ConnorArmstrong

Product & Delivery Leader

AI-enabled software, infrastructure and IT operations  |  Batesville, IN  |  Remote preferred, open to hybrid (Indianapolis, Cincinnati)

Product and delivery leader who took OnMapIT, an AI-powered IVR platform with a map-based service dashboard, from beta testing to launch ahead of schedule; it is now live with two early-adopter companies. Seven-plus years of hands-on infrastructure experience, including disaster recovery coordination, Active Directory and Microsoft 365, across insurance and education environments. Turns shifting executive direction into clear, repeatable frameworks. Practical expertise in enterprise AI adoption: proficient across multiple LLMs, with talks delivered to two companies on AI rollout and policy.

See my projects
Portrait of Connor Armstrong

Experience

Where a line has a project behind it, the project link goes straight to the work.

Co-Owner · Casket City Games

July 2025 – Present

Hobby game shop  |  casketcitygames.com

  • Co-founded a small retail business from the ground up and opened its first physical location.
  • Built the shop's own point-of-sale system and integrated it with PayPal.
  • Operate both physical and online retail sales.

Head of Product Pipelines, OnMapIT · Tekswork LLC

April 2026 – November 2026

Multi-region MSP  |  Previously Regional Solutions Manager and Solutions Architect

  • Led the product pipeline for OnMapIT, an AI-powered IVR platform that pairs voice automation with a map-based dashboard, ticketing and record keeping for customer-service and infrastructure organizations. View project
  • Shipped ahead of schedule while company priorities changed repeatedly; the product is live with two early-adopter companies. View project
  • Moved from regional expansion to product ownership as company direction shifted, and carried the product through to launch.
  • Built the cost and margin model behind the pricing, then turned it into three-tier packaging. Cost modelPackaging
  • Wrote sales training for the external field sales and internal sales teams, and trained them through live demos with Q&A. View project
  • Planned the 120-day launch campaign: prospect research, email sequences and sales enablement. View project
  • Designed an automated outbound email program, its CRM integration and a refinement loop for continuous improvement. View project
  • Designed a form-based pricing calculator that standardized sales data entry where the CRM had no SOP or training. View project
  • Aligned service delivery, sales and operations around aggressive year-over-year revenue growth targets.

IT Services Engineer · Eze Castle Integration

June 2022 – April 2026
  • Supported an insurance client environment of roughly 2,500 users, resolving 100–300 tickets daily on a 24-hour turnaround.
  • Headed coordination of the disaster recovery program, establishing protocols and procedures, and led the annual DR test.
  • Coordinated with all levels of the infrastructure IT team to align projects and incident response with organizational objectives.
  • Performed Level 1 and Level 2 troubleshooting across hardware, software and network systems to keep downtime low.
  • Administered Active Directory for secure, efficient user access management.

On-Site IT Technician · Five Star Tech Solutions

January 2021 – June 2022
  • Supported a school district of approximately 3,500 users and 4,500 devices across Windows, Mac and Chromebook.
  • Managed cloud-based device management software and sustained 99.9% uptime.
  • Resolved hardware, software and infrastructure issues as part of a lean three-person team.

AI Adoption Speaker and Educator

  • Presented to two companies on enterprise AI adoption and policy, and designed follow-on educational events; further sessions were paused when budgets froze.
  • Proficient with multiple LLMs and their best practices.

Freelance services

What I take on outside my day job.

VBA automation

Custom VBA automation for small business clients. Freelance since 2022, reducing manual reporting workload by up to 30%.

Available now
View details

AI adoption talks and training

Talks and educational sessions that help a company roll out AI and set policy for how it is used, built on working proficiency across multiple LLMs.

Available now

Skills and certs

Product & Leadership
Product Delivery, Project & Program Management, Process Documentation, Vendor & Stack Evaluation, Regional Operations, Change Management, Disaster Recovery Planning
AI
Multi-model LLM proficiency, Enterprise AI adoption and policy, AI best practices training
Platforms
ConnectWise PSA/Automate/ScreenConnect, Active Directory, Microsoft 365, ServiceNow, Five9
Technical
Windows, Linux (Ubuntu, RedHat, Debian, Igel), macOS, VBA, PowerShell, Bash, GDScript
Soft Skills
Stakeholder Communication, Cross-Functional Collaboration, Adaptability, Time Management

Education & certifications

  • Five9 Administrator Training2025
  • Microsoft 365 Administrator Certification2024
  • LinkedIn Learning Certification, IT Project Management2024
  • CompTIA A+ Certification2020
  • Self-directed AI coursework through AI Hero (aihero.dev)

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