Ashley Wilson
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AI consulting, fractional work, advisory, speaking, partnerships, or podcasts.

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Ashley Wilson · AI strategy and implementation · Operator · Founder

I help businesses put AI to work.

Cutting-edge tools. Teams that pull together. Process that works.

Twenty years building and scaling companies. Now I build with AI. Small projects for owners who want a level up. Long transformations for companies that want an expert at the helm. First products for founders ready to launch.

See the work ↓ Book a meeting ↗
20+ yrsBuilding and scaling companies
HarvardDistinction · Pitch Competition Winner
Insurtech400+ Agent Partners
AI EthicsSpeaker
2M+Organic views on $200 of ads
01
Who I help

Three kinds of client. One way of working.

The scale changes. The method does not.

Small business owners

A level up.

You run the business and you know what slows it down. I take one process, such as quoting, scheduling, follow-up or content, and make it faster with AI.

  • AI consulting by the project, fixed scope
  • Weeks, not quarters
  • Tools your team runs without me
How payment worksBy the hour, or a set rate for the project.
Established companies

Transformation, with an expert at the helm.

For companies ripe for digital transformation. I lead long-term work as a consultant or fractional COO: choose the right problems, build the systems, and bring the organization along.

  • Large, long-term engagements
  • Fractional COO or program lead
  • A subject-matter expert leading the work
How payment worksBy the milestone, priced to the complexity of the work.
New founders

Make it real.

You have the idea and the conviction. I get you to a working product, a plan to sell it, and a clear view of what launch will take.

  • Prototype to first customers
  • Go-to-market and capital plan
  • Advisory after launch
How payment worksA combination of equity, a board seat and cash.
02
Selected work

Browse the work.

Insurance, distribution, safety, media and legal tech. Different industries, the same job: take a tangled, high-stakes process and make it run.

1ParallelTurns a posted construction bid into an order-ready materials list.DistributionUnstructured plan sets into structured orders→ 2GroundworkTakes an insurance founder from an idea to a fileable program.InsuranceRegulation, pricing and capital in one model→ 3StormlineTurns a hail forecast into priced exposure, verified damage and routed adjusters by morning.InsuranceForecast to loss to claim in one map→ 4TailgateTurns a job said out loud in the truck into a priced quote before the driver is off the highway.TradesMessy speech into a priced quote→ 5HarborLets a person keep a private, timestamped record from their phone.SafetyPrivacy and record integrity at consumer scale→ 6FlywheelTurns one long-form piece into a week of social, then learns from it.MediaMulti-channel content operations on a closed loop→ 7TandemTurns a family's scattered records into a timeline a professional can verify.Legal techMessy records into a verifiable timeline→ 8NapkinTakes an idea on a napkin to a working booking tool, a launch kit and a simulated launch.Go to marketFrom a sketch to an MVP to a launch→ 9HandoffPuts every air traffic facility on one live board, so a report at one tower reaches all of them in a second.Public sectorSiloed facilities onto one shared picture→
1

Parallel

Turns a posted construction bid into an order-ready materials list.

The hard partPlan sets run to hundreds of pages of drawings, schedules and specs that rarely agree. Parallel reads them, maps every line to the catalog, and sends a person only the lines it cannot prove.

Open the demo →
2

Groundwork

Takes an insurance founder from an idea to a fileable program.

The hard partLicensing, filing rules, pricing and capital differ by line and by state. Groundwork holds them in one model, so the rater, the filing and the raise always agree.

Open the demo →
3

Stormline

Turns a hail forecast into priced exposure, verified damage and routed adjusters by morning.

The hard partTwenty-one forecasts, a hail swath measured by stone size, and thousands of policies, each with its own value and roof. Stormline turns them into one loss number that moves in real time against the reinsurance retention, then carries the worst roofs through drone inspection, an estimate sent by API and a morning adjuster route. From idea to prototype in one morning.

Open the demo →
4

Tailgate

Turns a job said out loud in the truck into a priced quote before the driver is off the highway.

The hard partA driver can't look at a screen, and speech comes in messy. Tailgate pulls the customer, the unit size, the options and the discount out of one run-on sentence, then prices them against preset rules so the quote is ready to send. Try it with your own voice.

Open the demo →
5

Harbor

Lets a person keep a private, timestamped record from their phone.

The hard partThe record has to stay discreet on the device, hold up when it is needed, and work for someone under stress. Encryption, AI transcription and translation, owner-controlled release, and a consumer and B2B business around it.

Open the demo →
6

Flywheel

Turns one long-form piece into a week of social, then learns from it.

The hard partFive channels, each with its own format and timing, plus images, approvals and partner payouts. One loop runs all of it and feeds the results into next week's picks.

Open the demo →
7

Tandem

Turns a family's scattered records into a timeline a professional can verify.

The hard partThousands of messages, documents and receipts in every format. Each fact is extracted, dated, tied to its fingerprinted original, and checked for what is missing.

Open the demo →
8

Napkin

Takes an idea on a napkin to a working booking tool, a launch kit and a simulated launch.

The hard partA sketch isn't a spec, and an MVP nobody hears about isn't a business. Napkin shows the whole trip in one place: every hand-drawn shape becomes a working part of the tool, and the tool comes with the page, the launch kit and the plan to sell it. Try booking a seat.

Open the demo →
9

Handoff

Puts every air traffic facility on one live board, so a report at one tower reaches all of them in a second.

The hard partMore than 400 U.S. facilities each keep their own copy of the weather, the outages and the pilot reports, and news moves between them by phone. Handoff maps 567 real towers, approach controls and centers from FAA data, ties them into one network, and shows the same report travelling both ways: by phone today, and on a shared board. Report wind shear and watch it cross the country.

Open the demo →

All nine run on sample data, and the client work is white-labeled. Open one and use it.

03
Approach

How the work gets done.

Tools

Cutting-edge, on purpose.

I build with the newest AI models and tooling, and I know which are ready for production and which are still a demo.

People

Teams brought together around innovation.

New technology fails when people are not with it. I put owners, operators and engineers in the same room and on the same plan.

Process

Process that works.

Every build ships with the process around it: who reviews, who owns it, and how it keeps running after I leave.

Ashley Wilson
04  Background

Some people see a gap. I build what fills it.

I built a direct-to-consumer insurance program from scratch, from underwriting to scale, and a multi-line program business with more than 400 agent partners. Then I founded a consumer safety platform and grew it to two million views on two hundred dollars of ad spend. I build the product and I run it.

400+Agent partners
Multi-line program business
D2CBuilt from scratch
Underwriting to scale
2MViews for a product I founded
On $200 of ad spend
125KLikes on the same launch
14K followers and growing
05  Speaking

Put me on your stage.

Keynotes, panels, podcasts, workshops, virtual or in person. Tell me about your event and I'll get back to you personally.

AI EthicsWomen in TechWomen's SafetyInsurance InnovationHypergrowth ScalingAI in Production

Goes straight to ashley@jawanalytics.com. Usually a reply within 48 hours.

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Start something

Book a call and bring the hard problem.

AI consulting, fractional work, advisory, speaking, partnerships, or podcasts.

Chat with Ashley for free ↗Invite me to speak