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MSI · 2 days ago

Head of Agile Development - MSI

United States

Full-time

Remote

Director/Executive

12+ years exp

MSI is a leading MGA that specializes in creating insurance solutions tailored to unique customer needs. The Head of Agile Development will be responsible for building and scaling a high-performing Agile delivery organization, optimizing team performance, and ensuring alignment with business value through effective technology delivery.

Financial ServicesInsurance

Responsibilities

Define and evolve the firm-wide Agile operating model (team topology, ceremonies, cadences, definitions of ready/done, flow metrics) to improve predictability, quality, and cycle time

Establish and run portfolio governance for planning, prioritization, and capacity management; introduce stage gates, quarterly planning, dependency visualization, and risk/issue management

Lead a team of Agile Delivery leaders (Agile Coaches, Scrum Masters, Release Train Engineers, Program Managers) and partner with Engineering leaders and Product Owners to ensure aligned roadmaps and clear commitments

Implement transparent delivery health and KPI dashboards (e.g., on-time delivery, throughput, DORA metrics, escaped defects, cycle and lead time, SLO/SLA attainment) for executive visibility

Drive engineering excellence with partners (DevSecOps, Platform, QA) including CI/CD maturity, automated testing, trunk-based development where appropriate, and release management quality gates

Mature scaled planning practices (PI/quarterly planning, cross-team dependency management, objective tracking), balancing capacity and demand with evidence-based forecasting

Embed secure-by-design and compliance controls across the SDLC in partnership with Security and Risk, ensuring audit readiness, data privacy, and regulatory alignment

Build a culture of continuous improvement: retrospectives at the team and portfolio levels, root-cause analysis, experimentation, and coaching to outcomes

Establish lightweight, consistent delivery artifacts (intake, business cases, OKRs, program increment objectives, release notes) that align on value and outcomes

Develop high-caliber leadership bench strength: recruit, mentor, and retain top Agile delivery talent; define career paths and competency models

Partner closely with the CDIO and functional executives to link technology delivery outcomes to business value, ensuring clear narrative, risk trade-offs, and stakeholder alignment

Qualification

Agile frameworksLeadership in AgileSoftware deliveryDevSecOps practicesData-driven leadershipStakeholder managementContinuous improvementRisk managementKPI reportingPortfolio governanceAgile certificationsCommunication skillsTeam mentoring

Required

12+ years in software delivery with 6+ years in leadership roles scaling Agile across multiple teams or portfolios in complex, regulated or enterprise environments

Demonstrated success maturing scaled agile frameworks (e.g., SAFe, Lean Portfolio Management, or similar) and implementing portfolio governance

Strong command of modern SDLC and DevSecOps practices, including CI/CD, automated testing, observability, and release management

Data-driven leader experienced with delivery and engineering KPIs (e.g., DORA, flow metrics, SLOs/SLAs) and building executive-ready reporting

Exceptional stakeholder management and communication; ability to translate strategy into clear delivery outcomes, constraints, and trade-offs

Bachelor's degree in Computer Science, Engineering, Information Systems, or related field

Preferred

Advanced degree and Agile certifications (e.g., SAFe, PSM/CSM, PMI-ACP) preferred

Company

MSI

MSI is a leading managing general agency (MGA) that thrives on solving challenges, delivering responsive service, and providing an easy insurance experience.

Founded in 2015

Keller, Texas, USA

501-1000 employees