If you're a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, connects effectively with senior executives, and is ready to embrace AI-driven sales execution, consider this opportunity. You'll take ownership of the renewals pipeline for high-value enterprise accounts, engage directly with decision-makers, and close multi-million-dollar contracts.

Trilogy isn't structured like a conventional SaaS sales organization with arbitrary targets, commission-based compensation, or excessive management layers. We operate as an AI-first organization, fundamentally transforming enterprise sales by optimizing deal execution, assessing risk, and managing stakeholder engagement through AI-powered intelligence. You'll join a team that operates with speed, iterates continuously, and applies AI to remove inefficiencies—enabling you to concentrate on the activities that actually drive deal closure. Rather than pursuing commission-based earnings, you'll benefit from a guaranteed compensation structure, giving you the freedom to refine your sales expertise without the uncertainty of variable income.

This isn't a passive renewals oversight role. It's a hands-on, execution-focused position where you'll manage a renewals pipeline, pinpoint key economic buyers, address objections head-on, and execute contract renewals with accuracy. You won't be managing a team or sitting through endless internal meetings. You'll operate on the front lines, negotiating high-value renewals and ensuring sustained customer retention.

What You Will Be Doing





Drive high-touch engagements with strategic customers, aligning on business value, addressing objections effectively, and securing renewals

Develop and refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and strategic frameworks designed to maximize retention and revenue growth

What You Won't Be Doing

Pursuing current logo acquisition or prospecting for net-new leads

Processing high-volume, low-value renewal transactions

Senior Customer Success Manager Key Responsibilities

Take full ownership of the renewals process 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 track record 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

Comfort selling value-added services and premium tiers based on business benefit rather than price

Practical experience with ChatGPT or Claude to enhance the quality and throughput of customer-facing work

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.

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.002

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