Executive Director, Product Strategy and Execution

📍 Job Overview

Job Title: Executive Director, Product Strategy and Execution

Company: Trustmark

Location: Remote (United States)

Job Type: FULL_TIME

Category: Product Strategy & Execution (with strong Revenue Operations implications)

Date Posted: May 22, 2026

Experience Level: 7-10 years

Remote Status: Fully Remote

🚀 Role Summary

• Drive strategic product development and execution for supplemental health products, including accident, critical illness, and hospital indemnity.

• Leverage deep market research, customer insights, and trend analysis to establish and maintain competitive advantage within the voluntary benefits marketplace.

• Develop and manage a prioritized product roadmap aligned with overarching business strategy and long-term growth objectives.

• Partner cross-functionally with underwriting, sales, marketing, and technology teams to ensure successful product implementation and market awareness.

• Establish and monitor Key Performance Indicators (KPIs) to measure product success, drive data-driven decisions, and enable continuous optimization.

📝 Enhancement Note: While the title is "Executive Director, Product Strategy and Execution," the responsibilities heavily lean into areas critical for Revenue Operations and Sales Operations. The focus on product performance, market competitiveness, sales enablement, and ROI directly impacts revenue generation and operational efficiency. Therefore, candidates with a strong understanding of Go-To-Market (GTM) strategies and operational execution will be highly valued.

📈 Primary Responsibilities

• Product Portfolio Leadership: Ensure the health product portfolio is top-tier by identifying gaps, leading prioritization, and developing offerings that meet market demands.

• Market Intelligence & Strategy: Conduct deep market and competitive analysis to define, position, and champion new product offerings, enhancing the company's product and business standing.

• Product Development Lifecycle Management: Lead all phases of product development, including research, design, sales strategy formulation, market analysis, requirement documentation, cost-benefit analysis, and seamless implementation.

• Risk Management & Mitigation: Conduct thorough risk analysis, identifying internal and external resources and capabilities necessary for successful new product launches.

• Financial Oversight: Establish and manage budgets, as well as operational plans for products under development and ongoing management.

• Claims & Customer Experience: Lead the development of health product claims strategy, including integration solutions and ongoing customer experience enhancements.

• Vendor & Partner Management: Manage relationships with external vendors and partners, overseeing RFP processes and collaborating internally to select optimal solutions for care delivery strategies.

• Sales Enablement & Storytelling: Act as the primary storyteller to support field partners, ensuring products are effectively sold, understood, and communicated across all channels.

• Performance Measurement & Optimization: Develop and own KPIs to measure new product initiative success, providing actionable insights for data-driven decisions and rapid course correction throughout the product lifecycle.

• Regulatory Compliance: Ensure all products adhere to compliance standards and proactively address regulatory changes.

📝 Enhancement Note: The emphasis on "Product Execution" and "Product Management" within the provided description indicates a strong need for operational rigor. Responsibilities like "Collaboratively works with underwriting, sales and marketing teams to competitively position and build awareness of new products with producers" and "Coaches direct reports on how to maintain product health across the organization; ultimately responsible for success, prioritization, and driving initiatives with internal technology and project partners" highlight the cross-functional operational coordination and project management skills required.

🎓 Skills & Qualifications

Education:

Experience:

• 7-10 years of industry experience, with a significant portion dedicated to product development, product management, and implementation.

Required Skills:

• Product Strategy & Vision: Ability to define and articulate a clear product vision and roadmap aligned with business objectives.

• Market Analysis & Research: Expertise in conducting deep market research, competitor analysis, and customer insight synthesis.

• Product Development Lifecycle: Proven track record of managing products from concept through launch and ongoing optimization.

• Cross-functional Leadership: Strong ability to lead and influence without direct oversight, fostering collaboration across departments.

• Strategic Planning & Execution: Proven capacity to develop and revise strategies and tactics to drive business growth and operational execution.

• Problem-Solving & Analytical Skills: Ability to analyze complex concepts and resolve intricate issues.

• Stakeholder Management: Experience building consensus and synergies across diverse teams, handling conflicts, and negotiating effectively.

• Innovation & Process Improvement: A creative mindset focused on improving existing processes and driving innovation.

• Communication: Excellent verbal and written communication skills, with the ability to effectively convey complex information.

• Integrity & Character: Demonstrated integrity and strength of character.

Preferred Skills:

• Deep broker/market connections within the voluntary benefits and adjacent markets.

• Sales-related experience, including client-facing roles (e.g., technology, partnerships, account executive/account management).

• Expertise in leading research projects and synthesizing consumer insights.

📝 Enhancement Note: The "Ability to lead/influence without direct oversight" and "Experience working collaboratively across the organization" strongly suggest a role that requires significant operational coordination and strategic alignment, typical of senior positions in Sales Operations or Revenue Operations that bridge product strategy and market execution.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Strategy Case Studies: Showcase examples of developed product strategies, including market rationale, target audience definition, and competitive positioning.

• Roadmap Development Examples: Present instances of creating prioritized product roadmaps, demonstrating how these aligned with business goals and resource allocation.

• Product Launch & Execution Documentation: Provide documentation or case studies detailing the end-to-end process of bringing a new product to market, highlighting cross-functional collaboration and key milestones.

• Performance Metrics & ROI Analysis: Include examples of KPIs developed for product success and demonstrations of how these metrics were used to track performance and achieve targeted ROI.

• Process Improvement Initiatives: Highlight instances where you identified and implemented improvements to product development or management processes, detailing the impact and outcomes.

Process Documentation:

• Workflow Design & Optimization: Demonstrate experience in designing and optimizing workflows for product ideation, development, testing, and launch.

• Implementation & Automation: Showcase understanding of how to effectively implement new products and leverage automation where applicable to streamline processes.

• Measurement & Performance Analysis: Detail approaches to measuring product performance, analyzing data, and generating actionable insights for continuous improvement.

📝 Enhancement Note: For an Executive Director level role, the portfolio should emphasize strategic impact and leadership. Candidates should be prepared to discuss how their product strategies and execution plans directly contributed to revenue growth, market share expansion, and operational efficiency within previous roles. Demonstrating an ability to manage complex projects and cross-functional teams will be crucial.

💵 Compensation & Benefits

Salary Range:

• $136,933 - $204,463 USD per year

Benefits:

• Comprehensive health insurance (medical, dental, vision)

• Life insurance

• Flexible Spending Accounts (FSA) and Health Savings Accounts (HSA)

• 401(k) plan with company match (implied)

• Employee Assistance Program (EAP)

• Back-up Care for Children, Adults, and Elders

• Numerous health and wellness initiatives

Working Hours:

• Expected 40 hours per week, typical for a full-time role. While remote, adherence to standard business hours within US time zones is generally expected for collaboration.

📝 Enhancement Note: The salary range provided is a competitive benchmark for an Executive Director level role in the US, especially for a remote position. The benefits package is robust, indicating a commitment to employee wellbeing and long-term financial security. For a remote role, understanding how benefits are administered across different US states might be a point of inquiry.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurance (specifically, supplemental health insurance and voluntary benefits). Trustmark operates within the broader financial services and healthcare sectors, focusing on improving wellbeing for individuals and businesses.

Company Size: Trustmark is a significant player in its industry, likely falling into the medium to large enterprise category. This implies established processes, a structured hierarchy, and a considerable market presence.

Founded: Trustmark has a long history, founded in 1914. This longevity suggests stability, deep industry expertise, and a commitment to long-term customer relationships and associate development.

Team Structure:

• The role likely sits within a Product Management or Product Development department, reporting to a VP or SVP of Product or Strategy.

• This Executive Director will lead a team of direct reports, including potentially Product Managers, Analysts, or Specialists focused on specific product lines.

Methodology:

• Data-Driven Decision Making: The role emphasizes using market research, customer insights, and KPIs to inform product strategy and execution.

• Agile & Iterative Approach: The mention of "continuous discovery and validation," "minimizing risk," and "accelerating time to market" suggests an agile or iterative product development methodology.

• Cross-functional Collaboration: A strong emphasis is placed on working collaboratively across departments to achieve shared goals.

• Customer-Centricity: The mission to "improve wellbeing" and focus on solving "meaningful customer problems" highlights a customer-centric approach.

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

📝 Enhancement Note: Trustmark's long history and mission to "improve wellbeing" suggest a company culture that values stability, employee welfare, and a commitment to its customers. For operations professionals, this often translates to a focus on robust processes, long-term strategic planning, and a supportive environment for continuous improvement.

📈 Career & Growth Analysis

Operations Career Level: This role is at an Executive Director level, indicating a senior leadership position responsible for significant strategic initiatives and team management. It bridges strategic product vision with operational execution.

Reporting Structure: The Executive Director will likely report to a Vice President or Senior Vice President within the Product, Strategy, or potentially a broader GTM organization. They will manage a team of direct reports, influencing their development and performance.

Operations Impact: The direct impact on revenue is substantial. By developing and refining competitive supplemental health products, this role directly influences sales effectiveness, market penetration, customer acquisition, and retention, all of which are critical drivers of top-line revenue and profitability. Ensuring products are well-positioned and understood by sales teams is key to maximizing revenue potential.

Growth Opportunities:

• Strategic Leadership Expansion: Potential to move into broader strategic roles, overseeing larger product portfolios or entire business units.

• Cross-functional Leadership Development: Opportunities to transition into senior leadership roles in Sales Operations, Revenue Operations, or GTM Strategy, leveraging deep product and market understanding.

• Mentorship and Team Building: Develop leadership skills by coaching and mentoring direct reports, building high-performing product teams.

• Industry Influence: Become a recognized leader in the supplemental health and voluntary benefits space, potentially contributing to industry forums or thought leadership.

• Business Unit Ownership: Potential to take on P&L responsibility for product lines or business segments.

📝 Enhancement Note: The blend of strategy and execution at this level offers a unique growth path for operations professionals looking to deepen their impact on product success and revenue generation. The ability to translate market needs into operational realities is a highly transferable skill.

🌐 Work Environment

Office Type: Fully Remote. This means the workspace is home-based, requiring self-discipline and effective remote collaboration tools.

Office Location(s): While the role is remote, it is specified for candidates located within the United States. This allows for flexibility in geographic location for the employee, but requires alignment with US business operations and potential tax/legal considerations for the employer.

Workspace Context:

• Autonomy & Flexibility: Remote work offers significant autonomy in managing one's workday and environment.

• Digital Collaboration Tools: Reliance on digital platforms for communication, project management, and data sharing is paramount.

• Cross-functional Virtual Interaction: The role requires active engagement with colleagues across various departments through virtual meetings, instant messaging, and collaborative software.

• Focus on Output: Success in a remote environment is measured by results and contribution rather than physical presence.

Work Schedule:

• Standard 40-hour work week is expected. While remote, flexibility in daily scheduling may be possible, but requires coordination with team members and stakeholders across different time zones within the US to ensure effective collaboration and timely responses.

📝 Enhancement Note: For operations roles, a remote environment necessitates strong organizational skills, proactive communication, and proficiency with collaboration tools. The ability to manage complex projects and drive initiatives without direct physical oversight is crucial.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or Recruiter call to assess basic qualifications, interest, and salary expectations.

• Hiring Manager Interview: In-depth discussion with the hiring manager (likely a VP/SVP) focusing on strategic thinking, leadership experience, product vision, and alignment with Trustmark's mission.

• Cross-functional Interviews: Interviews with key stakeholders from Sales, Underwriting, Marketing, and possibly IT/Operations to assess collaboration skills, understanding of operational execution, and ability to influence.

• Case Study/Presentation: Candidates may be asked to prepare and present a strategic product initiative, market analysis, or roadmap proposal, demonstrating their thought process, analytical skills, and communication abilities. This is a critical opportunity to showcase portfolio elements.

• Final Interview: Potentially with a senior executive for final assessment of strategic fit and leadership potential.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your most impactful projects that demonstrate success in product strategy, development, execution, and driving business results (revenue growth, market share).

• Quantify Impact: For each project, clearly articulate the problem, your solution, the process followed, and most importantly, the quantifiable outcomes (e.g., revenue increase, cost savings, market share growth, customer satisfaction improvement). Use specific numbers and percentages.

• Highlight Operations Integration: Emphasize how your product strategies were translated into actionable plans for sales enablement, operational execution, and cross-functional alignment. Showcase your ability to bridge product vision with practical implementation.

• Showcase Leadership & Collaboration: Use your portfolio to illustrate your ability to lead teams, influence stakeholders, and drive consensus across diverse departments.

• Structure for Clarity: Organize your portfolio logically, perhaps by product lifecycle stage or strategic objective. Use clear, concise language and compelling visuals where appropriate. Be ready to walk through your portfolio during the interview.

Challenge Preparation:

• Develop a Sample Product Strategy: Be prepared to outline a strategy for a hypothetical new supplemental health product or a significant enhancement to an existing one. This should include market analysis, target audience, value proposition, go-to-market considerations, and key success metrics.

• Analyze a Market Trend: Consider a current trend in the voluntary benefits or health insurance market and discuss its implications for Trustmark, including potential product opportunities or threats.

• Operational Execution Scenario: Think about how you would approach the launch of a complex new product, detailing the steps, key stakeholders, potential roadblocks, and how you would ensure successful execution and adoption by sales teams.

📝 Enhancement Note: Given the "Executive Director" title, expect a rigorous interview process that tests strategic thinking, leadership capabilities, and operational acumen. A well-curated portfolio that demonstrates quantifiable business impact and cross-functional execution is essential for this role.

🛠 Tools & Technology Stack

Primary Tools (Likely Utilized or Overseen):

• Product Lifecycle Management (PLM) Software: Tools for managing product roadmaps, requirements, and development processes (e.g., Jira, Aha!, Productboard).

• CRM Systems: For understanding customer segments, sales performance, and market feedback (e.g., Salesforce, Microsoft Dynamics).

• Analytics & Business Intelligence Platforms: For data analysis, KPI tracking, and reporting (e.g., Tableau, Power BI, Looker).

• Market Research & Competitive Intelligence Tools: Platforms for gathering market data, trend analysis, and competitor benchmarking.

• Project Management Software: For tracking project timelines, resources, and progress (e.g., Asana, Monday.com, Microsoft Project).

• Collaboration Suites: For communication and document sharing (e.g., Microsoft 365, Google Workspace).

Analytics & Reporting:

• Proficiency in analyzing data from CRM, sales reports, and customer feedback platforms to derive actionable insights.

CRM & Automation:

• Understanding of how CRM data informs product strategy and how product features can be integrated into sales processes.

• Familiarity with automation tools that can streamline product development workflows or customer onboarding.

📝 Enhancement Note: While this role is strategic, an appreciation for the underlying technology that supports product development, sales execution, and performance tracking is vital. Understanding how to leverage these tools to drive efficiency and better decision-making will be a key advantage.

👥 Team Culture & Values

Operations Values:

• Integrity & Trust: Paramount in the insurance industry and emphasized in Trustmark's mission. Operations must be conducted with unwavering ethical standards.

• Customer Well-being: A core value, driving decisions to ensure products genuinely benefit customers and improve their lives.

• Collaboration & Teamwork: Essential for driving complex initiatives across departments. Operations professionals are expected to be strong team players.

• Innovation & Continuous Improvement: A commitment to finding better ways of working, optimizing processes, and adapting to market changes.

• Data-Driven Decision Making: Reliance on facts and analytics to guide strategy and operational execution.

Collaboration Style:

• Partnership-Oriented: A collaborative approach is expected, working closely with sales, underwriting, marketing, and IT to achieve shared goals.

• Proactive Communication: Regular and transparent communication is key, especially in a remote environment, to ensure alignment and address potential issues early.

• Influence & Consensus Building: The ability to persuade and build consensus among diverse stakeholders is crucial for driving product initiatives forward.

• Feedback Integration: An open-door policy for feedback from all levels and departments to refine strategies and processes.

📝 Enhancement Note: Trustmark's emphasis on "wellbeing," "trust," and "diversity" suggests a culture that values people and ethical practices. Operations professionals are expected to embody these values in their daily work and interactions, fostering a supportive and results-oriented environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating a Competitive Market: The voluntary benefits market is dynamic; staying ahead of competitors requires continuous innovation and agility.

• Balancing Innovation with Risk: Developing new products involves inherent risks; effectively managing these while accelerating time-to-market is a key challenge.

• Cross-Functional Alignment: Ensuring seamless collaboration and buy-in from diverse departments (sales, underwriting, legal, IT) can be complex.

• Data Synthesis and Actionability: Extracting meaningful, actionable insights from vast amounts of market and customer data requires sophisticated analytical capabilities.

• Remote Team Management: Effectively leading and motivating a remote team requires strong communication, trust-building, and performance management skills.

Learning & Development Opportunities:

• Advanced Product Strategy & Management: Deepen expertise in product lifecycle management, market analysis, and strategic planning within the insurance sector.

• Leadership & Executive Coaching: Develop advanced leadership skills, mentorship capabilities, and strategic decision-making at an executive level.

• Industry Specialization: Become a subject matter expert in supplemental health products and the broader voluntary benefits landscape.

• GTM Strategy Enhancement: Gain further experience in aligning product strategy with go-to-market execution, sales enablement, and revenue generation.

• Digital Transformation & Automation: Explore opportunities to leverage emerging technologies to enhance product development, operational efficiency, and customer experience.

📝 Enhancement Note: This role offers significant challenges that are also rich learning opportunities. Overcoming these challenges will build a strong foundation for future leadership roles in operations, product, or GTM strategy.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you identified a significant market opportunity and how you translated it into a successful product strategy. What was your process, and what were the key results?" (Focus on market analysis, strategic thinking, and ROI.)

• "How do you prioritize product initiatives when faced with competing demands and limited resources? Walk us through your framework." (Assess prioritization skills, strategic alignment, and operational planning.)

• "Imagine a new competitor enters the market with a disruptive product. How would you assess the threat and what steps would you take to adapt Trustmark's product strategy and execution?" (Evaluate competitive analysis, strategic agility, and execution planning.)

Company & Culture Questions:

• "Based on your understanding of Trustmark's mission to improve wellbeing, how would you ensure our product development aligns with this core value?" (Assess cultural fit and alignment with company mission.)

• "Describe your experience leading and motivating teams, particularly in a remote environment. What are your key principles for fostering collaboration and accountability?" (Evaluate leadership style and remote team management skills.)

Portfolio Presentation Strategy:

• The "Problem-Solution-Impact" Framework: For each project, clearly articulate the business problem, your strategic solution (including product features and GTM considerations), and the quantifiable impact (revenue, market share, efficiency).

• Focus on Execution & Collaboration: Detail how you brought your strategies to life. Highlight your role in cross-functional collaboration, overcoming obstacles, and ensuring successful implementation.

• Showcase Strategic Thinking: Connect your product initiatives back to the broader business objectives and market landscape. Demonstrate your ability to think big picture while managing details.

• Be Prepared for Deep Dives: Anticipate questions about your decision-making process, the data you used, the risks you managed, and the specific challenges you faced during each project.

📝 Enhancement Note: Prepare to discuss specific examples that demonstrate your ability to not only strategize but also to execute effectively, especially in a GTM context. Your understanding of how product strategy directly feeds into revenue generation and operational efficiency will be key.

📌 Application Steps

To apply for this Executive Director, Product Strategy and Execution position:

• Submit your application: Navigate to the provided Workday job portal link and complete the online application.

• Tailor your Resume: Highlight experience directly related to product strategy, development, execution, voluntary benefits, market analysis, cross-functional leadership, and driving business growth. Quantify achievements with specific metrics and ROI where possible.

• Prepare Your Portfolio: Select 3-5 key projects that showcase your strategic thinking, execution capabilities, and quantifiable impact. Focus on how your work has positively influenced revenue, market position, or operational efficiency.

• Research Trustmark: Familiarize yourself with Trustmark's mission, values, product offerings (especially supplemental health), and the broader voluntary benefits market. Understand their commitment to "improving wellbeing."

• Practice Your Narrative: Be ready to articulate your experience using the STAR method (Situation, Task, Action, Result) and practice presenting your portfolio highlights, focusing on strategic impact and operational execution.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.