Head Of Sales $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Ready to revolutionize enterprise sales with AI? As our Head of Sales, you'll spearhead high-stakes negotiations, secure multi-million-dollar renewals, and redefine how AI drives sales execution. No arbitrary quotas. No commission games. Just pure, AI-powered deal-closing prowess.
At Trilogy, we're not just another SaaS company—we're the vanguard of AI-first sales. You'll leverage cutting-edge AI insights to optimize deal execution, assess risks, and engage stakeholders with unprecedented precision. Forget about chasing commissions; our guaranteed comp plan lets you focus on what truly matters: mastering the art and science of AI-driven sales.
This isn't a role for the faint-hearted. You'll be in the trenches, managing a high-value renewals pipeline, identifying key decision-makers, and driving contract renewals with laser-focused determination. No time wasted on babysitting teams or drowning in meetings—you'll be on the front lines, shaping the future of AI-powered sales.
Are you ready to own the renewals process for enterprise giants and redefine what's possible in sales? Apply now and let's transform the industry together.
What you will be doing
- Spearhead high-impact conversations with C-suite executives, aligning value propositions and overcoming objections to secure multi-million-dollar renewals
- Architect and continuously refine AI-driven B2B renewals strategies, leveraging data-driven insights to maximize retention and revenue
- Collaborate with our AI team to develop and implement cutting-edge sales execution tools, setting new industry standards for efficiency and effectiveness
What you will NOT be doing
- Chasing new logos or cold-calling prospects—your focus is on nurturing and growing our existing high-value relationships
- Processing high-volume, low-value renewals—we're after quality, not quantity
- Wasting time in endless internal meetings or managing large teams—your energy is dedicated to direct client engagement and deal execution
Key responsibilities
Drive and own the entire renewals lifecycle for our most valuable enterprise accounts, serving as the strategic linchpin between Trilogy and key decision-makers to maximize revenue retention and minimize churn, directly impacting our bottom line and long-term growth trajectory.
Candidate requirements
- North or South America-based sales professional with a proven track record
- Minimum 5 years of battle-tested experience in account management, renewal sales, or customer success, specifically in B2B software revenue retention
- Demonstrated success managing high-value accounts with $1 million+ ARR
- Forward-thinking mindset with the ability to embrace and champion an AI-first approach in all aspects of your work
- Advanced proficiency in CRM tools like Salesforce or HubSpot
- Exceptional negotiation skills and the ability to navigate complex stakeholder landscapes
- Strong analytical capabilities to leverage data-driven insights for strategic decision-making
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
Pass Cognitive Aptitude Test.
STEP 2
Pass English Proficiency Test.
STEP 3
Prove Real-World Job & AI Skills.
STEP 4
Ace An Interview Or Two.
STEP 5
Accept Job Offer.
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Why Crossover
Recruitment sucks. So we’re fixing it.
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.
