Head of Retention

For remote roles based inside the United States, applicants must be able to live and work full‑time in one of the following 19 states: CO, CT, DC, FL, GA, IL, KS, MA, MD, MI, MS, MO, NC, NJ, NY, OK, PA, TX, VA.

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.

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. Best‑in‑class service and thought partnerships allow us to establish long‑lasting strategic relationships with our clients.

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. Additionally, we believe in transparency in compensation. Total compensation for this role includes a base salary range of $110,000 – $130,000.

• 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 to support career progression into senior and leadership roles.
• Establish and maintain effective team rituals (e.g., standups, performance reviews, QA reviews) to ensure alignment, accountability, and support.
• Monitor workload distribution, capacity constraints, and burnout risk; proactively manage resourcing and advocate for the team when capacity thresholds are reached.
• Own hiring, onboarding, training, and, when necessary, performance management for retention team members.
• Partner closely with the retention analyst to:
  • Drive performance reporting and actionable insights.
  • Conduct program audits and identify growth opportunities.
  • Develop testing frameworks and optimization roadmaps.
• Act as executive sponsor for key accounts, participating in strategic planning sessions, QBRs, and escalations as needed (without serving as day‑to‑day account owner).

• Own the strategic direction and execution of retention programs across email, SMS, lifecycle, subscription, and direct mail integrations.
• Serve as the 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 to:
  • 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 (e.g., direct mail, subscription program management, advanced lifecycle services).Support sales…