Tech Bound
Tech Bound Podcast
Growth ideas for Calendly w/ Kieran Flanagan, CMO @ Zapier

Growth ideas for Calendly w/ Kieran Flanagan, CMO @ Zapier

The Tech Bound podcast

Today, I’m unpacking a fascinating conversation with Kieran Flanagan, CMO at Zapier and former SVP of Marketing at HubSpot. This discussion centers on Calendly, a scheduling app used by millions, and its strategic acquisition of Prelude.

We talk about the critical role of platforms in product-led growth (PLG) businesses. AI tools, for instance, are seen not as standalone products but platform features. Canva's freemium text image generator exemplifies a platform disrupting the market. Grammarly and Jasper also come up in the context of branding and market disruption.

Distribution is vital for platforms. Calendly's acquisition of Prelude, an HR enterprise tool, is a case in point. Flanagan compares Calendly's potential growth strategy to HubSpot's approach of building individual hubs around the contact record, each catering to different roles like marketing, sales, customer success, and operations.

We also explore the idea of Calendly morphing into a platform and integrating with other established products to multiply its value, for example, Gong, Outreach, Chorus, Jira, Monday, Asana, Dovetail, and Qualtrics.

Lastly, Flanagan shares some intriguing marketing ideas for Calendly, including acquiring a company like Lyre for its distribution capabilities and using Calendly to understand where time gets wasted or lost within an organization, thereby helping to optimize productivity.

About Kieran Flanagan

Introducing Kieran Flanagan:

Notes on the product, market, company and challenges


  • Calendly = scheduling app used by +10M people, from tech workers to yoga class instructors

    • Vision: be THE go-to platform for work and leisure life planning

  • Basic explanation: you want to schedule time with someone → all you need to do is share your Calendly, and they can pick a time

    • You can set a time limit, charge them for your time, and define time slots


  • Founded in 2013 by Tope Awotona

  • profitable today

  • Valued at $3b in 2020 by raising $350M from investors + Awotona’s life savings


  • Massive growth during the pandemic: 50% Y/Y revenue growth in 2021 (about $85M)

    • growing faster than companies like Zapier or DocuSign

    • 53% market share in the US


  • appointment scheduling market: ~$300M in 2021

    • 13-19% CAGR (compound annual growth rate)

    • predicted to reach $500-$700M in 2027

    • Direct competitors:, Setmore, Timetrade

    • Indirect competitors: Google, Hubspot, Drift

    • Trends:

      • big players like Google getting into the market

      • remote work = accelerant for scheduling software

      • More professions use scheduling software, e.g. doctors


  • Google entered the market: Google Workspace customers ($7.99) can provide scheduling with their Google Calendar

    • 2nd largest calendar app after Outlook, > 500M people

    • If Google Calendar was a social network, it would be bigger than Twitter or Snapchat

  • Calendly needs to win the enterprise segment

  • Calendly needs to build more features for verticals like Sales, HR or Productivity

Context of the episode

  • Calendly acquired Prelude

  • Predule = enterprise interview scheduling app for recruiting

  • Prelude raised $2.4M and has hundreds of customers

  • makes it easier to schedule a series of interviews (journey) with several stakeholders without the typical back and forth

  • more than just scheduling: provides information to applicants, Interviewer prep, and hiring analytics

Tech Bound
Tech Bound Podcast
Tech Bound is a podcast about inspiring Growth Ideas pitched by the best in the field.