Lifecycle Marketer

Established in 2021, Doubtless is a holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.

We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach includes our own insurance carrier, insurance brands and partner brands.

Spot, a subsidiary of Doubtless, is a team of pet-health-obsessed pet parents. We are driven by a shared vision to educate, empower, and engage pet lovers about the benefits of pet insurance to help them pay for covered vet bills so dogs and cats can live healthier, happier lives.

Job Summary:

Spot is seeking a Lifecycle Marketer The Lifecycle Marketerdrives customer retention through strategic lifecycle programs. You own the end-to-end customer journey from first touch through long-term renewal, with primary accountability for retention outcomes (New Business Retention and Renewal Retention) and contribution to AOV.

While your work spans the full lifecycle (quote follow-up, onboarding, engagement, renewal, winback, cross-sell), your performance is measured by retention metrics. You partner with the Digital Media Buyer and SEO Specialist on top-of-funnel work but do not own those channels.

You partner closely with Product, Data Science, and CRM teams to identify at-risk customers, design interventions, and improve renewal outcomes. You use AI tools (Claude, Claude Code, AI agents) to operate with the velocity of a much larger team.

Job Location: Miami, FL (4 days in office, 1 remote)

Main Responsibilities:

• Design and execute lifecycle programs targeting New Business Retention (Year 1) and Renewal Retention (Years 2 )
• Build customer segmentation using behavioral, transactional, and demographic data
• Identify at-risk customers and design intervention programs to prevent churn
• Own renewal campaigns end-to-end including timing, messaging, channels, and offers
• Design winback programs for lapsed customers
• Run a continuous experimentation roadmap that systematically improves retention metrics
• Partner with Data Science on churn prediction models and feed signals into lifecycle programs
• Use Claude and AI agents to draft copy variants, build automation, and analyze cohort behavior at scale
• Build agentic workflows that automate repetitive lifecycle tasks (segment generation, QA, reporting, copy variations)

Basic Qualifications:

Marketing experience

• 8 years of lifecycle marketing, CRM, or retention marketing experience
• Track record of measurably improving retention metrics (with specific examples)
• Experience with email service providers and lifecycle platforms (Customer.io, Iterable, Braze, or similar)
• Strong analytical skills including SQL fluency, cohort analysis, and A/B testing rigor
• Strong copywriting skills

AI fluency (required, not optional)

• Regular use of Claude, ChatGPT, or equivalent LLMs for marketing work (analysis, copywriting, ideation)
• Demonstrated ability to write effective prompts and structure AI workflows
• Experience building automations with AI tools (Claude Code, Zapier with AI, or similar)
• Comfort building or adapting AI agents for repetitive lifecycle task
• Willingness to identify new AI use cases and bring them to the team

Operating style

• Comfort with rapid iteration and 80/20 prioritization in a startup environment
• Bias toward shipping and learning over polishing in isolation
• Ability to own retention outcomes, not just campaign metrics

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