Associate, Enterprise Solutions & Automation

Company Description

Pebblebrook Hotel Trust (NYSE: PEB) is a publicly traded real estate investment trust (REIT) and the largest owner of urban and resort lifestyle hotels in the United States. With a portfolio of 44 hotels and approximately 11,000 guest rooms, the company operates across 13 major urban and resort markets. Pebblebrook is renowned for its focus on premium properties that deliver exceptional experiences for guests. For additional information, visit their website at www.pebblebrookhotels.com or follow them on social media at @PebblebrookPEB.

Role Description

The Associate, Enterprise Solutions & Automation will play a key role in helping design and build the systems, workflows and internal tools that make our corporate operating platform faster, smarter and more scalable. This role is ideal for a technical self-starter who enjoys turning messy business problems into practical solutions. You will work across Asset Management, Business Intelligence, Corporate Finance, Accounting, and Investments to develop applications, automations, data workflows, and integrations that reduce manual work, improve decision-making, and strengthen data integrity.

This is a full-time, on-site role based out of Bethesda, MD.

Key Responsibilities include:

Enterprise Application Development & Workflow Tools

Help enhance Pebblebrook’s internal property and corporate data tools, including the Pebblebrook Property Data Portal. Build new features, improve usability, strengthen backend logic, and streamline information flow among property teams, management companies, and the corporate office.

Actionable Intelligence & Data Pipelines

Partner with the Business Intelligence team to create clean, reliable datasets and data pipelines that support actionable intelligence and recommendations. Strong familiarity with Tableau to support proactive reporting structures and provide senior leadership with predictive insights.

Rapid Prototyping & Deployment

Utilize AI-driven development tools and workflows to move quickly from concept to production at an accelerated pace, focusing on high-level architectural execution rather than manual boilerplate.

Cross-Functional System Integration

Act as a technical liaison for Corporate Finance, Accounting, and Investment teams. You will identify reporting bottlenecks and engineer robust automations and custom API integrations to ensure data remains scalable and reliable.

Data Architecture & Maintenance

Contribute to the continuous evolution of the enterprise data architecture, maintaining high standards for accuracy, security, and system performance across all departments.

Candidate Profile

Builder’s Mentality

You are a self-starter who likes to create things, improve things, and fix things. You do not wait to be handed a perfect spec. You can spot inefficiencies, ask smart questions, and move a solution forward.

Creative, Practical Problem Solver

You enjoy solving real business problems, not just writing code in a vacuum. You are energized by finding simpler, faster, and more scalable ways to get work done.

Agentic Practitioner, Not AI-Dependent

An AI-native builder who views agentic coding systems as a force multiplier. You are comfortable directing AI agents to accelerate development cycles and are excited by the shift from syntax-level coding to architectural problem-solving. You use AI as leverage, not as autopilot.

Proactive Systems Architect

A solution-oriented thinker who possesses a strong mental model of how data moves between systems. You don’t wait for a ticket to fix a broken process; you take initiative to research and build sustainable, automated solutions that replace manual labor.

Effective Communicator

You can work with both technical and non-technical colleagues. You are able to translate business needs into technical requirements without losing sight of the “why.”

High Standards, High Ownership

You care about accuracy, reliability, and follow-through. You understand that even small errors can matter in a public company environment.

Education and Experience

Education

Bachelor’s degree in Computer Science, Information Systems, Finance, Data Analytics, or a related technical field, or comparable practical experience.

Required Experience

• 0–3 years of experience in software development, analytics, data engineering, automation, or a related technical role
• Demonstrated “hacker” mindset—curiosity-driven projects, automation scripts, or participation in open-source/technical communities
• Proficiency in Python and SQL with a demonstrated ability to build data-driven applications, automate multi-step workflows, and manage complex database integrations
• Exposure to or strong interest in Generative AI and LLM orchestration.
• Strong written and verbal communication skills
• Demonstrated curiosity, initiative, and comfort working in a fast-moving environment

Preferred Experience

• Financial & REIT Understanding: Familiarity with hospitality and real estate performance metrics (e.g., RevPAR, Occupancy, NOI), the construction of financial statements, and the operating and reporting structures unique to REITs.
• API & Systems Integration: Experience connecting and maintaining integrations across enterprise platforms, including but not limited to Azure PostgreSQL, TM1, and Oracle.
• Agentic AI Development: Hands-on experience working with large language models to design and develop reusable, extensible skill frameworks that leverage institutional knowledge through an MCP gateway.
• UI/UX Design for Internal Tools: Demonstrated ability to design and own the end-to-end delivery of clean, intuitive dashboards and internal business tools — with a track record of driving adoption among non-technical end users.

Our Technical Stack

• Backend & Data: Proficiency in Python (FastAPI preferred) and SQL (PostgreSQL).
• Frontend: Familiarity with modern JavaScript frameworks (Vue.js preferred).
• Intelligence: Proficiency in Tableau for data visualization and proactive reporting.

What Success Looks Like in the First 12 Months

• Deliver multiple high-impact automations or tools that meaningfully reduce manual work
• Improve the usability and adoption of Pebblebrook’s internal data portal and reporting tools
• Build trusted datasets and workflows that support faster, better management decisions
• Demonstrate strong judgment, ownership, and follow-through on cross-functional projects
• Become a go-to internal resource for solving practical business-system problems

When Applying for This Position, please include the answers to the following questions in your cover letter:

• Describe a time you encountered a manual, repetitive, or 'broken' process (at work, school, or in a personal project) that nobody asked you to fix, but you chose to automate anyway. What was the tool you built, what was the stack, and what was the specific outcome?

• Describe a project where you had to reconcile two conflicting datasets or integrate two systems that didn't want to talk to each other. How did you ensure the final output was 'one version of the truth'?

• Walk us through your current 'AI-augmented' development workflow. How do you use LLMs or agents to accelerate your building process, and more importantly, how do you audit the AI's output for accuracy and security? What specific tools are you using in this workflow?

• Describe a situation where you had to explain a complex technical limitation or a data discrepancy to a non-technical stakeholder. How did you frame the conversation to reach a business-focused solution?

• If you are tasked with using a new technology or framework (e.g., a specific API or an MCP gateway) that you’ve never seen before, what are the first three things you do to become proficient in it within 48 hours?