In partnership with
In the mid-2010s, traditional live chat tools were seen as customer support utilities, not revenue opportunities, past attempts to use chat for sales had largely failed because companies were trying to repurpose support software for selling. At the same time, B2B buyers were growing impatient with the old lead generation playbook of static web forms and delayed follow-ups.
📊 Snackable Stat: $5 Billion
In 2021 alone, Drift’s users generated over $5 billion in sales pipeline value through its conversational tools.
Here’s what you’ll learn:
Why naming the problem you solve can be more beneficial than naming the features you offer.
The definition of what it takes to own a category.
How to compete against market leaders by reframing the problem.
To Go Beyond Being “Better”
By the mid-2010s, live chat widgets had become table stakes for B2B websites. Intercom, founded in 2011, had established itself as the go-to solution for customer messaging, growing from $1 million to $50 million in annual recurring revenue between 2013 and 2016 while capturing thousands of paying customers. Rivals from LivePerson to Zendesk were crowding in, each pitching variations on the same theme: reactive support tools dressed up as engagement platforms.
Entering this market as another look-alike product was a recipe for obscurity. The challenge ran deeper than competition. The prevailing marketing funnel was fundamentally broken from the buyer's perspective. B2B buyers, accustomed to instant gratification from consumer apps, were being asked to fill out forms and wait hours or days for a reply. This disconnect created measurable friction: companies were effectively leaving their digital storefronts unattended, with prospects who had questions simply abandoning the site to look elsewhere.
Drift's CEO, David Cancel, who had been Chief Product Officer at HubSpot, noticed a striking paradox. Messaging apps like Slack were booming in workplace communication, yet B2B websites still treated interested prospects like support tickets in a queue. Live chat technology existed, but it was mostly confined to IT helpdesks and customer service departments. "Many people had tried to use live chat for sales... they weren't successful because they were using a support tool," Cancel explained. Companies had siloed their real-time conversations to support teams, while marketing and sales relied on slow, one-way methods like forms, emails, and drip campaigns.
The result was an overcrowded vendor landscape solving the wrong problem with outdated approaches that frustrated buyers and wasted seller opportunities. To win, Drift couldn't just build a better chat widget. It had to change the game entirely.
This free edition is supported by
Vibe code with your voice
Vibe code by voice. Wispr Flow lets you dictate prompts, PRDs, bug reproductions, and code review notes directly in Cursor, Warp, or your editor of choice. Speak instructions and Flow will auto-tag file names, preserve variable names and inline identifiers, and format lists and steps for immediate pasting into GitHub, Jira, or Docs. That means less retyping, fewer copy and paste errors, and faster triage. Use voice to dictate prompts and directions inside Cursor or Warp and get developer-ready text with file name recognition and variable recognition built in. For deeper context and examples, see our Vibe Coding article on wisprflow.ai. Try Wispr Flow for engineers.
How Free Education Beat Paid Advertising
Drift's strategy was to redefine the problem and create a category it could dominate. In 2016-2017, the company popularized the term "Conversational Marketing" to describe its approach: using chatbots and live chat to engage and qualify leads in real time, positioning chat as a revenue tool rather than a support utility. This wasn't just marketing spin. It was a deliberate category-creation play modeled after HubSpot's successful "Inbound Marketing" playbook.
Few startups successfully name and own a category, but Drift set out to do exactly that. As marketing strategist Al Ries wrote, "If you can't be first in a category, set up a new category you can be first in." Drift wasn't the first live chat tool, so it made Conversational Marketing the category.
Crucially, Drift didn't gatekeep the concept. It evangelized it. In January 2019, the company published "Conversational Marketing: How the World's Fastest Growing Companies Use Chatbots to Generate Leads 24/7/365," co-authored by CEO David Cancel and VP of Marketing Dave Gerhardt. The book walked readers through implementing real-time engagement strategies, complete with case studies and tactical playbooks. Drift also offered a free Conversational Marketing Certification through its Drift Insider training platform, spreading the methodology while training thousands of marketers in Drift's approach. By openly teaching its methodology, Drift turned marketing into education.
The strategy worked. "The idea didn't really take off until we gave it a name," Gerhardt later noted. By defining the rules of the emerging game, Drift positioned itself as Conversational Marketing's thought leader, forcing competitors to play on Drift's terms. Within two years, major platforms adapted to the narrative Drift set. HubSpot launched a "Conversations" tool in its Service Hub, Intercom rebranded around "Conversational Experiences," and Salesforce added chatbot offerings for Pardot. Instead of chasing incumbents, Drift made incumbents chase it.
And by freely teaching best practices through the book, certifications, and content, Drift ensured that marketers would associate success in this emerging category with the company that literally wrote the book on it.
Unicorn Status and New Vulnerabilities
By 2020, more than 50,000 businesses were using Drift. The approach moved from niche tactic to mainstream strategy, reaching mid-market and enterprise customers including ServiceNow, Okta, Adobe, and Snowflake. When a methodology reaches companies at that scale, it signals an industry shift rather than a passing trend.
The business impact was dramatic. Drift's annual recurring revenue grew from roughly $6 million in 2017 to over $100 million by 2021. In 2020 alone, ARR grew 70% year-over-year. By late 2022, Sacra estimated Drift reached approximately $135 million in ARR, up 35% from the prior year.
In September 2021, a majority investment from Vista Equity Partners pushed Drift into unicorn territory, valuing it at over $1 billion. The milestone carried cultural weight as Drift became one of the few Latino-founded tech unicorns. In 2021, Drift's customers created $5 billion in sales pipeline through conversational marketing. Lacework reported that implementing Drift reduced average days to close by 29% and saw over 100% increase in booking discovery meetings.
In February 2024, Drift was acquired by Salesloft to create an AI-powered revenue orchestration platform. However, in August 2025, the integration became the conduit for one of the largest SaaS supply-chain breaches in history. Attackers compromised Salesloft's systems and stole OAuth tokens, gaining unauthorized access to over 700 organizations' Salesforce and Google Workspace data, affecting companies including Cloudflare, Zscaler, and Palo Alto Networks. The breach highlighted the double-edged nature of deep platform integrations that made conversational marketing powerful.
Key takeaways to consider…
Speak to the Problem, Not Just the Product. Drift didn't compete on features against established players. They created an entirely new category that reframed the conversation. When you name the problem differently, you change how buyers think about solutions. Drift made it easier for prospects to understand why existing tools weren't working. If you're entering a crowded market, don't try to be better at what everyone else is doing. Define what everyone else is doing wrong.
Turn Your Methodology Into A Movement. Drift gave away its playbook and even offered certification that turned marketing into education. This transformed customers into evangelists who spread the methodology to their networks. And in the process, they built a category where they became synonymous with the solution itself. Education scales faster than sales.
Align Your Product With Real Buyer Behavior. Drift recognized that B2B buyers were frustrated by slow, form-based lead capture. Instead of iterating on existing tools, the company built its platform around real-time conversations, meeting buyers where they already expected immediacy.
This free edition is supported by
This Tech Could Be Worth 18X Nvidias
In 2017, legendary tech analyst Cathie Wood, CEO of ARK Invest, suggested this tech could present a “$17 trillion opportunity by 2037…roughly worth 35 Amazons.” Since then, advancements have gone absolutely insane, with market caps skyrocketing, valuations booming, and millionaires minted almost daily.
In fact, Wood has since revised predictions, saying: This technology could be worth $80 trillion by 2030. And The Verge claims one remarkable company is the backbone of this entire industry.
The Motley Fool laid out the full story on this incredible tech trend in an exclusive report. Details are already starting to leak out, so act quickly to capitalize.
🍫 Power Numbers
50,000+ - Businesses using Drift’s conversational marketing tools
30 million+ - Conversations powered by Drift in 2023 alone
35% YoY - Drift’s ARR growth from $100 million (2021) to $135 million (2022)
70% - ARR growth in 2020 during peak hypergrowth
$1 billion+ - Vista Equity Partners valuation (2021 unicorn milestone)
🍭 More Sweet Reads
What if the true measure of an exit is not the number of zeros in the outcome, but how much clarity and control a founder feels as the deal unfolds and life begins on the other side. The Joyful Exit explores how founders can ask better questions earlier, set healthier expectations with partners, and architect exits that feel intentional, aligned, and genuinely joyful.
Crowdfunding has quietly become a $2.4 billion engine for young companies, and the ACCESS Act is Congress’s latest bid to supercharge it by easing costly accounting rules and letting everyday investors put more money behind the startups they believe in.
The problem with enterprise AI isn’t GPUs or model choice, it’s that most organizations are running on vibes instead of P&L. Through war stories of overstretched “AI SWAT teams,” nervous executives, and biased systems, this piece shows how to rebuild AI initiatives around data discipline, clear ROI, governance, and change management so they actually ship and scale.
Most businesses waste 60% of their customer acquisition budgets on channels that don’t convert because there’s no systematic approach to moving prospects through their acquisition journey. The difference between winning deals and losing them comes with knowing exactly what to do at every stage. The From Prospect to Profit Playbook gives you actionable frameworks for mastering customer acquisition from end to end that you can deploy immediately.
Want to reach 40,000+ business-savvy readers, product leaders, and decision makers? Partner with us.
Was this shared with you?
