Pros
• Fully remote employment • Great hours (9:00am-2:00pm Pacific meeting window) • Great compensation (401k match and highly competitive base pay) • Great product (solves a real problem for many many many users) • Great brand (loyal promoters & global brand momentum)
Cons
EXECUTION MODEL Calendly's product development model most closely resembles a development agency, with the founding CEO as "the customer” who is choosing features to ship, setting all product priorities, and providing specific product requirements on each product project. And similar to customers working with development agencies, there is often continuous scope increase, constant re-prioritization, and discarding developed work in favor of something else. While there is a place for this type of development model in SaaS, it will likely frustrate product managers who seek autonomy and empowerment to objectively drive meaningful business results. Usage and experimentation data results are often disregarded in decision-making. Growth teams have struggled to achieve any traction or meaningful impact and progress as a result. PRODUCT LEADERSHIP C-suite turnover at Calendly has been remarkable and has materially affected the ability to execute strategic plans effectively. During my time at Calendly, there were changes or removals of key executives including the CTO, CMO (twice), CHRO, CCO, CRO, and CPO. Most notably, the product teams have experienced three different Chief Product Officers over the past five years with departures largely due to conflicts with the CEO over product vision and strategy. Product teams have reported low engagement scores without any outreach from product execs in response. On more than one occasion, the CPO has shifted stance to mirror the CEO's during executive reviews—leaving teams to defend their points of view with little air cover or support. MARKET THREAT Once an innovative solution to solve an acute problem, asynchronous scheduling has become increasingly commoditized in SaaS. There is an increasing number of startups developing similar products with more agility and disruptive technology. Behemoths like Google and Microsoft offer Calendly-like scheduling tools as part of their broader ecosystems at no additional cost. IT teams can too easily justify canceling Calendly in favor of these features that are included in Google or Microsoft workspace subscriptions. While Calendly remains "the Kleenex" of asynchronous scheduling, it must innovate more rapidly to address user needs beyond basic scheduling to maintain its market leadership.
