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