Crossover
Enterprise Sales Executive, Trilogy (Remote) - $100,000/year USD
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Unique Enterprise Sales Role
Most enterprise renewal roles chain you to one product and one quota. This one does neither. You'll sell across a portfolio of enterprise software products — learning each deeply enough to defend its value in front of a customer's decision-makers — and you'll compress years of sales development into months because of it.
At Trilogy, we don't track how many deals you close or how many customers you lose. We track the quality of the work: whether your renewal calls were prepared, whether the customer left understanding their options, whether your emails actually moved the renewal forward. Compensation is guaranteed, not commission-driven. And you won't be discounting your way to a signature — pricing isn't yours to negotiate. Your job is to make the value obvious.
You'll run renewal calls and customer correspondence for enterprise accounts, position AI capabilities, Platinum, and Prime, and guide customers through our Self-Serve Portal. AI is part of the work, not a talking point: you'll use it to prep opportunities, prioritize your inbox, and sharpen every email you send.
If you'd rather master a standardized, high-quality sales process than grind a quota, apply now.
What You Will Be Doing
- Running renewal sales calls with enterprise customers — preparing from Salesforce opportunity data and AI-generated summaries of current and prior renewals, setting the agenda, following the call script and quality bar, and closing with a clear, agreed next action
- Positioning AI features, Platinum, and Prime on their business merits, or guiding customers to the Self-Serve Portal to explore the content at their own pace
- Writing customer emails that advance the renewal — succinct, unambiguous, playbook- and template-compliant, and AI-enhanced
- Working the Renewals Cadence end to end and keeping Salesforce opportunity records clean enough that a non-expert can read the renewal status at a glance
- Raising internal action requests — quotes, invoices, legal, support, escalations — so customers never have to chase you for a promised follow-up
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What You Won’t Be Doing
- Hunting new logos or generating new leads
- Negotiating prices or discounting to win a signature
- Courtesy calls, relationship-building meetings, or happiness checks
Enterprise Sales Executive Key Responsibilities
Every renewal conversation and every customer email on your accounts is yours to own: prepared calls, clearly understood options, actionable outcomes, and a Salesforce record that tells the truth. Your work is assessed against the renewal call quality bar and the AI Opp Cadence Checker report — not a revenue target.
Basic Requirements
- 4+ 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+
- Full professional fluency in written and spoken English
- 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
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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.
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 $50 USD/hour, which equates to $100,000 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-3282-GB-London-EnterpriseSale
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