IT Leadership · Regulated Environments

Technology that holds up under audit, outage, and growth.

Director of Information Technology across regulated finance, MSP, and enterprise. Twenty plus years turning fragile IT operations into ones that pass examination, hold uptime, and stay governed under pressure.

James A. Sargent, Director of Information Technology
San Antonio · Austin · Remote
114 to 0
FFIEC Findings
99.9%
Uptime Held
$2.75M
Budget Directed
34
Client Orgs
9 of 10
Team Recruited
The Operating Belief

Most executives never touch the technology they decide on. My decade went the other way: back into the server room, on purpose, so the strategy would survive contact with the work.

Coming back to executive leadership meant bringing receipts. A budget run clean, uptime held through a full modernization, and zero material findings on federal examination.

About

Became a CIO at 29, then went back to the server room to learn what a boardroom hides.

James A. Sargent

Leadership came first. CIO and VP of Lending Operations at ACCION Texas, then the largest microlender in the United States, running an 18 person operation across 10 locations and originating more than 1,000 loans a year. Then came a deliberate decade in the work itself: infrastructure for 7,000 plus employees across 200 locations, offshore teams spanning three continents, enterprise security for Fortune 500 clients, and dual data centers under real load.

The return to executive leadership landed at Tyndall Federal Credit Union, a federally regulated environment inherited with 114 FFIEC examination findings and recurring multi day outages. Within one year the findings reached zero, the technology exam letter recorded no material findings, and the NCUA examination closed with zero IT findings. Reliability rose from 98% to 99.9% and still holds in 2026. Today the work is fractional IT Director for 32 of 34 client organizations at Bridgehead IT, directing more than 40 concurrent infrastructure, cloud, and cybersecurity initiatives across four continents.

20+ yearsLeading IT and infrastructure teams that own uptime end to end
Regulated by tradeNCUA, FFIEC, HIPAA, NIST, and SOX environments
Summa cum laudeB.S. Business Administration, Organizational Leadership
ITIL & CSM certifiedPlus Certified in Cybersecurity and Azure Fundamentals
The Signature Turnaround

One hundred fourteen findings. One year. Zero left standing.

The examination that defined the Tyndall turnaround, walked one workstream at a time. Step through the year and watch the ledger close.

114
FFIEC
findingsopen
114 0
Endpoints are examination verified: 114 findings inherited, zero at close, no material findings on the technology exam letter. Intermediate steps mark the workstreams behind the result, not a per phase count.
00Inherited State

A federally regulated environment, arriving broken.

Took over an underperforming IT operation at a credit union running dual data centers, one of them in hurricane zone Panama City. On arrival: 114 FFIEC examination findings and recurring multi day, multi layer outages hitting members.

Phase 1 of 8
What I Bring

Four things that stay fixed after the engagement ends.

Infrastructure that stays up

Replaced 10 servers, 4 core switches, and 2 storage arrays across dual data centers in a two month window with zero unplanned downtime. Reliability from 98% to 99.9%, still holding.

Compliance that passes

NCUA, FFIEC, HIPAA, NIST, and SOX environments. Findings closed, not managed. A layered security architecture with SIEM and MDR, vulnerability management, and DLP matured enterprise wide.

Teams that own outcomes

Recruited 9 of 10 across Infrastructure, Desktop Support, and Information Security, productivity up 25%. Service backlog cut from 200 plus tickets averaging 90 days to under 50 averaging 40.

AI with governance

Wrote a regulated financial institution's first Ethical and Responsible Use of AI Policy in 2023, still in force unchanged, and deployed governed access to generative AI for the organization.

Career

From CIO of the largest US microlender to IT Director in regulated finance.

DEC 2024 to PRESENTSan Antonio, TX
Fractional IT Director
Bridgehead IT · Title of record: Technical Account Manager

Serve as fractional IT Director for 32 of 34 client organizations across 8 plus industries, from 4 person firms to publicly traded global enterprises, directing technology strategy and risk and advising on budgets. Direct more than 40 concurrent infrastructure, cloud, and cybersecurity initiatives across four continents, and hold a dedicated vCISO engagement under NIST, HIPAA, and FFIEC frameworks.

34 Client Orgs40+ Initiatives97%+ CSATvCISO
JAN 2023 to SEP 2024Remote
Director of Information Technology
Tyndall Federal Credit Union

Recruited to rebuild IT at a federally regulated credit union. Drove FFIEC examination findings from 114 to 0 in one year, with no material findings on the technology exam letter and zero IT findings on the NCUA examination. Raised reliability from 98% to 99.9% across dual data centers, replaced 10 servers, 4 core switches, and 2 storage arrays with zero unplanned downtime, and built the first purchasing strategy that cut hardware costs about 35% from vendor quotes on a $2.75M budget. Wrote the organization's first AI policy, still in force.

Findings 114 to 098% to 99.9%$2.75M BudgetFirst AI Policy
MAR 2021 to JAN 2023San Antonio, TX
Service Delivery Manager
Computer Solutions

Built the Premier Response service line from zero to about $2M annual revenue across 20 to 30 clients and led an 8 person delivery team, a line that still runs today. Held a 94.7% positive customer satisfaction rating and extended resource planning visibility from 14 to 90 days. Recruited away by Tyndall, a Computer Solutions client, to run its infrastructure and service desk.

$2M New Line94.7% CSAT14 to 90 Day Forecast
JUN 2020 to MAR 2021Remote
Senior Consultant
Catapult Systems

Delivered enterprise Azure security programs, large scale Microsoft 365 migrations including G-Suite and tenant to tenant consolidations, and enterprise PKI as technical lead and project manager. Clients included Church & Dwight, a Fortune 320, alongside Austin Energy and Chromalloy, all delivered fully remote, on scope, and on schedule.

Azure SecurityM365 MigrationsEnterprise PKI
OCT 2019 to APR 2020San Antonio, TX
IT Manager, Server Systems
Zachry Group

Led a 7 person server systems team for the enterprise Windows server estate of a multi billion dollar construction and industrial firm. Raised server patch compliance from 45% to 88% in three months through process discipline, automation, and accountability, and led Active Directory and Microsoft 365 tenant consolidation across business units. Role ended in the April 2020 workforce reduction.

45% to 88% Patch7 Person Team
APR 2016 to OCT 2019New Braunfels, TX
Senior Systems Engineer
Rush Enterprises

Owned enterprise PKI on ADCS, Azure AD modernization, a staged 90 day Azure MFA rollout, and ServiceNow based provisioning for 200 plus locations and 7,000 plus employees. Senior escalation point for directory services, PKI, and authentication, automating licensing, reporting, and account lifecycle with PowerShell and System Center Orchestrator.

7,000+ Employees200+ Locations90 Day MFA
SEP 2012 to APR 2016San Antonio, TX
Senior Systems Engineer & Tower Lead
Argo Group

Led an 8 person US and India team running server and monitoring platforms across 3 data centers and 7 international offices for a SOX regulated global insurer, with audited change control for SOX reporting. Role ended when remaining infrastructure was outsourced.

3 Data CentersSOX RegulatedUS / India Team
1998 to 2005San Antonio, TX
CIO & VP of Lending Operations
ACCION Texas, now LiftFund · A CDFI and then the largest US microlender

Promoted from VP of Information Technology in 1998 to CIO and VP of Lending Operations in 2002, leading an 18 person lending and technology operation across 10 Texas locations originating more than 1,000 loans per year. Built ClientTrack, a loan lifecycle application spanning contact management through risk adjusted underwriting, and won a $300K HP technology grant in 2003, 1 of 9 selected from more than 500 applicants and covered by the San Antonio Business Journal.

18 Person Op$300K GrantBuilt ClientTrack
Capabilities

The full stack of an IT leader, from strategy to switch port.

Leadership & Strategy

IT Strategy & RoadmapsBudget OwnershipVendor ManagementTeam BuildingExecutive CommunicationChange ManagementService DeliverySLA Management

Infrastructure & Cloud

AzureMicrosoft 365Data Center OperationsVMwareHyper-VEntra IDActive DirectoryPKIPowerShellBusiness Continuity & DR

Security, Compliance & AI

Cybersecurity & RiskSIEMMDR / EDRVulnerability ManagementIncident ResponseIdentity & AccessAI GovernanceNCUAFFIECHIPAANISTSOX
Summa Cum LaudeB.S. Business Administration, Organizational Leadership, SNHU
ITIL & CSMITIL Foundation and Certified Scrum Master
Certified in CybersecurityISC2 CC and Microsoft Azure Fundamentals
AI FoundationsThree semester program, GPA 4.0, 2024
Get In Touch

Bring me the environment nobody wants to inherit.

Open to Director and VP of Information Technology roles across San Antonio, Austin, and remote. The harder the audit and the older the outage, the better the fit.

Email me LinkedIn