Lifecycle Marketing Expert - CRM

Obsidian; Toronto; On-site; CAD 90,000 - 130,000; Full time

Job summary

Obsidian is seeking a hands-on Lifecycle Marketing Specialist to design and pressure-test AI training environments and evaluation criteria for realistic marketing work.

You will orchestrate briefs, artifacts, and decision rubrics across ESPs, CRM platforms like Salesforce, and product analytics tools such as Amplitude, enabling robust agent benchmarking and measurement.

Qualifications

• Hands-on practitioner experience in lifecycle, CRM or retention marketing with ownership of sending program and incrementality.
• Familiar with ESPs, CRM platforms (e.g., Salesforce) and product analytics (e.g., 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 — the ability to explain why a decision is right.

Responsibilities

• Design task briefs drawn from lifecycle or CRM marketing work, 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.

Skills

Lifecycle marketing

CRM marketing

Clear written reasoning

Tools

ESP

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.