Director of Retention & Monetisation, Lodgify
SaaS Vacation Rental Software Company
Open for applications
SaaS Vacation Rental Software Company
201-500 employees
Open for applications
201-500 employees
Company mission
To empower the long-tail vacation rental host or property manager worldwide to get started and grow their business through technology, with the ultimate goal of making them independent.
Role
Who you are
- The Experience: 8–12 years in Growth, Lifecycle, or Retention within B2B SaaS. You’ve built a lifecycle system from scratch, not just managed an existing one
- The "Builder" Mindset: Your default mode is to build a prototype, not a slide deck. You get frustrated by slow feedback loops and use AI tools (n8n, Zapier, Claude, etc.) to break them
- Hard Requirement: You haven’t just "used" AI; you have shipped an AI-native automation or workflow that is currently in production
- Monetization Fluency: You understand value metrics, tier design, and willingness-to-pay research. You can talk NRR and LTV with a CFO, and "API architecture" with a CTO
- Technical Stack: Expertise in CRM orchestration (HubSpot/Braze), product analytics (Amplitude/Mixpanel), and SQL. You pull your own data; you don’t wait for a ticket
- Statistical Rigor: You understand ICE prioritization, cohort analysis, and statistical significance. You know when a result is a signal and when it’s just noise
What the job involves
- We are looking for a Director of Retention & Monetization reporting directly to the Chief Growth Officer
- You will lead the strategic direction for our Activation and CRM squads, while directly building and managing the Retention & Monetization Squad from the ground up
- This is a unique "Player-Coach" hybrid: you are a people leader setting the standard for your teams, but you are also an individual contributor, architecting and shipping our monetization experimentation roadmap
- Our goal is to build a Retention Engine that thinks for itself. You aren't just sending emails; you are building the infrastructure that identifies at-risk signals, triggers autonomous interventions, and scales pricing experiments at 10x the current industry velocity
- Architect a "Systems-First" Retention Model: Move Lodgify from reactive saves to proactive, behavioral interventions. You will define the data signals that matter and build the infrastructure (HubSpot, Braze, or equivalent) to trigger event-based actions, not just time-based sequences
- Own the Monetization Roadmap (Hands-on): You will personally design, run, and analyze pricing and packaging experiments. You aren't overseeing this from a distance; you are in the data, building the hypotheses, and reporting commercial read-outs directly to the CGO and CFO
- Drive AI-Native Execution: You reach for AI first. Whether it’s building a custom churn-prediction agent, automating segmentation, or using LLMs to personalize re-engagement at scale, you will lead the GTM organization’s AI transformation from within your function
- Bridge the Data Gap: Partner with Engineering and Data to instrument product events that turn "user behavior" into "actionable growth signals." You’ll ensure our stack has zero "coordination tax" and maximum experimentation speed
- Scale the Growth DNA: Elevate the Activation and CRM leads (Anabel and Alba) by setting a world-class standard for experimentation quality, statistical literacy, and delivery velocity
- Month 1 — Audit & Ship: Complete a full CRM debt audit and ship your first monetization experiment. Deliver one tangible AI automation into the hands of your team
- Month 3 — Compound: Live behavioral segmentation is active. Your first AI agent is in production. You've delivered a concrete recommendation on team structure and talent gaps to the CGO
- Month 6 — The Engine is Humming: Experimentation velocity has tripled. Retention, CRM, and Monetization are a single integrated system where signals in one automatically inform the others. NRR is measurably improving
- The Player-Coach Paradox: You must lead two squads while simultaneously acting as the IC lead for monetization. You aren't just a manager; you are a builder
- High-Volume, Low-ACV: With ~1,000 new customers a month, you can’t "white glove" your way to retention. This is a systems and architecture problem that requires scale-thinking
- No Playbook: We are defining what an AI-native growth org looks like. You’ll be building the plane while flying it, often influencing cross-functional teams (Product/Data) without direct authority
- The Clock is Running: We are at a critical scaling inflection point. The decisions you make on pricing and retention in the next 12 months will define the company’s trajectory for the next 5 years
Application process
- All applications and CVs must be submitted in English
Our take
For independent vacation rental owners or managers, creating and marketing a property can be challenging, and third-party portals can eat into profits with commissions and fees. Lodgify offers an efficient alternative with its vacation rental marketing software, enabling users to more efficiently manage their properties.
Lodgify enables users to quickly create mobile-friendly websites, manage reservations and payments, and synchronise property information across multiple rental portals. With the vacation rental market still booming, more and more people are looking to let out their spaces, which means demand for Lodgify's offerings is high.
This demand also means there's competition in the broader space, but Lodgify is one of the only companies focusing on long-tail, medium to small rental businesses. The company is well-funded and benefits from direct integrations with the likes of Airbnb, Expedia and Booking.com.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
39% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Nov 2022
$34.2m
SERIES B
May 2021
$8m
EARLY VC
Total funding: $49.6m
Company benefits
- Remote Flexibility: The freedom to work from home any day that works for you.
- Time to Recharge: 25 working days of paid vacation and Jornada Intensiva in August.
- Alan Health Insurance: Premium health, dental, and mental health support via Alan. Pre-existing conditions are covered.
- Meal Perk: €150/month allowance on your Alan card + 50% off Ametller Origen prepared dishes at the office.
- Tax-Free Savings: Increase your take-home pay by using Flexible Remuneration for extra meal costs (up to €70/mo) and public transport (up to €136/mo).
- Free Spanish classes
- Home Office Gear: We provide a table, ergonomic chair, and monitor for your home setup.
- Great culture & working environment with an international team of over 60 different nationalities
Company HQ
La Nova Esquerra de l'Eixample, Barcelona, Spain
Leadership
Dennis Klett
(Co-founder & Board Member)Previously worked as a Finance Analyst at Siemens Healthcare, then Philip Morris International.
Marco De Gregorio
(Co-founder & CAIO)Has extensive experience in web development, having done so both on a freelance basis and at 4D Interactive and Vueling Airlines. Was also the co-founder and CTO of Domegos Ltd., a holiday home web portal.
Shaun Shirazian
(CEO)Formerly CPO at Pipedrive, Country Manager at Intuit where they spent 12 years, and a Project Leader at Procter & Gamble.
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