Regional Sales Director
$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

Regional Sales Director   $100,000 USD/year

Description

You're an enterprise account manager tired of functioning as a polite renewal administrator. You understand how to maintain major client relationships, ensure contract integrity, and sustain revenue flow—all without requiring an army of CSMs, solution engineers, and enablement specialists to support you. You can communicate with a CMO about outcomes, with a content director about execution, and with compliance teams about risk. And you possess the ability to create automation that genuinely transforms your workflow, not just "I use ChatGPT."

Contently operates in the enterprise segment where errors carry significant consequences: regulated content. Financial institutions, healthcare organizations, and major consumer brands rely on us because brand safety, governance, and compliance are non-negotiable. What makes this compelling is that you won't be entering cold accounts. You're taking over an established enterprise portfolio where trust has already been built. Your responsibility is to convert that trust into sustained and expanding revenue by demonstrating ROI in the language your clients understand, then executing intelligent expansion. As you do this, you'll help shape what AI-driven account management looks like in 2026 for a content organization, because that playbook doesn't exist yet.

This role means owning renewals with a closer's mentality. It involves conducting QBRs that resonate with executives because you can connect usage data to business outcomes like compliance risk mitigation and brand authority. It requires proactively identifying expansion opportunities within accounts and in the broader market, then delivering proposals grounded in what the client is genuinely doing and what they genuinely need. It also means delivering automation on a quarterly basis that eliminates hours of repetitive account management tasks, reallocating your time toward strategy, negotiation, and growth. If your understanding of "AI skills" stops at writing better emails more quickly, you will not thrive here.

You'll join a lean team where accountability defines the culture and autonomy is the benefit. You'll collaborate cross-functionally with product, support, finance, and marketing specialists when necessary, but you're the operator responsible for driving results. If you want a portfolio of genuine enterprise clients, rapid feedback on your impact, and a position where AI development is a core requirement, please apply. If you're looking to learn AI building skills on the job and expect a ramp-up period, please do not apply (there are other Crossover opportunities designed for that).

What you will be doing

  • Account Renewals - Execute annual contract renewals on schedule, at or above existing ARR, with documented rationale for retention
  • Customer Success Plans - Maintain a success plan for each account that documents client objectives, health indicators, renewal schedule, and expansion strategy
  • AI Workflow Automation - Develop scripts or automation tools to manage routine activities (report generation, status communications, QBR data preparation)

What you will NOT be doing

  • Acquiring new logos or conducting cold outreach
  • Developing content marketing strategies on behalf of customers
  • Limiting AI tool usage to writing assistance or research support

Key responsibilities

  • Retain and expand revenue across Contently's established enterprise portfolio

Candidate requirements

  • A minimum of 2 years managing enterprise accounts valued at $200K+ ARR at a software company
  • Demonstrated experience leveraging data (usage metrics, renewal history, platform engagement) to construct business cases for executive decision-makers
  • Capability to develop AI workflow automations
  • Availability to work US work 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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STEP 2

Cognitive 
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Prove real-world 
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Interview with the hiring manager.
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Pass
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Accept job offer.
STEP 6

Accept job offer.

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