Scrum Master
Drawbridge - Boston / New York location preferred- Full-time - Reports to Head of Development
About Drawbridge
Drawbridge provides cybersecurity to the world's leading hedge funds, private equity firms, and portfolio companies through its Cyber Risk Intelligence platform.
The role
The role combines two in-demand fields, cybersecurity and AI, with agile delivery.
You'll serve two agile teams of developers and product managers, help strengthen the Scrum practice, and learn how AI changes the way teams plan and ship software. The teams build a cybersecurity platform for investment firms around the world, covering web applications, APIs, data pipelines, and AI-powered features. Agents propose, pipelines verify, and people decide.
This is a data-driven Scrum Master role. We expect you to use delivery data and AI tools, not only facilitation skills.
What you'll do
Facilitate sprint planning, daily stand-ups, refinement, sprint reviews, and retrospectives, so each event has a clear purpose and outcome.
Guide both teams and their product owners on Scrum practices, and help each team improve how it works.
Remove blockers quickly, and raise risks and dependencies early, including those between the two teams.
Keep the backlogs and sprint boards in Azure DevOps accurate, and make work visible to the teams and stakeholders.
Track delivery metrics such as velocity, cycle time, and sprint predictability, and use them to improve how the teams work, not to judge people.
Help the teams use AI tools for refinement, story writing, and retrospective analysis, with human review of the output.
Work with developers, product, and QA on release readiness, and keep each team's definitions of ready and done current.
Report progress, risks, and decisions clearly to the Head of Development and other stakeholders.
What you bring
3+ years as a Scrum Master, or in agile delivery, project coordination, or software development with hands-on Scrum experience. A PSM, CSM, or similar certification is a plus.
Working knowledge of Scrum and agile principles, used to serve teams rather than manage them.
Familiarity with modern development workflows, including Git, pull requests, and CI/CD.
Hands-on use of AI tools such as Claude, Copilot, or Cursor.
Comfort asking questions in the open.
Strong facilitation, curiosity, healthy skepticism of AI output, and clear written communication.
Nice to have
Azure DevOps boards and pipelines, Jira, Kanban or flow metrics, SAFe or other scaling frameworks, basic SQL or scripting, Microsoft Fabric, or cybersecurity or financial-sector experience.
What you'll grow into
How AI changes planning, estimation, and delivery for development teams.
Delivery for a cybersecurity product used by hedge funds and private equity firms, including their security and compliance expectations.
A larger part in the Scrum practice as the organization grows.
Skills Required
- 3+ years as a Scrum Master or in agile delivery, project coordination, or software development with hands-on Scrum experience
- Working knowledge of Scrum and agile principles
- Familiarity with Git, pull requests, and CI/CD workflows
- Hands-on experience using AI tools such as Claude, Copilot, or Cursor
- Strong facilitation, curiosity, healthy skepticism of AI output, and clear written communication
- PSM, CSM, or similar certification
- Experience with Azure DevOps boards and pipelines
- Experience with Jira, Kanban or flow metrics, SAFe, or other scaling frameworks
- Basic SQL or scripting experience
- Experience with Microsoft Fabric
- Cybersecurity or financial-sector experience
What We Do
Drawbridge is a premier provider of cybersecurity software and solutions to the alternative investment and wealth management industry. Its proprietary platform helps firms manage their governance, risk, and compliance (GRC) requirements while combatting sophisticated cyber threats and third-party risks. Drawbridge's platform connects business, compliance, and IT to empower firms to centralize and manage their most robust security programs, improve their risk profile and raise institutional capital. With a tested team focused on value delivery and an 800+ strong customer base, Drawbridge offers unmatched customer service and flexibility to help businesses proactively manage vulnerabilities, plan for growth, and reduce complexity.
