Head of Retention

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Simplistic, LLC is seeking a seasoned and strategic Head of Retention Marketing to lead and scale our retention and lifecycle marketing function. In this role, you will own the vision, performance, and growth of the retention department—driving client outcomes while building a high-performing, healthy team.

As a senior leader, you’ll oversee a team of retention account managers and strategists, partner closely with a dedicated retention analyst, and collaborate cross-functionally with Operations and other service leads (CRO, SEO, Development) to deliver integrated, best-in-class retention programs. You will also own the department’s P&L, ensuring strong commercial performance, efficient resourcing, and long‑term scalability.

This is a people-first leadership role with significant strategic and business responsibility. You’ll inherit a strong foundation—a growing book of business and a capable mid-level team—and be responsible for elevating our retention offering from a solid performer to an industry-leading practice.

$/yr - $/yr

For remote roles based inside of the United States, you may live in any of 19 states: CO, CT, DC, FL, GA, IL, KS, MA, MD, MI, MS, MO, NC, NJ, NY, OK, PA, TX, VA.

We are an eCommerce design, development, and optimization agency for D2C brands on the Shopify/Shopify Plus platform. As one of the founding Shopify Plus partners, we pride ourselves on being forward thinkers and experts in all things Shopify. Our mission is to craft tailored digital experiences to suit the voice and needs of each client.

Simplistic is committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.

• Lead, mentor, and develop a team of approximately 5+ retention account managers and strategists supporting a portfolio of ~30 clients.
• Provide ongoing coaching, structured feedback, and professional development plans.
• Establish and maintain effective team rituals (standups, performance reviews, QA reviews) to ensure alignment, accountability, and support.
• Monitor workload, capacity constraints and burnout risk; proactively manage resourcing.
• Own hiring, onboarding, training and, when necessary, performance management for retention team members.

• Own the strategic direction and execution of retention programs across email, SMS, lifecycle, subscription, and direct mail integrations.
• Serve as senior escalation point for complex lifecycle and technical challenges, including platform architecture, flow strategy, segmentation, experimentation, and deliverability.
• Ensure all retention outputs meet high standards for quality, brand alignment, and measurable business impact.
• Partner closely with the retention analyst:
• Drive performance reporting and actionable insights.
• Conduct program audits and identify growth opportunities.
• Develop testing frameworks and optimization roadmaps.

• Own the P&L for the retention function, including revenue growth, profitability, and expansion opportunities.
• Identify, develop, and refine adjacent and future retention offerings.
• Support sales efforts by contributing to pitches, audits, scopes, proposals, and pricing for retention and cross‑functional engagements.
• Collaborate with other service leaders (CRO, SEO, Development):
• Identify cross‑sell and upsell opportunities.
• Surface cross‑channel insights impacting retention performance.
• Present integrated strategies to shared clients.

• Partner closely with the Director of Operations to design and optimize delivery systems, including capacity planning and resource allocation models.
• QA standards and review processes.
• Project management workflows and toolsets (Monday, Jira, Slack integrations).
• Continuously improve operational efficiency through playbooks, templates, SLAs, and best practices.
• Foster a team culture centered on feedback, accountability, curiosity, and experimentation.