Senior Strategic Insights Analyst

A day in the life

You’ll report to the Director of Analytics and serve as the connective tissue across Calendly’s Analytics organization.

Our teams generate valuable insights across Product Analytics, Reporting Analytics, Marketing Analytics, and Data Science. But insights only create value when they influence decisions. This role exists to bridge the gap between analytical output and business action.

You’ll partner closely with analysts, analytics leaders, and business stakeholders to understand the underlying drivers behind findings, connect patterns that may not be visible within a single team or analysis, and identify the most important implications for the business. You’ll help determine what matters, why it matters, and what actions leaders should consider as a result.

You are not responsible for conducting analyses yourself. Instead, you’ll synthesize findings across the organization, connect them to broader business strategy and performance, and ensure they are communicated in ways that drive understanding, alignment, and action.

This is not a reporting or dashboarding role. It is a strategic synthesis, storytelling, and influence role focused on increasing the visibility, usability, and business impact of Calendly’s analytics investments.

On a typical day, you’ll:

• Partner with Analytics teams and business leaders to understand emerging trends, identify the most important business implications, and shape narratives around high-impact findings.
• Synthesize insights across Product Analytics, Reporting Analytics, Marketing Analytics, and Data Science, connecting findings to broader business strategy, customer behavior, product performance, and company goals.
• Create executive-ready communications including decision briefs, presentations, strategic memos, planning materials, and leadership updates.
• Curate and maintain recurring insight communications, including weekly and monthly business reviews, executive summaries, and stakeholder updates.
• Ensure critical insights reach the right audiences—from the board and executive team to functional leaders and the broader organization—in formats that drive alignment and decision-making.
• Develop foundational materials that improve organizational understanding of key business drivers, metrics, customer behaviors, and strategic priorities.
• Establish standards and best practices for analytics storytelling, insight packaging, discoverability, and communication quality across the Analytics organization.
• Help Analytics teams leverage AI and emerging tools to scale communications while maintaining editorial quality and analytical rigor.

What do we need from you?

Basic Qualifications

• 8+ years of experience in strategy, business operations, consulting, analytics enablement, product operations, research synthesis, or similar roles that translate complex information into business decisions.
• Exceptional written and verbal communication skills, with the ability to simplify complex concepts without losing nuance and adapt messaging for audiences ranging from individual contributors to executive leadership.
• Strong business acumen and analytical curiosity, with the ability to engage deeply with analytical findings, identify the most important insights, and connect them to broader company strategy, customer behavior, and business performance.
• Demonstrated experience creating executive-level narratives, recommendations, and decision-support materials from analytical, technical, or operational inputs.
• Experience working cross-functionally with analytics, product, GTM, finance, operations, and executive stakeholders.
• Strong organizational and prioritization skills, with the ability to manage multiple concurrent projects and stakeholders.
• High degree of ownership and comfort operating in ambiguous, fast-changing environments.

Preferred Qualifications

• Experience in management consulting, business strategy, chief of staff, business operations, analytics leadership, or similar strategic roles.
• Experience supporting executive leadership teams, strategic planning processes, board reviews, or company-level business reviews.
• Familiarity with analytics workflows, experimentation, metrics, forecasting, and data-informed decision-making environments.
• Track record of increasing the visibility, adoption, and business impact of analytical work across multiple functions.
• Familiarity with AI tools for content creation and knowledge management, including appropriate use cases and quality controls.

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