A guide who’s actually made the climb
I’m Cooper. I’ve spent ten years in IT — from the help desk to systems administration to infrastructure engineering — and today I run IT operations for a Denver insurance technology company.
Along the way I’ve taken an IT department through SOC 2 Type II and ISO 27001 at the same time, integrated more than five acquisitions, automated the full employee lifecycle from hire to termination, and built an office network that hasn’t gone down since cutover.
Sherpable is how I bring that to teams that aren’t ready for a full-time IT hire. The decisions that are cheap to get right early and expensive to fix later: how identity works, how the network is segmented, where the backups live, and who has the keys.
A sherpa doesn’t carry you up the mountain. They know the route, spot the hazards early, and make sure you get there safely — and can find your way back down.
Where I’ve been
- 2026 – now
IT Manager
Denver insurance technology companyOwn IT operations end to end: infrastructure, cloud, security, service desk, vendors, and the IT budget. Supervise systems and support staff, enforce change management, and act as the final escalation when something breaks.
- 2023 – 2026
Systems & Data Engineer
Denver insurance technology companyBuilt a high-availability office network with zero downtime since cutover. Led the rollout of Google Cloud, AWS, and the SaaS stack the company still runs on. Wrote custom SCIM and SAML integrations, and automated provisioning to keep up with rapid hiring.
- 2021 – 2023
Systems Engineer · Systems Administrator
High-growth cloud technology companyGuided IT through SOC 2 Type II and ISO 27001 certification at the same time, and wrote the IT, security, and compliance policies both audits required. Integrated 5+ acquisitions, fully automated the employee lifecycle from hire to termination, and led Azure reliability engineering through rapid growth.
- 2019 – 2020
Systems Administrator
Insurance brokerageRan on-prem servers, Active Directory, Exchange, SQL, and VDI. Designed a repeatable remote-access kit on OPNsense — preconfigured routers shipped to remote clients for secure VPN from day one.
- 2016 – 2019
Hosted Services Consultant → Escalation Specialist
Cloud hosting providerStarted on the help desk and worked up to escalations. Built and ran Citrix environments, and was a founding member of the root-cause-analysis team for problems that spanned network, server, and application.
Let’s see if we’re a fit.
A free 30-minute call to talk through your stack, your size, and the actual headache. You’ll leave with next steps, whether or not we work together.