Similar Jobs
About Us
TherapyNotes is the go-to superhero for behavioral health Practice Management and EHR software! Our top-notch SaaS solution handles scheduling, billing, documenting, telehealth, and more so clinicians can focus on awesome patient care.
We're a dynamic team of pros who love to innovate and push the envelope, keeping our software cutting-edge. Join us, and let's revolutionize behavioral health software together while making a real difference!
About The Position
The Senior Scrum Master is responsible for facilitating Agile execution across multiple infrastructure and engineering teams, ensuring consistent adherence to Scrum principles, sprint discipline, and continuous improvement practices. This role supports mulitple teams under a single Engineering Manager and partners closely with Technical Leads to optimize delivery, predictability, and team health.
This is not a traditional command-and-control project management role. It is a servant-leader position focused on enabling high-performing Agile teams while maintaining visibility and accountability across initiatives. In addition to Scrum leadership, this role provides light project management support for initiatives assigned to the teams, ensuring alignment with business priorities, transparency of progress, and proactive risk management.
What You'll Do
Agile Facilitation & Team Enablement
- Serve as Scrum Master for multiple engineering teams, facilitating sprint planning, daily standups, backlog refinement, sprint reviews, and retrospectives.
- Ensure Scrum ceremonies are productive, time-boxed, and outcome-driven.
- Promote Agile best practices and continuous improvement across teams.
- Identify and remove impediments that hinder team progress.
- Coach teams on sprint discipline, estimation practices, and commitment reliability.
- Monitor sprint health metrics (velocity, predictability, burndown, cycle time, etc.) and guide teams toward improvement.
Cross-Team Coordination
- Support coordination between engineering teams and external stakeholders.
- Ensure dependencies are identified early and managed effectively.
- Partner with Technical Leads to align sprint execution with technical strategy and delivery commitments.
- Reinforce clarity around scope, priorities, and acceptance criteria.
Project Management
- Provide structured oversight for projects assigned to the teams.
- Track milestones, risks, and deliverables without disrupting Agile flow.
- Ensure project artifacts (roadmaps, timelines, documentation, status updates) are maintained.
- Communicate project status, risks, and trade-offs to Engineering leadership.
- Facilitate cross-functional collaboration when projects involve other departments.
Reporting & Transparency
- Maintain dashboards and reporting to provide visibility into sprint performance, delivery status, and team capacity.
- Support the Engineering Manager with insights on delivery trends and potential risks.
- Ensure documentation is current and accessible in Jira, Confluence, or related systems.
What We're Looking For
- 5+ years of experience as a Scrum Master in an engineering or software development environment.
- Experience supporting multiple Agile teams simultaneously.
- Demonstrated success improving sprint predictability, team velocity, and delivery consistency.
- Strong understanding of Scrum, Agile principles, and incremental product delivery.
- Experience operating within a cloud-first, CI/CD environment.
- Working knowledge of modern web application architectures and cloud infrastructure.
- Proficiency in Jira, Confluence, or comparable Agile tooling.
Preferred Qualifications
- Certified Scrum Master (CSM), Professional Scrum Master (PSM), or equivalent.
- PMI-ACP or other Agile-focused certification.
- Experience coaching Agile maturity across engineering organizations.
- Familiarity with Lean or flow-based methodologies.
What We Offer
- Competitive salary - $100,000-$140,000
- Employer sponsored health, dental, vision, life, and disability insurance
- Retirement plan with company contribution
- Annual company profit sharing
- Personal development/training budget
- Open, collaborative work environment
- Extensive 2-week onboarding plan
- Comprehensive mentorship program
Equal Opportunity Employer Statement & Applicant Rights
TherapyNotes LLC is an Equal Opportunity Employer and does not discriminate based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status under federal, state, or local law. We are committed to providing a workplace free of discrimination and harassment.For more information about your rights under federal employment laws, please review the following:
- Know Your Rights: Workplace Discrimination is Illegal
- Family and Medical Leave Act (FMLA): Employee Rights Under FMLA
If you require a reasonable accommodation during the application process, please contact [email protected].
#LI-Remote
#LI-RH1
6/2/2026
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
