At a Glance
- Tasks: Lead high-stakes negotiations and manage renewals for enterprise clients using AI-driven strategies.
- Company: Join Trilogy, an innovative AI-first company transforming enterprise sales.
- Benefits: Enjoy a competitive salary, guaranteed compensation, and the chance to work remotely.
- Other info: Dynamic environment with opportunities for career growth and innovation.
- Why this job: Shape the future of AI-driven sales while owning impactful deals and driving customer success.
- Qualifications: 8+ years in customer success or account management with enterprise clients; fluent in English.
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.
If you want to shape the future of AI-driven sales while owning high-impact deals, here’s 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.
Key Responsibilities:
- 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 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:
- 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 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.
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.
Senior Customer Success Manager, Trilogy (Remote) - $200,000/year USD in London employer: Crossover
At Trilogy, we pride ourselves on being an innovative AI-first company that empowers our employees to excel in their roles without the constraints of traditional sales structures. Our remote work culture fosters collaboration and flexibility, allowing you to engage directly with high-value clients while enjoying a guaranteed compensation plan that prioritises your professional growth and stability. Join us to be part of a dynamic team that values creativity, efficiency, and the pursuit of excellence in customer success.
StudySmarter Expert Advice🤫
We think this is how you could land Senior Customer Success Manager, Trilogy (Remote) - $200,000/year USD in London
✨Get to Know the Company Culture
Before jumping into applications, it’s super helpful to understand the vibe at Crossover. Check out their social media, read reviews on sites like Glassdoor, and see how they engage with customers. It'll give you clues on their values and help tailor your conversation during interviews.
✨Join Customer Support Communities
Dive into online communities like those on Reddit or LinkedIn where customer support pros hang out. Participating in discussions or asking questions can make you more visible to potential recruiters and help you learn about job openings at companies like Crossover before they even post them.
✨Attend Job Fairs or Networking Events
Look out for local job fairs or events specifically for customer support roles. This is your chance to meet hiring managers face-to-face, and you might even get the opportunity to interview on the spot!
✨Show Off Your Skills with Customer Interactions
In the customer support world, showcasing your communication skills is key. Consider creating a short video introducing yourself or even doing a mock call to showcase your abilities. It's a memorable way to stand out, especially if you can share this during your interview process!
We think you need these skills to ace Senior Customer Success Manager, Trilogy (Remote) - $200,000/year USD in London
Some tips for your application 🫡
Show Off Your Communication Skills:In customer support, clear communication is key. Make sure your CV highlights any experience you've had in customer-facing roles and your ability to resolve issues. Don't shy away from including specific examples of how you've gone above and beyond to help customers – this really shows your potential in the role.
Tailor Your Cover Letter to Crossover:Your cover letter is your chance to shine! Tell us why you want to work at Crossover specifically. Mention any unique aspects of our company that resonate with you and how your skills can enhance our customer support. This personal touch will set your application apart from the rest!
Highlight Any Relevant Tools or Tech Skills:If you've used customer support software like Zendesk or Freshdesk or have experience with CRM systems, make sure to mention these in your application. Being familiar with industry-standard tools can be a big plus for us when we’re reviewing applications, as it shows you can hit the ground running!
Demonstrate Your Problem-Solving Skills:Customer support roles often require a knack for problem-solving. In your application, share examples of past experiences where you've tackled tough situations or resolved conflicts effectively. This will give us a good sense of how you handle challenges—an essential skill for success at Crossover!
How to prepare for a job interview at Crossover
✨Show Off Your People Skills
In customer support, it's all about communicating effectively. Prepare to share instances from your past experiences where you handled difficult customers or resolved conflicts. We want to hear how you empathised and found the best solutions, so think of specific examples to back up your stories!
✨Know the Tools of the Trade
Familiarise yourself with common customer support tools like Zendesk or Freshdesk, and make sure to review how you’ve used any similar systems in the past. During the interview, being able to discuss your hands-on experience with software or ticketing systems can really set you apart from the competition, so don’t skip this prep!
✨Show Genuine Enthusiasm
As this is a full-time role, employers want someone who isn’t just looking for any job, but wants to grow within customer support. Make sure to express your enthusiasm for helping customers and your desire to develop your skills. Show them why you're passionate about this field!
✨Practice Common Scenarios
Be prepared for role-playing scenarios where you might have to reassess a solution with a frustrated customer or explain a complex process in simple terms. Practising these common scenarios can help us feel more confident and demonstrate our practical skills effectively during the interview.
