Short Term Rentals Jobs in Silver Spring, MD (NOW HIRING)

Job Description: About Kasa Kasa is the leading tech-enabled hotel and apartment hotel brand and manager. We partner with owners of multifamily and boutique hospitality properties to deliver stylish, professionally managed accommodations to business and leisure travelers alike. We took the best that hotels and short-term rentals had to offer and created a new class of hospitality that is well-priced, reliable, and offers a large selection of great locations. Unlike traditional hotel operators, we prioritize automation, AI-driven pricing, and data-driven decision-making to optimize revenue and improve guest experiences. Behind the scenes, we build technology that combines with our innovative operations to grow a globally scalable offering that delivers high-quality stays to guests. Our guests enjoy seamless check-ins, caring service, and attractive amenities — and if anything comes up, our on-site and remote guest experience team is available throughout their stay, ensuring our hospitality is rarely seen but always felt.Day in the life of a Kasa Regional Director of Operations We are the leading tech-enabled hotel and apartment-hotel management company. We have built a hospitality operating system that fundamentally improves the profitability of hospitality assets while delivering a high-quality, digitally-forward experience to guests. We partner with owners of multifamily and hospitality properties to deliver stylish, professionally managed accommodations to business and leisure travelers alike. We took the best that hotels and short-term rentals had to offer and created a new class of hospitality that is well-priced, reliable, and offers a large selection of great locations. Unlike traditional hotel operators, we prioritize automation, AI-driven pricing, and data-driven decision-making to optimize revenue and improve guest experiences.The Role We are seeking a strategic, commercially-driven leader to oversee a regional portfolio of hotels, apartment-hotels, and multifamily short-term rental properties. Success in this role requires deep experience in hotel and full-building operations. You will manage a multi-market portfolio, ensuring regional goals both inform and align with Kasa's broader strategies and owner expectations. As Regional Director of Operations, you will operate as the senior business leader for your region, accountable for performance, leadership development, and owner outcomes. You will lead one of Kasa's defined regions, which will be composed of multiple areas, and each area will include several properties and/or markets. You'll be responsible for leading Area Directors, Area General Managers, General Managers, and their respective teams while ensuring commercial and operational success across a diverse portfolio. You will balance strategic vision, strong operational and financial execution, and a focus on elevating the guest experience at every touchpoint in the guest journey; leading high-performing teams to deliver signature guest experiences, optimize financial outcomes, and strengthen partner relationships. This role requires a leader who can effectively design and leverage the guest experience to drive revenue growth, ask the right questions, make the right operational calls, assess risk, manage escalations with sound judgment, and translate strategy into clear executional priorities. You will play a key role in translating strategies into actionable regional business plans that deliver measurable results. Your ability to bridge hospitality operations with business strategy will be essential to driving sustained profitability, guest experience, and reputation, as well as asset-level value creation.About the Team This role is part of our operations leadership team and reports directly to the Senior Vice President of Operations or his/her designee. You will lead a team of Area Directors, Area General Managers, and General Managers within your region while serving as the central leadership point for a Regional POD, working cross-functionally with Revenue Management, Sales, Marketing, Finance, People, and Guest Experience. You will also partner closely with Real Estate, Launch, Tech & Product, and Hospitality Operations to ensure strategies are effectively translated into property-level execution. Your influence will extend beyond day-to-day operations: shaping how resources are deployed, how performance is optimized, and how strategies are designed to strengthen both business outcomes and partner relationships. You will be accountable for ensuring your region's teams are high-performing, well-coached, and representative of Kasa's values, culture, and brand promise. Location & Travel This is an operationally immersive role, not a typical remote position. You'll spend 60% of your time traveling across markets to lead property teams, engage partners, and drive performance. When home, if you reside in a market where a Kasa property operates, you are expected to maintain a strong and consistent presence through frequent visits to your local property(ies) and regular engagement with onsite teams. If you do not reside in a market in which we operate, you will be based at home but given the scope of this role, visible and connected leadership across regional and onsite teams is essential to success, so travel may exceed 60%. You will need convenient access to a major airport to support the travel requirements of this role. Required AttributesExperience Management Expert - Demonstrates deep expertise in designing and operationalizing both Guest Experience (GX) and Employee Experience (EX) as interconnected drivers of business performance. Builds systems, standards, and feedback loops that elevate both GX and EX while strengthening team engagement, retention, and service consistency.Commercially Savvy Operator – Balances day-to-day operational excellence with strategic financial management. Uses data-driven insights to continuously improve the guest experience, drive profitability, manage risk, and identify growth opportunities at both the property and regional levels.Strategic Connector – Ensures alignment between regional operations, property partner priorities, strategic alliances, and company-wide objectives. Serves as a bridge between executive leadership and on-the-ground teams, translating strategy into action and providing insights that inform business planning and portfolio strategy.Effective Communicator – Demonstrates strong executive presence and communication skills. Engages credibly with ownership groups, institutional partners, and cross-functional executives through financial storytelling and clear performance narratives. Creates concise written narratives, owner update templates, and escalation briefs; coaches teams on owner-facing comms.People & Talent Leader – Holds a high bar for talent and acts decisively on hiring, coaching, performance management, and succession planning. Creates an environment of accountability, empowerment, and professional growth.Operational Excellence Driver – Establishes frameworks for consistency, efficiency, and quality across all markets. Continuously refines standards and processes to achieve top-tier guest experiences and operational reliability using Lean Six Sigma methodologies (or similar).Financial Steward – Owns financial performance and accountability across the region. Guides teams to proactively manage revenue, control costs, and make trade-offs that deliver sustainable profit and partner value.Transformation Driver & Problem Solver – Leads through ambiguity and transition, ensuring teams stay focused on results amid evolving priorities. Proactively identifies systemic issues and executes solutions with speed and clarity.Partner & Relationship Builder – Fosters trust-based relationships with ownership teams, key partners, and strategic alliances in the markets we operate in. Communicates proactively, manages expectations effectively, and ensures outcomes align with partner goals and brand standards.Growth Catalyst – Uses portfolio analysis and market insight to identify and execute opportunities for expansion, improvement, and innovation across the region.Expected ResultsObjective #1: Drive financial, operational, quality, and guest-experience performance across your region.Meet or exceed the Operating Profit per Unit goals set forth for your assigned properties and region.Embed Kasa's Hall of Fame Host values into daily operations, ensuring teams deliver exceptional guest experiences that translate into higher review scores, stronger property reputation, and long-term quality and other experience metrics gains.Develop and implement scalable financial processes that enable P&L owners to proactively manage revenue, expense, and profit goals.Partner with Revenue Management, Finance, and Operations to identify root causes of underperformance and implement targeted improvement plans.Establish frameworks for cost control and margin expansion that align with owner and partner expectations.Standardize regional KPIs and quality metrics to ensure balanced performance across guest satisfaction, profitability, and partner retention.Define and prioritize property CapEx and activation initiatives that place quality at the forefront, enhancing property performance, guest experience, and alignment with brand standards.Objective #2: Strengthen leadership and accountability across the region.Proactively identify risks, performance gaps, or emerging issues before escalation, setting the standard for what "good" looks like" across teams. Maintain an operating cadence that surfaces insights early and drives timely, data-informed action.Build and develop a bench of high-performing leaders, ensuring all leaders on your team have clear ownership of outcomes.Implement structured training, coaching and development programs to elevate commercial and operational acumen across teams.Coach leaders to confidently prepare and present budgets and performance narratives to ownership, ensuring clear alignment with owner expectations, market context, and the financial story.Enforce clear accountability mechanisms, ensuring every leader "knows their numbers" and manages to measurable business results.Reinforce a culture of performance, Fearless Feedback, and continuous improvement through consistent communication and structured review cadences.Objective #3: Elevate regional business planning and commercial alignment.Work with Real Estate / Growth teams to ensure that performance expectations included in underwriting are vetted and achievable.Develop and drive comprehensive regional business plans that connect operational execution with key commercial strategies - including Revenue Management, Sales, and Marketing - to achieve portfolio and partner objectives.Translate Kasa's strategic priorities into actionable, data-informed initiatives that improve revenue quality, profitability, and partner value creation.Ensure P&L leaders understand and activate the commercial levers available to them, fostering collaboration between Operations and commercial functions to maximize portfolio performance.Strengthen alignment with ownership and investment partners by clearly articulating strategic goals, progress, and financial outcomes, reinforcing Kasa's position as a trusted and proactive operator.Objective #4: Future-proof operational systems for scalability.Implement decision-making frameworks that enable faster execution and clarity of ownership.Create scalable processes that adapt to new property types and asset complexities (hotel, multi-family, apart-hotel).Live our value of Fearless Feedback: Champion continuous improvement through creating feedback loops and post-mortems to refine playbooks, staffing models, and service standards.Partner with the executive team to inform long-term regional growth and headcount planning based on portfolio performance and complexity.Experience12+ years of experience in progressively senior leadership roles within hotel and resort operations, hotel asset management, or multi-site service industries, with a proven ability to translate commercial strategy into operational execution. Previous General Manager experience in a full-service or select-service hotel environment with direct P&L responsibility is required, demonstrating firsthand understanding of property-level operations, team leadership, and P&L accountability.Demonstrated experience operating within established brand standards, quality assurance audits, or franchise compliance frameworks.Hands-on leadership experience across Rooms Division functions, including Front Office and Housekeeping operations, with demonstrated success improving experience scores and labor efficiency.Working fluency in hotel revenue management concepts including ADR, RevPAR, NRevPAR, occupancy mix, channel strategy, and demand forecasting.Experience partnering with engineering or facilities teams on PM programs, CAPEX prioritization, and life-cycle asset planning.Proven ability to manage multi-market P&Ls and lead geographically distributed teams of both salaried and hourly staff.Demonstrated success in balancing guest experience and operational excellence with financial performance and commercial partnership management.Strong background in people leadership: decisive in hiring, developing, and exiting talent as needed to maintain a high-performing culture.Experience managing owner or institutional partner relationships, with a track record of effective communication and performance reporting.Adept at financial storytelling, data-driven decision-making, and executive-level communication.Deep operational acumen, combined with the ability to think strategically and act as a business partner to cross-functional and ownership stakeholders.Comfortable navigating fast-paced, complex environments where innovation, problem-solving, and adaptability are critical.Plus if...MBA or equivalent degree preferred.Held multidisciplinary leadership roles in integrated hotels or resorts (hotel, F&B, entertainment, sales, etc.).Experience in a technology-enabled hospitality or real estate environment.Exposure to institutional partnerships or portfolio-level commercial management.Natural executive presence and polish; able to represent Kasa effectively with internal and external stakeholders.In one year, you will succeed at Kasa by:Achieving excellence across guest experience, financial performance, partner satisfaction, and team engagement, with your portfolio consistently meeting or exceeding budgeted goals.Building a high-performing regional team that raises the bar for operational and commercial execution.Strengthening Kasa's reputation as a preferred operator and strategic partner known for driving value creation, revenue growth, and bottom-line performance across your region.Establishing scalable operational systems that can support 10x future portfolio growth.Being recognized as a trusted advisor and strategic leader across Kasa