  • Bachelor’s degree from accredited institution required, master’s degree desired.


  • Medical, dental, and vision insurance
  • Paid Time Off (PTO) plus holidays
  • Retirement plan with employer contribution
  • Volunteer day (one paid day per year for company-sponsored volunteer work)
  • Gym membership reimbursement
  • Salary dependent on experience and qualifications


  • Fun, fast paced, hardworking office environment
  • Dog-friendly office
  • Half-day Fridays
  • Hybrid work environment: 3 days in office and optional 2 days working from home

Please submit a cover letter and resume to no later than April 15, 2023.

No phone calls or walk-ins.

Do not contact this company in solicitation of any product or service.

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