Senior Scrum Lead

ProSelect Insurance Company•Boston, MA

About The Position

The Senior Scrum Lead at Coverys plays a key role in advancing the organization’s Agile delivery model across insurance, risk analytics, and enterprise technology platforms. This role partners closely with business and IT leaders to deliver initiatives that modernize policy, billing, claims, and underwriting systems, enhance digital experiences, and support Coverys’ mission of protecting the healthcare community through innovative insurance and risk management solutions.

Requirements

Bachelor’s degree in business, Computer Science, or related field, required.
7+ years of IT delivery experience, with 5+ years as a Scrum Lead in an Agile or hybrid environment.
Experience in insurance systems, ideally in medical professional liability, commercial lines, or P&C insurance.
Extensive experience leading Agile delivery in the insurance domain.
Certified Scrum Master (PSM/CSM) or equivalent (PMI-ACP, A-CSM), required.
Exceptional facilitation, servant leadership, and communication skills.
Strong understanding of Agile methodologies (Scrum, Kanban, SAFe) and experience with Azure DevOps, SharePoint, or similar tools.
Hands-on experience supporting Release Trains and facilitating or participating in PI Planning events.
Delivery Excellence and Execution Discipline
Business and Technical Agility
Risk and Dependency Management
Continuous Learning and Improvement Mindset

Nice To Haves

Experience with Duck Creek, Guidewire or other core insurance systems, preferred.
Familiarity with cloud-based data platforms, Workday, or Salesforce ecosystems, preferred.
Prior exposure to compliance or audit-driven environments in insurance.
Ability to foster collaboration across teams with transparent and effective communication.

Responsibilities

Serve as Scrum Lead for two or more Agile teams within Coverys’ product and technology portfolio (e.g., core systems modernization, analytics, or digital experience).
Plan and facilitate all Scrum ceremonies sprint planning, daily stand-ups, sprint reviews, and retrospectives.
Partner with Product Owners and Business Analysts to maintain healthy, prioritized backlogs aligned with strategic business outcomes.
Identify and remove impediments impacting sprint progress while driving alignment across cross-functional teams (underwriting, Product Development, Actuarial, IT).
Leverage Agile metrics (velocity, burn-up/down, predictability) to guide performance and transparency.
Support Release Train level planning by ensuring team readiness for PI Planning and participating in coordination activities that align delivery across teams.
Work closely with product managers, delivery leads, architects, and business stakeholders to ensure sprint goals and deliverables support Coverys’ corporate strategy.
Collaborate with governance teams to maintain compliance with internal processes, audit standards, and regulatory expectations.
Communicate progress, risks, and dependencies clearly to leadership and business partners.
Mentor Scrum Leads and Product Owners across multiple teams to strengthen Agile maturity and consistency.
Foster a culture of accountability, empowerment, and continuous improvement.
Promote adoption of Agile practices, DevOps, and automation to improve delivery speed and quality.
Facilitate retrospectives to capture lessons learned and implement actionable improvements.
Ensure alignment with IT governance, risk, and compliance frameworks in the insurance space (e.g., data privacy, and audit readiness).
Maintain discipline in documentation, change management, and system testing in partnership with QA and release teams.
Support evolving business needs, as applicable.