Caldwell Securities Ltd. (“Caldwell”) is a majority employee-owned investment dealer that has been providing sophisticated and experienced investment and wealth management advice to individuals and corporations since 1981.

Caldwell’s primary business includes investment management services, mutual fund sales, and retail and institutional sales. Caldwell is a member of the Canadian Investment Regulatory Organization(“CIRO”) and runs its own self-clearing operations.

We are seeking an experienced Licensed Executive Assistant to support the President & COO of Caldwell Securities Ltd. The job is located at our Head Office in Toronto, Ontario.

What will you do?

Work closely with the executive and her clients

Draft and proofread correspondence

Conduct research, as required

Work on special sales projects; and interface with clients

Manage skilled and personal calendars and emails

Provide outstanding wealth management service to clients

Provide administrative support

Develop and maintain excel, word and power point documents

Use technology/systems to support clients

Maintain knowledge of client accounts by reviewing daily activity online and applicable reports

Research and resolve inquiries and issues related to accounts

Assist with personal administrative affairs, as required

Coordinate and schedule appointments and meetings

Scan documents, maintain files and records

File so that information remains updated and easily accessible

Assist with all office tasks

Other administrative projects, duties or responsibilities, as directed

What do you need to succeed?

A post-secondary degree (business related diploma or degree)

8-10 years of administrative experience





Previous financial service / brokerage industry experience

Required Preferred industry courses: Canadian Investment Regulatory Exam (“CIRE”), Retail Securities Exam (“RSE”)

Preferred industry Registration Categories designations: Investment Representative / Registered Representative Designation preferred

Note: Investment Representatives / Registered Representatives prior to December 31, 2025, are exempt from new proficiency requirements, if they are continuing in the same category of registration.They are not required to complete the Canadian Investment Regulatory Exam (“CIRE”) if they have a minimum two years of prior experience in the same registration category within three years prior to the date of application for approval.

Strong communication skills – verbal and written

Exceptional client service skills

Strong attention to detail

Ability to adhere to the highest level of privacy and confidentiality

Ability to plan, organize, and prioritize

Ability to deliver and follow through to the end on projects

Strong technology acumen: a willingness to learn industry software, WebEx / Zoom and

Excellent interpersonal skills

Great attitude and personable

Reliable member of the team

A can-do, proactive approach to learn and grow

Ability to plan, organize, prioritize and multi-task

Proficiency with PowerPoint, Excel, CRMs, and Outlook

What will we offer?

Base Salary of $80-115,000, depending on experience

Discretionary bonuses

Professional Development through Industry Courses

A progressive, and high performing team

Join Caldwell and be part of a highly engaged and collaborative team, where employees:

(i) can reach their full potential,

(ii) consistently deliver high-quality client experiences; and

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📌 Licensed Executive Assistant (Winnipeg)
🏢 Caldwell Securities
📍 Winnipeg