Lifecycle Marketing Expert - CRM - AI Trainer

Obsidian; Houston (TX); On-site; USD 120,000 - 180,000; Full time

Job summary

Obsidian seeks a hands-on lifecycle/CRM marketing expert to design and pressure-test realistic environments for evaluating AI agents in marketing tasks. You will define task briefs, required documents and tool states, and craft reference answers with clear decision criteria.

You will also review AI agent attempts, judge quality against your rubric, and analyze messy data to plan, execute, QA, and report across multiple tools.

Qualifications

• Hands-on practitioner experience in lifecycle, CRM or retention marketing.
• Owns the sending program and its incrementality.
• Comfortable across an ESP, a CRM such as Salesforce, and Amplitude.
• Experience building AI training environments, RL environments or simulated case studies is strongly preferred.
• Rubric Academy or Rubric Bootcamp certification is strongly preferred.

Responsibilities

• Design task briefs drawn from lifecycle or CRM marketing work, including what is tested and the decision the practitioner should reach.
• Specify documents, dashboards, personas and tool states required for tasks.
• Write or review the reference answer and the criteria that separate strong vs plausible-but-wrong responses.
• Review AI agent attempts and judge them against established standards.
• Diagnose what happened from messy data, prioritize, plan and execute, QA and reconciliation, and report across multiple tools.

Skills

Lifecycle marketing

CRM

Retention marketing

AI training environments

Written reasoning

Tools

ESP / Email service provider

Salesforce

Amplitude

Job description

About the work

We are building high-fidelity simulated work environments used to evaluate and improve AI agents on real marketing work. Each environment reproduces a marketing org's actual tool surface — email, storage, CRM, project management, social media management, web analytics, AEO/SEO, ads, CMS, product analytics and support — populated with realistic documents, dashboards, personas and deliberately planted problems.

You will help design and pressure-test the Lifecycle environments: the briefs, the artifacts, the judgment calls a strong practitioner would make, and the errors a weaker one would miss.

What you will do

• Design task briefs drawn from work you have actually done in lifecycle or CRM marketing, including what the task is really testing — the planted issue and the decision a strong practitioner should reach
• Specify the documents, dashboards, personas and tool states a realistic version of that task requires
• Write or review the reference answer and the criteria that separate a strong response from a plausible-but-wrong one
• Review AI agent attempts and judge them against your own standard

Tasks span the capabilities we measure: diagnosing what happened from messy or conflicting data, prioritizing and making tradeoffs, planning and executing, QA and reconciliation, triage and escalation, research and evaluation, reporting, and orchestrating multi-step work across several tools.

Lifecycle scope

Contact strategy, milestone campaigns, customer communications, deliverability and list health, and lifecycle portfolio optimization.

Who we are looking for

• Hands-on practitioner experience in lifecycle, CRM or retention marketing — you have owned the sending program and its incrementality, not only managed people who do it
• Comfortable across an ESP, a CRM such as Salesforce, and product analytics such as Amplitude
• Prior experience building AI training environments, RL environments or simulated case studies is strongly preferred
• Rubric Academy or Rubric Bootcamp certification is strongly preferred
• Clear written reasoning — much of the value is in explaining why a decision is right

Screening

Applicants complete a short multiple-choice knowledge screener specific to this sub-domain before review.