Job Description: Stay Healdsburg Executive Director
Reports To: Board of Directors
Department: Sales & Marketing / Destination Management
Position Type: Full-time
Job Summary
The Executive Director serves as the chief executive and strategic leader of Stay Healdsburg, providing vision, direction, and oversight for all destination marketing, sales, and organizational operations. This role is responsible for advancing Healdsburg as a premier leisure and meetings destination, driving sustainable visitor demand, maximizing economic impact, strengthening brand equity, and fostering strong partnerships with lodging partners, local businesses, city leadership, and regional tourism organizations.
As the primary ambassador for the destination, the Executive Director works closely with the Board of Directors to set strategy, manage resources responsibly, and ensure alignment with Stay Healdsburg’s mission, long-range goals, and community values.
1. Executive Leadership & Strategic Planning
- Develop and implement comprehensive annual and multi-year strategic plans for destination sales, marketing, and organizational growth in partnership with the Board of Directors.
- Provide thought leadership on tourism trends, competitive positioning, visitor research, and market opportunities to guide long-term decision-making.
- Establish, track, and report on key performance indicators (KPIs) including room nights, visitor spend, economic impact, and return on investment.
- Serve as the principal advisor to the Board of Directors, providing regular updates, data-driven insights, and strategic recommendations.
- Lead and oversee all destination marketing and branding initiatives, ensuring a cohesive and compelling brand story across all platforms.
- Direct the development and execution of marketing assets including visitor guides, digital campaigns, website strategy, social media, and content partnerships.
- Oversee public relations and communications strategies to generate earned media coverage and enhance Healdsburg’s national and international profile.
- Manage relationships with advertising agencies, PR firms, creative partners, and digital vendors to ensure consistent messaging and measurable results.
- Set the overall sales vision and strategy for key segments including leisure travel, meetings, events, and group business.
- Cultivate and maintain high-level relationships with lodging partners, attractions, wineries, tour operators, and tourism stakeholders.
- Represent Stay Healdsburg in regional, national, and international sales missions, trade shows, and industry events.
- Collaborate with regional partners such as Sonoma County Tourism, San Francisco Travel and other destination organizations to amplify reach and impact.
- Act as the primary liaison to the City of Healdsburg, ensuring alignment with municipal goals, funding requirements, and tourism policy considerations.
- Foster collaborative relationships with local businesses, residents, and community groups to support responsible and sustainable tourism growth.
- Serve as the public face and spokesperson for Stay Healdsburg, articulating the destination’s value to stakeholders and the broader community.
- Lead, mentor, and develop staff, fostering a high-performance, collaborative, and service-oriented culture.
- Oversee organizational operations including budgeting, financial management, contracting, and compliance.
- Manage Stay Healdsburg’s annual operating budget, ensuring fiscal responsibility, transparency, and alignment with strategic priorities.
- Prepare and present regular performance, financial, and strategic reports to the Board of Directors.
Education
- Bachelor’s degree in Marketing, Tourism Management, Business Administration, or a related field required.
- Advanced degree (MBA or similar) preferred.
- Minimum of 10–12 years of progressive leadership experience in destination marketing, hospitality, tourism, or a related industry.
- Prior experience working with a Board of Directors, public-sector funding, or a destination organization (DMO/CVB) strongly preferred.
- Demonstrated expertise in destination marketing, B2B sales, hotel sales, contracting, and tourism-related P&L management.
- Strong strategic planning, financial acumen, and organizational leadership skills.
- Exceptional communication, public speaking, negotiation, and relationship management abilities.
- Proven ability to collaborate effectively with board members, elected officials, business owners, and community stakeholders.
- Deep understanding of digital marketing, social media trends, CRM platforms, and tourism analytics tools (e.g., STR, Agency360, Demand 360).
Physical & Travel Requirements
- Ability to travel to industry trade shows, conferences, sales missions, and regional meetings (approximately 25% of the time).
- Physical: This position may occasionally require the ability to lift and carry up to 30 lbs., such as during event set up and breakdown.
- Benefits: Competitive benefits package including health insurance, paid time off, and professional development opportunities.
About Healdsburg Chamber of Commerce and Stay Healdsburg
Eyes are on Healdsburg. From traditional press outlets and influencers to other city governments and chambers, Healdsburg receives sustained attention for its high quality of life, renowned wineries and hotels, charming downtown, and unique local businesses. The Healdsburg Chamber of Commerce has been catalytic in generating this attention – through its events, civic engagement, and elevation of its business community. In partnership with Stay Healdsburg, the Chamber plays a pivotal role in the city’s economic success, business strength, and small-town way of life.
Apply
To apply for this position, please send your resume and a cover letter (no more than one page). In your letter, walk us through what you see as Healdsburg’s top two opportunities and top two challenges for its business community right now.
Apply to: Heidi Dittloff, Chair, Healdsburg Chamber of Commerce at info@healdsburg.com
The Healdsburg Chamber of Commerce is an equal opportunity employer committed to creating a diverse and inclusive work environment.
