- How to rapidly become a credible product expert across multiple enterprise software products
- How to position and differentiate a product based on business value rather than feature comparisons or discounts
- How to apply AI to prepare opportunities, prioritize customer communication, and elevate output quality
- A consistent, repeatable renewals methodology that applies to any enterprise sales position
Description
Most renewal roles at the enterprise level lock you into a single product and a single quota. This position does not. You'll work across a portfolio of enterprise software offerings — gaining sufficient depth in each to justify their value in front of a customer's executive team — and you'll condense years of sales training into a matter of months as a result.
Trilogy does not measure how many renewals you close or how many accounts you lose. We measure the quality of your work: whether your renewal discussions were well-prepared, whether the customer walked away with a clear understanding of their choices, whether your correspondence genuinely advanced the renewal. Compensation is fixed, not based on commissions. And you will not discount your way to a closed deal — pricing is not within your control. Your responsibility is to make the value self-evident.
You'll lead renewal discussions and customer communications for enterprise accounts, present AI capabilities, Platinum, and Prime, and direct customers through our Self-Serve Portal. AI is woven into the daily work, not a marketing line: you'll leverage it to prepare opportunities, prioritize communications, and refine every message you write.
If you prefer to master a consistent, high-caliber sales methodology over chasing a quota, apply now.
What you will be doing
- Conducting renewal sales discussions with enterprise customers — preparing using Salesforce opportunity data and AI-generated summaries of current and historical renewals, defining the agenda, adhering to the call script and quality standard, and concluding with a clear, mutually agreed next step
- Presenting AI features, Platinum, and Prime based on their business value, or directing customers to the Self-Serve Portal to review the materials independently
- Composing customer emails that move the renewal forward — concise, clear, aligned with playbook and templates, and enhanced by AI
- Executing the Renewals Cadence from start to finish and maintaining Salesforce opportunity records with clarity sufficient for any reader to understand renewal status immediately
- Submitting internal action requests — quotes, invoices, legal, support, escalations — ensuring customers are never left waiting for a promised follow-up
What you will NOT be doing
- Pursuing new logos or generating fresh leads
- Adjusting prices or offering discounts to secure a signature
- Conducting courtesy calls, relationship-building sessions, or satisfaction check-ins
Key responsibilities
Take ownership of the quality of every renewal conversation and every customer email on your accounts: well-prepared calls, clearly communicated options, actionable next steps, and a Salesforce record that accurately reflects reality. Your performance is evaluated against the renewal call quality standard and the AI Opp Cadence Checker report — not against a revenue goal.
Candidate requirements
- 4+ years of experience in a CSM or account management role at a software/SaaS/Cloud products company serving Enterprise clients
- Experience owning the full 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
- Proven success renewing complex, high-value B2B software (SaaS and on-prem) and related services with large enterprises
- Experience managing multiple products across different verticals or business units
- Confidence selling value-added services and premium tiers based on business benefit rather than price
- Practical experience with ChatGPT or Claude to improve the quality and efficiency of customer-facing work
Meet the hiring manager
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How it works
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
STEP 1
Chat-style
screening interview.
STEP 2
Cognitive 
aptitude test.
STEP 3
Prove real-world 
job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Pass
proctored test.
STEP 6
Accept job offer.
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Why Crossover
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The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
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