Loren Pudlewski

Buffalo, New York5 yrs in STRremote

About

For the past five years, I've built my career around helping vacation rental companies grow stronger businesses through the intersection of people, technology, operations, and guest experience. My perspective has been shaped by supporting the industry from multiple angles, partnering directly with vacation rental operators, leading Customer Success for a global hospitality technology company, and now advising nearly 100 property management organizations on hiring strategy, organizational design, and team development. As a Talent Strategy Specialist at Better Talent, I partner with founders and leadership teams to build scalable organizations through compensation strategy, behavioral assessments, recruitment marketing, structured hiring, and organizational planning. Previously, I helped build and lead Customer Success at Touch Stay, supporting hospitality businesses around the world, from independent operators to enterprise portfolios managing thousands of properties. I guided technology adoption, enterprise implementations, strategic partnerships, and customer growth while collaborating with property management systems and hospitality technology partners across the global vacation rental ecosystem. Alongside these roles, I've spent nearly five years partnering with Fireside Retreats to develop marketing strategy, guest communications, SEO, social media, and brand storytelling, providing valuable operator-side insight into what drives trust, bookings, and memorable guest experiences. Working with hundreds of professionals across global markets has reinforced one belief: sustainable growth happens when people, processes, and technology are intentionally aligned. I'm especially passionate about the thoughtful integration of AI and emerging technologies to improve operational efficiency, strengthen decision-making, and elevate both the guest and homeowner experience while preserving the authenticity and human connection that define unreasonable hospitality.

Core Skills

Property OperationsintermediateGuest ExperienceintermediateOwner RelationsintermediateTeam LeadershipintermediateVendor ManagementintermediateMarket AnalyticsintermediateCX StrategyintermediateBrand DevelopmentintermediateTraining & DevelopmentintermediateSales & Business Developmentintermediate

Experience

Talent Strategy Specialist

Better Talent · Remote

2025-08 – Present

- Own a portfolio of ~100 client accounts ranging from SMB to Enterprise size, managing the intersection of customer success, talent strategy, and revenue retention. - Serve as a trusted advisor to founders and operators, translating business goals into scalable hiring and team design strategies - Lead end-to-end hiring strategy including role design, compensation benchmarking, job ad optimization, and structured interview frameworks - Implement and coach clients on Predictive Index (PI) to improve candidate fit, team dynamics, and decision-making confidence - Write and optimize high-converting job ads, improving applicant quality and funnel conversion across multiple roles and markets - Drive client retention and expansion through consistent delivery, strategic guidance, and measurable hiring outcomes - Conduct compensation analysis and market benchmarking, advising clients on competitive and sustainable pay structures - Balance high-touch advisory with scalable systems, enabling consistent delivery across a large and diverse client portfolio

Head of Customer Success & Sales

Touch Stay · Remote

2022-07 – 2025-08

- Led the founding customer success strategy for a hospitality SaaS platform supporting operators from single-property owners to enterprise portfolios of 3,000+ units. - Helped guide Touch Stay through major growth milestones, including surpassing $1M and $2M ARR, by strengthening customer success operations and strategic partner relationships. - Supported post-acquisition transition efforts, working closely with customers, partners, and internal teams to maintain stability and retention during change. - Built and managed strategic partner relationships across property management systems, hospitality tech vendors, and enterprise clients to support large-scale implementations. - Served as primary liaison between customers, product, engineering, and partner teams to ensure adoption, retention, and long-term value realization. - Guided customers through digital transformation initiatives focused on guest experience, operational efficiency, and brand consistency. - Played a key role in enterprise negotiations, onboarding strategy, rollout planning, and multi-stakeholder alignment. - Maintained strong retention and expansion outcomes by positioning Touch Stay as a strategic partner rather than a transactional tool. - Led a team of Customer support, sales, and success members with coaching, and regularly cadenced meetings.