Trilogy isn't a conventional SaaS sales organization with arbitrary targets, commission structures, or excessive management layers. We are an AI-first organization redefining enterprise sales: refining deal execution, risk evaluation, and stakeholder engagement through AI-powered insights. You'll join a team that operates with speed, iterates continuously, and uses AI to remove inefficiencies, enabling you to concentrate on what truly drives closures. Rather than chasing variable commissions, you'll benefit from a guaranteed compensation structure, giving you the freedom to refine your sales expertise without the uncertainty of fluctuating earnings.
This is not a passive renewals oversight role. It's a hands-on, execution-focused position where you'll manage a renewals pipeline, identify critical economic buyers, address objections, and drive contract renewals with precision. You won't be managing a team or wasting hours in internal meetings. Instead, you'll be actively negotiating high-value renewals and ensuring sustained customer retention.
If you're looking to influence the future of AI-driven sales while owning high-impact transactions, submit your application today!
What You Will Be Doing
- Drive high-touch engagements with strategic customers, establishing value alignment, addressing objections, and securing renewals
- Develop and refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and frameworks designed to optimize retention and revenue growth
- Pursuing new logo acquisition or prospecting for new leads
- Managing high-volume, low-value renewal transactions
- Take full ownership of the renewals process for high-value enterprise accounts, acting as the main point of contact, with the objective of preserving revenue and reducing churn
- 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
- Proven history 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
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-GB-London-SeniorAccountM
