First Midwest Group For Ashwin

Commercial Real Estate: A 90-Day CTO Plan

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

If the IT seat can stay open another quarter, ignore this. If it can’t, the next two minutes are worth it.

What we noticed

Four decades of development since 1984, more than 10,000 residential lots, and a portfolio that runs from rental homes and a Radisson to self-storage and an adventure park.

Your Director of IT & Security posting went up on November 4, and it asks one person to run employee support, cybersecurity, physical security technology and the technology for every new building and acquisition.

Your portfolio Rental homes, commercial buildings, a hotel and event venue, self-storage, a pub, a senior living community and an adventure park. Each has its own systems and its own security needs. Affiliated entities page
Your security systems Self-storage is sold on gated access and video, which makes physical security technology a product for your customers as well as protection for your buildings. firstmidwestgroup.com
Your leadership team A CEO, a President, a CFO and a Chief Legal Officer sit on the leadership page. The new IT leader brings technology and security risk to that table. Leadership team page
Your land development Land development, site selection and infrastructure build-out give IT an early seat on every new project, before the cabling goes in. Land development page

Seen in your stack: Microsoft 365 · Cisco · HubSpot · Google Tag Manager · Cloudflare · access control · video surveillance

What your posting asks for

“Provide leadership and oversight for day-to-day IT support for FMG employees and business operations.”
“Maintain secure, reliable, and efficient network, wireless, telecommunications, cloud, and technology infrastructure.”
“Oversee access control and electronic entry systems, CCTV and video surveillance, intrusion detection and alarm systems, intercom and visitor management systems, remote monitoring solutions, and related network and communications infrastructure.”
“Lead IT and security technology planning and implementation for new construction, renovations, acquisitions, and major facility projects.”
“Develop and execute plans to integrate acquired properties into FMG's technology and security environment.”
“Identify opportunities to consolidate vendors, standardize systems, and reduce unnecessary technology expenses.”

From your Director of IT & Security posting, posted November 4, 2026.

What changes for your new Director of IT & Security

Your new Director of IT and Security starts with a plan: what to inventory across your properties first, how to standardize security systems, how to bring each acquisition into one environment, where AI saves your teams 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 IT & Security’s first 90 days

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

Days 1 to 30

Inventory the properties and the people

1
Visit each business and list its systems: office, network and security
The role covers offices, businesses and properties. A visit to each gives a first inventory and a view of how staff really work.
Source: Director of IT & Security posting
2
Build one asset list for devices, licenses and accounts
The posting asks for an accurate inventory of hardware, software licenses and devices. Everything else in the plan builds on it.
Source: Director of IT & Security posting
3
Check who still has access to what after role changes
New hires, transfers and terminations are named in the role. A one-time access review closes the most common security gap.
Source: Director of IT & Security posting
4
Find the recurring problems staff report
Your posting asks for practical fixes to recurring issues. The first list comes from the people who hit them.
Source: Director of IT & Security posting

Days 31 to 60

Security basics and vendor clean-up

5
Set the cybersecurity basics: backups, updates and who responds
The role covers endpoint security, backups and incident response. One page that says who does what in an incident is the starting point.
Source: Director of IT & Security posting
6
List the access control, camera and alarm systems at every property
The same kinds of system exist at many properties, often from different vendors. A list shows where standards are possible.
Source: Director of IT & Security posting
7
Review the IT and security vendors and contracts
Your posting asks to consolidate vendors and cut unnecessary spend. A review of what each vendor does and costs makes that concrete.
Source: Director of IT & Security posting

Days 61 to 90

Standards for new buildings and acquisitions

8
Write the technology and security checklist for a new building
The posting makes IT part of new construction. A checklist given to construction teams early avoids costly changes after the walls are up.
Source: Director of IT & Security posting
9
Write the playbook for bringing an acquired property into the environment
Assessing and integrating acquired properties is named in the role. A repeatable playbook makes each deal easier.
Source: Director of IT & Security posting
10
Set the technology budget and the three-year replacement plan
The role helps develop budgets, forecasts and capital planning. A replacement schedule built from the inventory turns surprises into line items.
Source: Director of IT & Security posting

Where AI pays off soonest

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

1 First-line answers for employee tech questions
The role oversees day-to-day support across several businesses. An assistant that answers common questions from your own how-tos gives the director time for the security and project work.
Source: Director of IT & Security posting
2 Drafting technology scopes and budgets for new projects
Each new building or renovation needs a scope, timeline and budget. A drafted first version from past projects speeds each one.
Source: Director of IT & Security posting
3 Tracking contracts, warranties and renewal dates
The posting asks for records of contracts and warranties. An assistant that reads them and flags upcoming renewals prevents missed dates and auto-renewals.
Source: Director of IT & Security posting

What the hire owns, and what a fractional lead covers

Your Director of IT & Security owns

Employee IT support across the businesses
Network, wireless, telecommunications and cybersecurity
Access control, cameras and alarm systems at each property
Technology for new construction, renovations and acquisitions
IT vendors, budgets and asset records

A fractional lead covers

Where AI and automation pay off soonest across the businesses
Standards for security and technology that apply to every property
Tool and vendor choices for anything AI, reviewed with you first
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

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

“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
“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

First Midwest Group sales playbook, in brief

First Midwest Group is a real estate developer and operator founded in 1984, with rental homes, commercial property, hospitality, self-storage and more.firstmidwestgroup.com, Our history page, Affiliated entities page

Its Director of IT & Security posting asks one leader to run employee IT support, cybersecurity, physical security technology and the technology for new buildings and acquisitions.Director of IT & Security posting

The first 90 days: visit every business, build one asset list, review access, set security basics and vendors, then write the checklists for new buildings and acquisitions.Director of IT & Security posting

AI pays off soonest in first-line employee support answers, drafted project scopes and tracking contracts and warranties.Director of IT & Security posting

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

Questions

Why a fractional lead instead of waiting for the full-time Director of IT & Security?

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 IT & Security 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.