Jo L

STR Operator & Automation Specialist

Airbnb • Self-employed

Dec 2024 - Present • 1 yr 6 mos

Converted two personal properties into fully automated short-term rental operations on Airbnb and Booking.com, building every system from scratch without any prior blueprint. Property one generates A$9,341/month at 81.1% occupancy with A$729 in additional revenue through Stripe add-ons across a range of guest add-ons tailored to each stays. Property two generates A$8,963/month at 76.7% occupancy with A$694 in add-on revenue. Combined monthly revenue: over A$18,000. Both run entirely hands-off. Built a custom AI knowledge base for each property covering every guest FAQ, house rule, check-in and check-out flow, local recommendation, and operational detail. Integrated into Hostaway so incoming guest messages trigger automatically drafted replies. Guest response time dropped to under 2 minutes. Active time spent on guest communications: near zero. Designed digital local guides and in-property collateral using Canva - QR code posters giving guests instant access to WiFi, property information, and curated local recommendations. Modern, on-brand designs placed throughout the property so guests find answers without needing to message at all. Integrated Hostaway's API with Claude (Anthropic) to build custom automations beyond the platform's native capabilities. Configured dynamic pricing via PriceLabs calibrated against live competitors, with rules for gap nights, weekend uplift, and minimum stay optimisation. Set up Stripe for add-on revenue collection - a stream most operators leave uncaptured. Prior to this, co-founded a short-term rental company and scaled from zero to six active properties across Sydney in eight months. Maintained 80%+ average occupancy across the portfolio. Built all guest operations, listing copy, pricing strategy, and automated workflows. Exited December 2025 with a full cash buyout, having systemised operations to run independently of any founder. Every system, every automation, every workflow - built and maintained independently.

AI Customer Success Manager

SaaS • Full-time

Oct 2025 - May 2026 • 7 mos

Served as the primary bridge between technical AI developers and non-technical business owners at an AI SaaS start-up. Owned all client-facing communication from solution scoping through delivery, translating complex AI systems into plain language for C-suite stakeholders. Maintained 90%+ gross revenue retention across a portfolio of 30 B2B accounts with five- to six-figure contract values. Led client discovery sessions to map workflows across departments, converting initial AI audits into broader organisational engagements. Monitored account health by tracking adoption and engagement signals, intervening early to prevent churn before it escalated. Consistently grew account scope beyond the initial contract through proactive expansion conversations. The skills built here - making complex systems simple, managing client expectations, and driving adoption - are directly applied when building AI knowledge bases and automation workflows for STR operators who are not technical.

Strategic Investment Property Consultant

Real Estate Specialists • Freelance

Nov 2024 - Jan 2026 • 1 yr 2 mos

Settled a combined A$10M in off-the-plan property transactions within the first three months, managing the full sales process from initial client consultation through to settlement. Guided clients through bespoke villa builds, managing expectations, timelines, and customisation decisions across long sales cycles with multiple stakeholders. Built genuine client relationships that made sales a natural outcome rather than a hard close. This role built a foundational understanding of property as an investment asset - how buyers think, what they're protecting, and what makes them trust an advisor. That same lens applies directly to STR consulting: operators aren't just running a listing, they're managing a financial asset. Understanding that distinction changes the quality of advice.