Scrum Master

At Ascendant Insurance Solutions, we're continuing to evolve how we build products, improve our operations, and deliver technology that supports our customers and employees. We're looking for a Scrum Master who can help teams work with greater clarity, focus, accountability, and momentum.

This isn't a role where you'll simply schedule stand-ups and maintain a Jira board. You'll help create the conditions for high-performing teams by removing obstacles, improving collaboration, facilitating meaningful conversations, and helping teams continuously improve how they plan and deliver work.

You'll work closely with Product Owners, engineers, business stakeholders, leadership, and cross-functional partners to make sure teams understand what they're trying to accomplish and have what they need to deliver it.

We're looking for a servant leader who knows when to facilitate, when to coach, when to challenge, and when to get out of the team's way.

If you enjoy helping people work better together, solving organizational problems, and turning ambiguity into progress, we'd like to hear from you.

What You'll Do

• Facilitate Scrum ceremonies including Sprint Planning, Daily Scrum, Sprint Reviews, and Retrospectives
• Help teams establish clear Sprint goals and realistic commitments
• Coach teams on Scrum principles, Agile practices, and continuous improvement
• Remove or escalate impediments that prevent teams from making progress
• Partner closely with Product Owners to support effective backlog refinement and prioritization
• Help ensure work is clearly defined, appropriately sized, and ready for development
• Facilitate collaboration between technical teams, business stakeholders, and leadership
• Identify dependencies, risks, bottlenecks, and potential delivery issues early
• Monitor team progress and help communicate meaningful delivery insights to stakeholders
• Use tools such as Jira, Azure DevOps, Confluence, or similar platforms to support transparency and workflow management
• Help teams use metrics responsibly to understand delivery performance and identify opportunities for improvement
• Encourage healthy team dynamics, accountability, psychological safety, and constructive communication
• Facilitate discussions when priorities, requirements, or expectations are unclear
• Help teams identify the root causes of recurring problems rather than treating symptoms
• Support Agile transformation and process-improvement initiatives across the organization
• Partner with other Scrum Masters, Product Owners, and Agile leaders to share best practices
• Help teams continuously improve their planning, estimation, communication, and delivery practices
• Protect the team from unnecessary distractions while maintaining appropriate stakeholder transparency

What Success Looks Like

Success in this role isn't measured by how many meetings you facilitate.

It's measured by whether teams are becoming more effective, predictable, collaborative, and capable of delivering meaningful outcomes.

You'll be successful when:

• Teams understand their goals and priorities
• Sprint commitments are realistic and aligned with business priorities
• Obstacles are identified and addressed quickly
• Stakeholders have appropriate visibility into progress and risks
• Retrospectives result in meaningful changes rather than repetitive conversations
• Teams become increasingly self-organizing
• Dependencies and risks are surfaced early
• Product Owners and delivery teams work effectively together
• Teams spend less time dealing with avoidable process problems
• Delivery becomes more predictable without sacrificing quality
• Teams continuously improve rather than simply repeating the same process

We're Looking for You If You Have

• 3+ years of experience as a Scrum Master, Agile Delivery Lead, Agile Coach, or similar role
• Strong understanding of Scrum principles, Agile methodologies, and servant leadership
• Experience facilitating Scrum ceremonies and coaching cross-functional teams
• Experience working with software development or technology teams
• Strong communication and facilitation skills
• Ability to work effectively with technical and non-technical stakeholders
• Strong conflict-resolution and problem-solving skills
• Experience identifying and removing organizational impediments
• Ability to manage competing priorities without becoming the team's project administrator
• Experience with Jira, Azure DevOps, Confluence, or comparable Agile tools
• Strong understanding of Agile metrics and delivery practices
• Ability to recognize when Scrum practices are helping—and when teams are performing ceremonies without achieving the intended outcome
• A coaching mindset and the ability to influence without relying on formal authority

Certifications

One or more of the following certifications is helpful:

• Certified ScrumMaster (CSM)
• Professional Scrum Master (PSM)
• Advanced Certified ScrumMaster (A-CSM)
• SAFe Scrum Master
• PMI-ACP
• Certified Agile Coach or similar credential

Certifications are valuable, but practical experience matters more than having a collection of certificates.

We're interested in how you've helped real teams navigate challenges, improve their processes, and deliver better outcomes.

The Kind of Person Who Will Thrive Here

You'll probably enjoy this role if you:

• Naturally bring structure to ambiguous situations
• Enjoy helping teams solve their own problems
• Ask thoughtful questions instead of immediately providing answers
• Can facilitate difficult conversations without creating unnecessary conflict
• Know how to challenge assumptions respectfully
• Are comfortable working with people at different levels of an organization
• Can communicate complicated situations clearly to executives and technical teams
• Care more about outcomes than following a process for its own sake
• Are comfortable saying, "This isn't working—let's figure out why"
• Have the patience to coach people while maintaining high standards
• Understand that successful Agile teams require trust, accountability, and transparency

Technology & Modern Agile Delivery

Technology and software development are changing rapidly, and modern Scrum Masters need to understand how emerging tools affect the way teams work.

At Ascendant Insurance Solutions, you'll have opportunities to work with modern collaboration, project-management, analytics, automation, and AI-enabled tools.

You may help teams explore how AI can improve requirements analysis, documentation, testing, research, sprint preparation, reporting, and knowledge management while ensuring that appropriate security, privacy, and governance practices are followed.

You don't need to be an AI engineer. We want someone who is curious about emerging technology and understands how to help teams adopt new tools thoughtfully.

Working at Ascendant Insurance Solutions

At Ascendant Insurance Solutions, we believe Agile isn't about having more meetings or following a checklist.

It's about creating an environment where talented people can understand the problem, make good decisions, collaborate effectively, and deliver value.

You'll work across technology and business teams and have the opportunity to influence how we plan, prioritize, communicate, and deliver important initiatives.

We value people who are:

Servant leaders. You help teams succeed without needing to be the person in control.

Outcome-focused. You care about business and customer outcomes—not simply completing tasks.

Transparent. You make risks, blockers, and difficult conversations visible early.

Collaborative. You create space for different perspectives and help teams reach better decisions.

Adaptable. You understand that Agile is a mindset, not a rigid set of ceremonies.

Continuous learners. You're constantly looking for ways to help yourself and your teams improve.

Career Growth

This position can lead to broader opportunities across Agile delivery, technology leadership, and organizational transformation.

Potential career paths include:

Scrum Master Senior Scrum Master Agile Coach Enterprise Agile Coach Agile Delivery Manager

or:

Scrum Master Senior Scrum Master Program Manager / Delivery Manager Technology Leadership

You may also develop expertise in:

• Agile transformation
• Product management
• Program management
• Engineering delivery
• Organizational change
• Digital transformation
• AI-enabled product development
• Enterprise Agile practices

Compensation & Benefits

Ascendant Insurance Solutions is committed to providing competitive compensation based on experience, qualifications, responsibilities, and internal equity.

Benefits may include:

• Competitive salary
• Medical, dental, and vision insurance
• 401(k) and retirement benefits
• Paid time off and company holidays
• Professional development and certification support
• Agile and leadership training
• Career advancement opportunities
• Employee assistance and wellness programs
• [Add company-specific benefits here]

Our Hiring Process

We want our hiring process to be practical and give you an opportunity to demonstrate how you think.

The process may include:

1. Initial conversation with our recruiting team
2. Interview with the hiring manager
3. Agile/Scrum scenario discussion
4. Facilitation or problem-solving exercise
5. Conversation with technology and business stakeholders
6. Final interview and offer

We're particularly interested in how you would respond to real situations—for example, a team that repeatedly misses Sprint goals, a Product Owner who constantly changes priorities, or stakeholders who bypass the team's agreed process.

Equal Opportunity Employer

Ascendant Insurance Solutions is an equal opportunity employer. We value a diverse workforce and do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other characteristic protected by applicable law.

Ready to Help Teams Do Their Best Work?

If you're an experienced Scrum Master who believes Agile is about empowering people, improving systems, and delivering meaningful outcomes, we'd love to hear from you.

Join Ascendant Insurance Solutions and help us build teams that don't just move faster—but work smarter, communicate better, and continuously improve.

Apply for the Scrum Master position today.