{"id":474,"date":"2025-01-13T17:45:37","date_gmt":"2025-01-13T18:45:37","guid":{"rendered":"https:\/\/howtobigisland.com\/?p=474"},"modified":"2025-01-21T16:29:31","modified_gmt":"2025-01-21T16:29:31","slug":"the-5-phase-framework-that-grew-outreach-from-0-to-230m-arr","status":"publish","type":"post","link":"https:\/\/howtobigisland.com\/index.php\/2025\/01\/13\/the-5-phase-framework-that-grew-outreach-from-0-to-230m-arr\/","title":{"rendered":"The 5-phase framework that grew Outreach from $0 to $230M ARR"},"content":{"rendered":"<div>\n<p><em>Hello and welcome to <strong>The GTM Newsletter by GTMnow <\/strong>\u2013 read by 50,000+ to scale their companies and careers. GTMnow shares insight around the go-to-market strategies responsible for explosive company growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind these strategies and companies.<\/em><\/p>\n<div>\n<hr \/>\n<\/div>\n<h2><strong>The 5-phase framework that grew Outreach from $0 to $230M ARR<\/strong><\/h2>\n<p><a href=\"https:\/\/www.linkedin.com\/in\/mkosoglow\/\">Mark Kosoglow<\/a> was Outreach\u2019s very first employee.<\/p>\n<p>He played a pivotal role in driving the company\u2019s growth from $0 to $230 million in ARR. Over the years, he built and scaled a world-class sales organization, creating a team that generated hundreds of millions in revenue.<\/p>\n<p>This success was underpinned by five distinct phases of growth, each requiring a unique type of sales leader and leadership approach.<\/p>\n<ol>\n<li>The Doer<\/li>\n<li>The Builder<\/li>\n<li>The Doctor<\/li>\n<li>The Architect<\/li>\n<li>The Communicator<\/li>\n<\/ol>\n<p>These phases highlight the evolving traits and responsibilities a sales leader must adopt to match an organization\u2019s growth trajectory.<\/p>\n<div class=\"captioned-image-container\">\n<figure>\n<div class=\"image2-inset\"><img loading=\"lazy\" class=\"sizing-normal lazyload\" src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\" width=\"1456\" height=\"1048\" data-src=\"https:\/\/howtobigisland.com\/wp-content\/uploads\/2025\/01\/f8c20df6-f4ef-4c36-b45e-647ced315f05_1456x1048.png\"><\/p>\n<div><\/div>\n<\/div>\n<p>\u00a0<\/p>\n<\/figure>\n<\/div>\n<h3>[Phase 1: The Doer]<strong> Hiring the first salesperson<\/strong><\/h3>\n<ul>\n<li><strong>Role: <\/strong>The first hire needs to be a hands-on \u201cdoer.\u201d Their primary responsibility is selling and generating revenue without worrying about other aspects like product meetings or board discussions.<\/li>\n<li><strong>Key characteristics: <\/strong>They must have the ability to execute independently, focus on sales, and have a clear role defined by the founder (e.g., seller, head of sales, or commercial cofounder).<\/li>\n<li><strong>Example:<\/strong> Mark achieved $1 million in sales in six months as Outreach\u2019s first hire on a 100% commission basis.<\/li>\n<\/ul>\n<p>In those scrappy early days, the first sales hire sets the tone for your entire go-to-market engine.<\/p>\n<p>This initial \u201cdoer\u201d isn\u2019t just another rep, they\u2019re the foundation on which you\u2019ll build momentum. Finding someone with an unwavering drive and a network to kickstart that first high-caliber team. Grit, passion, and relentless belief are all important at this stage.<\/p>\n<blockquote>\n<p>Mark\u2019s advice?<em> \u201cIf your first hire can\u2019t hire their first team of people they know, they shouldn\u2019t be your first sales hire unless you\u2019re just hiring a seller.\u201d<\/em><\/p>\n<\/blockquote>\n<h2>[Phase 2: The Builder] Establishing sales processes and culture<\/h2>\n<ul>\n<li><strong>Role: <\/strong>After initial revenue growth, the doer transitions to a builder. They focus on creating the initial sales team, building processes, and establishing a sales culture.<\/li>\n<li><strong>Key characteristics: <\/strong>They should be capable of hiring and leading a cohesive team, ideally from their existing network, to ensure trust and alignment.<\/li>\n<li><strong>Example:<\/strong> Outreach\u2019s first sales team comprised Mark\u2019s trusted friends and acquaintances who stayed for years and contributed significantly to the company\u2019s early success.<\/li>\n<\/ul>\n<p>With that initial team humming, it\u2019s time for the \u201cbuilder\u201d phase \u2013 developing those critical sales processes and fostering a winning culture.<\/p>\n<p>It\u2019s important to avoid the common pitfall of hiring reps before having enough pipeline. Instead, push them a couple deals more than their threshold, and then hire another rep into the pipeline. For Outreach, that threshold was 25 deals.<\/p>\n<h2>[Phase 3: The Doctor] Hiring for capacity<\/h2>\n<ul>\n<li><strong>Role:<\/strong> As the organization scales, the sales leader must become a doctor, diagnosing and solving specific issues in the sales process and team dynamics.<\/li>\n<li><strong>Key characteristics:<\/strong> They must identify bottlenecks, prescribe fixes, and implement changes to maintain performance.<\/li>\n<li><strong>Example:<\/strong> Outreach implemented a system where they hired new reps only after existing reps hit a threshold of active opportunities, ensuring the sales pipeline remained balanced.<\/li>\n<\/ul>\n<p>Reaching around $10 million ARR, most startups face a pivotal crossroads: do you hire ahead of demand to fuel future growth or risk being perpetually understaffed?<\/p>\n<p>That\u2019s when you go from being a builder to a doctor. In this phase, the \u201cdoctor\u201d leader must diagnose organizational constraints and prescribe proactive solutions \u2013 primarily by hiring for future capacity.<\/p>\n<p>Meaning, hire ahead to create capacity, then build demand to fill it.<\/p>\n<p>This is often the opposite of what you do up this point, where you\u2019re building pipeline first.<\/p>\n<p>Outreach went to around $25M under this stage.<\/p>\n<h2>[Phase 4: The Architect] Building the sales organization<\/h2>\n<ul>\n<li><strong>Role: <\/strong>The leader evolves into an architect who designs the blueprints for scalable sales processes and organizational structures. The focus shifts to creating a cohesive organization with second-line leaders who can sustain and adapt the company\u2019s culture.<\/li>\n<li><strong>Key characteristics:<\/strong> They focus on long-term planning, interdepartmental collaboration, and creating resources that enable the sales team to operate independently.<\/li>\n<li><strong>Example:<\/strong> By structuring the team for scalable growth, Outreach reached $50 million ARR. They developed a unified but nuanced culture across different teams, enabling smooth transitions for reps moving between segments.<\/li>\n<\/ul>\n<p>With that capacity in place, it\u2019s time to evolve into the \u201carchitect\u201d \u2013 the visionary responsible for designing and scaling the sales organization itself.<\/p>\n<blockquote>\n<p>As Mark puts it, <em>\u201cYou\u2019re no longer looking at the plans and building. You\u2019re the one that\u2019s responsible for the blueprints.\u201d<\/em><\/p>\n<\/blockquote>\n<p>This phase is about hiring second-line leaders\u2014directors and VPs\u2014who can carry the cultural torch while managing their own high-performing teams.<\/p>\n<p>Culture becomes the engine. Each segment, whether SMB, mid-market, or enterprise, has its own nuances, but they all share a familiar core. The goal is fostering an organization filled with second-line leaders that can create their version of your culture, but it still feels good.<\/p>\n<h2>[Phase 5: The Communicator] Aligning for strategic change<\/h2>\n<ul>\n<li><strong>Role:<\/strong> The leader becomes a communicator, aligning the entire organization toward a common goal, such as moving upmarket or entering new market segments.<\/li>\n<li><strong>Key characteristics: <\/strong>They must clearly articulate the strategy, rally cross-functional support, and drive company-wide initiatives.<\/li>\n<li><strong>Example: <\/strong>Outreach\u2019s shift to enterprise sales required an \u201centerprise state of mind\u201d across all teams, emphasizing company-wide commitment rather than relying solely on experienced enterprise sellers.<\/li>\n<\/ul>\n<p>As the organization matures, the leader must become a \u201ccommunicator,\u201d aligning cross-functional teams around strategic priorities\u2014especially when moving into new markets or upmarket opportunities.<\/p>\n<p>This phase is the most transformational. This phase requires a leader who can articulate a clear vision, rally support across departments, and communicate the why behind strategic shifts. It\u2019s about changing the company\u2019s DNA, not just the sales team\u2019s approach.<\/p>\n<p>\u00a0<\/p>\n<p><img loading=\"lazy\" class=\"alignnone wp-image-85381 size-full lazyload\" src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\" width=\"1456\" height=\"1048\" data-src=\"https:\/\/howtobigisland.com\/wp-content\/uploads\/2025\/01\/aa2dba7b-c0fe-4fe4-b084-c5098220db75_1456x1048.png\"><\/p>\n<p>\u00a0<\/p>\n<div class=\"captioned-image-container\">\n<figure><img loading=\"lazy\" class=\"alignnone wp-image-85387 size-full lazyload\" src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\" width=\"1456\" height=\"1048\" data-src=\"https:\/\/howtobigisland.com\/wp-content\/uploads\/2025\/01\/Mark-Kosoglow-Outreachs-first-employee.png\"><\/p>\n<p>\u00a0<\/p>\n<\/figure>\n<\/div>\n<p>At GTMfund, we\u2019re deeply committed to helping our portfolio companies build world-class teams. To date, we\u2019ve facilitated over 1,000 candidate introductions, resulting in many pivotal hires. To scale this support and extend it beyond our portfolio to the broader SaaS ecosystem, we\u2019ve partnered with <a href=\"https:\/\/www.pursuitsalessolutions.com\/gtm\">Pursuit<\/a> \u2013 a leader in go-to-market talent acquisition. This partnership enables companies to access top-tier talent on a non-retainer basis, ensuring flexibility and quality without unnecessary overhead.<\/p>\n<div>\n<hr \/>\n<\/div>\n<p class=\"button-wrapper\" data-component-name=\"ButtonCreateButton\"><a class=\"button primary\" href=\"https:\/\/thegtmnewsletter.substack.com\/p\/the-5-phase-framework-that-grew-outreach?utm_source=substack&amp;utm_medium=email&amp;utm_content=share&amp;action=share\">Share<\/a><\/p>\n<h6><em> Tag GTMnow so we can see your takeaways and help amplify them.<\/em><\/h6>\n<div>\n<hr \/>\n<\/div>\n<h4><strong> <img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\udca1\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f4a1.png\"> GTMfund Toolkit<\/strong><\/h4>\n<p>If your inbox looks anything like ours did after the holiday break, you know how overwhelming it can feel to get back to work. That\u2019s why we\u2019re grateful that we started using <a href=\"https:\/\/superhuman.com\/gtmnow\">Superhuman<\/a> last quarter, which helped us quickly get back to Inbox Zero. It was a seamless onboarding experience and Superhuman works with your existing Gmail or Outlook accounts.<\/p>\n<p>Superhuman studied the most efficient people and built the habits they use into their platform. The intentionality behind the product blew us away, even down to the analysis of proximity of your fingers to which keys so shortcuts can be as efficient as possible.<\/p>\n<p>It has already been a game changer for us and we love to see leaders implementing this kind of best in breed solution for their teams, allowing them to simplify and in turn speed up efficiency.<\/p>\n<p>New year, time to take back control \u2013 2025 is the year of inbox zero!<\/p>\n<p>If anyone also wants to take back control of their inboxes and empower their teams to do so, <strong>Superhuman is generously offering the GTMnow community exclusive access to 1 month free on the platform<\/strong>. If you add any teammates in January to your team, they\u2019ll get a free month too.<\/p>\n<p>To claim this offer, go to <a href=\"https:\/\/superhuman.com\/gtmnow\">www.superhuman.com\/gtmnow<\/a><\/p>\n<div>\n<hr \/>\n<\/div>\n<h4><strong><img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\udc42\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f442.png\"> More for your eardrums<\/strong><\/h4>\n<blockquote>\n<p><em><a href=\"https:\/\/gtmnow.com\/gtm-128-death-of-demos-selling-what-customers-need-fred-viet\/\">GTM 128: The Death of Demos and Selling What Customers Actually Need<\/a><\/em><\/p>\n<\/blockquote>\n<div id=\"youtube2-KyUVm57kpS4\" class=\"youtube-wrap\" data-component-name=\"Youtube2ToDOM\">\n<div class=\"youtube-inner\"><\/div>\n<\/div>\n<p><a href=\"https:\/\/www.linkedin.com\/in\/fredviet\/\">Fred Viet<\/a> serves as the Chief Sales Officer at Aircall, overseeing global sales and playing a key role in scaling the company\u2019s reach over the last four years. With a background that includes leadership roles at AWS, Microsoft, and Lenovo, Fred brings a wealth of experience in building high-performing teams and driving revenue growth.<\/p>\n<div>\n<hr \/>\n<\/div>\n<h4><img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\ude80\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f680.png\"><strong> Startup to watch<\/strong><\/h4>\n<p><strong><a href=\"https:\/\/www.linkedin.com\/posts\/sepehr-f_docunlock-streamlining-logistics-customs-activity-7272656394909040640-7fNm?utm_source=share&amp;utm_medium=member_desktop\">DocUnlock<\/a><\/strong><a href=\"https:\/\/www.linkedin.com\/posts\/sepehr-f_docunlock-streamlining-logistics-customs-activity-7272656394909040640-7fNm?utm_source=share&amp;utm_medium=member_desktop\"> \u2013 launched publicly with incredible traction, over 100% NRR through zero churn and multiple upgrades and expansions<\/a>. DocUnlock supercharges customs brokers and freight-forwarders by transforming commercial invoices, packing lists, ISFs, and other shipping documents into ready-to-file entries using artificial intelligence.<\/p>\n<p><strong><a href=\"https:\/\/www.linkedin.com\/posts\/createxyz_introducing-our-new-ai-templates-go-from-activity-7272288297819746305-SSiL?utm_source=share&amp;utm_medium=member_desktop\">Create <\/a><\/strong><a href=\"https:\/\/www.linkedin.com\/posts\/createxyz_introducing-our-new-ai-templates-go-from-activity-7272288297819746305-SSiL?utm_source=share&amp;utm_medium=member_desktop\">\u2013 launched AI Templates to make building even more accessible<\/a>. Create is AI text to app, allowing you to turn your words into sites, prototypes, and AI tools.<\/p>\n<div>\n<hr \/>\n<\/div>\n<h4><strong><img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\udc40\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f440.png\"> More for your eyeballs<\/strong><\/h4>\n<p><a href=\"https:\/\/sapphireventures.com\/blog\/selling-smarter-part-2-ai-sdrs-and-the-future-of-prospecting\/\">AI SDRs and the future of prospecting<\/a>. Why this shift is happening now, how the current prospecting software landscape is shaping up and what the future holds for AI in the space.<\/p>\n<p><a href=\"https:\/\/www.youtube.com\/shorts\/43HNvzx42lY\">How to use hashtags on LinkedIn (be aware of how many you use)<\/a>. Using more than 5 hashtags on a single post might signal to LinkedIn that you haven\u2019t naile<\/p>\n<div>\n<hr \/>\n<\/div>\n<h4><strong><img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\udd25\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f525.png\"> Hottest GTM jobs of the week<\/strong><\/h4>\n<ol>\n<li><a href=\"https:\/\/jobs.gtmfund.com\/jobs\/gtmfund\/f4750148-2fdf-4ff0-9f26-51248709b3ec\">Associate<\/a> at GTMfund <em>(Vancouver, Canada)<\/em><\/li>\n<li><a href=\"https:\/\/jobs.ashbyhq.com\/gorgias\/4755f737-4187-490d-a7bd-13da8a876bc6\">GTM Director, Marketing Suite<\/a> at Gorgias <em>(Toronto)<\/em><\/li>\n<li><a href=\"https:\/\/jobs.ashbyhq.com\/vanta\/220a7143-d0a5-4b42-8b6d-1bbd771a7a6f\">Senior Account Executive, SMB<\/a> at Vanta <em>(Sydney)<\/em><\/li>\n<li><a href=\"https:\/\/apply.workable.com\/document-crunch\/j\/8C851253B5\/\">Business Development Representative<\/a> at Document Crunch <em>(Hybrid \u2013 Atlanta)<\/em><\/li>\n<li><a href=\"https:\/\/jobs.lever.co\/NoibuTechnologies\/06780942-f32d-4bcb-b080-5338b59f2e39\">Enterprise Customer Success Manager<\/a> at Noibu <em>(Hybrid \u2013 Ottawa\/Toronto)<\/em><\/li>\n<li><a href=\"https:\/\/job-boards.greenhouse.io\/mutiny\/jobs\/4513935005\">Content Lead<\/a> at Mutiny <em>(Remote \u2013 US\/Canada)<\/em><\/li>\n<\/ol>\n<p>See more top GTM jobs on the <a href=\"https:\/\/jobs.gtmfund.com\/jobs\">GTMfund Job Board<\/a>.<\/p>\n<div>\n<hr \/>\n<\/div>\n<h4><strong><img src=\"data:image\/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==\" alt=\"\ud83d\uddd3\" class=\"wp-smiley lazyload\" style=\"height: 1em;max-height: 1em\" data-src=\"https:\/\/s.w.org\/images\/core\/emoji\/15.0.3\/72x72\/1f5d3.png\"> GTM industry events<\/strong><\/h4>\n<p><em>Upcoming go-to-market events you won\u2019t want to miss:<\/em><\/p>\n<ul>\n<li><a href=\"https:\/\/wynter.com\/spryng\/lp\">Spryng by Wynter<\/a>: March 24-26, 2025 (Austin, TX)<\/li>\n<li><a href=\"https:\/\/events.joinpavilion.com\/cmo-summit-2025\">Pavilion CMO Summit<\/a>: April 17, 2025 (Atlanta, GA)<\/li>\n<li><a href=\"https:\/\/events.bizzabo.com\/cro-summit-2025\">Pavilion CRO Summit<\/a>: June 3, 2025 (Denver, CO)<\/li>\n<li><a href=\"https:\/\/www.saastrannual.com\/\">SaaStr Annual<\/a>: September 10-12 (San Francisco, CA)<\/li>\n<li>Pavilion GTM Summit: October 14-16, 2025 (Austin, TX)<\/li>\n<li>GTMfund 2025 events TBA\u00a0(global)<\/li>\n<\/ul>\n<div>\n<hr \/>\n<\/div>\n<p class=\"button-wrapper\" data-component-name=\"ButtonCreateButton\"><a class=\"button primary\" href=\"https:\/\/thegtmnewsletter.substack.com\/subscribe?\">Subscribe now<\/a><\/p>\n<div>\n<hr \/>\n<\/div>\n<h6>This newsletter was entirely written and edited by <a href=\"https:\/\/www.linkedin.com\/in\/sophiebuonassisi\/\">Sophie Buonassisi<\/a> and <a href=\"https:\/\/www.linkedin.com\/in\/ssbarker\/\">Scott Barker<\/a> (not AI!).<\/h6>\n<\/div>\n<p>The post <a href=\"https:\/\/gtmnow.com\/the-5-phase-framework-that-grew-outreach-from-0-to-230m-arr\/\">The 5-phase framework that grew Outreach from $0 to $230M ARR<\/a> appeared first on <a href=\"https:\/\/gtmnow.com\">GTMnow<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Hello and welcome to The GTM Newsletter by GTMnow \u2013 read by 50,000+ to scale their companies and careers. GTMnow shares insight around the go-to-market strategies responsible for explosive company growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind these strategies and companies. The [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":476,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[12],"tags":[],"_links":{"self":[{"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/posts\/474"}],"collection":[{"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/comments?post=474"}],"version-history":[{"count":3,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/posts\/474\/revisions"}],"predecessor-version":[{"id":480,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/posts\/474\/revisions\/480"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/media\/476"}],"wp:attachment":[{"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/media?parent=474"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/categories?post=474"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/howtobigisland.com\/index.php\/wp-json\/wp\/v2\/tags?post=474"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}