Trust and Safety Operations 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.

The Product Operations team helps product development teams work more effectively by bringing structure, visibility, and consistency to how work moves across the product development lifecycle. Product Operations partners across functions to improve planning, coordination, communication, and execution — helping teams operate with greater clarity, confidence, and accountability.

Why do we need you? Well, we are looking for an Operations Analyst who will bring adaptability, ownership, and strong operational rigor to Calendly’s Trust & Safety workflows. You will report to the Senior Director of Product Operations and will be responsible for supporting the daily operations, escalations, investigations, and review cadences that help Calendly identify and respond to abuse patterns, customer reports, and platform risk.

In this role, you will partner closely with Product, Engineering, CX, Security, and other cross-functional teams to ensure Trust & Safety issues are reviewed, routed, documented, and resolved with the right level of urgency and context. You will help reduce operational overhead for Engineering, strengthen feedback loops across teams, and surface recurring issues that can inform tooling, process, detection, and product improvements.

On a typical day, you will: 

• Triage and resolve T&S escalations coming through internal channels, including suspension/reinstatement requests, CX escalations, host/user reports, and other abuse-related inquiries.
• Conduct daily enforcement operations, including account suspension, reinstatement review, bulk suspension workflows, and coordination with Engineering when tooling gaps require manual support.
• Review and investigate abuse reports from hosts, customers, support tickets, enforcement actions, and internal QA signals to determine whether additional action or deeper investigation is needed.
• Monitor risk and abuse signals across internal telemetry, detection outputs, undeliverable activity, product usage patterns, and investigation queues to identify trends, anomalies, and emerging abuse tactics.
• Perform in-depth investigations into suspicious behavior, distinguishing between legitimate outlier activity and true spam/abuse patterns using account history, velocity signals, behavioral context, and product interaction data.
• Develop and maintain playbook rules that standardize workflows, decision-making, and response protocols across customer interactions.
• Partner with Product and Engineering to identify weak points in detection, tooling, workflows, and enforcement controls, and translate operational findings into requirements, prioritization inputs, or mitigation recommendations.
• Maintain review cadences and operational reporting, including weekly investigation reviews, abuse trend summaries, SLA/volume tracking, and recommendations for improving T&S coverage, quality, and responsiveness.

Basic Qualifications

• 5+ years of experience in Product Operations, Technical Program Management, Risk Operations, Engineering Operations, or a related operational role supporting software, platform, or customer-facing teams.
• Experience managing operational workflows, queues, escalations, investigations, or review cadences in a cross-functional environment.
• Strong operational rigor, follow-through, and attention to detail, with the ability to manage recurring processes, document decisions, and ensure issues move to resolution.
• Ability to analyze signals from multiple sources — such as support tickets, customer reports, internal tooling, enforcement actions, product usage, or operational dashboards — and identify patterns or recurring issues.

• Strong communication skills, with the ability to provide clear status updates, summarize findings, and escalate risks or decisions to the right stakeholders.
• Experience partnering with Product, Engineering, CX, Security, Legal, or other cross-functional teams to improve workflows, resolve issues, and surface operational gaps.

Preferred Qualifications

• Experience in Trust & Safety, Risk Operations, Fraud Operations, Abuse Operations, Platform Integrity, Security Operations, or a related field.
• Experience reviewing abuse, spam, fraud, account enforcement, policy, or customer escalation workflows.
• Experience supporting operational reporting, health metrics, SLA tracking, queue management, or recurring business reviews.
• Experience working with technical teams to identify tooling gaps, manual process pain points, automation opportunities, or requirements for operational improvements.
• Experience in a high-growth SaaS, marketplace, communications, or platform business.
• Ability to balance speed, judgment, and accuracy when handling sensitive, customer-impacting, or risk-related decisions.

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