Commercial Underwriter

High Street Financial Services Corp.

Location: Calgary or Toronto (With regular collaboration across Edmonton, Calgary, and Toronto)

Reports to: Origination Team

Employment Type: Full-Time, Permanent

About the Role

High Street Financial Services is seeking an experienced Commercial Underwriter to support our origination team across Edmonton, Calgary, and Toronto. This role is central to evaluating, structuring, and recommending financing solutions for multifamily and commercial real estate transactions. The successful candidate will bring strong credit and financial analysis skills, along with hands-on experience in both CMHC-insured and conventional lending, to help drive sound, well-structured deals from origination through to approval.

The role can be based out of either Calgary or Toronto, with the expectation of close collaboration with originators and colleagues in Edmonton.

Key Responsibilities

- Underwrite multifamily and commercial real estate financing transactions, including acquisition, refinance, and construction/term deals
- Analyze borrower financial statements, rent rolls, operating statements, appraisals, and market data to assess credit risk and property performance
- Structure financing solutions that balance risk, return, and client needs, including loan sizing, pricing, covenants, and terms
- Evaluate and underwrite both CMHC-insured and conventional financing transactions, ensuring compliance with applicable program requirements and internal policies
- Partner closely with the origination teams in Edmonton, Calgary, and Toronto to support deal flow, client needs, and help structure competitive offers
- Conduct market research to inform underwriting assumptions and risk assessments
- Monitor portfolio performance and covenant compliance as required
- Maintain accurate and organized documentation in support of audit, compliance, and regulatory requirements

Qualifications
- Proficiency with Microsoft Excel and underwriting/financial modeling tools
- Post-secondary degree in Finance, Real Estate, Business, Economics,



or a related field
- Professional designation (e.g., CFA, MBA) considered an asset but not required
- 3–5 years of experience underwriting multifamily and commercial real estate transactions
- Demonstrated experience with CMHC-insured financing programs (e.g., MLI Select) as well as conventional lending products
- Strong financial analysis skills, including cash flow analysis, debt service coverage, and loan-to-value assessment
- Proven ability to structure and recommend financing solutions tailored to deal-specific risk and client objectives
- Solid understanding of commercial real estate fundamentals, valuation principles, and market dynamics across Canada
- Excellent written and verbal communication skills, with the ability to prepare clear, and concise lender submissions
- Strong organizational skills with the ability to manage multiple transactions and deadlines simultaneously

What We're Looking For
- A collaborative team player who can work effectively with originators and underwriters across multiple offices and time zones
- Strong attention to detail balanced with the ability to exercise sound judgment under time pressure
- A proactive, solutions-oriented approach to problem-solving
- High degree of integrity and professionalism in handling sensitive financial information

Why Join High Street Financial Services Corp. High Street Financial Services offers a collaborative, growth-oriented environment where underwriters play a direct role in shaping financing solutions for clients across Canada's commercial real estate market. We offer competitive compensation, comprehensive benefits, and opportunities for professional development.

To Apply: Please submit your resume and cover letter to [email protected].

High Street Financial Services is an equal prospect employer. We thank all applicants for their interest; however, only those selected for an interview will be contacted.

Pay: From $55,000.00 per year

Education

- Secondary School (required)

Experience:
- commercial underwriting: 3 years (preferred)

Location:
- Calgary, AB T2R 1M7 (preferred)

Work Location: In person

📌 Experienced Commercial Underwriter (Calgary)
🏢 High Street Financial Services
📍 Calgary