Head of Retention

For remote roles based inside of the United States can sit in any of the following 19 states: CO, CT, DC, FL, GA, IL, KS, MA, MD, MI, MS, MO, NC, NJ, NY, OK, PA, TX, and VA. Please only apply if you are able to live and work full-time in one of the states listed above. State locations and specifics are subject to change as our hiring requirements shift.

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.

About Simplistic:

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 expertise is under constant renovation to keep us at the forefront of the D2C eCommerce landscape.

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.

As the Head of Retention, this role could include:

Team Leadership & People Management

• 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.

Strategy, Delivery & Quality

• 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
• 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).

Commercial Ownership & Service Development

• 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 efforts by contributing to pitches, audits, scopes, proposals, and pricing for retention and cross-functional engagements.
• Collaborate with other service leaders (CRO, SEO, Development) to:
• Identify cross-sell and upsell opportunities
• Surface cross-channel insights impacting retention performance
• Present integrated strategies to shared clients
• Shape scalable, cross-functional delivery models

Process, Systems & Operations

• 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 (e.g., Monday, Jira, Slack integrations)
• Continuously improve operational efficiency through the development of playbooks, templates, SLAs, and best practices.
• Foster a team culture centered on feedback, accountability, curiosity, and experimentation.

Required Competencies

• 7+ years of experience in retention, lifecycle, or email marketing within ecommerce/DTC environments, with strong hands-on expertise in Klaviyo (flows, campaigns, segmentation, integrations, reporting).
• 3+ years of people leadership experience, including hiring, coaching, and performance management of cross-functional or client-facing teams.
• Deep understanding of lifecycle strategy and performance metrics, including retention, LTV, cohort analysis, deliverability, and list health.
• Strong familiarity with subscription and recurring revenue models; experience with direct mail as a performance channel is a plus.
• Proven ability to translate data into actionable business strategy, not just report on metrics.
• Comfortable operating in an agency environment, managing multiple clients and stakeholders simultaneously.
• Demonstrated ability to own financial outcomes, including P&L responsibility and tradeoff decisions across growth, quality, and capacity.
• People-first leader who prioritizes team health, development, and sustainable performance.
• Highly organized, process-oriented, and collaborative, with experience building scalable systems alongside operations.
• Confident communicator who can set boundaries, push back when needed, and advocate for quality and team capacity.