Chief Technology & Intelligence Transformation Officer

About LuxuryEstate

With 550,000+ luxury properties across 120+ countries and 1.8M monthly visitors, LuxuryEstate is the world's largest marketplace for $1M+ real estate. We connect 18,000+ elite agencies with global buyers seeking exceptional properties.

We're in transformation mode. Under new CEO leadership, we're repositioning from property aggregator to premium intelligence platform—and technology is our competitive advantage.

The Mandate

We need a Chief Technology & Intelligence Transformation Officer (CTITO) to architect and execute a complete technology overhaul. This is not optimization. This is reinvention.

You'll partner directly with the CEO (strategy, positioning, KPIs) and CTO (execution, engineering) to rebuild our technology foundation and embed AI-driven intelligence across every touchpoint.

• Reporting: CEO
• Location: Remote (European time zones) or Rome or Lisbon.
• Type: Full-time, Executive Level
• Start: Q2 2026

What You'll Drive

1. Strategic Transformation (30%)

• Translate business repositioning into concrete technology roadmap
• Transform technology from cost center to growth engine
• Align platform investments with revenue acceleration
• Define AI-native product strategy for premium differentiation
• Present to board and key stakeholders quarterly

2. AI-Heavy Product Pivot (30%)

• Embed AI across the entire value chain:
• Content intelligence: Auto-enrichment, scoring, quality assessment
• Listing insights: Pricing analytics, market trends, comparative intelligence
• Personalization: Smart search, recommendations, buyer-agent matching
• Lead optimization: Scoring, routing, conversion prediction
• Agent tools: Performance dashboards, market reports, content generation

Build differentiated capabilities competitors can't replicate. Establish data as strategic asset through governance, pipelines, ML infrastructure.

3. Architecture Overhaul (25%)

Execute modernization across:

• Cloud-native infrastructure: Scalable, cost-efficient, resilient
• Modular design: API-first, microservices where needed
• Data architecture: Real-time pipelines, warehouse, ML ops
• Performance: Observability, monitoring, optimization
• Technical debt: Structured reduction through phased migration

Rationalize legacy systems. Build for rapid experimentation and premium UX.

4. KPI-Driven Engineering (15%)

Embed business metrics directly into product and architecture:

• Real-time dashboards: traffic quality, conversion, engagement, revenue
• Performance feedback loops between usage and strategy
• Shift from vanity metrics to business-outcome engineering
• Instrumentation and analytics infrastructure
• A/B testing framework for continuous optimization

Who You Are

Experience Required

• 15+ years technology leadership (CTO, Chief Architect, CPO, CDO level)
• Proven turnaround experience: Modernized underperforming digital businesses
• AI/ML productization: Shipped ML-powered products at scale
• Platform modernization: Led cloud migrations, architecture overhauls (€M+ initiatives)
• Marketplace/SaaS background preferred (real estate tech, media platforms, or similar)

Core Capabilities

• Systems architect: Deep expertise in scalable, modern architectures
• AI strategist: Understand ML/AI beyond buzzwords—know how to productize
• Product thinker: Balance technical excellence with business outcomes
• KPI-driven: Obsessed with measurable impact, not just technology elegance
• Leader & executor: Strategic vision + hands-on ability to unblock teams
• Stakeholder manager: Align CEO, CTO, Board, engineering, product

Personal Traits

• Builder with turnaround DNA: You've rescued and rebuilt before
• Comfortable with ambiguity: Thrive in transformation, not steady-state
• Executive presence: Can present to board and inspire engineering teams
• Pragmatic visionary: Bold ideas grounded in execution reality
• Business-first technologist: Revenue and margins matter as much as architecture

Success Metrics (18-24 Months)

Technology Foundation

• Modernized, cloud-native architecture deployed
• Technical debt reduced by 60%+
• Platform performance improved 3x (speed, uptime, scalability)
• Development velocity increased 2x

AI Integration

• AI-powered features driving 30%+ engagement lift
• Content intelligence operational across all listings
• Predictive analytics informing pricing and lead scoring
• Data infrastructure supporting real-time ML models

Business Impact

• Technology directly attributable to revenue growth
• Premium positioning validated through product differentiation
• Key KPIs (conversion, engagement, retention) improved 40%+
• Technology recognized by board as central growth lever

Organization

• High-performance transformation culture embedded
• Engineering and product teams upskilled in AI/ML
• Clear 3-year technology roadmap with quarterly milestones
• Vendor/partner ecosystem optimized

Why This Role is Unique

Scope & Authority

• Shape the future of a globally recognized luxury platform
• Direct partnership with CEO on company strategy
• Executive mandate to redefine technology, data, AI
• Control significant budget and technology decisions

Transformation Scale

• One of the most ambitious AI pivots in luxury digital
• 550k+ properties, 120 countries, 18k+ agencies
• Greenfield opportunity within established brand
• Immediate impact on $M+ revenue business

Career-Defining Opportunity

• Lead a complete platform reinvention
• Build AI-native capabilities from scratch
• Turnaround story you'll showcase for years
• Path to Chief Product & Technology Officer or COO

Compensation & Benefits

Base Salary: Commensurate with experience and track record. We're looking for proven transformation leaders and will compensate accordingly for the right profile.

Bonus: Up to 30% of base tied to transformation milestones and business KPIs (conversion improvement, platform modernization progress, AI feature adoption, technical debt reduction)

• Flexible remote work (office in Rome or Lisbon)
• Technology budget for tools, conferences, learning
• Health insurance (location-dependent)

How to Apply

Send your CV with subject line "CTITO - [Your Name]":

• Resume/CV highlighting leadership experience
• Cover letter (max 750 words) addressing: Your most significant technology transformation and results; How you've productized AI/ML at scale; Why LuxuryEstate's transformation excites you; Your approach to the first 90 days (high-level)

Final Note

This role is for builders who've done it before.

If you want to optimize an existing architecture → this isn't it.

If you want to reinvent a platform at global scale → let's talk.

We're not looking for perfect. We're looking for proven.

Ready to architect the future of luxury real estate intelligence?

Key skills/competency

• Strategic Transformation
• AI Productization
• Architecture Modernization
• KPI-Driven Engineering
• Technology Leadership
• Cloud-Native Infrastructure
• Machine Learning (ML) Ops
• Data Architecture
• Stakeholder Management
• Business Outcome Focus