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Head of Risk & Insurance

VIA Rail Canada
Full Timedirector
New York City Posted 4 weeks ago

Role Overview

VIA Rail Canada is hiring a director-level Head of Risk & Insurance. This is a full-time role in New York City. Part of VIA Rail Canada's Risk hiring. Full responsibilities, required qualifications, and the apply link are listed in the description below.

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Job description

Via is using technology to transform transportation around the world. From changing a single person's daily commute to reducing humanity's collective environmental footprint — we've got huge goals.

As Head of Risk & Insurance, you will lead Via's insurance program, shaping its strategy, structure, and operations, as well as continuing to expand it as we take on new business lines.  Reporting to the COO, you'll be close to the integral parts of the business where risk shows up first. 

What You'll Do:

  • Own Via's insurance program end-to-end: assess our risk profile, identify the coverage we need, and put risk programs in place across the markets we operate in
  • Partner with senior leadership on risk strategy, including coverage decisions, alternative risk transfer (captives, self-insured retentions), and how risk and insurance figure into Via's broader operational and financial planning
  • Manage brokerage and carrier relationships: run renewals, evaluate quotes, negotiate terms, and select partners who can grow with us globally
  • Build the systems and team to manage claims and litigation efficiently: define how incidents are reported; how reserves are set; and how we run a highly effective claims management process 
  • Develop a risk management strategy that goes beyond insurance: partner with Legal, Finance, and other internal teams to identify and reduce loss exposure
  • Build the internal infrastructure: put policies, processes, dashboards, and reporting in place so the rest of the company has clear visibility into our risks 
  • Stand up the analytics that tell us whether the program is working: monitor loss ratios, claim frequency and severity, cost per mile, and retention thresholds and use them to inform every renewal
  • Lead, grow and develop Via’s risk team as the program scales

Who You Are:

  • You have built and run an insurance program before — ideally one with significant operational  exposure, and ideally at a company operating across multiple jurisdictions. You know what excellent looks like because you've built it.
  • You have at least 10+ years of experience in risk management, insurance, or a closely adjacent function
  • At the same time, you’re excited to build. You thrive in ambiguity and are excited to help scale a function at a rapidly growing company 
  • You think commercially. Insurance is both a cost to be optimized and a risk management tool to be wielded. You understand both sides and can make trade-offs that hold up to scrutiny
  • You are analytical and data-driven. You leverage claims, litigation, and operational insights to identify trends, evaluate risk, and drive decisions that improve outcomes and reduce costs
  • You are operationally minded. You know how to translate strategy into process, headcount, and tooling and how to do it in a way that scales
  • You are hands-on and low ego — no task is too small if it helps contributes to Via’s success 

Compensation and Benefits:

  • Final salary will be determined by the candidate's experience, knowledge, and skills. Salary reflected does not include equity or variable pay, where applicable.
  • Salary Range: $200,000 - $300,000 / year
  • We are proud to offer a generous and comprehensive benefits package, including free medical plans and 401K matching.

Ready to join the ride?

Via is an equal opportunity employer.

About VIA Rail Canada

VIA Rail Canada logo

VIA Rail Canada

viarail.ca

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Frequently Asked Questions

How do I apply for the Head of Risk & Insurance position at VIA Rail Canada?

Use the Apply button above to submit your application directly to VIA Rail Canada. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.

Where is the Head of Risk & Insurance position at VIA Rail Canada located?

This position is based in New York City. VIA Rail Canada has not indicated remote or hybrid options for this role, so candidates should plan for on-site work.

What does a Head of Risk & Insurance at VIA Rail Canada earn?

VIA Rail Canada has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.

When was the Head of Risk & Insurance role at VIA Rail Canada posted?

This role was posted on June 10, 2026 (32 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.

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