Fractional General Counsel · Risk Advisor
Calm.
Clear.
In Control.
Outside legal and risk leadership for companies that demand more than a vendor, without the cost of a full-time hire.
Serving middle-market companies with complex operations and real exposure.
Middle-market companies carry enterprise-level risk, with startup-level legal and risk infrastructure.
You're running a $20M–$200M business. Your contracts are complex. Your operations carry real liability. Your insurance program is renewing every year, and you're not sure if you're protected, or just paying premiums.
You need a General Counsel who understands risk financing. You need a Risk Advisor who understands the law. You need someone who has sat across from the insurer, the opposing counsel, and the CFO. Someone who knows how to speak all three languages.
Most companies your size can't justify a $300,000 in-house GC. And most outside counsel doesn't understand your insurance tower. That gap is where deals go sideways, claims get mishandled, and risk goes unmanaged.
"Every day I learn something new: about my client, the law, a business, or myself. I love learning about my clients' businesses and how they work."Brendan Bush · Wisconsin Law Journal
Your Fractional GC & Risk Leader.
Three ways to engage.
Designed for 6 to 8 client companies annually. This is not a retainer for reactive legal work. This is embedded, strategic partnership: a seat at your leadership table, built for the long term.
Foundation
For companies ready to establish a disciplined legal and risk foundation with an embedded advisor.
- Contract review and risk-posture guidance
- Insurance program assessment and annual review
- On-call legal and risk counsel
- Quarterly advisory cadence
- Vendor and supplier agreement support
Partnership
For companies ready for an advisor embedded in their leadership team, across legal, risk, and strategy.
- Contract drafting, review, and negotiation
- Vendor and supplier agreements
- Claims strategy and advocacy
- Insurance program oversight and structure
- Risk financing: captives, alternative structures, program design
- Board and leadership counsel
- Dispute strategy and pre-litigation management
- Ongoing advisory cadence throughout the year
Command
For companies with a specific, high-stakes challenge requiring deep expertise and a defined scope, without an ongoing engagement.
- Contract negotiation and review
- Insurance program restructuring
- M&A risk and legal diligence
- Litigation strategy and pre-suit assessment
- Captive feasibility: independent assessment of fit, structure, and partners
- Scope and pricing defined upfront
The practice is intentionally limited. If you're interested in any engagement level, the first conversation is always the right place to start.
Where law, risk, and operational complexity converge.
Brendan Bush has spent his career at the intersection of two disciplines that most companies treat as separate, and that separation is where problems live.
He began as a commercial litigator at a prominent trial firm in Milwaukee, representing corporations and business owners in complex disputes across federal and state courts nationwide. In that work, he learned something that shapes everything he does today: the outcome of a claim is rarely determined at the point of loss. It is determined long before: in how the contract was drafted, how risk was allocated between the parties, and how the insurance program was structured to respond when something goes wrong.
That litigation career earned national recognition. He was named an Up & Coming Lawyer by the Wisconsin Law Journal, a Rising Star by Super Lawyers four consecutive years (a distinction held by fewer than 2.5% of Wisconsin attorneys) and Top 40 Under 40 by the National Trial Lawyers. In 2013, he became the youngest graduate of the 25th class of the Trial Lawyers College, one of the most selective trial advocacy programs in the country.
The move into risk management and commercial insurance was not a departure from that work; it was the natural next step. The courtroom had shown him exactly where programs fail, where coverage gaps create catastrophic exposure, and where the absence of a coherent risk strategy costs companies far more than any premium ever would. He joined one of the largest independently owned insurance brokers in the country, where he led the firm's property and casualty captive practice.
From the courtroom to the boardroom, that dual experience is what Headwater Counsel LLC is built on. Most outside counsel has never read a captive feasibility study. Most brokers have never drafted an indemnity clause or managed a complex commercial dispute. Brendan has done all of it, at a high level, for companies that couldn't afford to get it wrong.
A record of results.
Three steps to embedded partnership.
Discovery Conversation
A focused, no-pressure conversation to understand your business, your risk profile, and your legal needs. We'll assess fit honestly, on both sides.
Risk & Legal Audit
An initial assessment of your contracts, insurance programs, and risk posture. We'll identify gaps, opportunities, and priorities before any engagement begins.
Ongoing Partnership
Monthly advisory rhythm, on-call access, contract review, risk program oversight, and strategic input, all included in your annual subscription.
The first conversation is always the right place to start.
Whether you're evaluating an engagement, have a specific question, or just want to understand if Headwater Counsel LLC is the right fit. Reach out directly.