Technical Delivery Lead- Hybrid Des Moines, Iowa

Wellabe is looking for a Technical Delivery Lead to join our team. The Technical Delivery Lead will function as both Project Manager & Technical Business Analyst. to translate business outcomes into high-quality, structured requirements and delivery plans that enable engineers-and AI-assisted development tools (including GitHub Copilot agents)-to implement solutions quickly, safely, and consistently. This role leads fast-paced delivery for a "startup within the company," applying modern, AI-enabled ways of working to accelerate planning, development, documentation, and release execution. In addition, works as a liaison with business units and technology teams to optimize costs and improve complex business processes, products, services, and software by strategically using data analysis to elicit, analyze, communicate, and validate requirements for change.
Be successful in this role

Someone in this role will:

• Research, identify, analyze, and model business processes and problems of high complexity to ensure a thorough understanding of current and proposed procedures and systems, identifying opportunities to improve departmental and corporate operations.
• Lead collaborations with project stakeholders to build business cases and prepare detailed requirements artifacts, including scope, assumptions, dependencies, cost/benefit analysis, and feasibility of identified opportunities.
• Lead and direct complex systems analysis and delivery efforts; including analyzing system requirements, drafting scope documents, and providing technical solution direction.
• Plan and execute delivery as a hybrid PM/BA:
  • Build and maintain delivery plans, milestones, and release timelines
  • Facilitate sprint planning, backlog refinement, demos, and retrospectives
  • Manage RAID (risks, assumptions, issues, dependencies), scope control, and change management
  • Provide regular status updates, decision logs, and escalation paths to leaders and stakeholders
• Produce "AI-ready" requirements and specifications that can be reliably implemented by development teams using GitHub Copilot agents and other AI development workflows:
  • Write clear user stories with strong acceptance criteria, including edge cases and non-functional requirements
  • Provide structured artifacts such as decision tables, workflow diagrams, data mappings, API/interface contracts, validation rules, and examples
  • Ensure requirements are testable, unambiguous, and traceable from outcome story acceptance criteria implementation validation
• Analyze and present documented requirements on small to large projects to business partners, technical teams, and software quality assurance teams to report progress and strategies; facilitate discussion around selecting the best solutions; and re-evaluate agreed-upon solutions to ensure feasibility and stakeholder alignment.
• • Research, identify, analyze, and model business processes and problems of high complexity to ensure a thorough understanding of current and proposed procedures and systems, identifying opportunities to improve departmental and corporate operations.
  • Lead collaborations with project stakeholders to build business cases and prepare detailed requirements artifacts, including scope, assumptions, dependencies, cost/benefit analysis, and feasibility of identified opportunities.
  • Lead and direct complex systems analysis and delivery efforts; including analyzing system requirements, drafting scope documents, and providing technical solution direction.
  • Plan and execute delivery as a hybrid PM/BA:
    • Build and maintain delivery plans, milestones, and release timelines
    • Facilitate sprint planning, backlog refinement, demos, and retrospectives
    • Manage RAID (risks, assumptions, issues, dependencies), scope control, and change management
    • Provide regular status updates, decision logs, and escalation paths to leaders and stakeholders
  • Produce "AI-ready" requirements and specifications that can be reliably implemented by development teams using GitHub Copilot agents and other AI development workflows:
    • Write clear user stories with strong acceptance criteria, including edge cases and non-functional requirements
    • Provide structured artifacts such as decision tables, workflow diagrams, data mappings, API/interface contracts, validation rules, and examples
    • Ensure requirements are testable, unambiguous, and traceable from outcome story acceptance criteria implementation validation
  • Analyze and present documented requirements on small to large projects to business partners, technical teams, and software quality assurance teams to report progress and strategies; facilitate discussion around selecting the best solutions; and re-evaluate agreed-upon solutions to ensure feasibility and stakeholder alignment.
  • Apply advanced questioning to identify, define, document, verify, and validate requirements to ensure accuracy and completeness
  • Design how and where the business will progress by continuously looking for improvements, evaluating effectiveness, and ensuring others follow the outlined approach.
  • Plan, manage, prioritize, schedule, and monitor all requirement activities such as elicitation, validation, change and scope control, and determination of approach, risks, solutions, priorities to ensure completion while providing guidance and communication of status to leaders.
  • Design strategies and select the best tools for business analysis practice such as field mappings, linking to DevOps for historical artifacts, etc.
  • Use AI tools responsibly to increase speed and quality across the delivery lifecycle:
    • Leverage AI as a drafting partner for requirements, documentation, research, and option analysis
    • Apply human judgment to validate correctness, compliance, and completeness
  • Serve as a leader in modern delivery practices-raising the bar for clarity, pace, and outcomes.
    • Coach stakeholders on writing outcome-based requirements and defining "done"
    • Mentor and support less experienced analysts by providing advice, coaching, and educational opportunities
    • Help shape team playbooks for AI-assisted development and documentation standards
  • Lead and facilitate Agile ceremonies with a strong focus on daily execution and team alignment:
    • Run daily Scrum stand-up meetings to track progress, surface blockers, and reinforce short-term priorities
    • Ensure commitments, impediments, and next steps are clearly documented and acted upon
    • Partner closely with engineering, QA, and product stakeholders to keep delivery on track and aligned to sprint goals
    • Reinforce Agile values of transparency, accountability, and continuous improvement within the team
  Qualifications
• Advanced knowledge of principles, processes, and practices related to technical business analysis and IT standards and procedures such as Teams, ProductPlan, SharePoint, systems development life cycle, and other related items
• Strong project delivery and facilitation skills, including planning, prioritization, stakeholder management, and transparent communication.
• Ability to understand, utilize, and communicate technical solutions.
• Strong knowledge of Agile delivery frameworks (e.g., Scrum, iterative delivery) and their practical application in fast-paced software development environments.
• Demonstrated experience running daily Scrum meetings, facilitating Agile ceremonies, and keeping teams focused on sprint goals and delivery outcomes.
• Bachelor's degree in business, insurance, computer science, or related. Combination of education and/or relevant work experience may be accepted in lieu of degree.
• 5+ years' related experience.
• Project management experience strongly preferred
• Experience delivering software in Agile/iterative environments preferred.
• Experience using AI-assisted tools (e.g., GitHub Copilot, documentation assistants, research copilots) in professional workflows preferred.

Benefits

• Hybrid availability
• 401(k) with company match
• Health insurance
• Paid time off, holidays
• Volunteer time off
• Lifestyle Spending Account (LSA)
• Paternity leave

Growth opportunities

We believe each of us has potential to grow and adapt with our business. We take your career as seriously as you do. Helping you develop your skills and talents leads to opportunities - not only for you, but also for our company. That's why we provide:

• LinkedIn Learning Premium access
• CliftonStrengths® assessment and coaching
• On-site and virtual workshops and cohorts featuring world-class content from FranklinCovey, Crucial Learning, Gallup, and more
• Free world-class insurance acumen courses through AHIP and LOMA
• Reimbursement and bonus opportunities for professional designations and certifications, including a tuition reimbursement program
• Opportunities to take part in Wellabe's mentorship programs

About Wellabe

Since 1929, Wellabe has been finding solutions to help our customers protect their health and financial well-being. And we're committed to fostering an internal culture of inclusivity, well-being, and development so each of our team members can succeed. Learn more about Wellabe's culture of betterment by visiting wellabe.com/culture.

Wellabe is full of smart, caring, hard-working people with a broad range of talents who understand collaboration is key. We bring our best selves every day, to connect with others to solve problems, spark innovation, and bring ideas to life. Meet the team and learn what makes Wellabe a great place to work by visiting wellabe.com/news/employee-spotlights.

Our core values:

• Be dedicated: Show unwavering commitment by proactively taking initiative, setting clear goals, and managing time effectively.
• Be trustworthy: Take accountability for actions, navigate difficult conversations with integrity, and build strong relationships through consistent, honest behavior.
• Be determined: Demonstrate enthusiasm and a relentless drive to overcome obstacles and achieve goals.
• Be collaborative: Foster teamwork by being self-aware, actively listening, and effectively communicating across all levels.
• Be open: Embrace diversity and new ideas to create an inclusive environment.
• Be generous: Embody generosity and compassion by serving a greater purpose and helping others.
• Be better: Commit to continuous improvement and adapt effectively to change.
• Be well: Prioritize physical and mental health, manage stress, and demonstrate emotional intelligence.

Equal Opportunity Employer
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