Why MSI? We thrive on solving challenges.

As a leading MGA, MSI combines deep underwriting expertise with insurer and reinsurer risk capacity to create specialized insurance solutions that empower distribution partners to meet customers’ unique needs.

We have a passion for crafting solutions for the important risks facing individuals and businesses. We offer an expanding suite of products – from fully-digital embedded renters coverage to high-value homeowners insurance to sophisticated commercial coverages, such as cyber liability and habitational property – delivered through agents, brokers, wholesalers and other brand partners.

Our partners and customers count on us to deliver exceptional service through a dedicated team that makes rapid resolutions a priority. We simplify the insurance experience through our advanced technology platform that supports every phase of the policy lifecycle.

Bring on your challenges and let us show you how we build insurance better.

Position Summary

The Head of Agile Development is a senior technology leader responsible for building and scaling a high-performing Agile delivery organization across product engineering, platforms, and data—driving predictable outcomes, quality, and speed-to-value for Baldwin. This role leads the Agile operating model across teams and portfolios, maturing practices in Scrum, Kanban, and SAFe/Lean Portfolio Management, while partnering closely with Product, Engineering, Data, Security, and Business leaders to translate priorities into measurable delivery results. The leader will optimize team topology, throughput, engineering excellence, and stakeholder transparency to enable the CDIO’s multi-year digital strategy.

Primary 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.

Qualifications

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

Special Working Conditions

• Fast-paced environment with enterprise-critical platforms; requires timely decision-making and clear communication.

Important Notice

This position description is intended to describe the general nature and level of work performed. It is not an exhaustive list of all responsibilities, duties, and skills required. Duties and responsibilities may change at any time with or without notice.

EEOC Statement

The Baldwin Group is an equal employment opportunity employer. We comply with all laws prohibiting discrimination based on race, color, religion, age, sex (including sexual orientation and gender identity), national origin or ancestry, disability, military status, marital status, and any other category protected by federal, state, or local laws. All such discrimination is unlawful, and all persons involved in operations are prohibited from engaging in this conduct.

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