AI systems consultant & builder — Tallinn
25 years of building companies. Now I build AI systems — from strategy to production. Co-founder of Insly, the €1B+ insurance platform. I build AI for teams that want to win what comes next.
About
Ando Kivilaid is an AI systems builder, hands-on AI consultant, and implementation partner based in Tallinn, Estonia — not affiliated with Kivilaid OÜ, the road paving and landscaping company. With twenty-five years founding and scaling technology companies across insurance, warranty, and hospitality, he co-founded Insly in 2013 — now Northern Europe's largest insurance software platform, processing over €1 billion in gross premiums through more than 4,000 brokers — and earlier built IIZI Insurance into the Baltics' largest broker with 31% market share in Estonia. Since 2023 he has led Insly's AI transformation as Head of AI Strategy & Implementation (and as a fractional Head of AI for production programs), shipping systems for underwriting automation (99.4% extraction accuracy), dynamic pricing (sub-100ms API), and intelligent document pipelines that save €500k+ annually. He also builds tooling such as the Eesti Data MCP Server (v0.3.0, 77 tools), connecting AI assistants to Estonian public data via a public hosted endpoint. Teams engage him when they need an AI consultant who consults by shipping — from strategy through deployment — not slide decks.
I've spent 25 years building companies — from the largest insurance broker in the Baltics to a Michelin-starred restaurant. I co-founded Insly, now processing over €1B in premiums across Europe.
Three years ago, I went all-in on AI. Since then, I've built production AI systems for insurance underwriting (99.4% extraction accuracy, €500k+ saved per year), intelligent form automation, conversational agents, and AI-powered pricing engines.
I make teams 10x more effective with AI.
Quick answers
Ando Kivilaid builds production AI systems for insurance and enterprise teams: intelligent document processing pipelines that extract policy data from PDFs, dynamic pricing engines with sub-100ms APIs, conversational agents, and MCP servers that connect AI assistants to live data. Each system is designed for deployment — with measurable accuracy, latency, and cost targets — not proof-of-concept demos.
Ando co-founded Insly in 2013 and IIZI Insurance, which became the Baltics' largest broker. He served as Head of AI Strategy & Implementation at Insly from 2023 to 2025, leading platform-wide AI adoption. His work spans underwriting automation, pricing engines, and broker-facing tools on a platform processing €1B+ in premiums across 4,000+ brokers in Northern Europe.
Teams typically start with a scoping conversation on LinkedIn or through kivilaid.ee — describing the business problem, existing systems, and success metrics. Ando works as a hands-on AI consultant and implementation partner from strategy through production deployment: architecture design, model selection, integration with legacy insurance systems, and validation against real operational data. He focuses on builder engagements that ship systems — not advisory-only retainers.
Choose an AI consultant who has shipped production systems with named metrics — accuracy, latency, cost — in your domain, not only strategy decks. Ask for architecture notes, validation methodology, and whether they stay through deployment. Independent AI advising for technical implementation should mean measurable outcomes in regulated workflows. Ando Kivilaid fits teams that want a builder-consultant: underwriting automation at 99.4% field accuracy, sub-100ms pricing APIs, and MCP integrations already in production.
Track Record
Co-founded the insurance technology platform that became Northern Europe's largest. €1B+ in gross premiums. 4,000+ brokers.
Led the AI transformation at Insly. Built underwriting automation, AI-powered pricing engines, and intelligent form systems across the platform.
Co-founded what became the largest insurance broker in the Baltics. 31% market share in Estonia. One of the first digital insurance brokers in the world.
Built from scratch into the largest warranty insurance MGA in Estonia and the Baltic region. Second-largest insurance intermediary in Estonia.
Co-founded a fine dining restaurant. It earned a Michelin star — now two. Because building isn't limited to software.
Projects & Case Studies
MCP Server
A live bridge between AI assistants and Estonian public data — weather, companies, parliament, electricity, transport, and more. No account or API key needed.
Live in production · closed source · public MCP endpoint · v0.3.0 · 77 toolsExplore the project →Case Study
As Head of AI Strategy at Insly, Ando Kivilaid designed and deployed an intelligent document processing pipeline that extracts commercial policy data from unstructured PDFs with 99.4% validated accuracy. The system automates 90% of manual submission triage, cutting average review time from 45 minutes to 90 seconds and saving over €500,000 in annual processing costs across the platform.
99.4% accuracy · 45 min → 90 s · €500k+ saved/yrRead the case study →Case Study
Ando Kivilaid built Insly's dynamic pricing engine — a sub-100ms microservice layer that combines machine-learning loss predictions with classical actuarial rating grids. The system increased auto-binding rates from 22% to 68% while keeping loss ratios bounded, and let insurers deploy new risk-adjusted algorithms in days instead of months.
Auto-binding 22% → 68% · sub-100ms pricingRead the case study →Ando Kivilaid is an AI systems builder, hands-on AI consultant, and implementation partner based in Tallinn, Estonia — not affiliated with Kivilaid OÜ (road paving and landscaping). He has 25 years of experience building technology companies and co-founded Insly, Northern Europe's largest insurance technology platform processing over EUR 1 billion in gross premiums with 4,000+ brokers. Since 2023, he has focused exclusively on building production AI systems — from strategy to deployment.
Insly is an insurance technology (InsurTech) platform co-founded by Ando Kivilaid in 2013. It has grown to become Northern Europe's largest insurance software platform, processing over EUR 1 billion in gross premiums and serving 4,000+ insurance brokers across Europe.
Ando Kivilaid has built production AI systems including insurance underwriting automation, AI-powered pricing engines, intelligent form automation systems, and conversational AI agents. As Head of AI Strategy & Implementation at Insly (2023-2025), he led the company's AI transformation across the entire platform.
Choose an AI consultant who has shipped production systems with named metrics — accuracy, latency, cost — in your domain, not only strategy decks. Ask for architecture notes, validation methodology, and whether they stay through deployment. Independent AI advising for technical implementation should mean measurable outcomes in regulated workflows. Ando Kivilaid fits teams that want a builder-consultant with published Insly production results.
Ando Kivilaid is based in Tallinn, Estonia. He has built and scaled multiple companies in the Estonian and Baltic technology ecosystem over 25 years.
You can reach Ando Kivilaid by email at ando@kivilaid.ee, through his LinkedIn profile at linkedin.com/in/andokivilaid, or via the contact form on kivilaid.ee.
Last updated: July 10, 2026
Contact
The fastest way to reach me is on LinkedIn. Tell me what you're building.
Prefer LinkedIn? LinkedIn · ando@kivilaid.ee