Sr. Director of Brand & Creative

Proper Hospitality is an independent hospitality company operating a growing portfolio of design-forward properties under the Proper Hotels, By Proper, and The Collective brands. We are not a large hotel chain. We build brands with texture rooted in place, culture, food and beverage, wellness, and community. Our creative output is a direct expression of that conviction.Position OverviewThis is a senior leadership position and one of the most senior creative roles in the company. The Senior Director of Brand & Creative owns the strategic and creative direction of the Proper portfolio. You set the standard, shape the point of view, and ensure that everything we put into the world across every brand, channel, and property is coherent, intentional, and differentiated.You will partner closely with the C-suite and founders to shape how Proper shows up in the world, and work in close partnership with F&B, wellness, programming, marketing, and property teams. You will lead an in-house creative and social team — including a Creative Director, design, and brand & campaign — bringing senior direction, editorial standard, and operating discipline to a function poised to scale with the company.The social media function will report directly into this role. This position is responsible for defining Proper's social strategy, creative voice, and content standards across all platforms, while leading and developing the social team to ensure social is fully integrated into the broader brand and creative vision.AI fluency — or strong systems thinking with active buy-in — is a requirement. You'll use AI tools meaningfully in your own practice and lead the work of translating brand voice, editorial standards, and creative judgment into systems that scale across the portfolio. This is one of the first functions at Proper where AI-augmented workflows will be visible, and you'll help define how.What You OwnBrand strategy and evolution across Proper Hotels, By Proper, and The CollectiveCampaign concepting and storytelling: defining the narrative, not just the lookCreative direction across all channels including digital, print, environmental, social, and brand partnershipsConsistency and integrity of brand expression across all properties and sub-brandsCross-functional creative collaboration with F&B, wellness, programming, sales, and operationsLeadership of the in-house design and creative team, setting direction, raising the standard, and ensuring consistent execution across all outputsExternal agency and vendor relationships: briefing, directing, and holding standardsBuilding the creative infrastructure and processes needed as the company scalesLeading AI adoption within the creative function: defining how brand voice and creative standards translate into AI-augmented workflows for ideation, production, and brand consistency, and holding the team accountable to using them wellEnsure brand and creative are a meaningful driver of commercial performance — supporting revenue growth across properties and reinforcing positioning with key partnersSocial media: leadership of the social function and team, defining social strategy, creative voice, content standards, and platform storytelling across all properties — including codifying how corporate and property-level social work together as the portfolio scalesWhat This Role Is NotThis is a leadership role focused on direction, systems, and quality. It is not a hands-on design production role — but it is a hands-on leadership role. You'll be close to the work and the team, not at 30,000 feet.What We Are Looking ForActive, demonstrated use of AI tools in your own creative practice — or a clear, evidenced point of view on systems and how creative work scales through them. We're looking for fluency or strong systems thinking with active buy-in, not theoretical interestAbility to assess and integrate new AI-powered creative tools and workflows at the team level10+ years of progressive brand and creative experience, with at least 3 in a senior leadership capacityDemonstrated experience leading integrated creative teams, including oversight of social media and content functionsDemonstrated ability to build and steward multi-property or multi-brand creative systemsBackground in lifestyle, hospitality, fashion, or culture-driven consumer brands preferredStrong strategic thinker: you connect brand to business, not just visual to visualProven collaborator across non-creative disciplines: ops, F&B, programming, real estateAbility to brief and direct external agencies and creative partners at a high levelClear, direct communicator with a point of view you can defendEnergized by team-building: comfortable leading and developing a team that includes junior and mid-level talent, raising both the standard and the capability of the people around youComfortable operating in a lean, fast-moving, entrepreneurial environmentEnergized by a blank canvas: this role will help define what Proper means creatively as we scale into new markets, properties, and residential projectsWhat Success Looks Like at 12 MonthsA clear brand architecture and voice for each Proper brand is documented and in active useAll major creative output across properties — including social channels — reflects a consistent, elevated point of viewThe in-house design and social teams have clear direction, stronger briefing processes, and higher output qualityCreative is operating as a strategic partner to F&B, wellness, and programming, not just a service functionAI-augmented workflows are embedded in how the team works — ideation, concepting, copywriting, and production all benefit from them — and brand voice and creative standards are encoded into the systems the team and its partners rely onYou have identified the gaps in tools, process, and talent and have a plan to close themSalary$200,000-225,000Proper Perks & BenefitsCompensation & RecognitionCompetitive Salary + Bonus: Rewarding exceptional talent and performance across all levels.Recognition Programs: Celebrating achievements big and small through company-wide appreciation and milestone rewards.Annual Performance Reviews: Regular opportunities for feedback, growth, and advancement.Culture of Growth & BelongingCulture of Growth: A collaborative, design-forward environment that values creativity, intelligence, and curiosity — where learning and excellence are a daily practice.Guided Skills Development: Access to training, leadership programs, mentorship, and cross-property mobility to encourage achievement and discovery.Diversity, Equity, Inclusion & Belonging: We honor individuality while fostering a culture of respect and belonging across all teams.Community Engagement: Opportunities to give back through local volunteerism, sustainability, and charitable partnerships.Health & WellnessComprehensive Health Coverage: Medical, dental, and vision plans through Aetna, designed to fit a range of personal and family needs.Wellness Access: Company-subsidized memberships with Equinox and ClassPass, plus wellbeing workshops and mental health resources.Employee Assistance Program (EAP): Confidential support for emotional wellbeing, financial planning, and life management through Unum.Time Off & FlexibilityPaid Time Off: Flexible PTO plus 11 paid holidays each year for corporate team members.Paid Parental Leave: Paid time off for eligible employees welcoming a new child through birth, adoption, or foster placement.Flexible Work Practices: Hybrid schedules for eligible roles and an emphasis on work-life balance.Financial Wellbeing & Core Protections401(k) Program: Company match of 50% of employee deferrals, up to the first 4% of eligible compensation.Employer-Paid Life & Disability Insurance: Core protections with optional additional coverage.Financial Education: Access to planning tools and workshops to support long-term stability and growth.Lifestyle & Travel PerksHotel Stay Benefits: 75% off BAR (floor of $100) across the Proper portfolio.Design Hotels Partnership: 50% off participating Marriott Design Hotels.Dining Discounts: 75% off food & beverage at all Proper Hospitality outlets.Lifestyle Perks: Complimentary or subsidized parking, cell phone reimbursement, and exclusive hospitality and retail discounts.Why Join Proper HospitalityAt Proper, we build experiences that move people — and that begins with the team behind them. As a best-in-class employer, we’re committed to creating one of the Best Places to Work in hospitality by nurturing a culture where creativity, excellence, and humanity thrive together.Everything we do is grounded in the belief that hospitality is more than a profession - it’s an opportunity to care for others and make lives better. Guided by the Pillars of Proper, we show up with warmth and authenticity (Care Proper), strive for excellence in everything we do (Achieve Proper), think creatively and resourcefully (Imagine Proper), and take pride in the style and culture that make us who we are (Present Proper).We believe our people are our greatest strength, and we invest deeply in their wellbeing, growth, and sense of belonging. From comprehensive benefits to meaningful development programs, Proper is designed to help you build a career, and a life, that feels as inspiring as the experiences we create for our guests.Our Commitment: Building the Best Place to WorkOur Best Place to Work initiative is a living commitment — a continuous investment in our people, our culture, and our purpose. We listen, learn, and evolve together to create an environment where everyone feels empowered to imagine boldly, achieve confidently, care deeply, and present themselves authentically.At Proper, joining the team means more than finding a job — it means joining a community that believes in building beautiful experiences together, for our guests and for one another.