Senior Customer Success Manager, Trilogy (Remote) - $200,000/year USD

If you're a customer success or enterprise sales professional who excels in complex negotiations, thrives when engaging C-level executives, and is eager to leverage AI in sales execution, this role offers the opportunity to own a high-value enterprise renewals portfolio, engage directly with key decision-makers, and close contracts worth millions. Trilogy is not your typical SaaS sales organization with rigid quotas, commission-driven incentives, or excessive management overhead. We operate as an AI-first enterprise, fundamentally transforming how enterprise sales functions: refining deal execution, assessing risk, and managing stakeholder relationships through AI-powered intelligence. You'll join a team that operates with speed, embraces continuous iteration, and uses AI to strip away inefficiency—freeing you to concentrate on the activities that actually drive deal closure. Rather than chasing variable commissions, you'll benefit from the security of a guaranteed compensation structure, enabling you to hone your sales expertise without the uncertainty of fluctuating earnings. This is far from a passive renewals oversight position. It's a tactical, execution-focused role in which you'll manage a renewals pipeline, identify critical economic buyers, navigate objections, and execute contract renewals with surgical precision. You won't spend time managing teams or sitting through endless internal coordination sessions. You'll operate on the front lines, negotiating high-stakes renewals and securing long-term customer relationships. If you're ready to help define the future of AI-enhanced sales while taking ownership of high-impact transactions, submit your application today! What You Will Be Doing Drive high-touch engagements with strategic customers, align on value delivery, address objections, and secure renewals Develop and refine structured B2B renewal playbooks, AI-enhanced sales methodologies, and frameworks designed to optimize retention and revenue growth What You Won’t Be Doing Pursuing new customer acquisition or generating fresh sales leads Processing high-volume, low-value renewal transactions Senior Customer Success Manager Key Responsibilities Take full ownership of the renewals lifecycle for high-value enterprise accounts, acting as the primary relationship owner, with the objective of retaining revenue and reducing churn Basic Requirements 8+ years of experience in a CSM or account management role at a software/SaaS/Cloud products company serving Enterprise clients Experience managing the entire renewal cycle — client engagement, value proposition, negotiation, managing paper process, and closing deals worth $100K+ Fluent English, with strong verbal and written proficiency Experience using AI tools in a professional setting Must be able to work during U.S. business hours Nice-to-have Requirements Proven success renewing complex, high-value B2B software (SaaS and on-prem) and related services with large enterprises Experience selling multiple products across different verticals or business units Ability to sell value-added services and premium tiers based on business value rather than pricing Practical experience using ChatGPT or Claude to enhance the quality and efficiency of customer-facing activities About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career in leaps and bounds. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5529-CA-Calgary-SeniorCustomer.001

Own the full renewals lifecycle for high-value enterprise accounts to retain revenue and reduce churn. Develop AI-enhanced sales methodologies and B2B renewal playbooks to optimize retention and growth.

Requires 8+ years of CSM or account management experience in SaaS/Cloud for enterprise clients, including closing deals over $100K. Must be fluent in English, proficient with AI tools, and able to work U.S. business hours.

• Guaranteed compensation structure

Identified from the job description. Confirm important requirements above.

• Enterprise Renewals
• C-level Engagement
• Complex Negotiations
• Customer Success Management
• Account Management
• AI Tool Proficiency
• B2B Sales Methodologies
• Churn Reduction
• Revenue Retention
• Stakeholder Management
• Contract Negotiation
• Value Proposition Development

• Sales
• Customer Service & Support
• Software
• Management & Leadership
• Technology

Minimum experience

10+ years

Apply by

Sep 11, 2026

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Calgary, Alberta, Canada

Seniority

Director