Director, Engagement Strategy

Position Overview:

Bloom Insurance, the insurance industry's trusted growth partner, is looking for a seasoned and visionary Director of Engagement Strategy to lead the strategic direction and execution of Bloom's multi-channel engagement programs. In this role, the Director serves as a senior leader responsible for shaping how Bloom connects with prospects and members across all touchpoints — from developing overarching engagement frameworks to driving measurable outcomes for health plan partners. The ideal candidate is a strategic thinker, a collaborative leader, and a data-driven decision-maker with a track record of building and scaling high-performing programs.

We are looking for an exceptional individual who can:

• Architect and own the strategic vision for multi-channel engagement programs, aligning campaign strategy with Bloom's growth objectives and the needs of health plan clients.
• Define and evolve program goals, audience segmentation frameworks, and channel mix strategy — ensuring each initiative is purposefully designed to drive enrollment, retention, and member engagement outcomes.
• Lead the evaluation, selection, and ongoing performance management of channel partners, platforms, and vendors — pivoting strategy based on performance signals and market conditions.
• Champion a consistent and compelling brand voice across all channels, partnering with content, creative, and client teams to ensure messaging is resonant, compliant, and impactful at scale.
• Oversee the development of detailed program roadmaps — setting strategic timelines, managing cross-functional dependencies, and ensuring execution aligns with both operational and financial targets.
• Translate audience insights and behavioral data into differentiated, channel-specific messaging strategies that drive engagement across the full member journey.
• Establish and own the analytics and reporting infrastructure for engagement programs — leading the team's use of KPIs, performance dashboards, and data storytelling to guide optimization and executive decision-making.
• Build and lead cross-functional alignment across internal teams, health plan clients, and external partners — serving as the senior point of contact for stakeholder communication on program strategy and performance.
• Institutionalize testing and optimization practices — including UAT, A/B testing, audience segmentation, and channel experimentation — to continuously elevate program effectiveness.
• Drive a culture of continuous improvement, translating performance data and post-campaign learnings into strategic refinements and program innovation.
• Serve as an executive-facing presence, delivering clear, compelling program performance narratives to leadership, clients, and board-level stakeholders as needed.
• Mentor and develop team members, building organizational capability in multi-channel strategy, operations, and analytics.
• Perform all other duties as assigned.

Qualifications:

• Bachelor's degree in Marketing, Communications, or a related Business or Data-oriented field; MBA or advanced degree preferred.
• 10+ years of experience in marketing, engagement strategy, or program operations, with demonstrated progression into senior leadership roles.
• Proven experience leading multi-channel programs at scale, ideally within healthcare, insurance, or a regulated industry.
• Strong background in cross-functional leadership, and executive stakeholder engagement.

  Required Skills and Abilities: 

• Exceptional leadership and communication skills — able to inspire teams, influence stakeholders, and represent Bloom's capabilities with credibility at the executive level.
• Strategic agility — able to navigate ambiguity, balance competing priorities, and lead teams through change with clarity and confidence.
• Deep analytical acumen with the ability to synthesize complex data into clear strategic recommendations.
• Strong business and financial acumen, with experience managing program budgets and optimizing for ROI.
• Innovative and solutions-oriented, with a bias toward action and measurable impact.
• Meticulous attention to detail balanced with the ability to think at the macro level.

What We Offer

Bloom operates with a people-first culture, which means listening to our employees to provide the benefits that mean the most to them. Our competitive compensation, comprehensive health coverage, long-term growth opportunities, and remote work environment are among the reasons that many of our employees have been with us since the beginning of our business. BeBloom™, our proprietary employee training and engagement program, helps you learn our business model and immerse yourself in everything our culture has to offer from day 1. From virtual live events to mentorship and leadership programs and employee-led councils, there are countless opportunities to get involved, build connections, and share your voice – because at Bloom, the real you belongs here.

Core Values:

1. Put People First: Uphold and promote a people-first culture within the organization, emphasizing empathy, kindness, and a commitment to making a positive difference.
2. Be Stronger Together: Embrace a team player mentality, leveraging the strengths of yourself and others to collaborate as one team.
3. Do What’s Right: Adhere to high ethical standards, acting with integrity to do what’s right for partners, customers, and colleagues.
4. Embrace a Growth Mindset: Embrace a culture of continuous learning, education, and professional development.
5. Drive Solutions: Demonstrate ingenuity and skill by sharing ideas and solutions that drive our mission forward.

About Bloom:

Bloom is a third-party insurance services provider that partners with Medicare health plans to enable high-quality Medicare enrollment and drive earlier health plan activation. Founded in 2007, Bloom has partnered with national and regional payers to implement solutions for every step of the member journey, from telesales and quote & enroll to health activation outreach. Supported by its Ascend technology platform, Bloom produces closer connections and better outcomes for Medicare beneficiaries and health plan stakeholders to deliver High Value Enrollment.