Learning & Talent Development Leader

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What Calendly is looking for in applicants

What is Calendly?

Calendly takes the work out of scheduling so our customers have more time to work on what’s really important. Our software is used by millions of people worldwide—with thousands more signing up every day. To maintain this exciting growth, we’re looking for top talent to join our team and help shape the future of our product.

Why join Calendly’s People & Organization Development Team team? 

The People & Organization Development team is at the epicenter of individual, team, and organizational growth at Calendly and encompasses People Operations (building the foundations for scale and enabling seamless experiences across the moments that matter), People Business Partners (providing strategic partnership to executive leaders and their teams), and the newly created Learning & Development function (you will get the chance to help develop the philosophy, strategy, and operational plans to enable the learning journeys at Calendly across core audiences - individuals, leaders, and teams).  This newly created role will report to the Head of People and Organization Development and will be a core member of her leadership team.  

We aspire to be the place where people have positive, career-defining experiences, while doing work that matters. This role has the opportunity to shape the types of experiences we have - the career pathways, the development opportunities, and the leadership development agenda.

What are some of the high impact opportunities you’ll tackle? 

  • Define the learning and development strategy and operational plans that meet us where we are today and allow us to scale through growth
  • Develop and source learning opportunities that meet our unique audience needs across individuals (individual development, career ownership), managers (leading and engaging teams, coaching, feedback, and career discussions), and leaders (leading the organization) all in a remote first environment.
  • Partner with People team and leadership stakeholders on developing a performance management strategy and approach that promotes feedback and individual development.
  • Design and develop a manager-as-coach model focused on creating awareness, promoting discovery, designing action, and managing progress and accountability through employee partnership.
  • Consult with departments and business units to identify gaps in individual and team competencies, and recommend solutions to close these gaps.
  • Use human capital data and assessments to identify needs, inform stakeholders, and measure effectiveness, and drive talent-centric outcomes related to team and organizational goals.


This opportunity is for you if you have/are:

  • Natural leader and trusted coach to talent throughout the organization (bonus points for professional coaching accreditation)
  • Thrive in an environment where you have the opportunity to put your thumbprint on a new role and workstream
  • Collaborate meaningfully with colleagues in the broader People team (HRBPs, Engagement, Comms, People Ops, DEI, etc) as well as organizational leaders to build relevant learning solutions 
  • ~10+ years of experience in Learning & Development, Talent Management, or as an HRBP where you led design, development, and delivery of L&D opportunities for your business unit or client groups 
  • Degree in HR Development, Business, Adult Learning, Organizational Development or relaHave experience creating strategies, building relationships, and executing talent-centric programs in a remote environment. 
  • Familiar with applying adult learning, design thinking and/or process knowledge as a mechanism to translate organizational talent needs into employee motivation, goal-setting, and action.
  • Experience with overseeing talent development budget and vendor relationships.ted field is preferred
  • Experience building or scaling L&D or Talent Development practices - great to have been part of a scrappy build as well as having visibility to more mature models as we scale 
  • Ability to operate in the gray and innovate to meet the needs of the business/industry; know industry best practice and how to adapt it
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time 

Calendly is registered as an employer in many, but not all, states. If you are not located in or able to work from a state where Calendly is registered, you will not be eligible for employment.


Want some tips on how to get an interview at Calendly?

What is Calendly looking for?
If this role looks interesting to you, a great first step is to understand what excites you about the team, product or mission. Take your time thinking about this and then tell the team! Get in touch and communicate that passion.
What are interviews for Learning & Talent Development Leader like?
Interview processes vary by company, role and team. The best plan is to see what others have experienced and then plan accordingly.
How to land an interview at Learning & Talent Development Leader ?
A great first step is organizing your path to an offer. Check out Kiter for tools to get started!