BUILD with Blake Bartlett

Annie Pearl (Calendly): Building Enterprise Products

Jun 8, 2022

Learn how PLG businesses can transition to enterprise, the importance of simplicity in product development, building tailored solutions for different personas, and the foundational steps towards enterprise success. Insights from Annie Pearl, Chief Product Officer at Calendly.

33:32

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Episode guests

Annie Pearl

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Quick takeaways

Establishing alignment on product philosophy for balancing end user experience with enterprise needs.

Adopting a platform strategy to offer tailored solutions and progressive customization for diverse organizational requirements.

Deep dives

Transition to Enterprise Market: Product and Go-to-Market Alignment

Transitioning from a product-led growth (PLG) model to embracing the enterprise market requires alignment on two crucial questions at the executive level. Firstly, defining the product philosophy involves balancing the end user experience with the needs of IT and administrators within organizations. Secondly, establishing the go-to-market strategy necessitates clarifying the types of teams to build and the corresponding talent, skills, and expectations required for success.

Introduction

2min

Navigating the Transition to Enterprise Solutions

14min

Navigating Complexity in Product Development

6min

Tailored Solutions for Enterprise Needs

7min

Foundational Step Towards Enterprise Transition

3min

Every PLG business will eventually have to build for the enterprise. Why? Bottom up adoption can indeed go “all the way up”...to the C-level of large organizations. But to get that 6- or 7-figure contract, you’ll need to beef up the product for the big leagues. Annie has gone through the journey at Glassdoor, and now at Calendly. She shares her playbook with us in today’s episode.

Calendly is an OpenView portfolio company. For a full portfolio list please visit ov.vc

Key Takeaways:

[2:10] What it looks like for PLG businesses to embrace enterprise

[4:42] Three components that make adopting enterprise easier said than done

[7:49] How to tackle the PLG plus enterprise transition in terms of people

[17:00] Maintaining simplicity and the end user experience as a philosophical north star

[19:51] Trades offs of embracing enterprise products from the PLG standpoint, and how to manage them

[22:57] Building solutions for personas and horizontal platforms

[28:06] Platforms and opting into layers of complexity

[30:01] Foundational step number one to building towards enterprise

Mentioned in this episode:

Annie Pearl, Chief Product Officer at Calendly