Engineering Manager, Calendly
Ecosystems
$193.9-294.2k
Salary dependent on location. Plus Top Performer Bonus program (or Sales incentive) and equity awards
More information about location
Automated appointment scheduling
Be an early applicant
Automated appointment scheduling
501-1000 employees
Be an early applicant
$193.9-294.2k
Salary dependent on location. Plus Top Performer Bonus program (or Sales incentive) and equity awards
More information about location
501-1000 employees
Company mission
To provide broad and deep support for various meeting scenarios, and make scheduling easier and more efficient.
Role
Who you are
- 5+ years experience managing a team of Software Engineers in a SaaS or technology company
- Proven experience hiring, coaching, and developing engineers at different levels, with a track record of building inclusive, high‑trust teams
- Strong communication skills with the ability to succinctly explain deep technical concepts to a range of audiences (engineers, PMs, cross‑functional partners, and leadership)
- Experience working in balanced product/engineering teams, partnering closely with Product, Design, and Data to define and deliver roadmaps
- Comfortable leading through ambiguity, making decisions with imperfect information, and bringing clarity and focus to your team
- 8+ years of overall software development experience, including building and operating web‑scale services and APIs. Experience with technologies like TypeScript/Node, Go, Ruby on Rails, and cloud platforms (GCP preferred) is a strong plus
- Deep proficiency with web application development, service‑oriented or microservices architectures, and event‑driven systems
- Experience designing and evolving public or partner‑facing APIs, webhooks, or integrations
- Demonstrated ability to plan and lead development efforts on large projects, breaking down complex work into sequenced milestones and aligning multiple teams
- Solid understanding of operational excellence: monitoring, alerting, incident response, and performance tuning for production services
- Experience leading or participating in Agile/Scrum ceremonies, and iterating on team processes to improve delivery and quality
- Empathy for both internal engineers (your platform’s customers) and external developers/partners, with a track record of building platform capabilities that unlock their work
- Experience balancing the needs of multiple stakeholders — product squads, security, compliance, GTM — while maintaining a coherent platform strategy
- Excitement about building the APIs, integrations, and workflow capabilities that extend Calendly into the broader SaaS ecosystem
- Availability for participation in on‑call rotation, ensuring prompt and effective responses to business‑critical alerts outside of regular working hours
- Authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time
What the job involves
- We are looking for an experienced Engineering Manager who combines strong people leadership, deep technical judgment in service‑oriented systems, APIs and integrations and a product mindset
- Your team will build and evolve platform capabilities and integrations that other Calendly product teams and external developers depend on daily
- Our platform and services play a pivotal role in driving adoption and integration, enabling agentic interactions, and powering key user interactions in the Calendly product
- Your work will directly empower product engineering squads to ship integrated features more efficiently and reliably, while making it simple for developers, customers and partners to extend Calendly through our ecosystem
- You will work directly with the Senior Manager of Engineering for our Core Platforms group, partnering closely with product, design, data, security, and go‑to‑market stakeholders to define and deliver the roadmap for Ecosystems
- A track record of leading teams that build and operate APIs & partner integrations that support both internal product teams and external developers
- A coaching mindset that grows engineers through clear expectations, actionable feedback, and regular performance and career conversations
- Strong technical judgment in distributed, service-oriented architectures and API design, with the ability to navigate trade-offs and guide engineers through complex decisions
- Comfort operating in ambiguous, cross-functional environments — partnering with Product, Design, Security, CX, and GTM to align on priorities and outcomes
- A bias for action, measurable outcomes, and continuously improving how your team executes, ships, and operates its services
- Ability to balance technical execution with team development and stakeholder management
- Familiarity with MCP servers or similar agent/orchestration frameworks, with a track record of building secure, multi‑tenant services that orchestrate workflows across internal services and external APIs
- As a Manager at Calendly, you have the chance to mentor and grow some of the best and brightest engineers in the world
- This role will work alongside our other Engineering teams to make Calendly even simpler and more powerful for our user base
- If chosen for this role, you’ll be responsible for the health, performance, and future of the Ecosystems team — from technical execution and operational excellence to people development and hiring
- At Calendly, you’ll have the opportunity to make a huge impact on a product used by millions
- On a typical day, you will be:
- Leading and growing a high‑performing engineering team
- Owning execution for Ecosystems services and integrations
- Guide your team through key architectural decisions across distributed systems, public APIs, webhooks, and integration patterns including agentic protocols like MCP
- Raise the bar on reliability, scalability, and performance, including SLIs/SLOs, observability, testing strategy, and incident readiness for the services you own
- Partner with other Platform and product squads to ensure Calendly experiences are API‑first and ecosystem‑ready
- Lead and refine agile practices to help your team deliver predictably and sustainably
- Provide feedback and guidance to help us continuously grow, scale, and evolve our operating model across the broader Engineering org
Our take
Calendly is a cloud-based scheduling service that is straightforward to use. It allows around 10 million customers per month to connect and make appointments based on their availability without having to send emails back and forth.
The platform offers four plans, allowing individuals, small companies, and large enterprises alike to make use of these services. Organic strategies have driven Calendly's growth. Its invites become links to Calendly itself, so people who like it can, and do, start to use it.
There are a handful of competing products on the market, including offerings from Doodle and Microsoft, but Calendly's customer-friendly design has won it attention and helped it to carve a space in the field. Impressive funding has contributed to the company's expansion, and its capitalised on the increasing popularity of home and hybrid working.
Freddie
Company Specialist at Welcome to the Jungle
Insights
21% employee growth in 12 months
Company
Funding (2 rounds)
Jan 2021
$350m
SERIES B
Apr 2014
$0.6m
SEED
Total funding: $350.6m
Company benefits
- Quarterly Bonus
- Equity
- Home Office Setup
- Technology
- Pick Your Own Perk
- Flexible Time Off
- Vacation Stipend
- Parental Leave
- Health and Wellbeing
- Fun Community Events
- 401k Company Match
Company HQ
Atlantic Station, Atlanta, GA
Leadership
Tope Awotona
(Founder & CEO)Having studied at the University of Georgia, they worked as an IBM Sales Rep and for Perceptive Software, Vertafore, and EMC as an Account Manager. They left the latter in 2014, having founded Calendly in February 2013.
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