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.

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 skilled 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 excellent 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.

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

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📌 Senior Customer Success Manager, Trilogy (Remote) - $200,000/year USD (Alberta)
🏢 Crossover
📍 Alberta