Head of Operations

Tali AI•Toronto, ON

23h•CA$170,000 - CA$220,000•Hybrid

About The Position

Tali AI is seeking a full-time Head of Operations to serve as the operational backbone of the company. This role is crucial for consolidating run-the-business functions, building scalable systems, and freeing up founders to focus on product, growth, and key relationships. The Head of Operations will be an operational anchor alongside a fractional CFO and VP of Sales, acting as a partner to the CEO during a significant growth phase. This is a senior leadership position with broad ownership and potential to evolve into a COO role. The company emphasizes an AI-native approach to operations, prioritizing automation and designing lean solutions from first principles rather than adhering to standard SaaS playbooks. Curiosity and a deep understanding of operational problems are key attributes for this role.

Requirements

8+ years in operations, including senior operational leadership at a startup/scaleup (Series A-C), ideally in B2B SaaS.
Hands-on experience standing up and running at least two of: RevOps/BizOps, People/HR, Security/Compliance, IT.
Player-coach mentality, comfortable with both strategy setting and hands-on execution.
AI-native operator, prioritizing automation and AI in process design.
First-principles, curious thinker, who analyzes problems deeply rather than relying on standard solutions.
Strong systems and data instincts.
Fluency with operational tooling (CRM/RevOps, HRIS, etc.).
High trust, low ego, calm under ambiguity, and excellent prioritization judgment.

Nice To Haves

Healthtech or another regulated industry experience.
Familiarity with PHIPA/PIPEDA, SOC 2, or healthcare data.
Experience supporting a financing round or other strategic corporate process operationally.
Canadian healthcare-system context.
HubSpot expertise.

Responsibilities

Run the company's operating rhythm, including annual/quarterly planning, OKRs, goal-setting, leadership meetings, and board preparation.
Drive cross-functional execution and program management to translate strategy into tangible outcomes.
Act as the CEO's force multiplier on special projects, including operational support for financing and strategic initiatives.
Own the People function, focusing on hiring velocity, onboarding, and performance and compensation frameworks.
Steward company culture and team health during periods of headcount growth.
Own Revenue Operations (RevOps) and Business Operations (BizOps), including CRM hygiene, pipeline and SLA reporting, lead definitions, and billing/renewals operations.
Partner closely with Sales, Marketing, and Customer Success to make the business measurable and the go-to-market machine efficient.
Own the security, privacy, and compliance backbone for a healthtech company, including SOC 2, PHIPA/PIPEDA compliance, data governance, information security, and vendor security reviews.
Manage contracts, vendors, and procurement, including partner and platform agreements.
Coordinate legal and corporate administration to maintain a tidy and audit-ready corporate operating foundation.