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Underwriter Development Program Jobs in Toronto, ON

Adi Development Group

Investment Associate

Burlington, ON · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • PTO

Lead underwriting on new opportunities - sources & uses, development budgets, lease-up assumptions ... Employee Home Ownership Program: Adians have the opportunity to live in the beautiful communities ...

Munich Re

Lead Cyber Treaty Underwriter

Toronto, ON · Hybrid

CA$140K/yr

  • Medical

  • Dental

Lead Cyber Treaty Underwriter will be responsible for driving growth and expanding HSB Canada ... Learning and development programs and resources, including unlimited access to LinkedIn Learning ...

Hibernian General Insurance

AVP, Marine

Toronto, ON · On-site

  • Medical

  • Retirement

With the support of technical underwriting resources, you will guide the continued development and ... Employee-driven programs focused on gender, LGBTQ+, origins, diversity, and inclusion. * Corporate ...

FCT

Director, National Underwriting

Oakville, ON · On-site

  • Retirement

  • PTO

Provide underwriting expertise and support at client meetings, presentations, industry events, and other business development initiatives. * Develop and deliver training programs and educational ...

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All JobsUnderwriter Development Program JobsUnderwriter Development Program Jobs in Toronto, ON

Underwriter Development Program information

What is an underwriter development program?

An Underwriter Development Program is a structured training initiative offered by insurance companies or financial institutions to prepare individuals for careers as underwriters. Participants typically receive a mix of classroom instruction, on-the-job training, and mentorship to learn about risk assessment, policy evaluation, and decision-making processes. The goal of the program is to equip trainees with the knowledge and skills needed to evaluate insurance applications, determine coverage terms, and assess potential risks. These programs often lead to full-time underwriting positions upon successful completion.

What can I expect from the training and mentorship provided in an underwriter development program?

Participants in an Underwriter Development Program typically receive a blend of classroom instruction, on-the-job training, and mentorship from experienced underwriters. You can expect to rotate through various lines of business, work on real case studies, and gradually take on more responsibility as you build your technical and analytical skills. Mentors and managers provide regular feedback and support, helping you to understand underwriting guidelines, risk assessment, and client interaction. This structured training approach prepares you for a successful underwriting career and often leads to advancement opportunities within the company.

What are the key skills and qualifications needed to thrive in an underwriter development program, and why are they important?

To thrive in an Underwriter Development Program, you need strong analytical abilities, attention to detail, and a bachelor's degree in finance, business, or a related field. Proficiency with risk assessment software, Microsoft Excel, and familiarity with industry regulations or progress toward certifications like CPCU are often valued. Effective communication, critical thinking, and strong organizational skills help candidates stand out in this role. These skills ensure accurate risk analysis, clear client interactions, and the ability to manage complex portfolios in the insurance industry.

What is the difference between Underwriter Development Program vs Underwriter?

AspectUnderwriter Development ProgramUnderwriter
CredentialsTypically requires a bachelor's degree, sometimes a certification like CPCU or ARMRequires similar credentials, often with additional experience or certifications
Work EnvironmentStructured training environment, often in corporate officesOperational, risk assessment, and decision-making roles in insurance companies
Usage in IndustryEntry-level training program for aspiring underwritersFull-time professional role responsible for evaluating insurance risks

The Underwriter Development Program is designed to train and develop new talent into underwriters, providing structured learning and mentorship. An underwriter, on the other hand, is a fully qualified professional responsible for assessing risks and making underwriting decisions. The program prepares individuals for a career as an underwriter, who then performs the core job functions within the insurance industry.

How hard is it to get an underwriter development program job?

Securing an underwriter development program position typically requires a relevant bachelor's degree, strong analytical skills, and sometimes prior internship experience. Competition can be moderate to high, and candidates often need to demonstrate proficiency in risk assessment, attention to detail, and familiarity with underwriting tools or software.

What are popular job titles related to Underwriter Development Program jobs in Toronto, ON?

For Underwriter Development Program jobs in Toronto, ON, the most frequently searched job titles are:

What job categories do people searching Underwriter Development Program jobs in Toronto, ON look for?

The top searched job categories for Underwriter Development Program jobs in Toronto, ON are:

Underwriter Development Program jobs near you
Infographic showing various Underwriter Development Program job openings in Toronto, ON as of August 2026, with employment types broken down into 1% As Needed, 80% Full Time, 15% Part Time, and 4% Contract. Highlights an 92% Physical, 4% Hybrid, and 4% Remote job distribution.

Investment Associate

Adi Development Group

Burlington, ON • On-site

Full-time

Medical, Dental, Vision, Life, PTO

Posted 22 days ago

Job description

ADI Development Group is a vertically integrated Canadian real estate developer and investment manager based in the Greater Toronto Area. With an established track record across Canadian markets, ADI develops, builds, and manages institutional-quality multi-unit residential communities, with a current focus on affordable rental development at scale. The platform brings development, construction, and property management capabilities together under one roof.

We are seeking an Associate to join the Investments team, with end-to-end responsibility for underwriting, structuring, and execution across the firm's acquisition and development activities. Reporting to the VP of Investments, the Associate will lead financial modeling and diligence on new opportunities, contribute to investment decisions through Investment Committee, and partner with senior leadership on capital formation and lender relationships. The position is intended for a candidate who assumes full ownership of the underwriting function and brings rigor, intellectual curiosity, and disciplined commercial judgment to every transaction.

What You'll Do
  • Lead financial modeling and underwriting for acquisitions, ground-up development, and value-add multifamily across the GTA
  • Lead underwriting on new opportunities - sources & uses, development budgets, lease-up assumptions, debt sizing, waterfall structures, and LP/GP returns - and present recommendations to the Investment Committee
  • Manage the deal pipeline and lead preliminary investment screens to filter opportunities before full underwriting
  • Lead third-party due diligence and project reporting workstreams - including appraisals, cost consultant reports, first draw reports, and market studies - through closing and into construction
  • Structure and model joint venture waterfalls, promote structures, and partner economics, working alongside legal counsel on key deal documents
  • Own monthly cost-to-date (CTD) and cost-to-complete (CTC) model updates across the active development portfolio, partnering with construction and project management teams to validate actuals, reforecast remaining spend, and flag variances to budget
  • Partner with senior leadership on capital raising and LP fundraising, producing model outputs, return scenarios, track records, and analytical content for PPMs, teasers, IC decks, and DDQ responses; participate in LP meetings as required
  • Lead debt raising and financing workstreams, including construction loan sizing, refinancing analysis, lender models, covenant testing, and term sheet negotiation support across senior, mezzanine, and CMHC-insured structures
  • Run sensitivity and scenario analyses to stress-test investment theses
  • Author Investment Committee memos and present transactions to IC; contribute to LP reporting, fundraising materials, and ODD responses
  • Conduct market research and comparable analysis across our active jurisdictions
  • Partner with development, construction, and property management teams to validate inputs and ground-truth assumptions
  • Contribute to the development of the firm's underwriting standards and templates
What We're Looking For
  • 3-6 years of experience in real estate private equity, real estate development, or real estate investment banking, with direct exposure to ground-up development underwriting
  • Development underwriting and modeling experience is required; multifamily experience strongly preferred
  • Hands-on experience with CTD/CTC reforecasting and development cost tracking is a strong asset
  • Advanced Excel and financial modeling skills - you can build a model from a blank sheet, not just plug into a template
  • MBA from a recognized program required
  • CAIA and/or CFA designation preferred
  • Bachelor's degree in finance, real estate, economics, or related field
  • Demonstrated ability to leverage AI tools and embed AI into modeling and analytical workflows to drive productivity is required
  • Demonstrated ability to lead transactions independently and present to senior leadership and external stakeholders, including LPs, lenders, and JV partners
  • A genuine self-starter who identifies issues independently, drives them to resolution, and does not require direction to move work forward
  • A track record of forming and defending a point of view - we expect the Associate to bring recommendations to the table, not just outputs, and to back them with sound analysis
  • Demonstrated ownership mentality - treats the underwriting function as their own and consistently goes beyond the brief to pressure-test assumptions and improve the work product
  • Comfortable operating with limited oversight in a team environment, working cross-functionally across departments, and proactive in flagging risks, gaps, and opportunities to senior leadership
  • Strong written and verbal communication - IC memos, LP communications, and lender presentations are central to the role
Why Adi?

You'll work directly with senior leadership on a platform pursuing one of the most important investment theses in North America: affordable rental housing at scale. The role offers genuine deal ownership, direct exposure to institutional capital partners and lenders, and a defined development path for a candidate who performs.

  • Learning & Development Reimbursement: Adi encourages team members to never stop learning and continuously improve.
  • Competitive Paid Time Off: Team members are provided with substantial paid vacation, wellness, and sick days annually.
  • Competitive Salaries: Adi regularly conducts compensation market reviews to ensure our total compensation package remains competitive.
  • Employee Home Ownership Program: Adians have the opportunity to live in the beautiful communities we create through our Employee Home Ownership Program. Eligible team members will receive a % discount off the total purchase price.
  • Comprehensive Benefits Plan: Adi provides all full-time team members and dependents with benefits coverage for dental, prescriptions, vision care, paramedical practitioners, life insurance and more
  • Flexible Health, Lifestyle & Wellness Personal Spending Account: Annual health, lifestyle & wellness spending accounts that can be used for fitness classes, gym memberships, family & pet needs, additional health benefits and more!
$95,000 - $120,000 a year
Adi Development Group is committed to fostering an inclusive, accessible environment where all employees and customers feel valued, respected and supported. We build teams that reflect the diversity of the communities we serve, and we hire based on merit and the principle of equity in employment. We welcome applications from all qualified individuals. Upon request, accommodation will be provided during the recruitment process to ensure equal access for applicants with disabilities. If you are selected for an interview and require accommodation, please inform Human Resources.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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