Senior Enterprise CSM - AI-Driven Renewals

Crossover; Vancouver; On-site; CAD 263,000 - 291,000; Full time

Job summary

Trilogy is seeking a Senior Customer Success Manager to own the renewals pipeline for high‑value enterprise accounts, negotiating renewals and driving long‑term retention.

You’ll lead executive conversations, define renewals playbooks, and apply AI‑driven insights to maximize revenue while avoiding low‑value work. This is a contractor‑of‑record role via Crossover with a guaranteed comp plan.

Qualifications

• 8+ years in a CSM or account management role serving Enterprise clients.
• Experience managing the entire renewal cycle—from client engagement to closing deals worth $100K+.
• Fluent English with strong written and verbal communication.
• Experience using AI tools in a professional setting.
• Must be able to work during U.S. business hours.

Responsibilities

• Own the entire renewals process for high‑value enterprise accounts, serving as the primary point of contact.
• Lead high‑touch conversations with key customers to align on value, overcome objections, and win renewals.
• Define and continuously improve structured renewals playbooks and AI‑driven strategies to maximize retention and revenue.
• Identify key economic buyers, navigate procurement processes, and drive contract renewals with precision.

Skills

Negotiation

Account management

Renewals management

English proficiency

AI tool experience

Tools

ChatGPT

Claude

Job description

Trilogy is seeking a Senior Customer Success Manager to own the renewals pipeline for high‑value enterprise accounts, negotiating renewals and driving long‑term retention.

You’ll lead executive conversations, define renewals playbooks, and apply AI‑driven insights to maximize revenue while avoiding low‑value work. This is a contractor‑of‑record role via Crossover with a guaranteed comp plan.