Engineering Manager
WFA Digital Insight
The demand for skilled engineering managers in the remote job market has surged, with over 27% of companies seeking leaders who can balance technical expertise with strategic vision. As Calendly continues to innovate in the scheduling space, this role offers a unique chance to drive impact. With the global shift towards remote work, companies are looking for professionals who can manage distributed teams and scale products efficiently. Calendly's commitment to empowering its engineers to grow and learn makes this an attractive opportunity for those seeking a challenging yet supportive environment. Before applying, candidates should be prepared to demonstrate their technical judgment, coaching mindset, and experience in leading high-performing teams.
Job Description
About the Role
The Engineering Manager at Calendly is a crucial position that combines people leadership with a strong technical background and a product mindset. This role is pivotal in defining and delivering the roadmap for new Scheduling products, working closely with cross-functional stakeholders including product, design, data, security, and GTM teams. The successful candidate will have a track record of leading teams that build and operate highly available products at scale and a coaching mindset that fosters growth through clear expectations, actionable feedback, and regular performance and career conversations.As part of the Calendly team, the Engineering Manager will play a key role in mentoring and growing some of the best and brightest engineers in the world. This involves working alongside other Engineering teams to enhance the simplicity and power of Calendly for its user base. The company is seeking a versatile technical leader who is passionate about impactful technology and can help accelerate and empower development teams.
The role is part of a dynamic environment where innovation and growth are paramount. Calendly's user base is vast, with millions of people relying on the platform for scheduling needs. The Engineering Manager will be at the forefront of driving product growth and making strategic decisions that impact the future of scheduling.
What You Will Do
- Lead agile ceremonies to plan and execute team work efficiently
- Coach, mentor, and onboard new engineering team members to ensure seamless integration
- Identify future technical needs and create plans to address them proactively
- Provide feedback and guidance to continuously grow and scale the team
- Work closely with GTM stakeholders to align on priorities and outcomes
- Develop and implement strategies for improving team execution, shipping, and operation of services
- Balance technical execution with team development and stakeholder management
- Hire and oversee engineers to build out new and existing squads for the company
- Collaborate with product, design, and data teams to define and deliver product roadmaps
- Operate in ambiguous, cross-functional environments with a bias for action and measurable outcomes
What We Are Looking For
- 2+ years of experience managing a team of Software Engineers
- Strong background in technical execution with a product mindset
- Experience in distributed, service-oriented architectures and API design
- Ability to navigate trade-offs and guide engineers through complex decisions
- Coaching mindset with a focus on growth through clear expectations and feedback
- Strong technical judgment and problem-solving skills
- Comfort operating in cross-functional environments with multiple stakeholders
- Ability to balance technical and team development aspects with stakeholder management
- Experience with agile methodologies and practices
- Strong communication and interpersonal skills
Nice to Have
- Experience in the scheduling or productivity software sector
- Knowledge of cloud-based technologies and scalability
- Familiarity with security and compliance principles in software development
- Experience with data-driven decision making and analysis
Benefits and Perks
- Opportunity to work on a product used by millions of users
- Collaborative and dynamic work environment with a team of skilled professionals
- Professional development opportunities with mentorship and growth plans
- Flexible remote work arrangements with a stipend for home office setup
- Competitive compensation package with equity options
- Comprehensive health insurance and benefits plan
- Generous PTO policy with paid holidays and vacation time
- Access to cutting-edge technologies and tools for professional growth
How to Stand Out
- Ensure your resume highlights specific examples of leading high-performing teams and driving technical growth.
- Prepare to discuss your experience with distributed architectures, API design, and cross-functional collaboration.
- Showcase your coaching mindset by providing examples of how you've grown engineers through feedback and career conversations.
- Be ready to walk through your approach to navigating trade-offs and making complex technical decisions.
- Demonstrate your understanding of GTM principles and how they apply to the engineering function.
- Tailor your cover letter to address the specific challenges and opportunities mentioned in the job description, showing you've taken the time to understand Calendly's unique context.
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