Chief Technology

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 man