Retail · Financial services · Fintech · Insurtech · Healthcare · IT

Jean Pierre
Quesada Castillo

Fractional C-Level in Artificial Intelligence, Technology and Project Portfolios

I turn board strategy into technology and artificial intelligence in production, with measurable results for retail, financial services, fintech, insurtech, healthcare and technology companies across Latin America.

Let’s talk about your next AI result Discover Ait
Jean Pierre Quesada Castillo
Chief AI OfficerCIO · jeanquesada.ai
Two MBAs George Washington University · MIT · INCAE CIO/CDTO of the Year 2024 · CIONET Central America Nominee Founder of 5 technology companies President, CIONET Costa Rica
Measurable impact
91%+

Project effectiveness, sustained year over year

Pending validation
100+

Technology projects per year

Pending validation
98%

Development delivered in-house

Pending validation
22+

Years in technology, 17 in executive leadership

Career

22 years building technology, 17 from the executive suite

  1. 2021 — present
    Grupo Monge · 6 countries

    VP & CIO · CDTO · Chief AI Officer

    >91% project effectiveness year over year; AI agents in production. Pending validation

    Regional leadership of IT, artificial intelligence, digital marketing, ecommerce and business intelligence strategy for retail and financial services in Costa Rica, Nicaragua, Honduras, Guatemala, El Salvador and Peru.

    AIITRetailFinancial servicesFintech
  2. 2025 — present
    Ait · Spin-off

    Founder & Chief AI Officer

    Ait Coach and Ait Cobros in market. Pending validation

    Brings the experience of implementing AI at scale to the regional market: AI strategy, custom products, implementation and AI PMO.

    AIProjects
  3. 2018 — 2021
    Grupo Monge · 6 countries

    VP & CIO · Regional IT Director

    Key result Pending validation

    Regional information technology leadership for retail and financial services in six countries.

    ITRetailFinancial services
  4. 2015 — 2021
    MAPO PMO

    Founder

    Key result Pending validation

    Project management services in Costa Rica, Central America, Peru and the United States.

    ProjectsEPMO
  5. 2011 — 2016
    Cloud & IT Consulting Services · Lógica Máxima Digital

    Founder

    Key result Pending validation

    IT consulting, software development and implementation, and technology project management in healthcare, mobile payments, insurance and ERP. Deputy general manager and regional operations manager (Central America and Panama) for a healthcare software company.

    HealthcareFintechInsurtechIT
  6. 2004 — 2011
    Dos Pinos · Costa Rica, Central America and Panama

    CTO · Information Technology Manager

    Key result Pending validation

    From IT project manager to head of infrastructure and operations, then regional CTO.

    ITManufacturing
Full career on LinkedIn →
Services

C-Level leadership when your company needs it, without the overhead of a full-time hire

Artificial Intelligence

Fractional Chief AI Officer

For companies that want to move from isolated pilots to AI in production with business impact.

  • AI strategy and roadmap tied to results
  • Prioritized portfolio of use cases
  • Governance, risk and adoption of AI agents
Technology

Fractional CIO / CTO

For organizations that need senior technology leadership through growth, transformation or transition.

  • IT strategy aligned with the business
  • Architecture, platforms and vendors
  • Regional digital transformation
Project Portfolios

EPMO Leadership

For companies with many initiatives and little certainty about which ones deliver value.

  • Portfolio governance and prioritization
  • Effectiveness metrics and executive tracking
  • AI PMO for artificial intelligence projects

Need it implemented? Ait, the company I founded, builds and deploys the AI solutions: custom products, agents and forward-deployed engineers.

Discover Ait
Ventures

Companies I founded to bring this experience to market

Ait
AI solutions with real impact

A spin-off that brings the experience of implementing artificial intelligence at scale to market, focused on business units.

Ait CoachConversational AI coaching
Ait CobrosAI-powered collections
AI strategy and productsRoadmap and custom solutions
AI implementation and PMOForward-deployed engineers and project management
goait.ai →
Ventures founded
  • AIAit
  • PMOMAPO PMO
  • IT consultingCloud & IT Consulting Services
  • HospitalityDivino Boutique Hotel & Restaurant
Speaking & recognition

Sharing the experience on stages across the region

2024 · CIONET Central America
CIO/CDTO of the Year · NomineeTechnology and digital transformation leader of the year, Central America
2024 · UTEC Graduate School, Peru
Expert faculty, Chief Technology Officer ProgramUTEC’s first CTO program, in collaboration with NTT DATA
2022 · Yalo Conecta
Pioneers in conversational commerce in Latin AmericaRecognition awarded to Grupo Monge
Jean Quesada at VeeamON Tour 2024
VeeamON Tour 2024 · San JoséPanelist: resilience, recovery and data protection
Jean Quesada at LATAM CISO Summit 2024
LATAM CISO Summit 2024International cybersecurity panel
Jean Quesada at Adobe CXM Forum 2022
Adobe CXM Forum 2022Success story: data, audience and conversion
Jean Quesada at Yalo Conecta 2022
Yalo Conecta 2022Transforming retail and financial services
Jean Quesada at CX4Future
CX4Future 2023 · Adobe and OMNI.PROTransforming customer experiences
Jean Quesada at Live case 2020
Live case 2020 · Virtual assistant AnaFirst WhatsApp payment channel in Central America

2025 · CIONETRegional webinar "CIOs leading with AI: from strategy to impact"

Contact

Let’s talk about your next result with AI

Direct conversations with boards, CEOs and business teams who want to take artificial intelligence from strategy to production.

WhatsAppMessage now→
Emailjean@jeanquesada.ai
LinkedInJean Quesada Castillo→ Aitgoait.ai→