OpenView

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&nbsp;<a href="http://ov.vc/" rel="noopener noreferrer" target="_blank">ov.vc</a> 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:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a><a href="https://www.linkedin.com/in/anniepearl/" rel="noopener noreferrer" target="_blank">Annie Pearl, Chief Product Officer at Calendly</a><a href="https://calendly.com/" rel="noopener noreferrer" target="_blank">Calendly</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

Before Calendly, Annie led Glassdoor's product vision and user experience for job seekers and employers around the world. She has led enterprise product teams at Box, including before and after its 2015 IPO, and was the VP of Product and a founding member of Xpert Financial. Annie was honored as one of the Most Influential Women in Bay Area Business in 2019 by the San Francisco Business Times. She holds a J.D. from Santa Clara University School of Law and a Bachelor's degree from Claremont McKenna College. She loves spending time outdoors, especially skiing hiking, and running.

Annie Pearl

Chief Product Officer at Calendly

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


Annie Pearl (Calendly): Building Enterprise Products

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.


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It takes 3 ingredients to build a software startup in today’s wild market: people, product and growth. Easier said than done. BUILD is here to help by featuring conversations between venture capitalist Blake Bartlett and the smartest folks in software. OpenView is a VC firm that invests in amazing companies like Datadog, Expensify and Calendly. Visit ov.vc for more details.

Adding a top-down sales motion is a make-or-break moment for PLG companies. If it’s done right, it can make you the next big thing in your category. If it’s not done right, it can break your team and ultimately compromise your position in the market. The answer? All-in commitment from the founders and key leaders. Enterprise PLG is a team sport!