Scrum-Master, Scrum-Master-(Technology), Agile-Coach Jobs

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.

Click here for some insight into our culture!

The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.

Originally posted on Himalayas

Job Family:

Travel Required:

Clearance Required:

AI Technical Scrum Master with Python Development

We are seeking an AI Technical Scrum Master with Python Development to lead Agile delivery for mission-focused, AI-enabled software products in a SAFe Agile environment while providing targeted, part-time Python development support.

This is an intentionally hybrid position, not two full-time roles combined into one. The primary responsibility is serving as the Scrum Master and Agile delivery lead for a cross-functional team. The secondary responsibility is contributing hands-on Python development for automation, APIs, integrations, data-processing utilities, testing, and selected technical backlog items based on sprint priorities and available capacity.

The successful candidate will facilitate Agile ceremonies, remove delivery impediments, strengthen team execution, coordinate dependencies, and foster continuous improvement across teams building trusted, secure, and scalable AI-enabled information systems. The candidate will also apply practical Python development skills to support delivery when additional technical capacity is needed, without compromising Scrum Master responsibilities, team coaching, or Agile leadership.

You will work closely with Product Owners, business stakeholders, Release Train Engineers, architects, software engineers, data scientists, testers, security teams, and operations teams to plan, coordinate, and deliver AI solutions that improve operational workflows, decision-making, and mission outcomes. The role requires strong Scrum Master leadership, experience with SAFe Agile delivery, an understanding of modern software engineering practices, and the ability to contribute maintainable Python code within an enterprise delivery environment.

This position is ideal for a technically capable servant leader who can enable a high-performing Agile team, communicate effectively with technical and non-technical stakeholders, and provide focused Python development support for well-defined backlog items.

Role Responsibility Model

Primary Role: Technical Scrum Master and Agile Delivery Lead

The primary focus of the position is Scrum Master leadership and Agile delivery. The individual is accountable for team facilitation, coaching, delivery coordination, impediment removal, continuous improvement, and support for successful sprint and Program Increment execution.

Secondary Role: Part-Time Python Developer

The secondary focus is hands-on Python development performed according to sprint priorities, team capacity, and technical need. Development assignments may include automation, APIs, integrations, data-processing utilities, testing tools, prototypes, and other clearly defined technical backlog items. The individual is not expected to perform the workload of a full-time Python developer in addition to full-time Scrum Master responsibilities.

What you will do

• Serve as the Technical Scrum Master and Agile Delivery Lead
• Serve as the Scrum Master for an Agile team delivering AI-enabled information systems in a SAFe Agile environment.
• Facilitate daily stand-ups, sprint planning, backlog refinement, sprint reviews, retrospectives, and other team synchronization activities.
• Support Program Increment Planning, iteration execution, dependency coordination, risk management, and alignment with broader program objectives.
• Partner with Product Owners, Release Train Engineers, technical leads, and stakeholders to promote transparency, delivery discipline, and predictable outcomes.
• Help maintain a healthy, prioritized, and sprint-ready backlog by facilitating effective collaboration among product, business, and technical stakeholders.
• Ensure Agile practices are applied consistently and pragmatically in alignment with SAFe principles and organizational delivery standards.
• Protect sufficient capacity for Scrum Master responsibilities while transparently planning any part-time Python development commitments.
• Enable Delivery of AI-Enabled Information Systems
• Support teams delivering AI-enabled capabilities such as document understanding, semantic search, summarization, recommendations, intelligent automation, conversational experiences, predictive analytics, and decision-support tools.
• Help the team manage AI-specific delivery considerations, including experimentation, iterative model improvement, data dependencies, integration readiness, model and prompt evaluation, and validation of AI-generated outputs.
• Coordinate across product, engineering, data science, testing, security, governance, and operations teams to help ensure AI capabilities are practical, usable, secure, supportable, and ready for release.
• Promote iterative delivery approaches that balance delivery speed, technical feasibility, quality, trust, governance, security, and mission value.
• Help translate complex technical work into clear plans, risks, dependencies, outcomes, and decisions for business and program stakeholders.
• Remove Impediments and Improve Team Performance
• Proactively identify, track, escalate, and help resolve impediments affecting delivery, quality, velocity, or team effectiveness.
• Coach team members on Agile practices, collaboration, self-organization, estimation, work management, accountability, and continuous improvement.
• Foster an environment of focus, transparency, inclusion, ownership, and continuous learning.
• Use Agile metrics and team insights to identify improvement opportunities and support more effective sprint and Program Increment execution.
• Help the team improve delivery flow, reduce bottlenecks, manage technical and delivery risks, and strengthen cross-functional coordination.
• Facilitate retrospectives that produce specific, achievable, and measurable improvement actions.
• Drive Cross-Team Coordination and Program Execution
• Coordinate dependencies, risks, constraints, decisions, and integration points across teams and stakeholders.
• Work with Product Owners and technical leads to clarify priorities, maintain sprint readiness, and establish achievable delivery commitments.
• Facilitate communication between technical and non-technical stakeholders to maintain alignment on scope, progress, risks, dependencies, and decisions.
• Maintain visibility into team progress, delivery health, impediments, technical challenges, and upcoming milestones.
• Contribute to release readiness and support the smooth transition of completed capabilities into testing, deployment, operations, and sustainment.
• Contribute Part-Time Python Development
• Contribute hands-on Python development for clearly defined technical backlog items after Scrum Master and Agile delivery responsibilities are appropriately planned and protected.
• Develop and maintain Python-based automation scripts, REST APIs, system integrations, data-processing utilities, testing tools, prototypes, and internal delivery utilities.
• Write clean, modular, reusable, documented, testable, and secure Python code in collaboration with software engineers, data scientists, and solution architects.
• Develop or support lightweight backend services and integrations using appropriate Python frameworks and libraries.
• Create unit and integration tests, troubleshoot defects, review logs, and support validation of Python components.
• Participate in Git-based source-control practices, pull requests, peer reviews, automated testing, CI/CD activities, defect resolution, and technical documentation.
• Work within established architecture, engineering, security, quality, and coding standards.
• Communicate development progress, risks, dependencies, and capacity constraints transparently during sprint execution.
• Avoid becoming the sole owner or single point of failure for business-critical Python components.
• Coordinate with the Product Owner and technical lead when Scrum Master duties or unplanned impediments affect development capacity or commitments.
• Support Quality, Governance, and Responsible Delivery
• Encourage Agile delivery practices that support quality, traceability, security, compliance, and operational readiness.
• Help incorporate architecture, governance, cybersecurity, testing, documentation, and release requirements into backlog planning and execution.
• Support delivery practices appropriate for systems processing PII, PHI, CUI, or other sensitive information.
• Promote responsible delivery of AI-enabled capabilities, including human-in-the-loop review, transparency, auditability, output validation, and appropriate governance controls.
• Ensure part-time development contributions follow the same engineering, testing, security, and documentation standards required of the broader development team.
• Champion Agile Maturity and Continuous Improvement
• Coach team members and stakeholders on SAFe Agile values, Scrum practices, and effective delivery behaviors.
• Help strengthen Agile maturity by sharing good practices, delivery insights, technical understanding, and lessons learned.
• Encourage collaboration, trust, adaptability, and evidence-based decision-making in response to evolving mission and business needs.
• Identify opportunities to use automation and responsible AI-assisted tools to reduce administrative effort and improve delivery visibility without replacing human judgment or accountability.
  
  What you will need
• Must be able to OBTAIN and MAINTAIN a Federal or DoD "PUBLIC TRUST"; candidates must obtain approved adjudication of their PUBLIC TRUST prior to onboarding with Guidehouse. Candidates with an ACTIVE PUBLIC TRUST or SUITABILITY are preferred.
• Bachelor’s degree in Information Technology, Computer Science, Engineering, Business, Data Science, or a related field, OR an additional FOUR (4) years of relevant experience in lieu of a degree.
• Minimum FOUR (4) years of experience as a Scrum Master supporting enterprise software delivery teams.
• Demonstrated experience serving as a Scrum Master in a SAFe Agile environment, including sprint execution, Program Increment Planning, dependency coordination, risk and issue management, and cross-team collaboration.
• Strong knowledge of Agile, Scrum, Kanban, and SAFe delivery principles and practices.
• Proven ability to facilitate Agile ceremonies, coach teams, remove impediments, manage competing priorities, and drive continuous improvement.
• Experience supporting cross-functional teams that include Product Owners, engineers, architects, data scientists, testers, security personnel, and operations staff.
• Strong understanding of the software delivery lifecycle, including planning, design, development, testing, security, release, deployment, and operational readiness.
• Experience supporting delivery in enterprise environments with governance, compliance, security, quality, and documentation requirements.
• Experience supporting AI-enabled information systems, advanced analytics platforms, machine learning solutions, intelligent automation, or other data-driven applications.
• Minimum TWO (2) years of hands-on Python software development experience supporting production applications, enterprise solutions, automation, data engineering, or system integration use cases.
• Demonstrated proficiency with Python fundamentals, including object-oriented programming, data structures, modules, exception handling, logging, package management, and development of maintainable and reusable code.
• Experience developing or integrating REST APIs, backend services, automation scripts, system integrations, or data-processing workflows using Python.
• Experience with Python testing and quality practices, including unit testing, debugging, code reviews, static analysis, dependency management, and secure coding standards.
• Experience using Git-based source control, branches, pull requests, peer reviews, and modern CI/CD practices.
• Ability to translate technical backlog items into appropriately sized development tasks and communicate implementation risks, assumptions, dependencies, and tradeoffs.
• Demonstrated ability to balance primary Scrum Master responsibilities with part-time Python development based on sprint priorities, available capacity, and team needs.
• Ability to recognize and clearly communicate when Agile leadership obligations require reprioritization, reassignment, or adjustment of development commitments.
• Strong communication, facilitation, organization, problem-solving, and stakeholder-management skills.

What would be nice to have

• SAFe Scrum Master, Certified ScrumMaster, PMI Agile Certified Practitioner, or a similar Agile certification.
• Experience with Python frameworks and libraries such as FastAPI, Flask, Django, Pandas, NumPy, Pydantic, PyTest, or equivalent tools.
• Experience creating API specifications, data-validation models, automated tests, and reusable Python packages.
• Experience developing Python solutions that integrate with AWS services such as AWS Lambda, Amazon API Gateway, Amazon S3, Amazon Bedrock, Amazon SageMaker, AWS Glue, Amazon DynamoDB, or related cloud services.
• Familiarity with containerized Python applications, Docker, infrastructure automation, application monitoring, logging, and observability practices.
• Experience supporting Generative AI, large language model, or AI-assisted software products involving summarization, intelligent search, document understanding, conversational experiences, retrieval-augmented generation, or decision support.
• Familiarity with AI/ML delivery concepts such as model evaluation, prompt iteration, human-in-the-loop workflows, retrieval-augmented generation, confidence scoring, output validation, and governance controls.
• Experience working with regulated or sensitive data, including PII, PHI, CUI, retention requirements, auditability, and security controls.
• Experience with Jira, Confluence, Miro, or similar Agile planning and collaboration platforms.
• Experience in government, healthcare, human services, case management, grants management, or other mission-oriented operational environments.
• Experience partnering with Product Owners, Release Train Engineers, architects, technical leads, and leadership teams to improve Agile maturity, engineering discipline, and release outcomes.
• Experience using Generative AI-assisted tools to improve meeting preparation, sprint reporting, action tracking, risk identification, backlog refinement, software development, testing, and documentation while maintaining security, governance, and human oversight.
  

What We Offer:

Guidehouse offers a comprehensive, total rewards package that includes competitive compensation and a flexible benefits package that reflects our commitment to creating a diverse and supportive workplace.

Benefits include:

• Medical, Rx, Dental & Vision Insurance

• Personal and Family Sick Time & Company Paid Holidays

• Parental Leave

• 401(k) Retirement Plan

• Group Term Life and Travel Assistance

• Voluntary Life and AD&D Insurance

• Health Savings Account, Health Care & Dependent Care Flexible Spending Accounts

• Transit and Parking Commuter Benefits

• Short-Term & Long-Term Disability

• Tuition Reimbursement, Personal Development, Certifications & Learning Opportunities

• Employee Referral Program

• Corporate Sponsored Events & Community Outreach

• Care.com annual membership

• Employee Assistance Program

• Supplemental Benefits via Corestream (Critical Care, Hospital Indemnity, Accident Insurance, Legal Assistance and ID theft protection, etc.)

• Position may be eligible for a discretionary variable incentive bonus

About Guidehouse

Guidehouse is an Equal Opportunity Employer–Protected Veterans, Individuals with Disabilities or any other basis protected by law, ordinance, or regulation.

Guidehouse will consider for employment qualified applicants with criminal histories in a manner consistent with the requirements of applicable law or ordinance including the Fair Chance Ordinance of Los Angeles and San Francisco.

If you have visited our website for information about employment opportunities, or to apply for a position, and you require an accommodation, please contact Guidehouse Recruiting at 1-571-633-1711 or via email at . All information you provide will be kept confidential and will be used only to the extent required to provide needed reasonable accommodation.

All communication regarding recruitment for a Guidehouse position will be sent from Guidehouse email domains including @guidehouse.com or . Correspondence received by an applicant from any other domain should be considered unauthorized and will not be honored by Guidehouse. Note that Guidehouse will never charge a fee or require a money transfer at any stage of the recruitment process and does not collect fees from educational institutions for participation in a recruitment event. Never provide your banking information to a third party purporting to need that information to proceed in the hiring process.

If any person or organization demands money related to a job opportunity with Guidehouse, please report the matter to Guidehouse’s Ethics Hotline. If you want to check the validity of correspondence you have received, please contact . Guidehouse is not responsible for losses incurred (monetary or otherwise) from an applicant’s dealings with unauthorized third parties.

Guidehouse does not accept unsolicited resumes through or from search firms or staffing agencies. All unsolicited resumes will be considered the property of Guidehouse and Guidehouse will not be obligated to pay a placement fee.

Originally posted on Himalayas