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Josh Siddon

Josh Siddon

Technology Executive (CIO/CTO/CISO) | Managed Wi-Fi, Cloud & AI Readiness for Multifamily and Multi-Site Operations

United States UTC-6
English
Native
Remote experience
3+ years
US overlap
Full overlap
Availability
2 weeks notice
Experience
30 yrs
Compensation
$200k – $275k

Technology executive with three decades of IT leadership across multifamily real estate, retail, hospitality and gaming, and the public sector. I have served as CIO, CTO, and CISO, leading organizations of 200+ people and budgets exceeding $30M. I am currently Founder and Principal of ResiQ, an independent, vendor-neutral technology infrastructure advisory. What I do: turn IT from a cost center into a business enabler. At MAA, an S&P 500 multifamily REIT, I designed and deployed a managed Wi-Fi product and standardized network architecture across 300+ properties. At Fred's Inc. I developed the digital transformation strategy — Azure data center migration and Dynamics 365 Finance & Operations — and remediated PCI infrastructure across 600 retail sites after a card security incident, delivering more than $10M in savings. I have cut vendor spend from $52M to $28M, realigned a $35M public-sector IT budget for $7M in annual savings, and rolled out 12,000 student laptops in eight weeks. Core strengths: IT strategy and digital transformation, managed Wi-Fi and network architecture, Azure cloud migration, cybersecurity and compliance (PCI, HIPAA, SOX), AI and automation readiness, vendor strategy and contract negotiation, IT turnarounds and M&A. I am looking for a remote CIO, CTO, CISO, or VP of technology role — full-time or fractional — where executive-level technology leadership is needed.

At a glance

Level Executive
Experience 30 years
Education Bachelor's
Business Administration (IT focus)
Compensation $200,000 – $275,000/yr
Looking for
Full-time Part-time Contract Freelance
Open to
Video Interview
Background Check
NDA
Messaging coming soon

Skills

Azure Networking Leadership Team Leadership Cybersecurity Project Management Strategic Planning Regulatory Compliance Cloud Computing Risk Management AI Automation Data analysis

Membership Details

Member Since

August 31, 2026

Last Active

2 days ago