AI-First VP 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 

Worldwide
Fully-remote
full-time (40 hrs/week)
Flexible schedule
Long-term role

AI-First VP of Sales   $200,000 USD/year

Description

Enterprise software doesn’t usually fail because of a lack of logos; it fails because revenue from the logos you already won erodes in silence. In long-cycle B2B, 70–90% of next year’s revenue is decided by how well you renew, expand, and rescue. Forecast slippage, messy SOWs, and weak escalation hygiene quietly torch margin and trust. The result is missed plans, CFO skepticism, and customers that treat you like a replaceable vendor instead of critical infrastructure.

We run a different playbook. This is a system-led commercial model where disciplined execution beats heroics. We engineer profitable, durable revenue from an existing Fortune-level base through clean renewals, precision expansions, and executive-level escalation control. Commercial structure is a first-class product: proposals that protect margin, contracts that enable clean delivery, and QBRs that actually move adoption.

This role isn’t a freedom-without-frameworks gig, and it isn’t a place to hide behind vibes or vanity pipeline. It’s for someone who gets energy from forecast accuracy, margin-safe deal structures, crisp SOWs, and executive conversations that end with clarity and commitments. You’ll bring real GenAI chops to speed analysis and communication, strong commercial judgment in ambiguous moments, escalation control that calms the room, and the coaching muscle to sharpen pricing, structure, and negotiation across the team. If you’ve led enterprise B2B software sales with responsibility for renewals, expansions, multi-year terms, SLAs, and pricing, then you’ll feel right at home.

If you’re currently leading or have recently led an enterprise sales org in SaaS, or you’ve progressed through senior roles like Sales Director, Regional VP, or Head of Enterprise Accounts after an early career built on rigorous pipeline management, we should talk. Step into a role where your craft isn’t diluted by chaos and own the engine that actually determines next year’s number. Apply if you’re ready to prove that disciplined commercial execution beats hope every time.

What you will be doing

  • Driving renewals and expansions from pipeline to signature
  • Running executive reviews and managing escalations
  • Shaping and approving commercial proposals and contracts that hold up under pressure

Key responsibilities

  • Increase enterprise account revenue and retention through disciplined commercial execution, strategic account leadership, and seamless customer integration

Candidate requirements

  • At least 5 years of experience managing renewals, expansions, or account growth in the B2B enterprise software industry
  • Experience using LLMs and other GenAI tools to streamline workflows
  • Experience managing multi-million-dollar enterprise accounts
  • Experience with CRM systems and Order-to-Cash (O2C) processes
  • Experience working with regulated industry customers (finance, healthcare, or pharma), including compliance-driven commercial structures
  • Experience leading sales or account management teams in quota-carrying roles and coaching on deal structure and negotiation

Meet a successful candidate

Watch Interview
Andres Ramirez
Andres  |  Senior Account Manager
Netherlands  

Globetrotting Andres moved to Amsterdam for love. Thanks to Crossover, that’s only the beginning of the story.

Meet Andres

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Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Accept job offer.
STEP 6

Accept job offer.

Pass
proctored test.
STEP 5

Pass
proctored test.

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