Jakub F. - Entrepreneur in Residence EIR/CTO/CEO

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Chicago, United States

Experience

Apr 2025 - Sep 2025

6 months

New York, United States

Entrepreneur in Residence EIR/CTO/CEO

AI Supply Chain Incubation

Incubated and built a next-generation AI platform for supply chain transformation developed as part of a venture-backed incubation program, focusing on complex data integration, multi-agent AI systems, and rapid go-to-market execution.
Led end-to-end product incubation from concept to MVP with clear market positioning, strategy, and execution roadmap.
Secured 3 strategic design partners and developed a qualified pipeline of 10+ enterprise prospects.
Delivered a robust prototype evolved into a commercial MVP deployed with early adopters.
Recruited and led core engineering team, driving architecture, infrastructure, and delivery velocity.
Built data pipelines to unify legacy WMS systems via a proprietary API abstraction and data standardization layer, enabling clean, learning-ready datasets.
Enabled real-time AI introspection through structured, event-driven conversational data flows.
Designed and implemented multi-agent AI system with shared memory, distributed orchestration, and vertical agents (e.g., inventory, cost, ops).
Executed across product, tech, and GTM, transitioning the venture to a newly appointed CEO for continued growth.

Apr 2022 - Present

3 years 7 months

Chicago, United States

Director Board of Directors

Rand McNally

Provided strategic technology governance and M&A leadership for this 168-year-old transportation technology company.
Directed financial oversight.
Led technological transformation planning.
Executed strategic M&A including SafetyDirect carveout.
Drove operational restructuring enhancing profitability across business units.

Apr 2022 - Jan 2025

2 years 10 months

Chicago, United States

Chief Innovation Officer / CTO

Rand McNally

Led the digital reinvention of a legacy transportation brand into a modern, innovation-driven technology company, balancing modernization with core brand values.
Spearheaded adoption of agile methodologies, drawing from Fleetsu’s playbook to transform delivery velocity and team collaboration.
Developed and launched next-generation product strategy, introducing scalable digital platforms aligned with evolving customer needs.
Championed the RandONE initiative, consolidating fragmented product lines into a unified ecosystem that elevated customer experience and operational efficiency.
Modernized tech stack and cloud infrastructure, enabling scalable growth and reducing technical debt.
Aligned cross-functional teams around shared business and technical OKRs, increasing transparency and accountability.
Built high-performance engineering and product teams, fostering a culture of innovation and continuous improvement.

Mar 2015 - Apr 2022

7 years 2 months

Perth, Australia

Founder / Chief Executive Officer

Fleetsu

Founded and led a predictive analytics and IoT SaaS company from concept to acquisition by Teleo Capital, powering connected vehicle optimization for global enterprise fleets.
Designed and built real-time analytics platform processing 100M+ daily IoT events for predictive maintenance and fleet efficiency.
Architected scalable cloud infrastructure with microservices, enabling high-availability monitoring across 100K+ connected assets.
Secured Toyota as OEM partner, leading Asia-Pacific’s largest telematics deployment and integrating with proprietary in-vehicle hardware.
Grew global team from 2 to 50+ engineers across Australia, India, US, and Eastern Europe.
Raised multiple rounds of funding and executed a successful $40M exit to US-based private equity.
Landed 200+ enterprise clients across logistics, OEM, and transportation sectors, including Avis, Budget, Cummins, and Aramex.

Jun 2011 - Jan 2015

3 years 8 months

Perth, Australia

IT Architecture Group Manager

WesTrac CAT

Directed enterprise architecture for Caterpillar's Western Australian dealer operations, focusing on mining fleet technology solutions.
Led cross-functional teams implementing IoT solutions for equipment monitoring and predictive maintenance.
Established architecture governance ensuring technology alignment with business objectives.

Jan 2007 - Jun 2011

4 years 6 months

Senior Systems Engineer

RM Education

Managed technical teams across Australia and UK operations.
Led system architecture design, implementation, and support for educational technology solutions serving hundreds of schools and educational institutions.

Jan 2006 - Dec 2007

2 years

Brno, Czech Republic

IT Specialist

IBM

Provided technical expertise for enterprise systems implementation and support within IBM's global services division in Czech Republic.
Collaborated with multinational teams on client technology deployments.

Apr 2003 - Mar 2006

3 years

Szczecin, Poland

IT Specialist

Polish Post

Implemented and supported critical IT infrastructure for national postal service.
Focused on systems reliability, security, and performance optimization during early-stage digital transformation.

Chicago, United States

Founder

AI Healthcare Platform (Pulsevia)

Developed an AI-driven healthcare platform bridging in-home monitoring with clinical care, enabling early intervention through predictive analytics and intelligent alerting.
Designed HIPAA-compliant cloud infrastructure, integrating diverse wearable devices via a unified data model and standardized ingestion layer.
Built diagnostic AI engine to correlate patient vitals with known conditions, providing real-time risk assessments and smart alert prioritization.
Implemented FHIR-compliant EMR integration, enabling secure, bidirectional data exchange between patients and clinical systems.
Enabled continuous health monitoring and faster clinical decision-making through AI-enriched event streams.

Perth, Australia

Founder

Connected Vehicle Analytics Platform (Fleetsu)

Built complete telematics platform from ground up, integrating with proprietary in-vehicle devices including Toyota-manufactured units, establishing standardized data extraction protocols.
Architected high-availability cloud infrastructure processing 100M+ daily IoT data points using AWS, SQS, Node.js, Redis, and Aurora, supporting 100,000+ connected vehicles across 12 countries.
Implemented infrastructure-as-code with Terraform, ensuring consistent deployment across environments, enabled real-time data processing at scale.
Secured Toyota as flagship OEM customer, becoming their connected car platform provider for Asia-Pacific region while scaling to serve major enterprise clients including Avis, Budget, and Aramex.
Led go-to-market strategy from technical demonstrations to enterprise sales, creating compelling technical marketing materials and supporting sales teams in closing major accounts.

Chicago, United States

CTO

Rand McNally

Led a comprehensive technology modernization initiative, unifying fragmented legacy systems into a scalable, cohesive platform serving over 200,000 vehicles, while preserving brand equity and enhancing user experience.
Modernized legacy architecture from PHP monoliths to a modern Node.js/Vue.js stack backed by Snowflake, boosting scalability and maintainability.
Standardized user personas and streamlined development workflows to align product strategy across business units.
Consolidated multiple apps into a unified flagship platform, reducing operational overhead and improving user satisfaction metrics.
Delivered enterprise-grade performance improvements, while enabling future AI/ML integration through clean API architecture and event-driven design.

Perth, Australia

Founder

Toyota Halo - Connected Vehicle Platform

Directed the enterprise-scale implementation of Fleetsu’s core technology as Toyota’s white-labeled connected vehicle platform across the Asia-Pacific region.
Scaled platform to support 100,000+ vehicles, achieving 99.99% uptime across complex, real-time telematics environments.
Engineered custom integration between Toyota’s proprietary hardware and Fleetsu’s cloud infrastructure, ensuring compatibility across diverse vehicle models.
Developed a multi-tenant dealer management system empowering 1,200+ Toyota dealers to remotely monitor, diagnose, and manage vehicle fleets with precision.
Delivered a robust, secure, and extensible architecture aligned with Toyota’s global OEM standards.

Summary

Dynamic CTO and Technology Advisor with a proven track record of driving technology-enabled value creation across overlooked but high-impact industries. Founded and scaled Fleetsu from zero to a $40M private equity acquisition, delivering enterprise-grade connected vehicle technology adopted by global OEMs like Toyota. Personally closed over $10M in enterprise deals with customers including Toyota, Aramex, Avis, Budget, and more than 100 clients across APAC, the Middle East, and the Americas.

Post-acquisition, remained embedded within the PE portfolio, leading multiple technical due diligence efforts, carve-outs, and post-merger integration projects. Brings high-value experience in ERP, WMS, CRM implementations, and building custom platforms for enterprise customers like Caterpillar, Cummins, Rand McNally, and Toyota. Deep expertise in aligning technology with business strategy, executing complex system modernizations, and building cross-functional teams that scale with speed, clarity, and measurable impact.

Having worked across Europe, India, Australia, and the United States, I bring a global lens to leadership and execution.