Want to be a bswifter?
At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces.
We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you!
Position Summary
You will join the team as a Scrum Master, responsible for guiding and enabling multiple Agile teams at bswift. This role is responsible for driving delivery excellence, strengthening Agile practices, and fostering a culture of continuous improvement across cross-functional product teams.
You’ll work closely with software developers, product managers, and cross-functional teams to deliver reliable, secure, and performant services that enable seamless user experiences.
Responsibilities
Lead and coach multiple Scrum teams to ensure predictable, high-quality, end to-end delivery.
Facilitate all Agile ceremonies and uphold Scrum principles, bswift standards, and delivery discipline.
Collaborate with Product Owners on backlog refinement, sprint readiness, and alignment with business priorities.
Proactively identify, escalate, and remove impediments to maintain smooth execution.
Coordinate cross-team dependencies, risks, and release planning while ensuring transparent communication with stakeholders.
Drive continuous improvement using metrics, retrospectives, and best practices to strengthen team performance and delivery.
Mentor and develop team members and junior Scrum Masters to foster a high-performance, self-organizing culture.
Ensure teams meet quality standards, maintain accurate Agile tracking systems, and deliver according to definition of done.
Support organizational initiatives including PI Planning, capacity planning, governance activities, and process optimization.
Knowledge, Education, and Experience
Education:
Bachelor's degree in computer science, Information Technology, Engineering, Business, or related field (or equivalent experience).
Experience:
2-5 years of hands-on experience as a Scrum Master supporting software development teams.
Proven success leading multiple Agile teams in a complex, scaled environment.
Strong experience in backlog management, sprint planning, release coordination, and cross-team delivery.
Demonstrated ability to manage dependencies, risks, and stakeholder communication across distributed teams.
Experience with Agile transformation, continuous improvement initiatives, and delivery governance.
Familiarity with DevOps workflows, release processes, and modern engineering practices.
Experience in enterprise SaaS, healthcare, HR tech, or benefits administration domains (preferred).
Knowledge & Skills:
Deep knowledge of Agile frameworks (Scrum, Kanban, SAFe) and practical application in real-world teams.
Strong skills in facilitation, conflict resolution, coaching, and servant leadership.
Hands-on expertise with Agile tools such as Jira, Azure DevOps, Confluence, or similar.
Ability to interpret and use delivery metrics to guide decisions and improvements.
Understanding of product lifecycles, SDLC, project management fundamentals, and quality standards.
Excellent communication and collaboration skills with the ability to influence across teams.
Certifications (Preferred):
CSM, PSM, SAFe Scrum Master, PMI-ACP, or equivalent Agile certifications.
At bswift, our mission is clear: Become the preeminent benefits administrator through exceptional people, innovative technology, and delighted customers. And our values are at the heart of everything we do to accomplish that mission. We Pursue Excellence, Embrace Accountability, Deliver Superior Service, and strive to Be A Great Place To Work. We take pride in having an engaged, collaborative team that goes the extra mile to get the job done right.
bswift has been regularly named one of Chicago’s Best and Brightest Companies to Work For®, as well as one of the Nation’s Best and Brightest Companies to Work For® year after year. We offer a fun, flexible, and creative environment where you can grow both professionally and personally.
If you have what it takes to join our award-winning culture, we’d love to hear from you!
Skills Required
- Bachelor's degree in computer science, information technology, engineering, business, or a related field, or equivalent experience
- 2-5 years of hands-on experience as a Scrum Master supporting software development teams
- Experience leading multiple Agile teams in a complex, scaled environment
- Experience with backlog management, sprint planning, release coordination, and cross-team delivery
- Experience managing dependencies, risks, and stakeholder communication across distributed teams
- Experience with Agile transformation, continuous improvement initiatives, and delivery governance
- Familiarity with DevOps workflows, release processes, and modern engineering practices
- Deep knowledge and practical application of Scrum, Kanban, and SAFe
- Strong facilitation, conflict resolution, coaching, and servant leadership skills
- Hands-on expertise with Jira, Azure DevOps, Confluence, or similar Agile tools
- Ability to interpret delivery metrics and use them to guide improvements
- Understanding of product lifecycles, SDLC, project management fundamentals, and quality standards
- Excellent communication and collaboration skills with the ability to influence across teams
- Experience in enterprise SaaS, healthcare, HR technology, or benefits administration
- CSM, PSM, SAFe Scrum Master, PMI-ACP, or equivalent Agile certification
bswift Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about bswift and has not been reviewed or approved by bswift.
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Healthcare Strength — Health coverage includes comprehensive medical, dental (with DMO/PPO options and preventive care at 100%), and a separate vision plan, alongside FSAs and wellness programming. Feedback suggests preventive services and wellbeing incentives (e.g., flu shots, healthy-behavior rewards) are accessible and valued.
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Retirement Support — Retirement programs feature a 401(k) with company match and immediate eligibility. Feedback suggests the matching contribution and straightforward participation enhance perceived retirement readiness.
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Leave & Time Off Breadth — Time off provisions include PTO that grows with tenure, company holidays, and civic leaves (jury duty, military, bereavement, community service). Feedback suggests extras like company-wide “You Days” and, in some areas, open PTO broaden practical time away.
bswift Insights
What We Do
bswift is a Chicago-based technology company that provides benefits administration for employers and exchanges nationwide. We pride ourselves on having a fun, friendly and smart staff that goes the extra mile to get the job done right. The reward is a fun, flexible and creative environment with ample opportunity for growth.
Why Work With Us
We offer the excitement and opportunity of a fast-growing company with the stability of an experienced management team, a blue-chip client base, and a proven track record of success. We're looking for motivated and goal-driven team members who possess the bswift values of higher standards, greater accountability and more fun.
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