Director of Digital Product & Conversion

📌 Core Information

🔹 Job Title: Director of Digital Product & Conversion

🔹 Company: Freebird

🔹 Location: United States (Remote)

🔹 Job Type: Full-Time

🔹 Category: E-commerce & Digital

🔹 Date Posted: May 26, 2025

🔹 Experience Level: 5-10 years

🔹 Remote Status: Fully Remote

🚀 Job Overview

Key aspects of this role include:

• Strategic leadership of eCommerce site performance, optimization, and evolution
• Ownership of digital product vision, roadmap, and experimentation program
• Cross-functional team management: CRO strategists, designers, and developers
• Global DTC experience scaling and technical platform oversight

ASSUMPTION: This role requires a strong background in DTC eCommerce, CRO, and Shopify Plus to drive measurable business impact through user-centered site strategy and rapid testing.

📋 Key Responsibilities

✅ Own the digital product vision and roadmap, aligning site performance with business goals and revenue targets

✅ Lead and operationalize a high-velocity CRO & experimentation program across all core web experiences

✅ Shape and prioritize the site experience around DTC metrics: conversion rate, AOV, repeat rate, and LTV

✅ Build and scale a dynamic, global DTC experience—ensuring pricing, currencies, shipping, and compliance are market-ready

✅ Drive insight-led, high-velocity A/B testing across landers, PDPs, cart/checkout, upsells, offers, bundles, etc.

✅ Collaborate cross-functionally with Paid Media, Creative, Retention, and Product to test offers, messaging, flows, and incentives

✅ Lead a cross-functional team: CRO Manager, UX/UI Designers, and Full-Stack Developer

✅ Create systems and sprints to prioritize, build, QA, and launch tests and experience upgrades

✅ Own the Shopify Plus tech stack—ensuring speed, compliance, and integration across apps, subscriptions, localization, and more

✅ Implement and manage tools for personalization, testing, analytics, and site enhancements

ASSUMPTION: This role requires a deep understanding of the Shopify Plus ecosystem and the ability to manage and optimize a high-velocity testing program.

🎯 Required Qualifications

Education: Bachelor's degree in Business, Marketing, or a related field (or equivalent experience)

Experience: 5-10 years of experience in DTC eCommerce, with a track record of growing revenue through site optimization and testing

Required Skills:

• Proven experience leading or building internal eCommerce and CRO teams, or working deeply with DTC brands at a CRO/Shopify agency
• Expertise in Shopify Plus: apps, checkout flows, subscription logic, localization, and customization
• Data-driven decision making and strong analytical skills
• Proven ability to lead cross-functional teams and drive rapid, aligned execution
• Fluency in English

Preferred Skills:

• Experience with global eCommerce infrastructure and market readiness
• Familiarity with subscription-based business models
• Experience with A/B testing tools (e.g., Optimizely, VWO, Adobe Target)

ASSUMPTION: Candidates with experience in DTC eCommerce, CRO, and Shopify Plus are most likely to succeed in this role.

💰 Compensation & Benefits

Salary Range: $120,000 - $180,000 per year (Based on industry standards for a Director of eCommerce with 5-10 years of experience in DTC)

Benefits:

• Comprehensive medical benefits
• Competitive compensation and bonuses
• 401(k) with company match
• Unlimited PTO
• Opportunities for growth

Working Hours: Full-time (40 hours per week) with flexible scheduling

ASSUMPTION: The salary range is estimated based on industry standards for a Director of eCommerce with 5-10 years of experience in DTC. Actual compensation may vary based on skills, experience, and performance.

📌 Applicant Insights

🔍 Company Context

Industry: Travel Arrangements (Freebird's core business before acquisition)

Company Size: 11-50 employees (as of 2025)

Founded: 2015 (Acquired by Capital One in August 2020)

Company Description:

• Freebird empowers travelers to skip the line and instantly book a new ticket after a flight disruption
• Offers a seamless, user-friendly experience for customers
• Provides a valuable service to travelers and partners with airlines to facilitate disruption management

Company Specialties:

• Flight disruption management
• Travel technology
• Customer-centric design

Company Website: https://www.getfreebird.com/

ASSUMPTION: Although Freebird's core business is travel-related, this role focuses on eCommerce and digital product strategy, which is more aligned with DTC and retail industries.

📊 Role Analysis

Career Level: Director-level role, reporting directly to the CEO or another C-level executive

Reporting Structure: This role will manage a team of CRO strategists, designers, and developers

Work Arrangement: Fully remote, with the flexibility to work from anywhere in the United States

Growth Opportunities:

• Potential to scale into a senior leadership position as the company grows
• Chance to make a significant impact on the company's eCommerce strategy and revenue
• Opportunity to learn and develop skills in global DTC expansion and technical platform management

ASSUMPTION: This role offers significant growth potential for the right candidate, as it is a critical function within the company's growth engine.

🌍 Location & Work Environment

Office Type: Fully remote, with no physical office requirement

Office Location(s): N/A

Geographic Context:

• The United States offers a large talent pool and diverse customer base for eCommerce businesses
• Remote work allows for greater flexibility and work-life balance
• Freebird's acquisition by Capital One provides stability and resources for growth

Work Schedule: Full-time (40 hours per week) with flexible scheduling

ASSUMPTION: The fully remote work arrangement allows for greater flexibility and the ability to attract top talent from across the United States.

💼 Interview & Application Insights

Typical Process:

• Initial phone or video screen to assess cultural fit and basic qualifications
• In-depth behavioral and technical interviews with the hiring manager and other team members
• Case study or take-home assignment to evaluate problem-solving skills and strategic thinking
• Final interview with the CEO or another C-level executive

Key Assessment Areas:

• CRO and eCommerce strategy
• Data analysis and interpretation
• Team leadership and management
• Technical proficiency with Shopify Plus and other relevant tools

Application Tips:

• Highlight your experience with DTC eCommerce, CRO, and Shopify Plus in your resume and cover letter
• Be prepared to discuss your approach to A/B testing, data-driven decision making, and team leadership
• Demonstrate your understanding of the role's responsibilities and the company's mission and values

ATS Keywords: Digital Product Strategy, CRO, UX, eCommerce, A/B Testing, Shopify Plus, Team Leadership, Data Analysis, Global Expansion, Site Optimization, Performance Marketing, Experimentation, Customer Insights, Site Operations, Subscription Logic, Cross-Functional Collaboration

ASSUMPTION: Freebird's interview process is designed to assess candidates' strategic thinking, technical skills, and cultural fit. Successful candidates will demonstrate a strong understanding of DTC eCommerce, CRO, and Shopify Plus.

🛠️ Tools & Technologies

• Shopify Plus
• A/B testing tools (e.g., Optimizely, VWO, Adobe Target)
• Analytics tools (e.g., Google Analytics, Mixpanel)
• Project management tools (e.g., Asana, Trello)

ASSUMPTION: The required tools and technologies for this role are standard in the eCommerce and CRO industries. Candidates should have experience with these tools or be willing to learn and adapt quickly.

👔 Cultural Fit Considerations

Company Values:

• Customer-centric
• Innovative
• Data-driven
• Collaborative

Work Style:

• Fast-paced and results-driven
• Data-driven and analytical
• Collaborative and cross-functional
• Adaptable and open to feedback

Self-Assessment Questions:

• How do you ensure that your decisions are driven by data and customer insights?
• Can you describe a time when you led a cross-functional team to achieve a significant business outcome?
• How do you approach A/B testing, and how do you ensure that your tests are valid and reliable?

ASSUMPTION: Freebird values candidates who are customer-focused, data-driven, and collaborative. Successful candidates will demonstrate a strong fit with these values and work styles.

⚠️ Potential Challenges

• Managing a remote team and ensuring consistent communication and collaboration
• Balancing the need for rapid testing and iteration with the need for thorough data analysis and validation
• Scaling the eCommerce experience and technical platform for global expansion
• Adapting to changes in the eCommerce landscape and consumer behavior

ASSUMPTION: These challenges are common in high-growth DTC eCommerce roles and can be overcome with strong leadership, strategic thinking, and a data-driven approach.

📈 Similar Roles Comparison

• This role is similar to a Director of eCommerce or Director of Conversion Optimization in a DTC or retail company
• However, this role has a stronger focus on global expansion and technical platform management
• Career paths for this role may include advancement to a Chief Revenue Officer, Chief Marketing Officer, or other senior leadership positions

ASSUMPTION: While this role shares similarities with other eCommerce and CRO director roles, its unique focus on global expansion and technical platform management sets it apart.

📝 Sample Projects

• Developing and implementing a comprehensive A/B testing roadmap to improve conversion rates and AOV
• Leading a cross-functional team to optimize the checkout process and reduce cart abandonment
• Managing the localization and compliance of the eCommerce site for global expansion

ASSUMPTION: These sample projects are representative of the types of initiatives a Director of Digital Product & Conversion might undertake in this role.

❓ Key Questions to Ask During Interview

• How does the company approach global expansion, and what are the key priorities for this role in that area?
• Can you describe the company's approach to A/B testing, and how does the team ensure that tests are valid and reliable?
• How does the company support the professional development and growth of its employees?
• What are the key performance indicators (KPIs) for this role, and how will success be measured?
• How does the company foster a culture of innovation and experimentation, and how can this role contribute to that culture?

ASSUMPTION: These questions are designed to assess the company's approach to global expansion, A/B testing, employee development, performance measurement, and innovation. Successful candidates will use these questions to demonstrate their strategic thinking and cultural fit.

📌 Next Steps for Applicants

To apply for this position:

• Submit your application through this link
• Tailor your resume and cover letter to highlight your experience with DTC eCommerce, CRO, and Shopify Plus
• Prepare for behavioral and technical interview questions related to eCommerce strategy, data analysis, team leadership, and Shopify Plus
• Follow up with the hiring manager one week after submitting your application to express your continued interest in the role

⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.