Operator-led advisory · Insurance · AI · Public sector

From the mesa to the coast, we’ve run it.

Judgment for the moments you can’t afford to get wrong, from a former state insurance regulator and CEO who has sat on both sides of the table.

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25 yearsinsurance, technology, government
Former regulatorNM Office of Superintendent of Insurance
Former CEO500+ agency and agent network
FedRAMP Class CAI platform certified 2026
40+regulatory bodies briefed on AI

Five ways we help

One senior operator, five practice areas. Every engagement is led by Heather, start to finish.

Regulatory Strategy & Compliance

Stay in good standing with your regulators, and be ready when they call.

For example: a market-conduct exam on the calendar, or complaints climbing 02

AI Strategy & Governance

Know where AI will, and won't, move the needle, then put it into production under controls a regulator would accept.

For example: a vendor pitch you want a second opinion on 03

Crisis & Turnaround Leadership

Interim, hands-on leadership when the business is under real pressure.

For example: a carrier exit, a sudden departure or a cash-flow crunch 04

M&A Transition Support

Pre- and post-close support from someone who has integrated an acquisition as CEO.

For example: diligence before you sign, or the first 100 days after 05

Major Initiatives & Modernization

Senior oversight for the complex initiative your team can't run while running the business.

For example: a system replacement, a state expansion, or retiring the spreadsheet everyone secretly hates

Proof, not theory

Results from the operating seat and the regulator’s side of the table.

01Cut combined state DOI and carrier consumer complaints 80% with a compliance program built from scratch.
02Uncovered an industry-wide ACA fraud pattern, co-presented it to the NAIC, and wrote the data call commissioners used.
03Led an AI platform through the FedRAMP 20x pilots to Class C (Moderate) certification.
04Briefed commissioners and staff at 40+ state and federal regulatory bodies on AI governance.
05Led several hundred employees and a 500+ agency and agent network, and expanded into seven new states.
06Kept agencies and policyholders whole when carriers exited states or discontinued products.
07Spoke for New Mexico's insurance regulator through wildfire and flood response and public rate hearings.
08Took an AI company from concept to revenue. U.S. patent co-inventor.

See the full track record →

Who we work with

The discipline doesn’t change. The scale does.

Insurers, MGAs & agencies

Regulated distribution, run right

Compliance, carrier relations, licensing and growth from someone who has run a 50-state MGA and FMO.

Public sector & regulators

Change that survives scrutiny

AI governance, pilots and procurement designed for public records requests, hearings and audits.

Small & mid-sized businesses

Budget-aware, vendor-honest

Independent advice on AI and operations, sized to what you can actually spend.

Large & enterprise organizations

An outside operator’s judgment

Interim leadership and senior capacity for crises, transitions and major initiatives.

Why organizations choose Lost Tree

Both sides of the table

Former state insurance regulator and former CEO. We know what regulators look for because we’ve been the regulator, and we know what it costs because we’ve run the P&L.

Fixed fees up front

Scoped, written pricing before work begins. No open-ended billing, no surprise invoices.

Every relationship disclosed

Independent advice. If we have any relationship with a vendor we recommend, including a referral fee, you’ll know in writing before you decide.

“You don’t hire us for a slide deck. You hire us because you need someone who has run the business before.”

Heather Widler, Founder & Principal

From the blog

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For SMBs

Not sure where to start?

Book a free 20-minute call. You'll get a candid read on whether, and how, we can help.

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