NOTE: This is a FULLY remote role, but the candidate must be within the North America or EMEA region to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within the North America or EMEA region.

Trusted by 20,000+ property managers worldwide, Hostaway is an industry leading, AI-powered vacation rental management platform designed for professional short-term rental operators. Hostaway brings everything together for greater efficiency and faster growth.

Profitable, high-growth, and the first short-term rental PMS unicorn 🦄. Join us at our most exciting stage yet! Learn more about our recent valuation and story here.

Hostaway is seeking a highly motivated Senior Director of Content & Brand to join our team and drive our growth in the market.

About the role

Hostaway is looking for a Senior Director of Brand and Content to build and lead the brand, content, and creative engine for our next stage of growth as a leading B2B SaaS platform for professional short-term rental operators. This is a high-impact SaaS marketing leadership role for someone who can shape our market narrative, elevate our category presence, and create content and creative programs that support awareness, pipeline, customer acquisition, and revenue growth.

You’ll build the function largely from the ground up, including the team, operating model, workflows, AI-enabled production systems, and quality standards. This role will partner closely with Product Marketing, Demand Generation, Sales, Marketing Operations, and Product to ensure Hostaway’s brand, content, and creative output is aligned with SaaS GTM priorities, buyer journeys, product launches, demand generation, and measurable business outcomes.

Your mission

• Build and lead a team that will own the modern content engine that produces high-quality, high-velocity editorial, thought leadership, and demand-supporting content.

• Build and lead a small team that will define and own Hostaway's brand strategy, positioning, narrative architecture, and visual identity system for a fast-growing global vertical SaaS company

• Build the in-house Creative team from scratch including designers, copywriters, motion/video, and production talent.

• Across Content/Brand/Creative, utilize AI teammates who will drive efficiency while humans drive quality, designing workflows where generative tools handle research, drafting, variation, localization, and asset production, while humans own strategy, narrative, taste, and final quality.

• Partner closely with Product Marketing, Demand Generation, Sales, Marketing Operations and Product to align brand, content, and creative to support GTM priorities and drive revenue growth.

• Hire, mentor, and develop the brand, content, and creative team, making smart early bets on senior leaders, hands-on makers, and hybrid AI-native talent.

• Decide the right mix of in-house team, agencies, freelancers, and AI-augmented partners; manage vendor relationships and budget accordingly.

• Define KPIs across brand health, content performance, creative effectiveness, AI productivity gains, LLM/AI discoverability, and revenue contribution.

• 12+ years of progressive experience across content, brand, and/or creative leadership, with significant experience in B2B SaaS marketing.

• 5+ years of experience building and leading teams, including hiring senior talent and developing high-performing creative or editorial professionals.

• Experience marketing to SMB or mid-market SaaS buyers, ideally in a high-velocity, transactional sales and marketing environment.

• Proven ability to build a SaaS marketing function or sub-function from the ground up, including strategy, team structure, workflows, tools, and execution standards.

• Strong understanding of SaaS GTM motions, buyer journeys, product marketing, demand generation, lifecycle content, and sales enablement.

• Strong editorial instincts, storytelling ability, and creative judgment, with a clear sense of what makes B2B SaaS content and creative effective.

• Hands-on fluency with AI tools for content, brand, and creative work, including a practical point of view on where AI improves quality, speed, and scale.

• Strong cross-functional leadership skills, executive presence, and a track record of connecting brand, content, and creative work to measurable SaaS business outcomes such as pipeline, revenue, retention, and category authority.

What we offer

• Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant.

• 100% Remote: Enjoy the freedom to work from anywhere within your country of residence—be it a co-working space, your home office, or even your dining room table. The choice is yours. Just don’t ask to work in our office (we don’t have one).

• Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. This ensures we all share in the company’s success.

• Values-Driven Leadership: Our Core Values are not just words we’ve written to make us feel good. We leverage them daily when making strategic and tactical decisions.

• Professional Growth: Our rapid growth offers unparalleled learning and development opportunities, along with a multitude of career advancement opportunities.

• Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms.

• Geographic Specific Benefits: As an international employer, we offer different country-specific benefits such as Health Insurance and Pensions in countries where these perks are customary. The specifics depend on the country of the applicant.

• Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity, providing a key pillar to our success (and making it a lot of fun to work here).

Thank you for your interest. If you apply for this role, you will receive an email from our Talent Acquisition team after your application has been reviewed alongside the qualifications for this role and the qualifications of others who have applied.