James Mastrocovo

Operations Associate

Chicago, Illinois, United States21 yrs 11 mos experience
Highly Stable

Key Highlights

  • Proven expertise in enterprise-level IT support.
  • Strong background in system administration across diverse environments.
  • Exceptional communication and problem-solving skills.
Stackforce AI infers this person is a SaaS-focused IT professional with extensive experience in system administration and user support.

Contact

Skills

Core Skills

Information TechnologySystem AdministrationCreative Problem SolvingCommunication

Other Skills

Technical SupportDocumentationCustomer ServiceSocial MediaSocial NetworkingCustomer ExperienceAdobe Creative SuiteApple CertifiedSalesTrainingRetailMicrosoft OfficeLeadershipTroubleshootingTime Management

About

Seeking a fulfilling and challenging experience with a passionate team. Looking forward to working alongside creative thinking and customer focused colleagues.

Experience

Olivine, inc.

Business Applications Administrator

Nov 2025Present · 5 mos · Chicago, Illinois, United States · Remote

Legacy.com

IT Systems Administrator

Mar 2025Jun 2025 · 3 mos · Chicago, Illinois, United States · Hybrid

  • Deliver enterprise-level IT support and infrastructure management for over 300 users across Legacy.com and its sister companies, including direct support for executive leadership. Champion operational efficiency, security, and compliance through strategic system administration, process optimization, and collaborative project execution.
  • Key Responsibilities:
  • Provide full-spectrum technical support across macOS and Windows environments, resolving hardware, software, and network issues with a strong focus on user experience and security.
  • Administer critical SaaS platforms and infrastructure including Barracuda (backups), Kandji & Intune (MDM), Sophos (endpoint protection), Apple Business Manager, and Zoom Rooms.
  • Maintain and optimize cloud infrastructure, including AWS WorkSpaces and EC2 instances.
  • Manage access control systems via Keyscan Aurora, and oversee physical infrastructure including servers and networking equipment in Legacy’s Chicago office.
  • Drive compliance and risk mitigation efforts through software audits, e-waste procedures aligned with PCI standards, and secure asset reclaiming.
  • Document repeatable IT solutions and training procedures in Atlassian Confluence, ensuring knowledge continuity and operational consistency across teams.
  • Facilitate onboarding for new hires and contractors across business units, aligning IT processes with HR and executive needs.
  • Collaborate cross-functionally with Accounting, HR, Executives, and department leads to support IT procurement, invoicing, and strategic technology planning.
Information TechnologySystem AdministrationTechnical SupportDocumentationCreative Problem SolvingCommunication

23andme

4 roles

IT Systems Administrator I

Apr 2024Apr 2025 · 1 yr

Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Information Technology Engineer

Sep 2023Apr 2024 · 7 mos

Information Technology

Information Technology Administrator

Feb 2022Sep 2023 · 1 yr 7 mos

Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

IT Support Administrator

Oct 2021Feb 2022 · 4 mos

  • Experienced IT Admin delivering robust on-site and remote support across global sites. I manage cloud-based environments and enterprise apps (Okta, G‑Suite, Atlassian, Jamf, Microsoft O365, InTune, Desktop Central, Box, etc.) on Mac OS and Windows, and coordinate end-to-end IT implementations for diverse teams. I streamline new hire setups, maintain IT ticketing, and resolve complex system issues in collaboration with Corp IT. I also provide audiovisual support and IT staff training.
Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Intuit

Service Desk Tech II

Jan 2020Nov 2021 · 1 yr 10 mos · Mountain View, California, United States

  • Support hundreds of employees spanning multiple locations, remote imaging and delivery of computers to users, update internal knowledge base documentation, assist with new hire orientation, manage ticketing system, restock and maintain inventory at Help Desk, setup computer repairs with offsite vendors
Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Palo alto networks

IT Desktop Support Level 2

Jul 2019Jan 2020 · 6 mos · Santa Clara, CA

  • Assist users with laptop refreshes in a timely manner resulting in increased customer satisfaction
  • Provide technical assistance to customers via telephone, email or in person
  • Assist in imaging & provisioning laptops for new hires in a week resulting in a smooth on-boarding experience for new employees
  • Facilitate weekly new hire orientation ensuring new hires gained a better understanding of IT Helpdesk roles
  • Track work completion and ticket progression through ServiceNow / JIRA
  • Setup desk, deliver equipment, and provide assistance deskside to users
Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Twitter

IT Support Technician

Nov 2017Jun 2019 · 1 yr 7 mos · San Francisco, California

  • Interfacing with employees, assisting with New Hire Orientation, asset management, troubleshooting internal services (Google Apps/Admin, JAMF, Windows Active Directory, VM management, Atlasssian suite)
Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Apple retail

5 roles

QA Engineer

Mar 2012Nov 2014 · 2 yrs 8 mos

  • Software, web, and app testing to ensure quality of multiple tools. Communicate test results to software engineers and QA leads. Maintain detailed steps of recreation of bug testing in RADAR (bug tracking software). (Note: From Mar 12’ to Nov 14’ was not working full time in this position)
Creative Problem SolvingCommunication

Creative

Jan 2012Nov 2017 · 5 yrs 10 mos

  • Providing personal, one-on-one training and adjusting my teaching style and pace to meet the needs of the individual.
  • Conducting presentations and workshops using Apple-approved training techniques and materials as well as customer tailored elements.
  • Being one of the go-to people for creative knowledge in the store.
  • Patiently showing customers such basic computing skills as double-clicking, browsing the Internet, organizing and editing photos.
  • Teaching customers how to make a movie, record a song, draw digitally or edit photos, or create a graphically pleasing document.
  • Encourage and facilitate learning in groups from fundamental concepts of the Mac OS to more advanced Final Cut Pro editing techniques.
Information TechnologySystem AdministrationCreative Problem SolvingDocumentationCommunication

Technical Specialist

Jan 2010Jan 2012 · 2 yrs

Creative Problem SolvingDocumentationCommunication

Concierge

Jan 2008Jan 2010 · 2 yrs

Creative Problem SolvingCommunication

Specialist

Aug 2007Jan 2008 · 5 mos

Communication

Compusa

Retail Associate / Small Business Associate

Jul 2005Jul 2007 · 2 yrs · San Jose, CA

  • Assist with business sales staff training, interact with
  • customers both over the phone and in person, participate in
  • physical inventory checks, inform and help customers
Communication

Mac-pro

Technician

Aug 2003May 2005 · 1 yr 9 mos · Campbell, CA

  • Install and repair numerous components on all models of Apple
  • computers, interact with customers both in store and over the
  • phone, prepare items and computers for shipment, extensive
  • management and transfer of customer data
Communication

Education

Evergreen Valley Community College

Graphic Design

Jan 2004Jan 2006

Santa Teresa High School

High school

Jan 2001Jan 2004

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