Senior Compliance and Risk Analyst

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

Our Compliance and Risk team is a strategic partner that enables the business to grow securely and responsibly. We work across Engineering, Security, Product, Legal, HR, and Business Operations to build scalable compliance and risk programs that support innovation while maintaining customer trust.

As a Senior Compliance and Risk Analyst, you will own and mature our compliance program, ensuring the organization maintains certifications such as SOC 2 and ISO 27001 while building scalable, automated processes that support a rapidly growing SaaS business.

This is a high-impact role for someone who enjoys both strategy and execution. You'll design and operationalize controls, strengthen our common controls framework, optimize compliance automation, and embed compliance into business processes and product development. Beyond maintaining audit readiness, you'll help shape how compliance evolves as the organization grows, driving continuous improvement and fostering a proactive culture of risk management.

• Own and manage the organization's compliance program, including SOC 2 and ISO 27001 readiness, certification, and ongoing maintenance.
• Develop and execute a compliance roadmap aligned with business objectives, regulatory requirements, and organizational risk appetite.
• Lead internal and external audits by coordinating evidence collection, managing auditor relationships, and driving timely remediation of findings.
• Monitor changes in regulatory and industry frameworks, assessing their impact on the organization's compliance program.
• Own the enterprise risk management process, including risk identification, assessment, treatment planning, and ongoing monitoring.
• Conduct periodic risk assessments and partner with stakeholders to identify control gaps and prioritize remediation activities.
• Develop and present compliance metrics, risk dashboards, and executive reports for senior leadership.
• Design, document, and improve internal controls aligned with SOC 2, ISO 27001, and other applicable frameworks.
• Lead control testing, including evidence collection, effectiveness validation, remediation tracking, and continuous improvement.
• Expand and mature the organization's common controls framework to support evolving compliance requirements.
• Administer and optimize compliance automation platforms, improving workflow efficiency and reducing manual effort.
• Perform User Access Reviews (UARs) and support continuous compliance monitoring through automation and reporting.
• Partner with Engineering, Security, Product, Legal, HR, and Operations to integrate compliance into business processes and product development.
• Develop training, playbooks, and self-service resources that empower teams to meet compliance requirements efficiently.
• Manage multiple compliance initiatives simultaneously while ensuring projects remain on schedule and stakeholders stay informed.

• 5+ years of experience in compliance, risk management, audit, or Governance, Risk, and Compliance (GRC) roles within a technology or SaaS environment.
• Experience owning or leading compliance programs supporting frameworks such as SOC 2 and ISO 27001.
• Working knowledge of security and privacy frameworks including NIST, ISO 27001, GDPR, and HIPAA.
• Experience administering compliance automation platforms such as Drata, Vanta, Tugboat Logic, or similar solutions.
• Experience performing User Access Reviews (UARs) using GRC or compliance automation platforms.
• Strong understanding of internal controls, risk assessment methodologies, and audit processes.
• Demonstrated ability to manage multiple initiatives and deliver results in a fast-paced environment.
• Excellent project management, analytical, and problem-solving skills.
• Strong communication skills with the ability to translate technical and regulatory requirements into practical business solutions.
• Proven ability to collaborate effectively with technical and non-technical stakeholders across the organization.

• Experience leveraging AI to improve compliance processes or automate workflows.
• Experience scaling compliance programs within a high-growth SaaS organization.
• Hands-on experience developing or expanding a common controls framework.
• Advanced expertise configuring compliance automation platforms, including integrations, custom controls, and reporting.
• Familiarity with additional compliance frameworks such as PCI DSS, FedRAMP, or other industry standards.
• Experience developing compliance training, awareness programs, or self-service enablement resources.
• Professional certifications such as CISA, CRISC, CISSP, CCSK, or equivalent.

This role may require occasional travel for company events, team collaboration, or offsites.