Senior Digital Product Manager

Who We Are

The Digital Stronghold is a modern commerce collective built around four distinctive, high-performance menswear brands: Taylor Stitch, The Tie Bar, Boston Scally, and Pedal Mafia. Each brand stands powerfully on its own, with a loyal community and a clear sense of purpose, yet together they form a connected portfolio shaping what contemporary menswear looks like across lifestyle, tailoring, and performance apparel.

We are creators, builders, and collaborators. We believe in design-led thinking, thoughtful storytelling, and delivering products and experiences that customers truly love.

About the Role

We're looking for a Senior Digital Product Manager to lead the digital product roadmap across our portfolio of direct-to-consumer brands. This role is responsible for defining, prioritizing, and executing digital product initiatives spanning our websites, eCommerce platforms, and supporting technologies.

You'll bridge business goals with user experience and technical execution—ensuring each brand delivers a premium, seamless, conversion-driven digital experience. Working closely with design, engineering, merchandising, analytics, and marketing teams, you'll continually elevate site performance, engagement, and revenue while honoring each brand's unique identity and customer promise.

What You'll Do

Product Strategy & Roadmap

• Drive the digital product roadmap in alignment with brand goals and revenue targets.

• Identify opportunity areas and define product requirements, informed by data, research, testing, and cross-functional insights.

• Champion the voice of the customer across all digital experiences.

Execution & Collaboration

• Translate business objectives and brand strategies into actionable digital initiatives.

• Manage and prioritize the product backlog across multiple brand sites and apps.

• Partner with engineering and design teams to deliver best-in-class, on-brand digital experiences on time and within scope.

• Collaborate with QA to ensure seamless implementation, testing, and deployment of releases.

Optimization & Performance

• Optimize customer journeys, conversion funnels, and site performance through continuous testing and iteration.

• Lead A/B and multivariate testing to validate improvements in UX, engagement, and conversion.

• Monitor key site metrics—traffic, conversion rate, AOV, retention—and share performance trends with leadership.

• Conduct competitive benchmarking and user behavior analysis to identify new growth opportunities.

Brand & Experience Stewardship

• Ensure digital platforms reflect brand standards, merchandising strategies, and promotional moments.

• Stay ahead of emerging eCommerce trends, mobile innovations, and technologies shaping modern fashion retail.

What We're Looking For

Education & Experience

• Bachelor's degree in Business, Marketing, Computer Science, or a related field; MBA a plus.

• 5+ years in digital product management within a consumer-facing eCommerce or retail environment (apparel or lifestyle preferred).

• Strong familiarity with Shopify (both headed and headless) and its ecosystem.

• Experience driving cross-functional initiatives across creative, technical, and commercial teams.

• Deep understanding of digital analytics tools (GA4, Hotjar, etc.), UX/UI principles, and product development methodologies.

• A track record of using data to inform decisions and elevate user experiences.

Skills & Competencies

• Exceptional communication, prioritization, and stakeholder-management skills.

• Ability to balance brand aesthetics with performance-driven decision making.

• Working knowledge of SEO, CRM, and digital marketing integrations.

• Passion for menswear, retail trends, and DTC commerce.

• Confidence collaborating with engineering teams and navigating code/architecture discussions (engineering background a plus, not required).

Work Environment & Requirements

• Fully remote role. US or Canada preferred in CST/EST timezones

• Ability to sit or stand at a workstation for extended periods.

• Occasional travel (up to 10%) for brand events, vendor meetings, or onsite collaborations.

• Flexibility to support major digital launches or seasonal campaigns as needed.