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 & A