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How Calendly's Product Marketing Team Successfully Launched an Enterprise Offering

Jeff HardisonJeff Hardison
Calendly Head of Product Marketing

In this playbook, I share how we launched Calendly’s Enterprise offering as we moved up market. Our launch exceeded our target revenue goals, successfully positioned Calendly as an enterprise solution, and generated a large pipeline (45 percent increase) of enterprise deals.

Many successful product-led growth (PLG) companies struggle to move upmarket to sell enterprise deals because they fail to properly position themselves for an enterprise buyer. Already a successful PLG company, Calendly prepared to launch its enterprise subscription plan of advanced security, privacy, and administrative controls, but knew it needed a marketing approach that better explained our value to larger companies. I was hired to lead product marketing during this period.

Who is this for:

This playbook will be useful to product marketing professionals at PLG companies, particularly those launching new products targeted at enterprise customers and supporting new sales team members.

What you will learn:

  • How marketing to enterprise buyers differs from marketing to PLG buyers

  • How to build messaging for enterprise buyers

  • How to drive the culture change needed for the company to message to enterprise buyers

  • How to drive a successful product launch from start through launch and post-launch

Table of Contents:
Playbook Content


Calendly is a leading Software-as-a-Service (SaaS) company providing a scheduling automation platform that improves scheduling for individuals and businesses. The company's self-serve, e-commerce-style sales approach had been attractive to both individuals and businesses of all sizes who wanted to quickly get up and running with an easy-to-use scheduling tool that integrates with other productivity applications. However, some larger companies with advanced security, privacy, and administrative control needs not only sought “enterprise features” tailored to them, but were also seeking enterprise salespeople who could assist them and their teams in the buying process.

Calendly launch goal

The goal with the launch of the Enterprise subscription plan was to both deliver these advanced features and generate a pipeline of enterprise-sized deals to the sales team. The Product Marketing team focused on nailing the messaging to enterprise IT buyers who focus on business outcomes, and on specific IT requirements (e.g., SSO, SCIM) rather than just improving time savings as individual contributors (ICs) often look to do.

Key internal stakeholders:

  • Product managers

  • Marketing leaders and ICs

  • Sales and CS 

  • Company leadership


You're likely familiar with the standard steps of a product launch, which typically involve research, testing, executive decision-making, preparation, announcement planning, sales and customer success enablement, and ongoing adoption. However, the art of product marketing lies in framing the product launch as part of the company’s journey to address more customer needs. In the case of this launch, doing this meant framing the launch of Calendly for Enterprise as a strategic milestone in continuing to serve millions of buyers of all company sizes while also addressing more and more needs of Enterprise buyers.

In order to do this, we focused on understanding the distinction between these two types of buyers. We first had to recognize their contrasting perspectives: Individual contributors who sign up for free often focus on the jobs-to-be-done (JTBD) framework, while Enterprise buyers desire business outcomes before paying for your product. You can’t simply save time for an Enterprise buyer’s team; you must also offer a secure and controllable platform that increases sales, expands customer relationships, and hires better talent. Being able to recognize and understand these perspectives is crucial, as they significantly impact messaging strategies.

Framework call out

6-step product launch process

Building upon these insights, my framework for launching this product included these steps:

  1. Research

  2. Message Testing

  3. Go/No-Go with Executives

  4. Preparing the Announcement

  5. The 30-90 Day Marketing Sprint

  6. Ongoing Adoption Marketing

While executing the often-tactical launch process, it's important to remain flexible and adapt to the specific needs of your company and product. Avoid blindly following a process you’ve used before that may prove ineffective in a different situation. Additionally, investing significant time in initial research and diligently tracking the success of your efforts through reports and analytics is invaluable.

Step 7

Finally, remember that your journey doesn’t end on the day of the launch. Continuously driving product adoption and ensuring customers derive maximum value from all the product’s features — after launch day — are critical goals throughout the customer journey.

Diagram: Calendly product launch process

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