Skyler Vaughn
Co-Founder | Operations & Client Success Lead
Hudson
Summary
Relationship-driven operator with experience managing a $1M+ short-term rental portfolio and overseeing 50+ projects from concept to completion. Proven ability to build strong client relationships, coordinate cross-functional teams, and deliver high-quality outcomes in fast-paced environments.
Overview
6
6
years of professional experience
Work History
Co-Founder | Operations & Client Success Lead
For the Love of Upstate
09.2023 - Current
- Co-built and managed a portfolio of 8 short-term rental properties generating ~$1M+ annually
- Maintained 80%+ occupancy rates across properties through strong operational execution and guest experience optimization
- Served as primary point of contact for clients, partners, and vendors, building and maintaining high-trust relationships
- Managed end-to-end operations including guest communication, vendor coordination, and performance optimization
- Coordinated and oversaw 8 renovation and design projects with budgets ranging from $80K–$500K
- Led communication across contractors, partners, and stakeholders to ensure alignment and successful project delivery
- Implemented systems and workflows using tools like Asana, Jira, Slack, and PMS platforms (Hospitable, Hostaway) to improve efficiency and consistency
- Resolved time-sensitive operational and client issues, ensuring strong customer satisfaction and repeat business
Operations & Construction Manager
Techvestor
02.2022 - 06.2024
- Managed over $4,000,000 of renovation and furnishing spend which resulted in 40+ single-family home flips into active short-term rentals
- Virtually managed flips in multiple markets (Pocono Mountains, Upstate New York, Florida, Illinois, and Joshua Tree, CA)
- Project managed renovations and furnishings of homes using project management tools like Confluence, Jira, and Monday.com
- Created processes for the operations team and built best practices and SOPs for the team
- Tracked and analyzed best amenities to add to homes to generate above-market average revenue
- Filed for and completed all short-term rental and building permits needed to successfully renovate and list on Airbnb & VRBO
Marketing & Operations Manager
The Sunrise Homes
01.2020 - 02.2022
- Increased e-commerce sales by 400% in less than 8 months.
- Grew the company’s combined following by 13,900% (500 to 70,000) in less than 2 years
- Engaged with followers to cultivate a highly engaged community of brand advocates
- Built and led a short-term rental mentorship program, coaching over 60 one-on-one clients to define and achieve their business goals
- Managed social platforms like Instagram and TikTok
Education
Bachelor of Science - Marketing And Economics
University of San Francisco
San Francisco, CA 05.2001 -
Skills
- Client Relationship Management
- Customer Success & Retention
- Account Management
- Cross-Functional Coordination
- Operations Management
- Process Improvement & SOP Development
- Revenue Optimization
- Customer Experience Strategy
- Conflict Resolution
Timeline
Co-Founder | Operations & Client Success Lead
For the Love of Upstate
09.2023 - Current
Operations & Construction Manager
Techvestor
02.2022 - 06.2024
Marketing & Operations Manager
The Sunrise Homes
01.2020 - 02.2022
Bachelor of Science - Marketing And Economics
University of San Francisco
05.2001 -