At a Glance
- Tasks: Drive high-value enterprise renewals and engage with C-level executives using AI-driven sales methods.
- Company: Trilogy, a leader in innovative software solutions with a focus on talent and technology.
- Benefits: Guaranteed $200,000/year salary, flexible remote work, and no arbitrary quotas.
- Other info: Work in a fast-paced environment with opportunities for significant career growth.
- Why this job: Join a dynamic team transforming enterprise sales and make a real impact on customer retention.
- Qualifications: 8+ years in enterprise sales or customer success, fluent in English, and experience with AI tools.
If you're a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, engages comfortably with C-level executives, and is ready to leverage AI-driven sales methodologies, this opportunity offers ownership of a high-value enterprise renewals pipeline, direct access to decision-makers, and responsibility for closing multi-million-dollar agreements. Trilogy operates differently from conventional SaaS sales organizations—we've eliminated arbitrary quotas, commission volatility, and excessive management overhead.
As an AI-first organization, we're fundamentally transforming enterprise sales: refining deal execution, assessing risk intelligently, and optimizing stakeholder engagement through AI-powered analytics. You'll join a team that operates with speed, iterates relentlessly, and applies AI to remove inefficiencies, enabling you to concentrate on activities that truly drive 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 anxiety of fluctuating earnings.
This role is not a passive renewals oversight position. It's a hands‑on, execution-focused responsibility where you'll manage a renewals pipeline, pinpoint critical economic buyers, address objections head‑on, and execute contract renewals with surgical precision. You won't be managing teams or sitting through endless internal status meetings. You'll be directly negotiating high-value renewals and safeguarding long-term customer retention.
What You Will Be Doing
- Drive high-touch engagements with strategic customers, aligning on delivered value, addressing objections, and securing renewals
- Develop and refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and operational frameworks designed to optimize retention and revenue outcomes
What You Won’t Be Doing
- Pursuing new logo acquisition or prospecting for net-new business
- Managing high-volume, low-complexity renewal transactions
Enterprise Renewals Executive Key Responsibilities
- Assume full accountability for the renewals lifecycle across high-value enterprise accounts, acting as the principal relationship owner, with the objective of preserving 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
- Demonstrated success renewing sophisticated, high-value B2B software (SaaS and on-prem) and associated services with large enterprise organizations
- Background selling multiple product lines across diverse verticals or business units
- Proficiency in selling value-added services and premium offerings based on business outcomes rather than pricing
- Practical application of ChatGPT or Claude to enhance quality and productivity of customer-facing deliverables
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.
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.
Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD employer: Crossover
Crossover is an exceptional employer that champions educational innovation and personal growth, making it an ideal place for the Chief Learning Architect for Accelerated Mastery role. With a competitive compensation package and a commitment to fostering a collaborative work culture, employees are encouraged to lead transformative initiatives while benefiting from ongoing professional development opportunities. Located in the United Kingdom, Crossover provides a unique environment where academic leaders can thrive and make a significant impact on the future of learning.
StudySmarter Expert Advice🤫
We think this is how you could land Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD
✨Leverage Your Network
In sales and business development, who you know can often be as important as what you know. Get involved with local networking events or industry meetups to connect with key players. Don't be shy—share your passion for the field and let folks know you're on the lookout for opportunities!
✨Show Your Skills Through Real-World Results
When targeting a full-time role like Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD at Crossover, presenting tangible results from your previous sales experience can set you apart. Bring along case studies or examples of how you've closed deals or expanded accounts, and don't forget to showcase your problem-solving prowess. It’s all about quantifying your success!
✨Engage with Sales Communities
Dive deep into online sales communities, like Sales Hacker or LinkedIn groups dedicated to sales professionals. Engaging in discussions and sharing insights can boost your visibility and might just put you on the radar of hiring managers looking for fresh talent in business development.
✨Direct Applications Matter
While we all know the online application route, consider sending direct applications to companies you admire, including Crossover. Tailor your message to explain why you’re drawn to them and how you can contribute as a Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD. Sometimes, a personal touch can grab attention faster than a generic application!
We think you need these skills to ace Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD
Some tips for your application 🫡
Show Off Those Sales Skills:In your CV and cover letter, highlight any previous sales or business development experience you have. Use numbers and examples to showcase your achievements – did you exceed sales targets or bring in new clients? Make those accomplishments shine!
Tailor Your Message for Crossover:When writing your cover letter, make sure to tailor your message specifically for Crossover. Show that you know the company’s mission and how your skills align with their goals in the sales landscape. This personalised touch will grab their attention!
Keep It Professional Yet Engaging:Sales is all about relationships, so while you want to maintain professionalism in your application, don’t be afraid to let your personality shine through. Engage the reader and demonstrate your enthusiastic approach to sales and business development!
Proof of Performance:Include any relevant certifications or training you’ve undertaken in sales or negotiation tactics. If you’ve attended workshops or courses, list these to showcase your commitment to professional development. This extra touch can set you apart from the competition!
How to prepare for a job interview at Crossover
✨Know Your Sales Methodologies
Brush up on popular sales methodologies like SPIN Selling or Challenger Sales. Being able to discuss these techniques and how you've applied them will show Crossover that you understand the role and can hit the ground running in the sales game.
✨Demonstrate Your Deal-Making Skills
Prepare to share stories from your past experiences where you closed deals, overcame objections, or started new client relationships. We want to show Crossover that you’re not just about numbers but also about building lasting connections in business development.
✨Prepare for Role-Play Scenarios
In a full-time sales interview, don’t be surprised if they throw in a role-play exercise to test your pitching skills. Practising how you would pitch a product or handle an objection will help us shine in this simulation—think of it like a dress rehearsal for your future sales calls!
✨Align Your Goals with the Company’s Vision
Take a moment to reflect on how your career ambitions align with Crossover’s objectives. When we articulate how our personal growth ties in with the company’s goals, it shows commitment and a genuine interest in contributing to their success.
