JOHN TROTTA
I design and build technology, security, and AI programs for regulated industries.
I've spent 17 years in regulated financial services across technology, security, and operations. I design and review security controls, assess cyber and third-party risk, and partner with engineers to architect systems that pass audits without slowing the business: SOC 2 Type II, PCI-DSS, and HIPAA stood up from nothing and mapped to NIST CSF, 10+ audits passed with zero material findings, zero major incidents over eight years. And I still build: AI products that carry real revenue, compliance monitoring that replaced manual spot-checks with full coverage, and the secure data flows a 300-person firm runs on. I'm the technical voice to ownership, clients, legal, and regulators on risk acceptance, control strategy, and emerging technology. Operations background, CISSP, daily user of agentic AI, and I still write code when it's the fastest path to the answer.
Experience
Chief Technology & Security Officer
RTR Financial Services, Inc.
August 2019 - Present
Staten Island, NY
Own technology, product, and operational systems for a regulated mid-size financial services firm running across hybrid on-prem and cloud. Full accountability for what gets built, how it runs, and the security and compliance behind it.
- Conceived and built an AI phone system that turned a manual call workflow into a self-service revenue channel now worth an estimated 10% of company revenue. Thousands of calls a day, routed and handled automatically.
- Built and own an AI call-monitoring platform across 65+ agents and thousands of daily calls: logging, sentiment, and automatic verification of required legal disclosures and consent, replacing manual spot-checks with full coverage and giving managers a real-time view they never had.
- Build AI ops tooling: agentic workflows that monitor, remediate, and report on their own, with anything risky routed back for approval.
- Built the secure data flows the business runs on: site-to-site VPNs across data centers, API connections from internet-facing systems into isolated back ends, API and FTP transfers, and BI wired straight to production databases, all change-managed and auditable.
- The technical voice to ownership, clients, legal, and regulators: turn vague business problems into things that ship, and carry the proposals, RFPs, and security reviews that underpinned more than $10M in regulated-client revenue.
- Automated 80 to 100 hours of manual work a month across clerical, operations, and compliance, and cut technology spend roughly 30% through architecture rationalization and vendor consolidation while the business grew fourfold.
- Built the company's first real disaster recovery and continuity and drove uptime to 99.99%, scaled the environment from 75 to 300 employees, and moved to multi-state remote operations in a week when COVID hit, opening up 8+ states.
- Stood up the company's security and compliance from nothing: SOC 2 Type II, PCI-DSS, and HIPAA, first-time certification on each, zero major incidents in eight years.
IT Manager
RTR Financial Services, Inc.
2016 - August 2019
Staten Island, NY
- Ran the WannaCry ransomware recovery with no DR plan in place, pulling together internal staff and vendors to restore full operations in 48 hours.
- Owned availability, security, patching, and compliance across every enterprise system.
Infrastructure & Security Lead
RTR Financial Services, Inc.
2014 - 2016
Staten Island, NY
- Transformed how the existing environment was used: reworked current tools, standardized automation with PowerShell and Python, added new systems as extensions to what was already in place, and built the procedures to meet new client requirements.
Systems Administrator
RTR Financial Services, Inc.
2012 - 2014
Staten Island, NY
- Administered the company's core systems day to day, keeping a lean environment running under the IT manager who owned the network.
Business Analyst
RTR Financial Services, Inc.
August 2008 - 2012
Staten Island, NY
- Worked across reporting systems, analytics, and business processes to measure and improve operations.
Press
All from AccountsRecovery.net
AI 101: Back to the Basics
April 2026
Getting to Know John Trotta of RTR Financial Services
December 2025
Teaching Prompt Engineering to Your Staff
March 2025
Using AI as a Research Tool and for Creation of Policies and Procedures
January 2025
Artificial Intelligence: Empowering Human Agents for Better Efficiency
November 2024
View all speaking engagements
Archive
Skills
Product & Systems
Security and Compliance
Infrastructure and Cloud
Engineering and Automation
Executive Leadership
Certifications
Certified Information Systems Security Professional
ISC2
Project Management Professional
PMI, in progress (2026)
VMware Certified Professional
Data Center Virtualization 6.7
Microsoft Certified Solutions Expert
Windows Server Security and Core Infrastructure
Cisco Certified Network Associate
Implementing and Administering Cisco Solutions
Education
CUNY Baruch College
Zicklin School of Business
Bachelor of Business Administration, Operations Management
New York, NY
Projects
AI Phone System (IVR)
An AI-driven phone system that turned a manual, rules-based call workflow into a self-service revenue channel. Handles thousands of calls a day with routing, self-service, and follow-up. Contributes an estimated 10%+ of company revenue.
Tech: Cloud Telephony, SIP, Python, LLM APIs, Speech-to-Text
Compliance Monitoring Platform
AI platform that replaced manual spot-checking with full-coverage legal disclosure verification and sentiment analysis on customer calls. Closed the compliance blind spots that sampling could never catch.
Tech: Python, Speech-to-Text, LLM APIs, Sentiment Analysis
Homelab
Production-grade k3s cluster on ProxMox, GitOps-managed with Flux. Runs 25+ services across monitoring, automation, media, document management, and AI workloads. Bare metal.
Tech: ProxMox, k3s, Flux, Kube-Prometheus, Velero, Loki
OpsMan
Semi-autonomous AI ops manager for the homelab. Watches ProxMox and Kubernetes, runs approved Day-2 operations, logs everything. Anything risky comes back for approval.
Tech: Python, ProxMox API, Kubernetes API, Pushover
What I Build With
The core of what makes me productive. The rest of my stack lives in GitHub.