Are you an enterprise sales or customer success pro who thrives in high-stakes negotiations, enjoys engaging senior executives, and wants to master AI-driven sales execution? If so, here's a role where you can own the renewals pipeline for high-value enterprise clients, leading direct conversations with decision-makers, and securing multi-million-dollar contracts.

At Trilogy, we're not running a traditional SaaS sales org with arbitrary quotas, commission games, or bloated layers of management. We're an AI-first company that’s rewriting how enterprise sales works: optimizing deal execution, risk assessment, and stakeholder engagement with AI-powered insights. You'll be part of a team that moves fast, iterates constantly, and leverages AI to eliminate inefficiencies, so you can focus on what actually closes deals. Instead of chasing commissions, you'll have the stability of a guaranteed comp plan, allowing you to sharpen your sales craft without the stress of unpredictable payouts.

This is not a cushy renewals overseer job. It's a hands‑on, execution-driven position where you'll be responsible for managing a renewals pipeline, identifying key economic buyers, overcoming objections, and driving contract renewals with precision. You won't be babysitting a team or wasting time in endless internal meetings. You'll be on the front lines, negotiating high-value renewals and ensuring long‑term customer retention.

What You Will Be Doing

Lead high-touch conversations with key customers, aligning on value, overcoming objections, and winning renewals

Define and continuously improve structured B2B renewals playbooks, AI‑driven sales strategies, and frameworks to maximize retention and revenue

What You Won’t Be Doing

New logo sales or hunting for new leads

High volume, low value renewal processing

Enterprise Renewals Executive Key Responsibilities
Your single mandate is to own the entire renewals process for high‑value enterprise accounts, serving as the primary point of contact,



with the goal of retaining revenue and minimizing 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 robust 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

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 on business benefit rather than price

Hands‑on use of ChatGPT or Claude to raise 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 contemporary 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-Toronto-EnterpriseRene

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📌 Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD (Ontario)
🏢 Crossover
📍 Ontario