CS

Head of Operations

Cold Start
Posted onJan 22, 2026
LocationMontréal, Quebec, Canada | Toronto, Ontario, Canada (On-site)
Employment typeFull-time

Head of Operations

About Cold Start Ventures

Cold Start Ventures partners with world-class founders to launch and scale category-defining startups at the intersection of healthcare and AI. Each company we incubate is backed by tier-1 VCs with $1.5M+ in committed day-one capital. Our ventures benefit from a tested playbook that drives a 6× higher survival rate to Series B than the industry average — creating over $2B in portfolio value, including breakout successes such as 3Y Health and Berry Street.

The Role

We’re seeking a Head of Operations to own and scale Cold Start’s internal operations while supporting the growing portfolio of venture-backed startups. This is a high-impact, high-visibility role suited for a dynamic operator with a finance or consulting background — someone equally comfortable modeling cash flows, negotiating vendor agreements, and structuring multi-entity operations.

This is an ideal fit for a former investment banker, management consultant, Chief of Staff, or business operations leader — especially someone who’s worked in VC-backed, early-stage, or high-growth environments and thrives in fast-paced, ambiguous settings.

Responsibilities

  • Lead day-to-day operations for Cold Start Ventures and provide operational support to incubated startups

  • Oversee financial planning, reporting, and compliance — from multi-entity structuring and capital allocation to vendor management and audit readiness

  • Develop and present partner- and investor-ready materials, including performance dashboards and partner updates

  • Drive special projects with founders including market analysis, fundraising processes, and GTM support

  • Serve as a strategic partner to leadership on business development, venture structuring, and growth initiatives

Qualifications

  • 5–8+ years of experience in investment banking, management consulting, venture/business operations, or finance leadership roles

  • Strong financial acumen, with the ability to interpret data, manage budgets, and build scalable operational systems

  • Proven experience operating in startup or early-stage environments, comfortable with rapid change and context-switching

  • Exceptional communicator — able to synthesize complex information for executives, founders, and investors

  • Resourceful, execution-driven, and detail-oriented, with a track record of leading cross-functional initiatives

Bonus Points

  • Experience in healthcare, fintech, or AI-driven businesses

  • Familiarity with fund administration, venture capital, or legal ops

  • Multi-entity or international operations experience

Why Join Us?

  • $2B+ portfolio value created – including 3Y Health and Berry Street

  • True co-founder influence – your voice, equity, and leadership directly shape our future companies

  • High autonomy and direct exposure to exceptional founders, investors, and early-stage building

  • Competitive compensation and equity

Ready to help us build the next generation of startups? Apply now.

Cold Start is an incubator focused on building and investing in generation-defining companies.

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