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 passive renewal administrator. You understand how to maintain satisfaction among major accounts, ensure contract integrity, and sustain revenue flow—without requiring extensive support from customer success managers, solution engineers, or enablement teams. You can communicate with a CMO using outcome-focused language, with a content director about execution details, and with compliance teams about risk management. And you possess the capability to develop automation that fundamentally transforms your workflow, not simply surface-level AI usage.

Contently operates in the enterprise segment where errors carry significant consequences: regulated content. Financial institutions, healthcare organizations, and recognizable brands rely on us because brand protection, governance, and compliance are non-negotiable requirements. What makes this opportunity compelling is that you won't be entering unfamiliar territory. You're taking over an enterprise account portfolio with established trust. Your objective is to convert that existing trust into sustained and expanded revenue by demonstrating ROI in terminology that resonates with clients, then pursuing intelligent expansion strategies. As you execute, you'll contribute to defining AI-enabled account management practices for 2026 at a content enterprise—a blueprint that doesn't yet exist.

This position means owning renewals with a closer's mentality. It involves conducting quarterly business reviews that resonate with executive stakeholders because you connect usage analytics to measurable outcomes like reduced compliance exposure and enhanced brand credibility. It requires identifying expansion opportunities proactively—both within accounts and across the broader market—and delivering proposals grounded in the client's actual activity and genuine needs. It also means deploying automation on a quarterly basis that eliminates hours of repetitive account management tasks, allowing you to redirect your focus toward strategy, negotiation, and revenue growth. If your understanding of "AI capabilities" is limited to generating better-written emails more quickly, this role will not be a fit.

You'll join a focused team where accountability defines the culture and autonomy is the reward. You'll collaborate cross-functionally with product, support, finance, and marketing specialists as situations demand, but you are the operator responsible for driving results. If you want responsibility for a portfolio of legitimate enterprise accounts, rapid feedback on your impact, and a position where building with AI is a core requirement, please apply. If you're seeking this role to gradually develop AI-building skills over time, please do not apply (other opportunities at Crossover support that learning path).

What you will be doing

  • Account Renewals - Execute annual contract renewals punctually, maintaining or exceeding current ARR, supported by documented retention reasoning
  • Customer Success Plans - Maintain per-account success documentation that captures client objectives, health indicators, renewal schedules, and expansion pathways
  • AI Workflow Automation - Develop scripts or automation solutions to manage repetitive activities (data extraction for reports, status communications, QBR preparation materials)

What you will NOT be doing

  • New logo acquisition or cold outreach
  • Building content marketing strategies for customers
  • Using AI tools only for help with writing or research

Key responsibilities

  • Retain and grow revenue across Contently's existing enterprise portfolio

Candidate requirements

  • At least 2 years of experience managing enterprise accounts valued at $200K+ ARR at software company
  • Experience using data (usage metrics, renewal history, platform engagement) to build business cases for executive buyers
  • Ability to build AI workflow automations
  • Willingness 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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