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Jonathan Wolff

creative solutions to technical problems


PROFESSIONAL SUMMARY

Jamf 300 Certified Mac IT specialist with a proven record of scaling infrastructure, improving device compliance, and training teams to support secure, efficient Apple ecosystems.

5+ years experience in Enterprise Healthcare and Financial environments.


TECHNICAL SKILLS

  • Operating Systems: macOS, iOS, Linux
  • MDM Tools: Apple Business Manager, Jamf Pro (Jamf 300 Certified), Mosyle (Certified Admin)
  • Security/Reporting Tools: macOS Security Compliance Project, SysTrack (L1/L2/L3 & Engineer certified)
  • Tools: Atlassian, ConnectWise, Docker, GitHub, GitHub Desktop, Service Now, Slack, Terminal, Visual Studio Code, Xcode
  • Open Source Tools (Mac): Erase-Install, Escrow Buddy, Nudge, Setup Your Mac, Support App, Suspicious Package
  • Scripting: Bash, CSS, HTML, Markdown, Swift/SwiftUI
  • Other: Active Directory, Change Management, DevOps, FileVault, Microsoft 365 (Certified: Fundamentals), Patch Management, Software Documentation, VMs, Zoom

PROFESSIONAL EXPERIENCE

Soultions Engineer

SECOND SON CONSULTING
Remote
July 2025 - present

Mac Technology Engineer

RANDSTAD DIGITAL
Wayne, PA
October 2024 - April 2025

  • Supported end users during migration from on-prem to Jamf Cloud environment.
    • Take tickets in ServiceNow and create escalations in Jira.
  • Interfaced with external vendors for technical troubleshooting.
    • Facilitate calls in Apple, Microsoft, Zoom.
  • Software packaging and patch management via DevOps.
    • Use Visual Studio Code and integrations with GitHub for version control.
  • Developed and led the creation of how-to and troubleshooting documentation in GitHub.

Mac Solutions Engineer

DIGITAL FIX CONSULTING
Pittsburgh, PA
March 2022 - September 2024

  • Configured, implemented, and maintained a brand-new Jamf Cloud instance for a healthcare client migrating from an on-premise solution, including vetting new software.
  • Implemented macOS Security Compliance Project for security baselines.
  • Performed software packaging and patch management.
  • Developed cadence of automated reports in Jamf to monitor device and application statuses.
  • Implemented custom-branded zero-touch automated device enrollment and support tools.
  • Developed with by ideas from MacAdmins Slack and teammate feedback.
  • Utilized Cherwell for user tickets and Jira for Engineering tasks.

Mac Technician II

DIGITAL FIX CONSULTING
Pittsburgh, PA
October 2019 - March 2022

  • Resolved user tickets and served as “Apprentice” to the Engineering team.
    • Used ServiceNow and Cherwell for ticketing.
  • Developed end user training for troubleshooting basic issues; mitigating concerns, building goodwill, and minimizing tickets.
    • Created and deployed using Microsoft 365 suite.
  • Inventory maintenance.

Creative Pro & Expert

APPLE INC
South Hills Village, PA
July 2016 - June 2019

  • Led Today at Apple Sessions; instructed all ages on general and technical aspects of Apple devices and services. Specialized in iPhone, iPad, Mac, Music, and Photography.
  • Assisted customers with questions about Macs and music creation in an elevated sales role.

Store Management

BOSE CORP
Washington, PA | King of Prussia, PA | Philadelphia, PA
August 2010 - July 2016

  • Managed teams of 6-12 at three separate store locations.
  • Led multiple teams to YOY comp growth, including 112% growth one year at Philadelphia International Airport location.
  • Spearheaded hiring, scheduling, team training, customer service, and sales.

Sales Specialist

SONY INC
Pottstown, PA
February 2009 - August 2010

  • TVs, Computers, and Digital Cameras.

EDUCATION & CERTIFICATIONS

EDUCATION

Bachelor’s Degree
Lebanon Valley College
Annville, PA

Major: Music Recording Technology | Minor: Physics

Specialty Certificate
Montgomery County Community College
Blue Bell, PA

Concentration: Business Marketing & Management

CERTIFICATIONS

  • Agile Foundations
  • Atlassian
    • Confluence Fundamentals
    • Jira Fundamentals
  • DevOps Foundations
  • Git Mastery: Beginner to Expert with GitHub & GitLab
  • Jamf
    • Certified Admin
  • Microsoft
    • Microsoft 365 Certified: Fundamentals
    • Microsoft Certified: Azure Fundamentals
  • SysTrack
    • L1/L2/L3
    • Desktop Engineer
  • Technical Writing: How to Write Software Documentation

OTHER SKILLS

  • Audio Recording
  • Music Production
  • Guitar & Bass

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