Head Of Sales
$100,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

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

Head Of Sales   $100,000 USD/year

Description

You're an enterprise account manager who's tired of operating as a glorified renewal coordinator. You understand how to maintain marquee clients, ensure contract integrity, and sustain revenue momentum—all without requiring an army of CSMs, solution engineers, and enablement resources to support you. You can speak to a CMO in business outcomes, a content director in tactical execution, and compliance teams in risk mitigation. And you can genuinely develop automation that transforms your workflow, not just "I prompt ChatGPT."

Contently operates in the enterprise space where errors carry significant consequences: regulated content. Financial institutions, healthcare organizations, and recognized consumer brands rely on us because brand protection, governance, and compliance are non-negotiable. What makes this compelling is you're not entering cold relationships. You're taking ownership of an enterprise book where credibility is already established. Your mission is to convert that credibility into sustained and expanded revenue by demonstrating ROI in terms your clients understand, then scaling intelligently. As you execute, you'll help shape what AI-enabled account management means in 2026 for a content platform—because this playbook doesn't exist yet.

This position is about owning renewals with precision. It's facilitating QBRs that resonate with senior leadership because you connect platform usage to measurable outcomes like reduced compliance exposure and strengthened brand equity. It's identifying expansion opportunities within accounts and the broader market proactively, then delivering proposals grounded in actual client activity and genuine needs. It's also delivering automation on a quarterly cadence that eliminates hours of manual AM tasks, freeing your capacity for strategic planning, negotiation, and growth initiatives. If your understanding of "AI capability" stops at generating better emails more quickly, this role isn't for you.

You'll join a streamlined team where accountability defines the culture and autonomy defines the benefit. You'll collaborate cross-functionally with product, support, finance, and marketing specialists as required, but you are the driver who delivers results. If you want ownership of genuine enterprise accounts, immediate visibility into your impact, and a position where building with AI is mandatory, we encourage you to apply. If you're joining to develop your AI skills on the job and expect a gradual ramp period, please do not apply (other roles at Crossover offer that path).

What you will be doing

  • Account Renewals - Execute annual contract renewals on schedule, at or exceeding current ARR, with documented justification for retention outcomes
  • Customer Success Plans - Maintain per-account success documentation that captures client objectives, health indicators, renewal schedules, and expansion opportunities
  • AI Workflow Automation - Develop scripts or automation systems to manage repetitive activities (data extraction, status communications, QBR preparation)

What you will NOT be doing

  • Acquiring new logos or conducting cold prospecting
  • Designing content marketing strategies on behalf of clients
  • Limiting AI tool usage to writing assistance or research support

Key responsibilities

  • Retain and expand revenue within Contently's current enterprise account portfolio

Candidate requirements

  • Minimum 2 years managing enterprise accounts with $200K+ ARR at a software company
  • Proven experience leveraging data (usage analytics, renewal records, platform activity) to construct business justifications for executive decision-makers
  • Demonstrated ability to create AI workflow automations
  • Availability to work US business hours (EST time zone)

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
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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.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

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