What does Lost Tree Consulting do?
We’re an operator-led advisory practice with five practice areas: Regulatory Strategy & Compliance, AI Strategy & Governance, Crisis & Turnaround Leadership, M&A Transition Support, and Major Initiatives & Modernization.
Who leads the work?
Heather Widler, our founder, leads every engagement herself. She is a former state insurance regulator and the former CEO of Entratus AI and Insurance Care Direct.
Do you work with insurers, MGAs and agencies?
Yes. Insurance distribution is our home turf: compliance programs, carrier audits, DOI inquiries, licensing, carrier exits and new-state expansion.
What does a regulatory engagement cost?
Most start with a Regulatory Readiness Assessment, from $7,500 over three weeks. Compliance program builds and ongoing oversight are scoped individually as a fixed fee or retainer.
Do you work with large or enterprise companies?
Yes. Crisis and turnaround, M&A transition and major initiative work often involve larger private companies and enterprise business units.
How much does AI consulting cost for a small business?
Most small business engagements start around $4,500 for an AI Readiness Snapshot and $12,500 for a full roadmap and vendor match. Ongoing implementation support runs from $6,000 per month.
Do you sell AI software, or are you independent?
We don’t sell software. Our recommendations are built around your requirements.
Do you take referral fees from vendors?
We always disclose. If we have any relationship with a vendor we recommend, including a referral fee, you’ll know in writing before you decide.
Are you affiliated with any AI company?
Yes, and we say so up front. Heather is a founding shareholder and strategic advisor of Entratus AI. If Entratus AI could be relevant to your needs, we disclose that relationship in writing, and we’ll always show you independent alternatives.
Can you help our agency with an AI-related RFP or pilot?
Yes. Heather has led an AI platform through the FedRAMP 20x pilots to Class C certification, and helped write and run multi-million-dollar CMS grants at a state insurance regulator.
We don’t have an IT department. Can you still help?
Yes. Most small businesses don’t have dedicated IT or data teams. We explain everything in plain language.
How long does an AI readiness assessment take?
Typically two to three weeks from kickoff to delivery, depending on the size of your organization.
Is our data safe with you?
We sign mutual confidentiality agreements before any engagement begins, and we limit our review to the workflows and information the work requires.
Do you work outside Florida?
Yes. We’re based in Melbourne, Florida and work with clients nationwide, mostly by video.
What if AI isn’t right for us yet?
That’s a legitimate outcome, and we’ll tell you plainly if that’s what the assessment shows.
Still have a question?
Book a free 20-minute call. You'll get a candid read on whether, and how, we can help.