Email Retention Marketing Specialist

About Us The Digital Stronghold is a modern commerce collective built around four distinctive, high-performance brands: Taylor Stitch, The Tie Bar, Boston Scally Company, and Pedal Mafia. Each brand stands on its own with a loyal community and a clear sense of purpose—yet together, they define what contemporary menswear looks like across lifestyle, tailoring, and performance apparel. We are creators, builders, and collaborators who believe in the strength of design-led thinking and thoughtful storytelling across every product we make. Our Values Own the outcome Move with purpose Speak truth, listen fully Learn and share Drop the ego Build for the long haul About the Role We’re looking for a strategic and data-driven Email Retention Marketing Specialist to support the retention marketing lifecycle across our portfolio of brands. Reporting to the Senior Retention Marketing Manager, this role is responsible for executing and optimizing Email, SMS, and Direct Mail campaigns that drive measurable revenue and customer engagement. You won’t just be scheduling campaigns—you’ll help shape marketing calendars, support testing strategies, and leverage platforms like Klaviyo, Attentive, and Shopify to improve the customer journey. This is an ideal opportunity for someone who combines creative thinking with analytical problem-solving and thrives in a fast-paced eCommerce environment. What You’ll Do Retention Marketing Campaign Execution Execute Email, SMS, and Direct Mail campaigns aligned with marketing calendars and brand standards Build and deploy campaigns in Klaviyo and Attentive, including segmentation, personalization, and scheduling Coordinate with cross-functional teams to ensure campaigns launch accurately and on time Campaign Quality & Brand Consistency Perform thorough QA checks including link testing, audience validation, and creative review Ensure all campaigns maintain consistent brand voice, messaging, and visual standards across channels Support the creation of campaign briefs and collaborate with creative teams on copy and asset needs Data Analysis & Optimization Track and report on campaign performance metrics including engagement, conversion, and revenue contribution Assist with A/B testing initiatives across subject lines, content, send times, and audience strategies Analyze results and provide recommendations for continuous optimization and incremental growth Lifecycle Marketing Support Support the planning and maintenance of retention marketing calendars Assist in optimizing automated lifecycle flows, including setup, updates, and performance monitoring Document processes, test learnings, and best practices to improve team efficiency and knowledge sharing Platform & Technical Expertise Utilize Klaviyo, Attentive, Shopify, and related marketing tools to execute campaigns effectively Stay informed on platform updates, retention marketing trends, and emerging best practices Continue developing technical expertise across the retention marketing ecosystem What We’re Looking For 3–5 years of experience in eCommerce or digital marketing Hands-on experience with Klaviyo, Attentive, and the Shopify ecosystem preferred Strong attention to detail in campaign setup, QA, reporting, and execution Analytical mindset with the ability to interpret performance data and identify opportunities Comfortable balancing creative thinking with technical execution Familiarity with A/B testing and conversion rate optimization principles Ability to collaborate across multiple brands and stakeholder groups Bachelor’s degree in Marketing, Communications, Business, Analytics, or a related field preferred Proactive, curious, and eager to learn in a fast-moving environment Work Environment This is a fully remote role requiring prolonged computer and screen use in a professional home office environment. The role involves frequent collaboration via email, messaging, phone, and video conferencing, with occasional flexibility needed to support different time zones. Why Join Us? Work across a portfolio of distinctive, growing consumer brands Opportunity to shape retention strategy and customer experience at scale Collaborative, entrepreneurial team culture Fully remote work environment with flexibility and autonomy Competitive compensation and benefits package including medical, dental, vision, 401(k), flexible PTO, and paid parental leave