{"id":14309,"date":"2026-07-08T10:00:03","date_gmt":"2026-07-08T04:30:03","guid":{"rendered":"https:\/\/gtm360.com\/blog\/?p=14309"},"modified":"2026-07-05T22:08:51","modified_gmt":"2026-07-05T16:38:51","slug":"aspirational-selling-may-scale-new-heights-in-enterprise-ai","status":"publish","type":"post","link":"https:\/\/gtm360.com\/blog\/2026\/07\/08\/aspirational-selling-may-scale-new-heights-in-enterprise-ai\/","title":{"rendered":"Aspirational Selling May Scale New Heights In Enterprise AI"},"content":{"rendered":"<p><!--SIDEBAR RIGHT, GREEN--><\/p>\n<blockquote class=\"skr-bq-noline-right\">\n<div style=\"background-color: #00c89640; padding: 15px 30px;\"><em>Aspirational Selling<\/em> is selling to aspirational goals of the customer, with a proven track record of achieving those goals for other customers in the past, and every intention of achieving them for the said customer at present. &#8211; <a href=\"https:\/\/gtm360.com\/blog\/2017\/10\/13\/aspirational-selling-is-not-overselling\/\" target=\"_blank\" rel=\"noopener\">Aspirational Selling Is Not Overselling<\/a><\/div>\n<\/blockquote>\n<p>In our GTM work around Enterprise AI with nearly 100 prospects and customers, we have observed three major trends:<\/p>\n<ol>\n<li>Overestimation of ability to change<\/li>\n<li>Renegotiations<\/li>\n<li>Alternative pricing models<\/li>\n<\/ol>\n<p>I forsee that they will take aspirational selling, which is already a common practice in the software industry, to another level in Enterprise AI sales.<\/p>\n<p><strong>1. Overestimation of ability to change<\/strong><\/p>\n<p><em>Enterprises overestimate their ability to change.<\/em><\/p>\n<p>This is a chronic issue in Enterprise IT. Before the implementation of any large and complex enterprise software begins, companies believe they can do whatever it takes to succeed. But, after the implementation begins, there are sudden references to cybersecurity, legal, compliance, and other bogeys. Their ability to change wanes with time.<\/p>\n<p>Account managers need to manage expectations. But expectation management is an art. If a vendor highlights change management challenges during pre-sales, customers may rush to brand it as pessimistic and \/ or conclude that it&#8217;s not capable of making things happen, and remove it from their shortlist.<\/p>\n<p>While AI demands greater need for enterprises to change, the hype around AI boosts enterprises&#8217; confidence in their ability to change.<\/p>\n<p>So, aspirational selling, which has been a practice <em>du jour<\/em> in Enterprise IT sales for all technologies, might scale new heights in Enterprise AI.<\/p>\n<blockquote class=\"twitter-tweet\">\n<p dir=\"ltr\" lang=\"en\">&#8220;Underpromise and Overdeliver&#8221; worked in 20th century. In 21st century, success mantra has changed to &#8220;Overpromise and Overdeliver&#8221;. Anyone who underpromises will get wiped out without even getting the chance to showcase their delivery capabilities.<a href=\"https:\/\/t.co\/c63j8CpWyC\">https:\/\/t.co\/c63j8CpWyC<\/a><\/p>\n<p>\u2014 SKR (@s_ketharaman) <a href=\"https:\/\/twitter.com\/s_ketharaman\/status\/1521784235262193665?ref_src=twsrc%5Etfw\">May 4, 2022<\/a><\/p><\/blockquote>\n<p><script async src=\"https:\/\/platform.twitter.com\/widgets.js\" charset=\"utf-8\"><\/script><\/p>\n<p><strong>2. Renegotiations<\/strong><\/p>\n<p><em>There are re-negotiations.<\/em><\/p>\n<p>Renegotiations in AI deals may go beyond <em>cost<\/em> and <em>timelines<\/em> and include <em>success criteria<\/em>.<\/p>\n<p>To this extent, AI will echo ERP.<\/p>\n<p>Per <a href=\"https:\/\/x.com\/GTM360\/status\/1250763460817944576\" target=\"_blank\" rel=\"noopener\">survey conducted in 2020<\/a>, the percentage of companies that rated their ERP project a success went up from 58% in 2015 to 58% in 2019. The key reason for the sharp increase was &#8220;To avoid reputational damage coming from failure, customers redefine success as whatever they get.&#8221; Not because there was a significant increase in the ability to change or improvement in expectation management.<\/p>\n<p><strong>3. Alternative pricing models<\/strong><\/p>\n<p><em>AI-based contracts are abuzz with alternative pricing models.\u00a0<\/em><\/p>\n<p>IT Services companies have traditionally followed <em>time-and-material<\/em> and <em>fixed price<\/em> engagement models.<\/p>\n<p>There&#8217;s a lot of talk about <em>outcome-based pricing<\/em> in AI deals.<\/p>\n<p><a href=\"https:\/\/gtm360.com\/blog\/wp-content\/uploads\/2026\/04\/AI-AI-AI-TILE-fi.jpg\" target=\"_blank\" rel=\"noopener\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14319 size-full\" src=\"https:\/\/gtm360.com\/blog\/wp-content\/uploads\/2026\/04\/AI-AI-AI-TILE-fi.jpg\" alt=\"\" width=\"630\" height=\"280\" srcset=\"https:\/\/gtm360.com\/blog\/wp-content\/uploads\/2026\/04\/AI-AI-AI-TILE-fi.jpg 630w, https:\/\/gtm360.com\/blog\/wp-content\/uploads\/2026\/04\/AI-AI-AI-TILE-fi-500x222.jpg 500w\" sizes=\"auto, (max-width: 630px) 100vw, 630px\" \/><\/a><\/p>\n<p>But it is not such a paradigm shift as it&#8217;s made out to be in the popular narrative.<\/p>\n<p>IT Services companies have attempted outcome-based pricing in the past. The challenge is, at early stages, customers expect vendors to take on risk with uncertain returns, which leads to severe margin pressure; whereas, at later stages, customers balk at paying vendors a percentage of cost saved or revenue gained, want predictable billing, and demand a return to fixed price, so vendors can&#8217;t fully encash the upside.<\/p>\n<p>Therefore, outcome-based pricing never worked at scale in the IT Services industry.<\/p>\n<p>To cite an example from our firsthand experience, an <a href=\"https:\/\/www.gtm360.com\/customers\/#c111\" target=\"_blank\" rel=\"noopener\">LMS vendor<\/a> quoted a fixed price for its software. Prospects demanded outcome-based pricing. We crafted a new marketable item around outcomes that elevated the product&#8217;s appeal and ticket size to a new level.<\/p>\n<p>But you&#8217;d be wrong in thinking that everything was gung-ho after that.<\/p>\n<p>The same customer that demanded outcome-based pricing model before shuddered at having to part with a percentage of reduced costs after a year, and insisted on returning to the fixed pricing model. We agreed but we also switched from guaranteed benefits to contingent benefits.<\/p>\n<p>We&#8217;ve already started seeing early signs of this in Enterprise AI. <em>Microsoft<\/em> and <em>Anthropic<\/em> recently switched from seat-based to usage-based pricing. Many customers are displeased. Some are trying to switch to other LLM providers.<\/p>\n<blockquote class=\"twitter-tweet\">\n<p dir=\"ltr\" lang=\"en\">Banks should be jumping with joy when Anthropic recently changed its pricing from per-seat to usage-based. But they&#8217;re doing the opposite &#8211; reconsidering their use of Anthropic. If Anthropic shifts to outcome-based pricing, I can bet that customers will totally dump Anthropic.<\/p>\n<p>\u2014 SKR (@s_ketharaman) <a href=\"https:\/\/twitter.com\/s_ketharaman\/status\/2047619798771843511?ref_src=twsrc%5Etfw\">April 24, 2026<\/a><\/p><\/blockquote>\n<p><script async src=\"https:\/\/platform.twitter.com\/widgets.js\" charset=\"utf-8\"><\/script><\/p>\n<p>Then there are many output-based pricing deals packaged as outcome-based pricing deals, as I highlighted in my blog post entitled <a href=\"https:\/\/gtm360.com\/blog\/2025\/12\/10\/outcome-washing-in-ai-deals\/\" target=\"_blank\" rel=\"noopener\"><strong>Outcome Washing In AI Deals<\/strong><\/a>.<\/p>\n<hr style=\"width: 70%;\" \/>\n<p>Aspirational Selling is not misselling.<\/p>\n<blockquote class=\"twitter-tweet\">\n<p dir=\"ltr\" lang=\"en\">Due to internal constraints, not every customer can implement every feature supported in ERP, CRM and other enterprise software. But it&#8217;s not overpromising for sales to talk about them &#8211; as long as they&#8217;ve been implemented by some other customer. <a href=\"https:\/\/t.co\/c63j8CpWyC\">https:\/\/t.co\/c63j8CpWyC<\/a><\/p>\n<p>\u2014 SKR (@s_ketharaman) <a href=\"https:\/\/twitter.com\/s_ketharaman\/status\/1644286924830437376?ref_src=twsrc%5Etfw\">April 7, 2023<\/a><\/p><\/blockquote>\n<p><script async src=\"https:\/\/platform.twitter.com\/widgets.js\" charset=\"utf-8\"><\/script><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Aspirational Selling is selling to aspirational goals of the customer, with a proven track record of achieving those goals for other customers in the past, and every intention of achieving them for the said customer at present. &#8211; Aspirational Selling Is Not Overselling In our GTM work around Enterprise AI with nearly 100 prospects and &#8230; <a title=\"Aspirational Selling May Scale New Heights In Enterprise AI\" class=\"read-more\" href=\"https:\/\/gtm360.com\/blog\/2026\/07\/08\/aspirational-selling-may-scale-new-heights-in-enterprise-ai\/\" aria-label=\"Read more about Aspirational Selling May Scale New Heights In Enterprise AI\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":14319,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[17,4,8,1],"tags":[],"class_list":["post-14309","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-b1-integrated-marketing","category-digital-marketing","category-it-marketing","category-mandatory-category"],"_links":{"self":[{"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/posts\/14309","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/comments?post=14309"}],"version-history":[{"count":13,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/posts\/14309\/revisions"}],"predecessor-version":[{"id":14506,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/posts\/14309\/revisions\/14506"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/media\/14319"}],"wp:attachment":[{"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/media?parent=14309"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/categories?post=14309"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/gtm360.com\/blog\/wp-json\/wp\/v2\/tags?post=14309"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}