Director of Lifecycle

The Opportunity

As the Director of Lifecycle, you will own the end-to-end lifecycle business — not just channels, but the customer economics that drive repeat revenue and profitability at Caraway. This role is accountable for defining how lifecycle contributes to company growth, including LTV expansion, repeat purchase velocity, margin efficiency, and customer cohort quality.

This is a senior, strategic leadership role. You are not managing campaigns — you are building and operating a lifecycle system that influences how the business acquires, converts, retains, and grows customers over time. You will set the lifecycle strategy, define KPI ownership, and lead cross-functional initiatives that materially change customer behavior and financial outcomes.

You will partner closely with Growth, Finance, Data, Creative, and Digital Product to ensure lifecycle is fully integrated into acquisition strategy, product experience, and company planning. You will also own the operating model for lifecycle, ensuring the team is structured, prioritized, and accountable to business outcomes — not just execution.

Who You Are:

You are a strategic lifecycle leader with deep experience building retention and customer growth systems within high-growth DTC or ecommerce businesses. You understand lifecycle not simply as a marketing channel, but as a core business driver — using customer insights, cohort analysis, and financial rigor to influence LTV, repeat purchase behavior, contribution margin, and long-term profitability. Commercially minded and highly analytical, you know how to identify structural growth opportunities across the customer journey and build scalable strategies that materially impact business performance.

You are a thoughtful and direct communicator who can influence cross-functional stakeholders. Comfortable operating at both the strategic and operational levels, you thrive in fast-paced environments, bring a strong sense of ownership and accountability to your work, and are energized by building high-performing teams, challenging existing assumptions, and driving meaningful business impact.

Responsibilities:

• Own lifecycle as a business function, with direct accountability to LTV, contribution margin, repeat purchase velocity, and cohort performance
• Define and operationalize lifecycle KPIs, ensuring they are consistently measured, reported, and tied to financial outcomes (not attributed revenue)
• Build a long-term lifecycle strategy that identifies structural growth levers across the customer journey, including onboarding, repeat behavior, cross-category expansion, and reactivation
• Lead the development of lifecycle architecture, including segmentation strategy, automation systems, personalization frameworks, and channel orchestration across Email, SMS, Direct Mail, and emerging channels
• Design and implement pricing and incentive governance across lifecycle to balance growth and margin, including testing frameworks for offer strategy, discounting, and payback
• Partner with Finance and Data to establish clear incrementality measurement, cohort analysis, and forecasting models tied to lifecycle performance
• Drive cross-functional initiatives that improve lifecycle outcomes at a systems level (e.g., welcome offer strategy, product merchandising alignment, PDP/onsite conversion improvements, post-purchase experience)
• Translate complex data into clear strategic direction, identifying root causes of performance issues and defining actions that unlock scale
• Establish a disciplined experimentation framework focused on high-impact lifecycle changes, not incremental campaign testing
• Own lifecycle forecasting and planning, ensuring retention is a core input into company revenue and profitability targets
• Build and lead a high-performing lifecycle team, setting a high bar for strategic thinking, ownership, and accountability
• Define how lifecycle integrates with acquisition, ensuring full-funnel alignment and maximizing total customer value

Knowledge, Skills & Abilities:

• 8–10+ years of experience in lifecycle, retention, or growth roles within a high-growth DTC or ecommerce business
• Proven experience owning lifecycle as a business driver, with demonstrated impact on LTV, repeat pur