I help leadership teams in regulated, data-heavy industries go from AI ambition to systems in production. I learn your business fast, take stock of what you already have, build an adoption plan your executives will back — and stay to deliver it.
Leading innovation for Washington DC’s for-hire vehicle regulator and other city agencies
$500M
Largest technology contract I’ve closed, in a career of selling to CIOs and CEOs
385M
Ride-hail trips analyzed to give DC a measured baseline for autonomous vehicle rules
96%
Fewer rides with an unverified driver, within weeks of my automated compliance system going live
+173%
Growth in app-hailed trips in one year after the universal e-hail program I led
Approach
Get inside the business quickly. Then act.
I’ve done this across media, insurance, HR technology, government and transportation. The industry changes; the method doesn’t.
Learn the business
Days, not months. KPIs, data, systems, meetings and the people who run them — until I can explain the operation back to its leaders.
Take inventory
Systems, data, vendors, contracts and constraints, including regulatory ones. Most of the value is already sitting in your data.
Plan adoption
A sequenced roadmap with owners, costs and early wins, built with the executives who fund it and the teams who will run it.
Build and launch
Hands-on delivery: data pipelines, APIs, agentic workflows and internal tools — layered on top of legacy systems instead of waiting years for a rewrite.
Services
Where I help
AI adoption strategy
Where AI pays off in your operation, what it takes to get there, and a roadmap leadership can act on.
Agentic workflows & automation
Custom AI agents and automations for high-volume, high-stakes work — designed, built and put into production.
Enterprise sales & partnerships
Complex deals and partnerships for technical products. I translate the technology into value that executives and agencies will buy.
Data platforms & APIs
Unlock legacy data with APIs and pipelines so new services can launch now, not after a multi-year rebuild.
Regulated markets & government
Rules, data standards and partnerships for new technology, including autonomous vehicles, in transportation and the public sector.
New products & ventures
Concept to launch for new products inside established organizations — from business model to first customers.
Selected work
Proof, not promises
A sample of recent engagements. Most of this work is public record.
Government · Data platform · 2014–present
Building the digital backbone for DC’s for-hire vehicle regulator
For the District of Columbia’s Department of For-Hire Vehicles, I drew up the plan that replaced every analog meter in the city with software: app-based smart meters that report each trip and vehicle position to the city in real time. It is the same kind of platform that ride-hail and autonomous fleets run on. I product-managed the city-sponsored meter for two years and wrote the technical rules every meter and payment provider must meet. I have tested providers every summer since the first approvals in 2017, and in 2018 I developed the 32-point test, from in-vehicle equipment to back-end data, that each must still pass before it is authorized to operate. Today 10 technology providers build on the API platform, and I lead the technical work with their developers across the US, Europe and Asia.
35M metered trips recorded since 201820M+ rides on the digital meter10 technology providers32-point annual provider test
DC requires every driver to be verified before each shift. It had the rule and the data, but no way to see whether the technology companies running the meters enforced it. I designed a system that checks every trip against the driver’s verification record each night and grades each provider A to F. It holds five companies accountable, not thousands of drivers. Fairness rules, such as automatic forgiveness when the city’s own service fails, make the grades defensible. DFHV’s performance team uses the findings in its operating-authority reviews, and providers stay conditionally approved until they fix what the tools surface. I wrote the Databricks SQL and built the working front end, with AI assistance. After one change I directed at the largest provider, verified trips rose from 68–81% to nearly 100% in three days.
Trips driven without verification, average per day, 2026View the data
Period
Trips a day
Mar
759
Apr
732
May
677
Jun
659
Jul
487
Aug
259
Sep
464
Oct 1–17
593
Oct 24– Nov 10
21
Oct 18–23 excluded: system downtime.
1.8M trips graded across five providers137,000 unverified trips flagged in eight monthsFrom about 580 a day to about 20
A toolset that turns raw trip, payment and GPS data into risk signals, next to a live fleet map. One tool finds drivers who start the meter before the ride begins. It scans about 200 million GPS records a month, sent every three seconds by each vehicle, and flags only habitual patterns that hold up in an enforcement conversation. More than 450 drivers are on that report today. I train the agency’s enforcement and legal teams on the tools myself and work closely with its policy team. Legal, policy, complaints, performance and IT staff all work from them.
200M GPS records scanned a month35+ officers and staff700+ vehicles flagged for officers100+ notices of infraction issued
Autonomous vehicles · Policy data
Modeling how autonomous vehicles change a city
I build the data models that compare taxis, ride-hail and autonomous vehicles by time of day, drawing on hundreds of millions of trip records. DC’s regulator and Council staff use them as they write new for-hire and AV rules. I also shape the monitoring and data frameworks behind new legislation, so the rules can be measured once they pass.
385M ride-hail trips analyzedUsed by agency and Council staff
Invention · Civic tech
Roof lights as a civic messaging network
I invented the idea of treating vehicle roof lights as a shared public–private asset: advertising revenue for the industry, plus emergency alerts, Amber Alerts and neighborhood messages for the city. I worked with hardware vendors on prototypes, APIs and connectivity, helped the vendor invent a companion app that handles the messaging logic, so technology providers need no integration work of their own, and ran beta tests with out-of-home advertisers and national sports teams.
1,000+ lights and growing2-year economic impact study under way
Managed a grant program to build universal e-hail across DC’s metered fleet and led the deep integrations between e-hail apps, digital meters and vehicles.
E-hail trips +173% (105K → 287K)16% of metered trips now e-hailed
Bringing Square into regulated in-vehicle payments
When DC moved its fleet to software meters, I brought Square into the city-sponsored meter app, including early work with Square’s developer kit for taking payments inside other apps. It opened a regulated market to a global payments company.
One customer service system for DC’s building regulator
For DC’s Department of Consumer and Regulatory Affairs, now the Department of Buildings, I mapped every department and customer touchpoint, inventoried the systems, wrote the functional specs and steered vendor selection through government procurement. The result was a single system built around customer conversations, from chat to support teams. I also inventoried the agency’s legacy systems and led the plan to open them up with APIs, so new services could be built on top instead of replacing them.
When DC passed protections for properties next to construction sites, I was asked to create an insurance product to match. I called insurance CEOs until I found a willing carrier, then sorted through hundreds of thousands of building-project records so its actuaries could price a low-cost add-on policy for neighbors. I also built the agency’s Insurance Education Center, which DC still runs today.
A building operations platform for a Manhattan condominium
As a board member of a 73-unit condominium, I couldn’t buy software that fixed daily operations, so I built it: mobile ticketing for staff and management, automated board reports, AI that reads and files incoming forms, and an AI assistant that answers questions from the building’s own documents, with a citation for each answer. It runs on Google Workspace with Gemini and Claude, on no new software budget.
In daily use by staff, management and the Board
Before KH²
Operator, not just advisor
Hailo
Co-President, North America
Ran four live markets for the London ride-hailing app (New York, Boston, Washington DC and Atlanta) and readied two more (Miami and Philadelphia), including city and state approvals. In New York, Hailo was part of the city’s e-hail pilot, reporting data to the regulator as the rules were written. Hailo later merged into Daimler’s mytaxi.
Dow Jones
General Manager, Dow Jones Ventures
Hired to invent, build and grow FINS.com, a startup inside Dow Jones built on Wall Street Journal assets: 200% annual growth, 1M+ monthly visitors and 12 sites across the US, Europe and Asia.
Jobster
Chief Revenue Officer
Took a venture-backed SaaS platform from launch to $8M in first-year sales, signing 15% of the Fortune 100 in year one.
Yahoo!
VP Sales, Enterprise Services
Built an enterprise software business to $28M in recurring revenue across 300+ Fortune 1000 accounts in 23 countries.
Selected clients
About
Kevin Hatfield
I wrote my first BASIC programs in third grade, interned at Apple in college and moved to Silicon Valley after USC. Early on I closed technology deals worth up to $500 million with CIOs who told me I understood their operations better than they did. That’s still the job: get inside an organization quickly, see what it really runs on, show the people in charge a better way — and then build it.
Since 2014 I’ve run KH² Consulting, working across transportation, government, insurance, media and venture-backed startups, including more than a decade leading innovation for Washington DC’s for-hire vehicle regulator and work with New York City’s TLC on the evolution of its technology and data platforms. Before that I co-led North America for Hailo, built FINS.com inside Dow Jones, and led revenue teams at Jobster and Yahoo!.
Today most of my work is AI: helping leadership teams decide where it pays off, and building the agents, data pipelines and tools that make it real. Early in my career I helped large companies turn their assets and relationships into new internet businesses. AI is that wave again. Clients describe me the same way: I explain complex technology in terms everyone can understand, then I build it.
BS, USC Marshall School of Business · UC Berkeley Executive Education, AI: Business Strategies and Applications · Databricks, AI Agent Fundamentals · Based in New York City
Contact
Tell me what you’re working on.
A new AI initiative, a legacy system that’s holding you back, or a launch in a regulated market — I’m glad to talk it through.
KH² Consulting
