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Sales Enablement Manager III, Instructional Design

  • Remote
  • Sales

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 Enablement team? 

The Enablement Manager, Instructional Design, will have the unique opportunity to be the first instructional designer on our small, but mighty, enablement team.  As we’re in our first year of building out the enablement function, you will have the ability to help shape the way our team operates, how we serve our stakeholders across the business and how our sales team goes to market. Calendly has aggressive goals for 2021- after experiencing exponential growth in 2020- and our high-impact enablement programs will be critical to the sales team successfully scaling at the pace of our viral, product-led growth company.  

To support Calendly’s rapid growth, you will help build learning programs that drive sales performance through predictable, repeatable and scalable sales motions. You will partner closely with our enablement team members and cross-functional partners to design and develop training courses and collateral that are engaging and effective. Once created, you will co-manage and maintain content in our Learning Management System (Lessonly) and report out on training feedback and the impact on business outcomes. Other competencies you might tackle include negotiation skills, communicating product value, account planning and consultative selling.

We know we wouldn’t be where we are—or make it to where we’re going—without our people. And when it comes to walking the talk, we think actions speak louder than words. Our people are shown appreciation through a formal rewards and recognition program, a competitive benefits package, and countless quality-of-life perks such as our home office stipend and an annual vacation stipend. If you’re seeking an opportunity to make your mark and be part of a groundbreaking team, then this is the job for you.

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

  • Develop learning objectives for all enablement-driven training initiatives including, but not limited to: onboarding, product launches, sales training, process training and company off-site meetings
  • Identify best training modality and use appropriate course design and development tools to create effective asynchronous, VILT and occasional in-person courses
  • Build systems for training needs analysis and metrics to report out on the effectiveness of training content and the impact of training on sales behaviors
  • Work across teams (sales, product, product marketing, customer success, etc.) to diagnose the performance gap and build the appropriate solution (job aid vs. training)
  • Help build, execute and reinforce training around new product launches
  • Dream, design and build e-learning courses deployed through our Learning Management System (LMS) to facilitate skill and knowledge-building opportunities for our Account Executives (AE’s), based on our sales competencies and desired proficiency levels
  • Work with our enablement team to build and drive our enablement strategy and over-deliver on our success metrics

This opportunity is for you if you have/are:

  • 5+ years of instructional design and sales enablement experience 
  • Desire to work in a fast-paced sales environment
  • Understanding of adult learning principles and instructional design frameworks
  • Experience with related tools including: Learning Management System (Lessonly), Enablement Platform (Highspot), CRM (SalesForce) and Google Apps
  • Strong organizational skills and experience managing multiple projects and priorities
  • Experience building relationships across multi-functional teams, working collaboratively to achieve goals
  • Flexibility and a willingness to roll up your sleeves for the needs of the business.
  • 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.


Not the right time to come onboard?

No problem! We’re all about making connections that make great things happen, so if the time’s not quite right for you to join us, but you’re keen to stay in the loop, just register your details, and we’ll add you to our talent pool.

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