{"id":2324,"date":"2024-12-18T12:07:49","date_gmt":"2024-12-18T17:07:49","guid":{"rendered":"https:\/\/paulsyng.com\/blog\/?p=2324"},"modified":"2025-01-07T14:58:36","modified_gmt":"2025-01-07T19:58:36","slug":"why-calendlys-2024-shift-misses-the-bigger-opportunity","status":"publish","type":"post","link":"https:\/\/paulsyng.com\/blog\/why-calendlys-2024-shift-misses-the-bigger-opportunity\/","title":{"rendered":"REIMAGINING CALENDLY: OWNING TIME"},"content":{"rendered":"\n<p>(<em>Recent analyses have noted Calendly\u2019s shift toward competing with other scheduling tools, reflecting a response to market maturity. However, this approach misses a larger opportunity\u2026 Please see Anthony&#8217;s <a href=\"https:\/\/www.linkedin.com\/posts\/anthonypierri_productmarketing-positioning-b2b-activity-7273350967150960640-a0c1?utm_source=share&amp;utm_medium=member_desktop\" target=\"_blank\" rel=\"noopener\">post<\/a> first.<\/em>)<\/p>\n\n\n\n<hr class=\"wp-block-separator aligncenter has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Why Calendly\u2019s 2024 Positioning Shift Misses the Bigger Opportunity<\/h3>\n\n\n\n<p>In 2024, Calendly made its first major positioning shift in eight years. For nearly a decade, the company positioned itself as the antidote to back-and-forth emails. Now, it has chosen to compete directly against other scheduling tools like Chili Piper and Doodle.<\/p>\n\n\n\n<p>At first glance, this shift seems logical. The market has matured, competitors have emerged, and enterprise clients now compare scheduling tools rather than email chains. But while this move might align with conventional wisdom, it reveals a fundamental misunderstanding of positioning\u2014and more importantly, what it could be.<br><br>And it&#8217;s the &#8216;Peloton&#8217; mistake.<\/p>\n\n\n\n<figure class=\"wp-block-embed alignwide is-type-video is-provider-youtube wp-block-embed-youtube wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\n<iframe loading=\"lazy\" title=\"WHY GREAT PRODUCTS FAIL\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/9lqDTogqn1M?feature=oembed\" frameborder=\"0\" allow=\"accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share\" referrerpolicy=\"strict-origin-when-cross-origin\" allowfullscreen><\/iframe>\n<\/div><\/figure>\n\n\n\n<p>As Calendly\u2019s CEO Tope Awotona said, <em>\u201cIn my life, I&#8217;ve benefited from not taking the conventional wisdom. It\u2019s benefited me personally, and I think it has benefited the business.\u201d<\/em> This quote perfectly frames what\u2019s at stake. Calendly\u2019s move to follow the market\u2019s narrative reflects conventional thinking, but the real opportunity lies in redefining the narrative entirely.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Positioning: The Power of Owning Mental Territory<\/h3>\n\n\n\n<p>Positioning is not about where you sit in a market\u2014it\u2019s about what you own in the minds of your audience. The strongest brands don\u2019t compete within a category; they create concepts that make comparisons irrelevant.<\/p>\n\n\n\n<p>Consider these examples:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Volvo<\/strong> doesn\u2019t just sell safe cars\u2014it owns <em>safety<\/em> itself.<\/li>\n\n\n\n<li><strong>Tesla<\/strong> doesn\u2019t just sell electric vehicles\u2014it owns the <em>future of transportation<\/em>.<\/li>\n\n\n\n<li><strong>Red Bull<\/strong> doesn\u2019t just sell energy drinks\u2014it owns <em>human potential<\/em>.<\/li>\n<\/ul>\n\n\n\n<p>Calendly has the potential to move beyond \u201cscheduling tools\u201d and own a larger, more transformative concept. As Tope has said, <em>\u201cDo things the way they should be done so they can turn out the way they should turn out.\u201d<\/em> The \u201cway it should be done\u201d is not fighting for share in a crowded category but elevating the brand to a space where it defines the rules.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">The Missed Opportunity<\/h3>\n\n\n\n<p>Calendly\u2019s 2024 shift reveals three critical mistakes:<\/p>\n\n\n\n<ol class=\"wp-block-list\">\n<li><strong>Playing Too Small<\/strong><br>By focusing on the scheduling tools category, Calendly confines itself to incremental competition in a space that\u2019s becoming commoditized. This is a classic example of playing the game others have already defined.<br><\/li>\n\n\n\n<li><strong>Focusing on Features Over Fundamentals<\/strong><br>Scheduling tools are often reduced to functionality\u2014automation, integrations, and interface simplicity. But true positioning transcends features and speaks to deeper human needs, such as professional respect, time optimization, and connection.<br><\/li>\n\n\n\n<li><strong>Following Instead of Leading<\/strong><br>Rather than shaping a new market category, Calendly\u2019s shift suggests a reactive response to competitors. As a company built on bold moves, this feels at odds with its DNA.<\/li>\n<\/ol>\n\n\n\n<p>Tope himself has articulated a broader vision for Calendly: <em>\u201cWe want Calendly to be much more than scheduling\u2014we want to be the go-to platform for the entire meeting lifecycle.\u201d<\/em> Achieving this requires more than competing in the current scheduling tools category\u2014it demands rethinking the category itself.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">The Bigger Opportunity<\/h3>\n\n\n\n<p>Instead of competing, Calendly could own a transformative concept that redefines professional interactions. Here\u2019s how:<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>1. Find and Own a Deeper Concept<\/strong><\/h4>\n\n\n\n<p>At its core, scheduling is about more than logistics. It touches on fundamental human truths:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Time Value:<\/strong> Meetings reflect how professionals prioritize and value time.<\/li>\n\n\n\n<li><strong>Professional Respect:<\/strong> A well-scheduled meeting signals boundaries, importance, and courtesy.<\/li>\n\n\n\n<li><strong>Human Connection:<\/strong> Meetings are relational, not just transactional.<\/li>\n<\/ul>\n\n\n\n<p>Calendly has an opportunity to position itself as a champion of these deeper values, moving beyond \u201cbetter scheduling.\u201d<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>2. Redefine the Category<\/strong><\/h4>\n\n\n\n<p>Rather than competing as a \u201cscheduling tool,\u201d Calendly can create a new category entirely. Some possibilities include:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Make Time Work For You<\/strong><\/li>\n\n\n\n<li><strong>Take Back Your Time<\/strong><\/li>\n\n\n\n<li><strong>Bring People Closer Together <\/strong><\/li>\n<\/ul>\n\n\n\n<p>These categories emphasize transformation over tools, aligning with Tope\u2019s goal of making Calendly essential for the entire meeting lifecycle.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>3. Amplify Human Patterns<\/strong><\/h4>\n\n\n\n<p>To make this shift, Calendly must recognize and amplify the patterns underlying professional interactions:<\/p>\n\n\n\n<p><strong>Pattern 1: <em>Time Value<\/em><\/strong><br>Scheduling isn\u2019t just about setting a time; it\u2019s about signaling how time is valued. Calendly could become synonymous with optimizing time for maximum productivity and respect.<\/p>\n\n\n\n<p><strong>Pattern 2: <em>Power Dynamics<\/em><\/strong><br>Meetings are also about professional respect and boundaries. Calendly could lead conversations on how respectful scheduling enhances collaboration and trust.<\/p>\n\n\n\n<p><strong>Pattern 3: <em>Connection Quality<\/em><\/strong><br>Great meetings are about more than efficiency; they\u2019re about building relationships. Calendly could emphasize the importance of meeting quality, not just quantity.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Strategic Implementation<\/h3>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Concept Ownership<\/strong><\/h4>\n\n\n\n<p>Calendly can align its messaging, product development, and customer experience around owning a fundamental idea like time optimization or professional respect. As Tope\u2019s entrepreneurial approach shows, <em>\u201cI realized that to be successful, I needed to start a business in a more organic way.\u201d<\/em> This organic approach applies to positioning, too\u2014growing naturally from an unshakable core concept.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Category Definition<\/strong><\/h4>\n\n\n\n<p>Communicate a bold vision: \u201cCalendly isn\u2019t just a scheduling tool\u2014it\u2019s how professionals optimize their most valuable resource: time.\u201d Educate the market on why this matters and inspire loyalty by leading the conversation.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Amplifying Patterns<\/strong><\/h4>\n\n\n\n<p>Integrate features that support these deeper values, such as:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Meeting quality analytics<\/li>\n\n\n\n<li>Sentiment tracking for professional interactions<\/li>\n\n\n\n<li>Features that enhance relational depth, not just efficiency<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Metrics for Success<\/h3>\n\n\n\n<p>Traditional metrics like market share or feature parity are insufficient. Instead, focus on:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>Concept Penetration:<\/strong> How strongly is Calendly associated with its chosen concept?<\/li>\n\n\n\n<li><strong>Category Leadership:<\/strong> Is Calendly seen as the definitive leader of a new category?<\/li>\n\n\n\n<li><strong>Transformation Impact:<\/strong> How has Calendly changed the way professionals think about time and meetings?<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Final Thoughts<\/h3>\n\n\n\n<p>Calendly\u2019s current pivot reflects conventional thinking, but its future lies in bold moves. As Tope Awotona has demonstrated throughout his career, success comes from rejecting the status quo and charting a new path.<\/p>\n\n\n\n<p>The opportunity isn\u2019t to compete in the scheduling tools category. It\u2019s to redefine professional interactions, own a transformative concept, and create a category that makes competitors irrelevant.<\/p>\n\n\n\n<p>For any business, the lesson is clear:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Don\u2019t fight for market share\u2014own mental territory.<\/li>\n\n\n\n<li>Don\u2019t compete\u2014lead.<\/li>\n\n\n\n<li>Don\u2019t play the game better\u2014change it entirely.<\/li>\n<\/ul>\n\n\n\n<p>What concept could Calendly own? What patterns could it amplify? What category could it create? Answering these questions could unlock a future far greater than any scheduling tool ever imagined.<br><br>Go deeper in <a href=\"https:\/\/paulsyng.com\/blog\/calendly-from-scheduling-to-owning-time-part-2\/\">part 2<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>(Recent analyses have noted Calendly\u2019s shift toward competing with other scheduling tools, reflecting a response to market maturity. However, this approach misses a larger opportunity\u2026 Please see Anthony&#8217;s post first.) Why Calendly\u2019s 2024 Positioning Shift Misses the Bigger Opportunity In 2024, Calendly made its first major positioning shift in eight years. For nearly a decade, [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":2325,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_coblocks_attr":"","_coblocks_dimensions":"","_coblocks_responsive_height":"","_coblocks_accordion_ie_support":"","footnotes":""},"categories":[75],"tags":[],"class_list":["post-2324","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-feature"],"_links":{"self":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/2324","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/comments?post=2324"}],"version-history":[{"count":11,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/2324\/revisions"}],"predecessor-version":[{"id":2452,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/posts\/2324\/revisions\/2452"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/media\/2325"}],"wp:attachment":[{"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/media?parent=2324"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/categories?post=2324"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/paulsyng.com\/blog\/wp-json\/wp\/v2\/tags?post=2324"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}