Intermediate Systems Administrator

Caldwell Financial Ltd., through its wholly-owned subsidiaries Caldwell Securities Ltd., Caldwell Investment Management Ltd. and Caldwell Insurance Services, has managed significant financial assets for families, individuals, corporations, trusts and foundations since 1980. Our broad investment, insurance, family office, estate and foundation management services are based on having highly qualified professionals working on a “client first” basis.



The purpose of this position is to provide 1st-level operational support. This position requires excellent communication and problem-solving skills. The individual must possess an expert-level technical knowledge in the field of backup/server operations. The ideal candidate will be a highly motivated self-starter with a desire to learn. He/She will also understand that well-run computer operations rely both on process and on knowledge. The company is located at King and University in downtown Toronto.



Issues Management and Resolution:

  • Analyze issues and formulate solutions
  • Troubleshoot system, application and hardware issues
  • Use external information to research and resolve issues when needed
  • Manage multiple issues, priorities and goals
  • Document and adhere to standard processes

System Administration:

  • Perform backups and restores
  • Perform configuration of hardware including disk drives, network interfaces, memory, processors, and peripherals
  • Perform installation and configuration of software including operating system, patches, and 3rd party products
  • Document processes and systems along with tracking of assets
  • Understanding of server network configuration: Ethernet, Port Trunking, VLANs
  • Design, build and configure PC Hardware/Software
  • Manage VOIP Telephone system


  • Demonstrate sound written and oral communication and organizational skills
  • Document solutions, systems and procedures
  • Identify and suggest process and/or procedure improvements
  • Ability to follow documented commonly-used concepts, practices, and procedures
  • Deliver personal, user focused and professional service to varying levels of end-user sophistication
  • Works effectively both as an individual and as lead to a junior administrator and in conjunction with the rest of the IT oriented staff
  • Attend and participate within IT team meetings and functions
  • Lead/Contribute to meetings to discuss problems/solutions with stakeholders and peers
  • Provide status and issue updates to managers and peers as required
  • Gather knowledge of technology changes through training, conferences, textbooks, journals, case studies
  • Perform product evaluations and deliver results and/or recommendations

Weekends – After Hour Work – On Call:

  • Must maintain a flexible schedule and be available to work non-standard business hours upon request or as needed, estimated to be less than 10% of total time
  • Must be available via cell phone for issue resolution and assistance after hours
  • Time-off in-lieu will be available in full for non-standard hours


  • This position may involve some travel to branch offices within the Greater Toronto and Niagara areas, estimated to be less than 3% of total time


Education and Certifications:

  • Bachelor's Degree from an accredited University, preferably in Computer Science, Information Systems or equivalent program or IT experience required
  • Technical certifications (e.g. MCSE, VMWare)


  • Minimum 5 years of IT-related experience
  • Minimum 3 years experience in field of expertise
  • Experience leading small projects
  • Expertise with Veeam, VMWare, MS Server 2003 – 2012, Windows 10 and 7

Additional Skills

  • Knowledge of Brokerage and/or Wealth Management businesses a plus
  • Networking, Active Directory a plus
  • Knowledge of Bell Total Connect a plus

Other duties:

  • This job description reflects management’s assignment of essential functions, it does not prescribe or restrict the tasks that may be assigned

Job Type: Full-time, Permanent

To apply for this position, please send your covering letter and resume to

We thank all applicants; however, only those selected for an interview will be contacted.