How to apply for Head of Risk & Insurance

About Via Transporation

Via Transportation is revolutionizing global transit systems by replacing traditional fixed-route buses with dynamic, on-demand software. As a mission-driven company with a focus on sustainability and equity, you'll work on technology that directly impacts millions of daily commuters in over 30 countries.

About the role

As Head of Risk & Insurance, you'll own Via's entire insurance program, from assessing risk across diverse global markets to negotiating with carriers and building an in-house claims team. Your work directly enables Via's rapid expansion into new geographies while protecting the company from operational and financial risks.

A typical day

You might start the day reviewing a claims report from a new market, then jump on a call with a broker to negotiate renewal terms. After lunch, you'll meet with the VP of Operations to discuss a new city launch's risk profile, and end the day building a dashboard to track claims trends across all markets.

Who Via Transporation is looking for

• You have 10+ years in risk/insurance, with hands-on experience building insurance programs from scratch for fast-growing tech companies or multi-jurisdictional operations.
• You're data-driven: you use claims analytics and operational data to identify risk patterns, optimize coverage, and drive decisions.
• You're low-ego and hands-on—comfortable both negotiating with C-suite and diving into claims administration details.
• You thrive in ambiguity and can scale processes as the company grows, managing relationships across different cultures and regulatory environments.

Tips for this application

• Highlight your experience with alternative risk transfer (captives, self-insurance) and how you've used data to reduce total cost of risk.
• Show specific examples of managing insurance programs across multiple countries or states, including regulatory nuances.
• Tailor your resume to emphasize operational risk management (e.g., claims handling, safety programs) not just insurance buying.
• If you have experience in mobility or transportation (rideshare, logistics), explicitly connect it to Via's business model.
• Quantify your impact: e.g., 'Reduced claims frequency by 20% through data-driven safety initiatives' or 'Negotiated 15% premium reduction across 10 markets.'

What to cover in your cover letter

["Your passion for Via's mission of making transportation efficient, affordable, and sustainable.", 'Your ability to build and scale insurance programs in a fast-paced, global tech environment.', 'Specific examples of using data and analytics to drive risk decisions, not just insurance purchasing.', "Your hands-on, low-ego approach: you're willing to do the work yourself while building a team."]

Research before applying

• Read Via's blog posts and news about their expansion into new cities (e.g., Berlin, Sydney) and understand the different regulatory landscapes.
• Look at Via's recent partnerships (e.g., with public transit agencies) to understand the operational risks involved.
• Review Via's sustainability reports or mission statements to align your risk strategy with their values.
• Check LinkedIn for current risk/insurance team members to understand team structure and where this role fits.

Likely interview topics

Based on the job description, expect questions about:

• Walk us through how you would design an insurance program for a new market like Japan or Brazil.
• How do you use claims data to inform risk mitigation strategies? Give a specific example.
• Describe a time you had to negotiate with a difficult carrier or broker. What was the outcome?
• How would you build a risk management culture in a company that moves fast and prioritizes growth?
• What's your approach to managing claims litigation while controlling costs? Any experience with self-insurance?

Common mistakes to avoid

• Focusing only on buying insurance without discussing risk mitigation, claims management, or operational improvements.
• Being too high-level—this role requires hands-on involvement, so show you're willing to dive into details.
• Ignoring the unique risks of Via's business model (e.g., driver classification, public-private partnerships, autonomous vehicles).