Head Of Sales, Trilogy (Remote) - $200,000/year USD at Crossover
Torino, Piemonte, Italy -
Full Time


Start Date

Immediate

Expiry Date

26 May, 25

Salary

200000.0

Posted On

27 Feb, 25

Experience

0 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

No

Skills

Salesforce, Business Operations, Hubspot

Industry

Marketing/Advertising/Sales

Description

Are you an enterprise sales 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, apply now!

CANDIDATE REQUIREMENTS

  • At least 5 years of experience in an account management role selling B2B software products
  • Experience managing an entire sales cycle, closing deals worth at least $1 million
  • Ability to adopt an AI-first approach in all tasks, looking for ways to use AI to optimize personal work and transform business operations
  • Proficiency in CRM tools like Salesforce or HubSpot

THIS POSITION IS ALSO KNOWN AS:

  • Regional Sales Director
  • Sales Leader
  • Enterprise Sales Director
Responsibilities

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 WILL NOT 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
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