Head of AI Content Operations

About Outgoing Media

Outgoing Media builds, powers, and scales email programs that people actually want to read. Our focus is sending relevant, respectful, and high-performing email content that earns its place in the inbox. We work across advertising, editorial, and client-branded sends—always guided by our values of trust, accountability, experimentation, and scalable excellence.

Role Overview

The Head of AI Content Operations owns the systems, prompts, and processes that fuel Outgoing Media’s AI-driven content engine. You’ll sit at the intersection of technology, editorial, and performance—responsible for maintaining and evolving the tools that enable our teams to create, test, and scale great email and blog content across brands.

This role blends AI operations, editorial leadership, and technical problem-solving. You’ll manage and optimize AI prompts and Python-based systems that produce content at scale—ensuring performance, reliability, and continuous improvement as new brands and campaigns come online. You’ll also lead a small team of full-time and contract contributors, fostering a culture of precision, accountability, and innovation.

Key ResponsibilitiesAI Systems & Tools

• Own, maintain, and optimize AI prompts, templates, and workflows for email and blog content generation.
• Monitor AI system performance—identify and resolve prompt timeouts, latency issues, and output quality problems.
• Continuously test and refine prompts for tone, accuracy, and engagement to “dial in” brand-specific article performance.
• Collaborate with engineers to improve and automate content production tools written in Python.
• Document prompt logic, parameters, and workflows to ensure consistent results across brands.

Editorial Operations

• Oversee the editorial calendar and QA process for all owned and partner brands.
• Build systems that ensure high-quality, brand-safe, and compliant content delivery.
• Collaborate with analytics and product teams to convert performance data into prompt and content improvements.
• Manage editorial workflows and maintain standards for tone, readability, and engagement.

New Brand Setup

• Lead setup for new brands—establishing content structures, prompt parameters, and automation rules.
• Create scalable templates, naming conventions, and tagging systems for rapid brand deployment.
• Partner with stakeholders to ensure brand voice and performance targets are met from day one.

Cross-Functional Leadership

• Work closely with ad ops, engineering, and creative teams to ensure seamless content generation and delivery.
• Lead post-send reviews, root-cause analyses, and prompt optimization cycles.
• Manage a team of 1–2 full-time employees and contract writers/editors, providing clear goals, training, and accountability.
• Champion Outgoing Media’s core values—Earn the Inbox, Test Boldly, and Build to Scale.

RequirementsExperience & Background

• 3+ years in content operations, AI-driven editorial systems, or marketing operations.
• Proven experience managing AI content tools and optimizing prompt performance.
• Demonstrated success overseeing editorial systems, blog networks, or large-scale content programs.
• Familiarity with email production, content marketing, and audience engagement analytics.

Technical Skills

• Proficiency in Python — able to troubleshoot, optimize, and code to support AI workflows.
• Hands-on experience in AI prompt engineering and optimization using models such as ChatGPT, Claude, or Gemini.
• Experience monitoring AI performance (timeouts, throughput, latency) and resolving production issues.
• Comfort with version control (Git) and structured documentation for reproducible systems.
• Understanding of automated content pipelines and publishing workflows.

Short-Term Maintenance Expectations

• Performance Management: Ensure AI prompts run reliably without timeouts or API failures.
• Prompt Optimization: Continuously refine and test prompts to improve article quality, tone, and relevance.
• New Brand Setup: Lead configuration, testing, and deployment of prompt systems for new brands on schedule.

Soft Skills & Attributes

• Excellent writing and editing background—able to spot tone, clarity, and structure issues quickly.
• Analytical and detail-oriented; balances creativity with precision.
• Strong communicator who can bridge technical and creative disciplines.
• Systems thinker who thrives in a test-and-learn culture.
• Proactive, accountable, and process-driven; thrives in a fast-paced environment.
• Capable people leader—able to manage, mentor, and inspire small, high-performing teams.

You’ll Thrive Here If You Believe In

Earn the Inbox: You build content that respects audiences and measures wantedness, not just clicks.Test Boldly, Learn Fast: You experiment with purpose—hypothesis, test, learn, scale.Accountability: You take full ownership from idea to send, and fix root causes, not symptoms.Trust: You value transparency, compliance, and brand integrity.Build to Scale: You turn creative processes into systems that grow without breaking.

What Success Looks Like

• Daily Automation: All core content is generated, QA’d, and published by 8:00 AM daily.
• Operational Resilience: When prompts fail, systems are restored and publishing resumes within 5 hours.
• New Brand Integration: New brand agents, prompts, and templates are live and functional within their scheduled launch windows.
• Team Performance: Your direct reports meet deadlines, improve quality metrics, and uphold company standards.
• Scalable Infrastructure: Content production remains consistent, efficient, and high-quality as Outgoing Media grows.
• Editorial Consistency: Voice, tone, and quality are uniform across all brand outputs.

What You'll Get

• 100% covered for insurance with BCBS and Guardian
• HSA employer contribution
• 13 Paid Company Holidays
• 5 "No meeting" Fridays designated throughout the year for deep work
• Unlimited paid time-off

Job Type: Full-time

Pay: $110,000.00 - $120,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Parental leave
• Vision insurance

Work Location: Remote