Senior Sr Scrum Master- MSI

Why MSI? We thrive on solving challenges. As a leading MGA, MSI combines deep underwriting expertise with insurer 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.

The Problem

Platform Architecture is our most overloaded cross-cutting team. Priorities are pushed down onto them from every direction. They're also the final gate in the PR approval chain (Platform Review → Staff Engineering → Platform Architecture) — not the only reviewers, but the ones who carry the heaviest review load and have the most influence over how that process is designed — which makes them a bottleneck with limited ability to control their own inbound work.

Infrastructure has a related but distinct problem. They just stood up a formal SDLC and are early in adopting ADO, and teams with dependencies on them often reach out at the last minute rather than planning ahead — disrupting their flow of work the same way competing top-down asks disrupt Platform Architecture's. They also need to get better at communicating outward: proactively flagging when scrum and product teams need to test architectural changes or enhancements, rather than that falling through the cracks after the fact.

Both teams need their capacity protected from poorly-timed, uncoordinated demands, and both need a partner who can build the two-way communication habits — inbound planning lead time and outbound impact visibility — that neither currently has.

We also want dedicated Agile coaching capacity across the broader team eventually — someone who can dig into how each team runs planning, standups, and retros, and help our strategic Agile plan translate into practice, not just theory. That's not this role's starting focus: given the depth of what's already being asked for Platform Architecture and Infrastructure, we don't want to set this person up to juggle too much on day one. We see broader coaching as a natural growth path for this role once the Platform Architecture and Infrastructure work is stable, and only if/when they have the capacity for it.

The Role

Reports to the Head of Agile or Head of AI Enabled Delivery with a dotted line to the other. Serves as the embedded Scrum Master for Platform Architecture and Infrastructure, and acts as mentor/lead to the other Scrum Masters across the organization to drive consistent execution of our Agile strategy. No direct reports.

Key Responsibilities

Core Responsibilities (Day One)

• Prioritization gatekeeping: Push back on stakeholders, convene cross-team prioritization sessions, and protect Platform Architecture and Infrastructure capacity from competing top-down asks, maintaining clear cross-portfolio dependency maps so trade-offs are visible to stakeholders.

• Cross-team visibility & coaching: Coach Platform Architecture and Infrastructure to proactively communicate their work, roadmap, and potential downstream impact to dependent scrum and product teams; facilitate a recurring cross-team forum until this becomes routine practice, and use it to support prioritization decisions.

• Capacity protection for bottleneck relief: Influence and partner with Platform Architecture leadership to reduce the volume of competing top-down asks landing directly on their team, freeing their capacity to redesign the release-approval process they anchor (Platform Review → Staff Engineering → Platform Architecture). This role does not own that approval process itself — it protects the time Platform Architecture needs to fix it.

• Ceremony-level coaching: Run and coach ceremonies for both teams, tailoring facilitation and training to each team's specific needs and maturity rather than a one-size-fits-all approach.

• Strategic accountability: Report directly to the Heads of Agile on team health, blockers, and adherence to the strategic plan.

• Compliance & documentation: Ensure delivery routines for Platform Architecture and Infrastructure align with applicable security, risk, and governance requirements across Baldwin partner organizations; support accurate delivery documentation and audit/accreditation readiness where required.

Growth Opportunity (As Capacity Allows)

• SM mentorship: Provide informal lead guidance to the Scrum Masters on other teams, ensuring our strategic Agile plan is executed consistently across the org.

Qualifications

• Proven experience as an embedded Scrum Master or Agile Coach supporting highly technical, cross-cutting engineering or infrastructure teams.

• Strong negotiation and stakeholder-alignment skills, with the ability to balance competing priorities and drive alignment across business units and portfolios.

• Working knowledge of Azure DevOps (ADO); familiarity with DevSecOps, multi-cloud, or CI/CD delivery environments a plus.

• Experience with cross-portfolio dependency mapping, OKRs, and delivery/quality metrics reporting.

• Agile certification (CSM, PSM, SAFe SSM/Advanced SM, or equivalent) preferred.

Success Metrics (6–12 Months)

• Platform Architecture reports measurably more protected capacity (e.g., reduced ad hoc/competing asks), enabling them to own redesign of their release-approval process.

• Recurring cross-stakeholder prioritization cadence established and adopted.

• Recurring roadmap/impact forum between Platform Architecture, Infrastructure, and dependent teams established and running independently of this role.

• Visible execution of the Heads of Agile's strategic plan across team ceremonies.

Growth Opportunity (As Capacity Allows)

• Tailored coaching plans rolled out for Scrum Masters.

• Informal coaching practices shared with Scrum Masters on other teams, if bandwidth allows once core scope is stable.

#LI-JW2

#LI-REMOTE

Click here for some insight into our culture!