26 Outreach Playbooks CEOs Used to Add $5M Pipeline

In this article, you will learn exactly how top software CEOs use cold outreach to land their first customers and scale revenue into the millions, with real-world examples and actionable playbooks. These founders have turned cold outreach from a dreaded task into a powerful growth engine, acquiring thousands of new users and building multi-million dollar companies from the ground up. You’ll hear directly from CEOs like Allan Duza of Reachbox.ai, who scaled his AI email platform to $6 million in ARR in just 18 months by perfecting his outreach strategy, and Manny Medina of Outreach.io, who built a massive sales engagement platform by first mastering the art of the outbound play.

You’ll get the 5-part playbook to launch your own Cold Outreach campaigns, in addition to over 40 case studies you can use as inspiration. These examples are from top founders who have keynoted Founderpath events, sharing the exact tactics they used to build their companies.

The 5-Part Playbook For Cold Outreach

1. Define Your Ideal Customer Profile (ICP) and Build a Targeted List. Before sending a single email, know exactly who you’re targeting. The most successful founders are relentlessly specific. They don’t just target “SaaS companies”; they target “Heads of Product Marketing at B2B SaaS companies with 100-400 employees.” Use tools like LinkedIn Sales Navigator, Apollo, or ZoomInfo to filter by industry, company size, revenue, and even specific technologies they use. Tony Tommy of Products AI secured his first customers by using Apollo and ZoomInfo to find product managers at companies doing $10M-$100M in revenue, proving that a well-defined list is the foundation of any successful campaign.
2. Craft a Compelling, Hyper-Personalized Message. Generic templates don’t work. Your email needs to be short, relevant, and provide immediate value. The key is to make it about them, not you. Research your prospect. Mention a recent LinkedIn post, a company award, or a specific challenge their industry is facing. Allan Duza of Reachbox.ai got his first 100 customers by sending hyper-personalized emails that included a video specifically about the prospect’s company and the top three things they could do to get more customers using his platform. This value-first approach gets replies.
3. Your Subject Line Should Spark Curiosity, Not Sell. Nobody opens an email with the subject line “Book a Demo with Me.” Successful founders use simple, intriguing subject lines that feel personal. Try “Quick question,” “Trying something new,” or referencing their company name. Matt Archer of Mahana.io landed his first beta customers with the simple subject line, “Trying something new within the collaborative space.” It was enough to pique curiosity and start a conversation, which is the only goal of the subject line.
4. Ask for Feedback, Not a Sale. When you’re just starting, one of the most powerful cold outreach tactics is not to sell, but to ask for advice. People are often more willing to give 15 minutes of feedback on a new idea than to sit through a sales demo. Yash Siobhan of GetSorale.com pre-sold his software to the first five customers by reaching out and saying, “Hey, I’m building a software that solves this specific pain point. Would you mind hopping on a 15-minute call to review it?” This approach validates your idea and builds your first relationships.
5. Execute, Track, and Iterate. The best founders use their own tools to run their outreach, a strategy often called “eating your own dog food.” This not only gets them customers but also provides invaluable product feedback. The team at Instantly.ai grew to $200,000 in MRR in just nine months by using their own tool to send thousands of cold emails daily. They tracked what worked, what didn’t, and constantly iterated on their copy and targeting to improve results. Whether you use your own tool or another, you must track open rates, reply rates, and meeting booked rates to understand what’s effective.

40+ Examples of Cold Outreach That Generated Millions

• The CEO of Reachbox.ai explained how their first 100 customers came entirely from using their own tool. They targeted SaaS companies, researched their specific value proposition, and sent a hyper-personalized email with a custom video, leading to $6 million in ARR within 18 months.
• The founder of Instantly.ai used his own cold outreach tool to grow his company to $2.4 million in ARR in just 9 months. His simple, effective email copy was: “Hey [Name], we built a tool that helped us get 100k MRR in a few months. Do you want to see if we can do the same for you?”
• Kyle Van Voris, a sales consultant, emphasizes the power of targeted outbound. He scaled an SDR team from 3 to 14 people, taking a company from $120M in assets under management to over $1B in just 20 months by defining a clear ICP and using a repeatable cold outreach process.
• Matt Archer at Mahana.io secured his first two beta customers, with 15 total seats, through direct cold email. His subject line was simply “Trying something new within the collaborative space,” which was intriguing enough to get a response and a demo.
• Yash Siobhan, CEO of getsourl.com, pre-sold his first five customers at $99 each before writing a single line of code. He did this by sending Loom videos of Figma mock-ups to influencer marketing managers on LinkedIn and asking for feedback, scaling to $34,000 in MRR within 6 months.
• Manny Medina, the CEO of Outreach.io, built his initial growth engine on heavy outbound sales. He scaled his sales team by meticulously breaking down outreach into 15 different personas across 4 segments, constantly testing language and direct mail packages to optimize reply rates before reaching $10M in new bookings per quarter.
• Max Armbruster of Talkpush got his first enterprise customers for his recruitment software by cold emailing and messaging two to three hundred CMOs on LinkedIn, asking for feedback on his product. This strategy landed Zappos as his first major client, helping him grow to over $100,000 in MRR.
• Yannick Dickel, co-founder of Conveino.de, got his first customers after spinning out of a large corporation through traditional cold outreach. With no prior sales experience, he and his team started making calls and sending emails, which led to their first 5 paying customers and $30,000 in ARR.
• The team at Fullfunnel.io used engagement-based outreach triggers on LinkedIn to drive growth. They reached out to people who engaged with their content, achieving over 80% acceptance rates and 40%+ response rates, leading to 61 inbound five-figure deals in their first year.
• Tony Tommy of Product.AI used Apollo and ZoomInfo for a fully outbound strategy to get his first customers. He targeted companies with 100-400 employees and $10M-$100M in revenue, using cold calls to land his first five clients and reach $60,000 in ARR.
• Andre Cvijovic of Referrizer built a 20-person remote, commission-only call center that makes 20,000 cold calls a week. This brute-force outbound strategy took his company from $60,000 in ARR to $1.4 million in just 12 months.
• Zach Hedges, the CEO of Aimisocial.com, acquired his first 300 customers within 72 hours by running a pre-launch campaign in a Facebook group. He nurtured a group of over 1,000 interested people for four months before offering them a special monthly price, hitting $25,000 in MRR right out of the gate.
• Stefan Smulders of Expandi scraped the Facebook groups of his competitors to build a highly targeted list. He then reached out with a personalized cold message, which helped him book over 40 appointments every week and scale to $7M in ARR.
• The CEO of FirstHive leveraged his past relationships from his marketing services company to get his first few enterprise customers. He had direct access to CMOs, which allowed him to land initial contracts worth around $250,000 each, helping him grow to $2.4M in ARR.
• Jayson DeMers of EmailAnalytics used his SEO expertise to get his first 100 customers. He acquired the exact match domain emailanalytics.com for just $5,000 and ranked #1 for his target keyword, driving all of his initial growth to $9,000 MRR organically.
• Arno, the founder of Breakcold, got his first five paying customers a week after launching his MVP by building in public on Twitter. He grew his following from 0 to 1,000 and used the audience to launch his personalized outreach tool, reaching $2,000 in MRR within four months.
• The founder of Archie used his consultancy network to land his first 28 customers for his AI-based document management tool. He focused on user engagement and proving a willingness to pay, which helped him secure his first $1,600 in MRR.
• Gadi Eliashiv of Singular got his first leads by answering questions on Quora related to marketing ROI and funneling them to a self-service mock-up of his product. This inbound interest from users asking “how do I understand my marketing?” helped him land his first enterprise customers and grow to over $26M in ARR.
• Justin McGill from LeadFuze started with a productized service doing done-for-you cold outreach. This allowed him to validate the market and self-fund the development of his software, eventually converting his service clients into SaaS customers and growing to $30,000 in MRR.
• Jonathan Lacoste of Jebbit used cold outreach on LinkedIn and attended niche networking events to get his first customers. This direct approach helped him land deals with major enterprises and grow his declared data platform, which has raised over $10M.
• Michael McCarthy of Inkit got his first customer, Bite Squad, by sending the head of demand gen 15 emails over the course of a month. This persistent, direct cold email approach helped him land over 100 customers and break a $1M run rate.
• Baird Hall, the founder of Wavve, got his first 100 customers through brute-force outreach. He scraped the iTunes API for new podcasters, found their emails in the RSS feed, and sent 30-50 personalized cold emails daily, helping him bootstrap to over $1.3M in ARR.
• Jake Atwood from BuzzBuilder used his own tool for cold email campaigns to find customers. His system identifies prospects based on trigger events (like new hiring posts on Indeed for recruiters) and uses personalized messaging based on DISC personality profiles, scaling to over $1.2M in ARR.
• The CEO of VanillaSoft initially grew his sales engagement platform by focusing on inbound leads from content marketing. This strategy helped them acquire 650 organizations and grow to over $10M in ARR before they even began to ramp up outbound efforts.
• Prayag Narula, CEO of LeadGenius, got his first customers for his B2B data platform by joining Y Combinator and leveraging the network. His first few sales were licensing the core technology via an API to other startups he met through the incubator, which eventually helped him raise $25M.
• Ken Hoppe of Modigie used a “brute force” cold outreach strategy to land his first 29 customers. He and his team targeted CROs and VPs of Sales in Silicon Valley, got their mobile numbers (using their own data enrichment methods), and called them directly, leading to just under $300,000 in bookings in the first year.
• The founder of HyperProspect landed his first client, Canopy Management, by finding the CEO in a relevant LinkedIn group for e-commerce entrepreneurs. He sent a personalized message about how he could create an impact for their business, which led to a booked meeting and his first $510/month contract.
• Chris Federspiel of Blackthorn, who has bootstrapped his company to $14M in ARR, focused his early go-to-market strategy on a very specific niche: higher ed and non-profits on the Salesforce platform. This laser focus allowed him to tailor his outreach and messaging to solve their specific payment and event management needs.
• Spencer Farber of Cliently got his first 70-80 customers by offering to personally create their sales engagement campaigns. This hands-on approach for annual plans was a powerful incentive for early adopters, helping him secure his first $8,000 in MRR within 9 months of launch.
• The team at Fincom.co used cold calling as their primary growth channel to get their first customers. This sales-driven approach, while waiting for their brand and inbound content strategy to develop, was critical for their early growth, helping them raise $1M in their pre-seed round.
• Luna’s CEO, Steven Nelman, used a freemium model with a viral loop to get his initial traction. He offered 25 free emails/month, with the ability to earn more by inviting colleagues. This strategy resulted in 37% of his 10,000 signups coming from referrals and helped him scale to over $24,000 in MRR.
• John Doherty of GetCredo leveraged relationships and referral traffic to get his business off the ground. A single mention from Rand Fishkin on a Moz Whiteboard Friday about “how to hire an SEO agency” drove over $300,000 in revenue to his business over five years.
• The CEO of Nittiolearn used outbound sales via email and LinkedIn to get his first 15 enterprise customers. By targeting Heads of Operations with a message focused on training for a distributed workforce, he scaled the LMS tool to $20,000 in MRR.
• Steven Messer, founder of Collective[i], got his first paying customers by offering to act as an outsourced data science arm for large, publicly traded companies. He solved their hardest problem—forecasting—which got his foot in the door and allowed him to scale to tracking 5% of the globe’s B2B economy.
• Isaac Pohl-Zaretsky, co-founder of Pocus, stressed that top sellers don’t spray and pray. Instead, they use a “warm outbound” framework, focusing on accounts where there are existing intent signals, which helped one of their early AEs close $700,000 in new ARR in her first quarter.
• Shaheem Alam, CEO of Five Rings Marketing, uses the same outbound playbook for his own agency that he provides for clients. He leverages LinkedIn, email, and cold calling to book meetings, which has grown his outsourced SDR firm to $30,000 in MRR across 15 clients.
• The founders of Prospectify got their first 100 customers paying an average of $352/month by eating their own dog food. They used their own sales intelligence tool to find prospects, hyper-target them using Google search for terms like “sales hacker,” and automate outreach.
• Andrei Breaz of Bant.io got his initial traction from a $200 AdWords campaign. This small, targeted spend was enough to get the flywheel started, leading to word-of-mouth referrals that have grown the B2B lead generation service to nearly $400,000 in annual revenue.
• Martin Macas of Fincom used cold calling as the primary driver to get early customers for his financial data platform. This direct sales approach allowed him to get initial traction while his content and inbound strategies were still maturing, helping him secure $1 million in pre-seed funding.
• Aaron De Cruz of Maynu gets customers for his restaurant ordering platform by sending cold DMs on Instagram. He complements this with word-of-mouth referrals from friends and existing customers to grow to $3,000 in monthly revenue.

Conclusion

You’ve just learned the 5-part playbook for cold outreach and seen over 40 examples of how top SaaS founders used this exact tactic to build their companies from the ground up. The recurring theme is clear: success comes from a specific, value-driven, and personalized approach. By defining your target, crafting a compelling message, and iterating based on results, you can turn cold outreach into your most powerful channel for customer acquisition. To get started tracking your own SaaS metrics and see how your growth compares to these founders, check out the free tools available at Founderpath.

Founderpath invests in ambitious founders looking to grow fast. Click here to submit a capital request