Senior Director of Web Development

Group 1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Why This Role Matters:

Hands-on technical/design manager accountable for the tactical execution of the web development and UI design team. Oversees the three Web/UI Developer roles (Lead, Senior, and Web/UI Developer levels) and is personally accountable for the quality, performance, and brand integrity of all marketing web properties and design systems across Group 1001 member companies (Delaware Life, Wellspring Health, Gainbridge, Clear Spring P&C, RVI Group, and Group 1001 Corporate). This is explicitly a working manager role — not a people-only manager.

Scope and Complexity:

• Direct people-management of Lead, Senior, and entry-level Web/UI Developers (FTE and contractor mix)
• Tactical accountability for sprint-level delivery, design reviews, and visual/UX standards across all web properties
• Supports web property and UI design needs across all Group 1001 member companies: Delaware Life, Wellspring Health, Gainbridge, Clear Spring P&C, RVI Group, and Group 1001 Corporate
• Expected to maintain hands-on design and Webflow contribution on critical-path work, personally conduct design reviews, and prototype design solutions to de-risk delivery
• Must meet or exceed the Lead Web/UI Developer technical bar in Figma, Webflow, and design systems
• Operates in an Agile environment using Jira and User Stories, with AI-assisted design and content expected throughout the team

How You'll Contribute:

• Hands-On Design and Build: Contribute production-quality design and Webflow build work on critical-path web properties; personally conduct design reviews; prototype solutions in Figma and Webflow to de-risk new initiatives.
• Product Ownership of Portfolio Applications: Serve as the accountable Product Owner for the applications and web properties in the team's portfolio, including ongoing responsibility for security posture, accessibility compliance (WCAG AA minimum), and regulatory compliance applicable to the supported Group 1001 member company (e.g., insurance regulatory, privacy, and data-protection requirements).
• Architectural Fitness and Operational Resilience: Own the architectural health of every application in the portfolio — including business continuity and disaster recovery posture, data backup and retention policy adherence, operating-system and runtime version currency, third-party library currency, and timely application of security patches.
• Tooling and Access Enablement: Ensure every team member has access to the correct application development and support tooling at the appropriate access level — including IDEs, design tools, source control, CI/CD systems, cloud consoles, monitoring/observability platforms, ticketing systems, and any production-support tooling required for their role. Partner with IT, Security, and Identity teams to provision, review, and revoke access on an ongoing basis.
• Short-Range Planning: Own the team's quarterly and sprint-level design and build plans; align capacity against committed scope across member-company marketing initiatives.
• Sprint Operations: Either lead or actively participate in Agile sprint planning, backlog refinement, and retrospectives; partner with marketing stakeholders and product owners on story sizing and readiness.
• Story Readiness Review: Personally vet user stories for design fitness, acceptance criteria clarity, content-readiness, and dependency identification before they enter a sprint.
• Staff Assignment: Match designers to projects based on skill, brand-fluency, and capacity across member-company workstreams.
• Day-to-Day People Management: Schedule management, 1:1s, goal-setting, performance reviews, compensation recommendations, and corrective action.
• Designer Growth: Build individual development plans; provide design and technical mentoring; develop senior and lead designers' craft, design-system thinking, and stakeholder skills.
• Design System Stewardship: Own the enterprise design system strategy — governance, contribution model, and cross-member-company reuse.
• SEO/GEO Program Ownership: Oversee the team's SEO and Generative Engine Optimization strategy and continuous monitoring across all managed web properties.
• Performance Measurement: Own the team's web analytics and BI feed strategy — ensuring KPIs flow into Group 1001's enterprise BI platforms.
• Continuous Delivery Improvement: Drive measurable improvements in design throughput, design-to-dev handoff quality, and Webflow build velocity.
• M&A Web Property Integration: In partnership with the AVP, lead the hands-on assessment, re-platforming (typically onto Webflow), and brand-integration of marketing web properties acquired through M&A across member companies.
• Standards and Governance: Set and enforce team design standards, accessibility (WCAG AA minimum), brand compliance, and Webflow build conventions.

What You're Looking For:

• 10+ years of professional web design and front-end build experience with progressive responsibility
• Demonstrated professional experience in the financial services and/or insurance sector, with a clear commitment to deepening domain knowledge across the markets in which Group 1001 member companies compete — including life and annuity, health, property and casualty, and specialty insurance.
• Demonstrated ability to meet or exceed the Lead Web/UI Developer technical bar — see Lead Web/UI Developer requirements as the technical floor
• Figma — expert-level (HARD REQUIREMENT)
• Webflow — expert-level for building and governing client-maintainable sites (HARD REQUIREMENT)
• Deep design-system experience — building, evolving, governing, and scaling design systems across multiple product lines
• Strong typography, layout, interaction, and visual-design fundamentals
• Experience producing developer-ready Figma files for handoff to engineering teams
• Experience defining and executing SEO and GEO (Generative Engine Optimization) strategy and continuous monitoring
• Experience instrumenting web properties to feed enterprise BI platforms
• Content creation capability — copy, visual assets, campaign artifacts
• Requirements-gathering fluency with business stakeholders (Marketing, Sales, Communications)
• Agile environment experience (Jira, User Stories)
• Confident, fluent use of AI tools to accelerate design and content work
• Demonstrated technical/design management experience — running a team of 3+ designers
• Demonstrated grounding in software engineering or design concepts and theory — acquired through formal education, professional training, or equivalent industry experience

Preferred Qualifications:

• Prior experience integrating acquired-company web properties during M&A activity
• Insurance, life/annuity, or financial services marketing domain experience, particularly intermediary-distribution channels (IMOs, banks, broker-dealers)
• Experience with Contentful, headless CMS architectures, or similar
• HTML/CSS/JS proficiency sufficient to extend Webflow capabilities via custom code

Behavioral Competencies:

• Hands-on design credibility — earns respect by doing, not just delegating
• Outstanding tact and diplomacy — this role sits at the seam between business stakeholders, marketing leadership, and a creative team; conflict-management skill is non-negotiable
• Team-oriented and collaborative — models the customer-facing behavior expected of every member of the Web/UI team
• Strong taste — defends design quality without alienating stakeholders
• Coaching mindset — develops senior and lead designers as future leaders
• Stakeholder empathy — translates business goals into design decisions and back
• Calm under marketing-deadline pressure
• Intellectual curiosity and forward-thinking, especially on AI-accelerated design and content generation

Benefits Highlights: 

Employees who meet benefit eligibility guidelines and work 30 hours or more weekly, have the ability to enroll in Group 1001’s benefits package. Employees (and their families) are eligible to participate in the Company’s comprehensive health, dental, and vision insurance plan options.  Employees are also eligible for Basic and Supplemental Life Insurance, Short and Long-Term Disability. All employees (regardless of hours worked) have immediate access to the Company’s Employee Assistance Program and wellness programs—no enrollment is required.  Employees may also participate in the Company’s 401K plan, with matching contributions by the Company.

Group 1001, and its affiliated companies, is strongly committed to providing a supportive work environment where employee differences are valued. Diversity is an essential ingredient in making Group 1001 a welcoming place to work and is fundamental in building a high-performance team. Diversity embodies all the differences that make us unique individuals.  All employees share the responsibility for maintaining a workplace culture of dignity, respect, understanding and appreciation of individual and group differences.

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