Bridgehead Prepared for Amy at The Estate Lawyers
The Estate Lawyers For Amy

Estate Litigation Attorney: A 90-Day CTO Plan

Amy, here’s your new Director of Operations and Technology’s first 90 days. What to fix first, where AI pays off soonest, and what the hire should own.

If the Director of Operations and Technology seat can stay open another quarter, ignore this. If it can’t, the next two minutes are worth it.

What we noticed

A 4.8 rating across 104+ Google reviews, more than 20 years since you founded the firm, and a site that already says AI is part of how the firm runs.

Your Director of Operations and Technology posting went up on November 3, and it asks one person to build the roadmap, run every approved project, raise the standard in each department and prepare new offices and acquired teams for day one.

  • Your own service Probate and trust litigation across Irvine and San Diego, including work for other estate planning firms that need a litigation department. theestatelawyers.com
  • Your data Every inquiry arrives through a form with a Referral ID, and every case produces dates, filings and billing. That is the data a baseline and a dashboard are built from. Contact page
  • Your team Attorneys, paralegals, a Director of Operations, a Director of Marketing and Business Development and an office manager. The posting adds a leader over operations and technology together. About page
  • Your tech Your site says AI is already part of how the firm responds to clients, and your posting names EOS and Ninety.io as the operating system you run on. theestatelawyers.com

Seen in your stack: Microsoft 365 · EOS · Ninety.io · online scheduling · contact forms with Referral ID

What your posting asks for

  • “Build and maintain written 12–24 month roadmap: each initiative states the problem, expected benefit, proposed owner, estimated cost, dependencies, and timing.”
  • “Maintain an inventory of all software tools: costs, contract renewal dates, business owners, and actual use. Identify duplicates, unused licenses, and unnecessary subscriptions.”
  • “Before any major project launches, establish baseline data: current costs, error rates, time spent, and performance benchmarks.”
  • “Require each department leader to name an owner who maps current steps, improves the process, writes SOPs and checklists, and trains the team.”
  • “Build and maintain a reusable integration plan covering physical infrastructure, staffing, systems, billing, files, and training — with a department owner and deadline for each component.”
  • “Hold outside IT providers and technology vendors to agreed scope, cost, service standards, and timelines.”

From your Director of Operations and Technology posting, posted November 3, 2026.

What changes for your new Director of Operations and Technology

Your new Director of Operations and Technology starts with a plan: the operations and software to fix first, where AI saves your paralegals and attorneys time soonest, and a clear line between what they own and what a fractional lead can carry while they settle in.

Your new Director of Operations and Technology’s first 90 days

Three phases, each item with the reason it’s there and where that came from.

Days 1 to 30

Assess and baseline

  1. 1
    Meet every department leader and write down their top three problems

    The posting starts with regular assessment of staffing, processes, software, reporting and capacity gaps. The conversations are the first draft of the roadmap.

    Source: Director of Operations and Technology posting
  2. 2
    Build the software inventory with cost, renewal date and owner

    The first quick win is usually money. Duplicates and unused seats are the cheapest cuts, and renewal dates set the order.

    Source: Director of Operations and Technology posting
  3. 3
    Measure the baseline for intake, case set-up and billing

    The posting wants current costs, error rates and time spent before any project. Measure those three first, since each touches every matter.

    Source: Director of Operations and Technology posting
  4. 4
    Review how outside IT is scoped, and what the response times are

    Vendors are held to scope, cost and service standards, and you can’t hold them to one you haven’t written down.

    Source: Director of Operations and Technology posting

Days 31 to 60

Rank and start the first projects

  1. 5
    Write the first roadmap with each initiative’s problem, owner and cost

    This is the posting’s core deliverable. Rank by client impact, employee impact, cost, risk and growth.

    Source: Director of Operations and Technology posting
  2. 6
    Take the Leadership Team through the roadmap and agree what to approve, defer or stop

    The posting asks for a quarterly review. The first one sets how decisions get made.

    Source: Director of Operations and Technology posting
  3. 7
    Set up the master project list with owners, budgets and dates

    Approved work needs an owner, scope, budget, milestones and a definition of done, or it drifts.

    Source: Director of Operations and Technology posting
  4. 8
    Pick the first process to document and automate

    One department with a clear owner and a visible delay proves the method for the others.

    Source: Director of Operations and Technology posting

Days 61 to 90

Make it repeatable

  1. 9
    Finish the first SOPs and train the team on them

    Each department leader names an owner who writes the SOPs and checklists. Finish one set so the rest has a template.

    Source: Director of Operations and Technology posting
  2. 10
    Draft the integration plan for a new office or acquired team

    Growth in locations and acquisitions is the reason the role exists, and one reusable plan beats rebuilding each time.

    Source: Director of Operations and Technology posting
  3. 11
    Report what changed, what it cost and what comes next

    The posting asks for plain results against the estimate, which builds the trust to approve the next project.

    Source: Director of Operations and Technology posting

Where AI pays off soonest

Workflows from your own business, in the order they save your team time.

  1. 1 Inquiry intake sorted and summarized before it reaches a person

    Your contact form takes a detailed description of the legal matter. A first read that tags the matter type and urgency, and drafts the intake summary, speeds up the first call.

    Source: Contact page
  2. 2 First drafts of pleadings and motions from your own prior filings

    Your litigators draft pleadings and motions on every matter. A draft from your own prior filings gives an attorney something to edit and not a blank page, with every cite checked by a person.

    Source: Careers page
  3. 3 Case chronologies built from the documents in each file

    Disputes about trusts and conservatorships run on dates and documents. A chronology drafted from the file saves paralegal hours before an attorney reviews it.

    Source: Careers page
  4. 4 Client updates drafted from the case status

    Your site promises prompt replies. A drafted status note for each active matter, approved by the attorney, keeps that promise as volume grows.

    Source: theestatelawyers.com
  5. 5 Billing and collections follow-up from the matter record

    Reconciling time and invoices is routine work for finance. A first pass that flags unbilled time and overdue accounts is a measurable return the posting asks you to verify with Finance.

    Source: Director of Operations and Technology posting

What the hire owns, and what a fractional lead covers

Your Director of Operations and Technology owns

  • The operations and technology roadmap and its quarterly review
  • The master project list and every owner’s commitments
  • Software inventory, vendors and outside IT
  • SOPs and process standards across departments
  • Integration of new offices and acquired teams

A fractional lead covers

  • Where AI pays off first in intake, drafting and chronologies, and what gets built first
  • Security and confidentiality choices for any AI that touches client files
  • Vendor and build-or-buy calls while the hire gets settled
  • This 90-day plan, run alongside the hire until it’s theirs

Your first 90 days of tech leadership, planned

The plan above is yours either way.

Email Kash

We build a handful of these a month, for founders hiring now.

90 days

from the first day to a written roadmap

  • What to fix first, with the reason
  • Where AI pays off soonest
  • What the hire owns and what a fractional lead covers
  • A roadmap your team can run
Kash Badami

Who’s building it

Kash Badami was Chief Architect of a national health information network and closed the CMS deal behind Healthcare.gov’s data infrastructure. He runs his own company on AI today.

Chief Architectof a national health information network for HHS, aligning 23 federal agencies
$27MCMS deal that became core Healthcare.gov data infrastructure
  1. “he was singularly responsible for the company’s single largest customer by revenue - the Center for Medicare & Medicaid within the US Department of Health and Human Services.”

    RLRobert Liebowitz, worked with Kash on MarkLogic’s Public Sector team; now First Ascent VenturesLinkedIn recommendation, April 2026

  2. “Kash and I built ERT Credit together in 2021. He took my MVP and turned it into a SaaS that hit $10M ARR in twelve months.”

    Jordan Anderson, CEO, PayStreetgobridgehead.ai/about

The Estate Lawyers sales playbook, in brief

The Estate Lawyers is a probate, trust and estate litigation firm founded by Amy Gostanian, with offices in Irvine and San Diego and a 4.8 rating across 104+ Google reviews.theestatelawyers.com, About page

Its Director of Operations and Technology posting asks one leader to build the roadmap, deliver approved projects and prepare new offices and acquired teams.Director of Operations and Technology posting

The first 90 days: assess each department, inventory the software, set baselines, write and rank the roadmap, then make the first SOPs and integration plan repeatable.Director of Operations and Technology posting

AI pays off soonest in intake summaries, first drafts from prior filings, case chronologies, client updates and billing follow-up.Contact page, Careers page, theestatelawyers.com, Director of Operations and Technology posting

Prepared by at Bridgehead · November 9, 2026 · Every source

Questions

Why a fractional lead instead of waiting for the full-time Director of Operations and Technology?

You don’t have to choose. The hire owns the product and the team; a fractional lead covers the AI and software side and runs this plan until it’s theirs, so nothing waits on the search.

What does it cost?

The first engagement is a fixed price, quoted on a call once we’ve seen what you need. After that there’s an optional monthly retainer, and you can stop at any point.

Will it get in the way of the Director of Operations and Technology we hire?

No. The line between what they own and what a fractional lead covers is on this page, and the plan is handed to them to run.

Where does our data live, and is it secure?

In your own accounts. Nothing runs on our side, and every tool or vendor we suggest is reviewed with you before anyone connects it.

Is this only about AI?

No. AI is one part. Most of the first 90 days is the work your posting describes, and the AI items are the ones that save your team time soonest.

Your first 90 days of tech leadership, planned

The plan above is yours either way.

Email Kash

We build a handful of these a month, for founders hiring now.

90 days

from the first day to a written roadmap

  • What to fix first, with the reason
  • Where AI pays off soonest
  • What the hire owns and what a fractional lead covers
  • A roadmap your team can run
The research behind this page 8 sources
  1. Director of Operations and Technology posting, November 3, 2026
  2. theestatelawyers.com
  3. About page
  4. Attorneys page
  5. Careers page
  6. Firm news page
  7. FAQ page
  8. Contact page
  • Sources: the Director of Operations and Technology posting on LinkedIn and 7 pages of theestatelawyers.com, saved on November 9, 2026.
  • The only technology seen in the page code is the site itself; the mail record points to Microsoft 365.