Enterprise Customer Success Manager (AI)

Location: Vancouver, Canada; hybrid workplace. Regular travel of at least 25% across Canada and the US is required, including onsite customer workshops and strategic meetings. The role also allows working anywhere in the world for 60 calendar days per year.

Compensation: CAD 145,000–175,000 annual OTE, depending on experience.

Company

hirify.global develops an AI operating system that helps insurance agencies and brokerages automate workflows and improve policyholder service across North America.

What you will do

• Own end-to-end relationships with large enterprise insurance customers as their primary advocate and trusted advisor.
• Drive product adoption through tailored guidance, adoption sessions, change management, and workflow consulting.
• Build multithreaded relationships with executive, operational, and technical stakeholders.
• Lead strategic business reviews, executive alignment sessions, onsite workshops, and working sessions.
• Create data-driven success plans, forecast renewals, identify risks, and support retention and expansion opportunities.
• Partner with Sales, Product, Engineering, Implementation, Support, and Marketing to resolve issues and communicate customer insights.

Requirements

• 5+ years of experience in Customer Success or Account Management in a SaaS environment, including at least 3 years managing strategic enterprise accounts.
• Knowledge of insurance brokerage workflows, personal lines insurance, or related financial services.
• Strong data literacy and the ability to translate product usage into measurable ROI.
• Experience managing multiple projects and orchestrating multi-region or business-unit transformation programs.
• Ability to mobilize VP- and Director-level sponsors, communicate flawlessly in English, and demonstrate strong executive presence.
• Ability to travel at least 25% across North America and lead onsite customer engagements.

Nice to have

• Experience with HubSpot or similar CRM platforms.
• Proficiency with Microsoft Word, Excel, PowerPoint, or G-Suite equivalents.
• Experience identifying product gaps, configuration issues, and adoption blockers.

Culture & Benefits

• Customer-focused, AI-first environment with high ownership and urgency.
• Employee stock options based on experience level and subject to a standard vesting schedule.
• Comprehensive health benefits, including a CAD 500 Lifestyle Spending Account.
• Four weeks of paid vacation per year.
• Work anywhere in the world for 60 calendar days per year.
• Parental leave top-ups of six months for birthing parents and eight weeks for non-birthing parents, up to a CAD 100,000 annual salary.