Calendly

Engineering Manager

• Recruit, manage, and mentor a diverse team of Identity and Trust & Safety engineers, fostering a culture of collaboration, accountability, and continuous improvement
• Provide hands-on mentorship, guidance, and decision-making to help engineering teams deliver effective, high-quality solutions
• Own and drive execution on critical initiatives, ensuring timely, high-quality outcomes while promoting incremental delivery and impact
• Define and evolve our Identity and Access management capabilities to meet future demands while shaping the Trust & Safety roadmap in alignment with company priorities and emerging threats
• Design and implement scalable systems to detect, prevent, and respond to fraud and abuse, leveraging key metrics to measure effectiveness
• Partner with Product, Security, Design, Engineering, Legal, and Compliance teams to embed security and safety considerations throughout the development lifecycle
• Shape technical strategy and North Star Architecture while guiding the design and implementation of key services and components

Engineering Manager, IAM – Trust & Safety

Support Engineer

• Design, build, and operate services and APIs for contacts, companies, syncing third party data sources, deduplication, enrichment, and search - prioritizing reliability, performance, and maintainability.
• Partner with Product and Design to shape requirements, sequence milestones, and deliver incremental value that supports our customers.
• Contribute to our data model and storage strategies for people and related objects, ensuring consistency, privacy, and scalability.
• Improve platform resilience with robust observability, fault-tolerant patterns, and production readiness; participate in on-call to support business critical services.
• Collaborate with adjacent squads to evolve architecture and shared components; participate in code reviews and provide mentorship to peers.
• If you have React/TypeScript experience, contribute to end to end delivery by partnering on UI contracts and occasionally implementing UI that integrates with your services.

Senior Full Stack Engineer – Support Engineering

Director

• Define and evolve Calendly's integrated brand amplification strategy, setting a 1–3 year vision for how we show up across social, PR, and advocacy channels to grow awareness, share of voice, and brand affinity. Translate company and product priorities into coordinated programs that make Calendly's story impossible to ignore.
• Lead and develop your team — a Social Media Lead, Customer Advocacy Lead, and PR Contractor — by setting clear goals, providing coaching, and creating an environment where each person can do their best work. Hold the team accountable to outcomes while removing blockers and advocating for resources needed to execute.
• Oversee Calendly's social media strategy and execution, partnering with the Social Media Lead to develop platform strategies, content pillars, editorial calendars, and channel-specific playbooks that grow reach and drive meaningful engagement. Ensure social content is on-brand, audience-first, and connected to the broader marketing narrative.
• Guide and provide strategic direction to our PR contractor, helping shape Calendly's narrative, prioritize media opportunities, and ensure PR efforts are tightly connected to broader brand and business goals. Serve as the internal voice of the brand in all communications decisions, translating company priorities into clear story angles and messaging frameworks the PR contractor can execute against.
• Build and scale customer advocacy programs that identify, activate, and nurture brand champions — turning customer success into reviews, testimonials, case studies, speaking opportunities, and community engagement that amplify Calendly's story at scale. Design the systems and incentive structures that make participation easy and sustainable.
• Partner with Internal Communications, Employee Experience, and the Social Media Lead to activate employees as authentic brand voices on social and professional networks. Provide strategic direction, content toolkits, and brand guidance that makes it easy for employees to share Calendly's story in ways that feel genuine and impactful.
• Partner cross-functionally with creative, product marketing, demand gen, and executive communications teams to develop compelling content and campaigns that feed all brand and advocacy channels. Ensure creative quality, message consistency, and strong alignment between brand moments and business objectives.
• Establish KPIs and a reporting cadence to measure the impact of brand, PR, and advocacy programs — tracking reach, share of voice, engagement, and pipeline influence. Use data and insights to continuously optimize strategy and communicate program effectiveness to senior leadership.

Director of Brand – Advocacy

• Define and evolve Calendly’s Customer Education strategy, setting a clear vision for how educational content — video demos, self-serve tutorials, Help Center articles, Learning Hub courses, and live programming — maps to customer segments, product surfaces, and lifecycle stages from onboarding through deep feature adoption.
• Lead and develop your team of education specialists and multimedia content producers, setting clear goals, providing coaching, and building an environment where each person can do their best work. Hold the team accountable to outcomes while advocating for the resources needed to execute.
• Partner closely with Product Marketing to ensure education content is embedded in every product launch — developing Help Center articles, demo videos, feature walkthroughs, and in-product guidance that help customers understand and adopt new capabilities quickly.
• Partner with Customer Success and Support to identify where customers are getting stuck, surface education content gaps that are contributing to support volume or churn risk, and build content that proactively answers the questions customers have before they need to ask.
• Build and scale the Calendly Learning Hub as a best-in-class self-serve education destination — developing a curriculum strategy, overseeing course development, and creating a content roadmap that keeps pace with Calendly’s product evolution.
• Raise the bar on multimedia content quality across the education function, partnering with your multimedia producer and the broader creative team to develop demo videos, feature tutorials, and educational experiences that are compelling, on-brand, and built for how customers actually learn.
• Establish KPIs and a reporting cadence to measure the impact of education content — tracking metrics like feature activation rates, Help Center deflection, Learning Hub engagement, and time-to-value for new users. Use data and insights to continuously improve strategy and communicate program effectiveness to senior leadership.
• Build the operational systems and workflows that allow your team to produce high-quality content at the speed of Calendly’s product cadence, including processes for content planning, review, localization, and maintenance.

Director, Customer Education

Product Marketing

• Design and deliver full-lifecycle enablement programs (onboarding, product training, skill-building, and ongoing process training) across our Sales & Customer Success and 24/7 Support organizations
• Lead and develop your team of two as a player-coach, building and delivering programs yourself while delegating, mentoring, and raising the bar for the team
• Define repeatable operating playbooks and program cadences for GTM initiatives (launches, operational changes, vertical programs), partnering cross-functionally with Sales, Support, Product Marketing, GTM Ops, and Product
• Own release and launch readiness for all customer-facing teams, defining the activities, workflows, and deliverables (trainings, documentation, etc.) tied to each release tier and playbook, in partnership with Product and Product Marketing
• Own and build out Calendly's GTM coaching and quality programs — including a Sales coaching program leveraging tools like Gong and a Support QA program with a focus on auto-QA
• Build and maintain a mix of live and asynchronous training experiences, including hands-on, demo-based formats that reflect how our teams actually work
• Build AI-native enablement experiences that help our teams learn and apply skills faster
• Define and track measurable impact metrics for all enablement programs, connecting training to business outcomes
• Partner with GTM managers and senior leaders to identify skill gaps and design targeted 1:1 training support for individuals who need additional development

Senior Manager, GTM Enablement

Full-stack Engineer

• Collaborating within your squad to build and iterate on commerce features that drive measurable business impact across self‑serve and enterprise customers.
• Contributing to platform scaling initiatives while improving reliability and performance in user critical flows.
• Meeting regularly with Product and Design to fine tune requirements, define MVPs, and instrument experiments that validate value quickly.
• Attending agile ceremonies to help your team plan out their work and get it done with predictable delivery.
• Working across squads to improve engineering practices and evolve shared monorepo tooling and service boundaries.
• Reviewing implementation plans and pull requests from your peers with a focus on simplicity, maintainability, and incremental delivery.
• Contributing to a high trust, professional casual culture grounded in respect and ownership.
• Using AI assistants thoughtfully to scaffold code, generate tests, draft documentation, analyze logs, and accelerate experiments. Choosing when not to use AI based on risk, privacy, and correctness considerations.

Full Stack Engineer, Commerce

• Mentoring and growing engineers.
• Leading agile ceremonies to help your team plan out their work and get it done.
• Identifying future technical needs and creating plans to meet them.
• Providing feedback and guidance to help us continuously grow and scale.
• Hiring engineers to build out both new and existing squads for the company, with oversight on all team members that get hired onto the squad.
• Working on products and services aimed at simplifying scheduling for millions of users.

QA Automation Engineer

• Identifying opportunities to eliminate manual security workflows and replace them with scalable, automated solutions
• Building internal tools and integrations that automate processes such as vulnerability triage and prioritization, alert enrichment and routing, and GRC evidence collection
• Partnering with security and engineering stakeholders to understand pain points and translate them into practical technical solutions
• Designing and building reusable “paved road” solutions that standardize how security workflows are executed across teams
• Using AI-assisted development tools and LLM APIs to accelerate implementation
• Continuously improving, maintaining, and scaling solutions to handle increasing volume, complexity, and organizational needs
• Supporting Product Security workflows as needed, such as security reviews, vulnerability triage, or tooling
• Supporting the secure usage and development of AI/LLM-powered features across Calendly as needed

Security Automation Engineer

DevOps Engineer

• Building tools and applications to extends Calendly’s infrastructure platform
• Evaluating and deploying cloud native open source tools
• Exercising expertise in cloud infrastructure concepts and patterns
• Instituting resilient infrastructure through Infrastructure as code
• Maintaining and improving observability of our infrastructure platform, and offers patterns for application teams to consume for application observability
• Participating in an on-call rotation to support the infrastructure platform
• Fostering a collaborative environment of learning and knowledge dissemination
• Defining standard practices and tooling around new services, changes, incidents, postmortems, and capacity management, and work with application engineering teams to adopt those practices