How Billionaire Melanie Perkins Closed Canva’s First Sales After 100 Rejections
EdTech, First-Time EdTech Founder Sales, Melanie Perkins, Future of Selling System
How Billionaire Melanie Perkins Closed Canva’s First Sales After 100 Rejections — A Sales Guide for First-Time EdTech Founders
This is a story about walking into rooms where no one knows you, selling a product no one believes in yet, and choosing to keep going anyway. Jason wants every first-time EdTech founder leading sales to see themselves in Melanie Perkins’ journey — and walk away with a kinder, stronger system for their next meeting.
From a Small Classroom in Perth to a Product Nobody Wanted Yet
Picture a small classroom in Perth. Melanie Perkins is teaching students how to use complex design software — the kind that needs thick manuals, long lessons, and a lot of patience. Her students are frustrated. She’s frustrated too. Not because they’re slow, but because the tools weren’t built for them.
Out of that frustration, an idea forms. What if design were as simple as drag and drop? What if anyone could create something beautiful without training? No Silicon Valley network. No deep-pocketed investors. Just a young founder, a partner, and a belief that design could be easier for everyone.
If you’re a first-time EdTech founder, this should feel familiar. You see broken learning experiences in classrooms, universities, or corporate training. You build something better. Then you walk into your first real sales meetings — and the world greets you with raised eyebrows, slow head nods, and polite lines like “We’ll think about it.”
As Jason teaches at AuthorJason.com, founders who treat those first classrooms as learning labs — not just prospects — discover how to get your first EdTech sales as a startup founder and close the next ten schools faster.
100+ Investor Rejections — and Still Turning Doubt into Momentum
Perkins didn’t walk into friendly rooms. She flew to the United States, pitched investors who had never heard of her, and heard “no” again and again. Reports describe more than 100 investor rejections before Canva found real momentum. In a market already dominated by Adobe and other design tools, her idea seemed too simple, too early, or too risky to many of the people with capital and power.
This is the part most founders underestimate. It’s not one big “no.” It’s a steady drumbeat of rejection. Meetings that feel promising but end with “We’ll be in touch.” Calls that never get returned. Emails that go quiet. The same questions on loop: “Who are your customers?” “Why you?” “Why now?” “How will you compete?” The same doubts you hear when you pitch your learning platform to schools, universities, or corporate buyers who already have tools that “sort of work.”
And yet, while investors were saying no, early users were quietly saying yes. Canva’s first revenue didn’t come from flashy brands or huge budgets. It came from a simple product that solved real problems better, and from a founder willing to keep showing up even when gatekeepers stayed unconvinced. It was product-led growth before the term was trendy — and it grew into a global company that now blends mass adoption with serious enterprise sales, as recent reports on Canva’s expansion and growing corporate ARR from sources like The Information show.
As Jason teaches at AuthorJason.com, learning how to get your first EdTech sales as a startup founder means accepting that early doubt is data — and using it to sharpen your story, not shrink your ambition.
Perkins proves you can sell long before the world knows your name.
The Credibility Gap Every New EdTech Founder Must Cross
If you’re leading sales for your EdTech startup today, you walk into rooms carrying a silent weight. The buyer isn’t just judging your product. They’re judging your company’s chances of staying alive. Will you still be around in two years? Will your support team still exist? Are you a safe choice when their career and their students are on the line? This is the credibility gap — the invisible distance between what you know about your product and what they’re willing to believe right now.
Perkins faced the same gap. Investors compared her to giants. You face it when buyers compare you to legacy platforms or big publishers. Market data shows EdTech is growing fast — with global spending expected to keep rising at double-digit rates according to Grand View Research — but that doesn’t make your next meeting easier. Sector growth doesn’t automatically turn into trust in you. That trust has to be earned, conversation by conversation, often while your logo is still unknown and your team is still small.
Jason sees this pattern in almost every founder he works with. Smart, caring, hard-working people who’ve built real value, but feel like they’re always on trial. When buyers ask, “Who else is using this?” or “What happens if you shut down?”, it can feel like a personal attack. It isn’t. It’s the buyer trying to protect their students, staff, and budget. Your job isn’t to fight that fear. Your job is to guide them across the bridge from doubt to trust, as Perkins did — one proof point and one honest answer at a time.
As Jason teaches at AuthorJason.com, the EdTech founder who treats their first school as a relationship and a learning opportunity — not just a logo — learns how to get your first EdTech sales as a startup founder and turns that trust into faster follow-on deals.
Why Almost Every New Founder Gets About the Same Number of Rejections
There’s a quiet truth about startup life that almost no one tells you at the beginning. Every first-time founder, in every industry, gets their own version of 100 rejections. Perkins got hers from investors and early skeptics. You get yours from school leaders, deans, heads of L&D, and procurement teams who “love the idea” but “can’t move forward this quarter.”
When Jason looks at EdTech founders in 2026, he sees the same movie playing on repeat. The global market is growing. Funding is still flowing, though more cautiously, as reports from firms like Hyde Park Capital show. And yet first-time founders often get stuck in the same place: a handful of pilots, a few small contracts, and a long list of “we almost” that never turned into signed deals. The number of rejections is not what separates the breakthrough stories from the burnout stories. The difference is the system they use to turn conversation #101 into a yes.
Think of it like learning to drive. Almost everyone stalls the engine at some point. The question isn’t whether you will. The question is whether someone sits beside you, shows you a repeatable way to recover, and helps you stay calm enough to try again. Perkins had mentors, supportive partners, and a clear vision of who she served. You deserve the same level of support — not just in product, but in how you sell.
As Jason teaches at AuthorJason.com, the founder who sees every early school conversation as a “repetition” — not a referendum — learns how to get your first EdTech sales as a startup founder without burning out along the way.
How Melanie Perkins Sold Before She Was “Credible”
Perkins didn’t wait to become credible before she started selling. She sold her vision while she was still teaching in that Perth classroom. She sold the earliest versions of Canva when the product was far from perfect. She sold the idea that design could be different to investors who had never backed a founder like her before. Her strength wasn’t a polished résumé. Her strength was clarity, persistence, and a deep understanding of who she was building for — everyday people who wanted to create without friction or fear of “getting it wrong.”
You can do the same in EdTech. Buyers may not care about your age, your accent, or the size of your office. They care whether your product makes teachers’ lives easier, improves outcomes, or saves time and money. When you walk into a meeting, you don’t need to look like a seasoned enterprise seller. You need to look like someone who understands their world better than anyone else — and has done the work to turn that understanding into a usable, reliable product. That’s how founders like Richard Branson and Sara Blakely built trust long before the world knew their names: by staying close to the problem and the people, not by chasing perfect credentials.
When Sara Blakely was selling Spanx in the early days, she didn’t start with big retail chains. She walked into stores herself, convinced floor staff to try the product in fitting rooms, and sold one conversation at a time. That grassroots approach helped her land Neiman Marcus, after she personally showed the product to a buyer in a bathroom stall — a specific, bold moment that turned skepticism into belief.
Richard Branson followed a similar pattern with Virgin Atlantic. Before he owned a full airline, he chartered a single plane when his original flight was cancelled, then sold tickets to other stranded passengers with a handwritten sign. That improvised move proved real demand and gave him a story investors and customers could feel — not just understand intellectually.
Perkins had her own version of this. In interviews, she’s described how early Canva prototypes were tested heavily with friends, teachers, and non-designers, watching where they clicked and where they froze. Every session was both a mini sales call and a usability lab — a way to prove the promise of “anyone can design” long before Canva had millions of users or a multi-billion-dollar valuation.
As Jason teaches at AuthorJason.com, the EdTech founder who behaves this way — selling small, specific wins to real educators — learns how to get your first EdTech sales as a startup founder long before the brand name looks “credible” on a slide.
Owning the room starts with breathing through hard questions, not dodging them.
The Future of Selling System: A Kinder Way to Lead Your Own Sales
Jason built the Future of Selling System because he kept meeting brilliant builder-founders who were exhausted by selling. They weren’t failing. They were just tired of guessing. Tired of rewriting the same follow-up emails from scratch. Tired of walking into meetings hoping today would be the day the buyer would finally “get it.” Tired of feeling like every “no” was a verdict on their worth as founders, not just a data point on the journey.
The Future of Selling System isn’t about turning you into an aggressive closer. It’s about giving you a calm, reliable rhythm for your sales conversations. A way to prepare, show intent, teach, close, and build habits without burning yourself out. It’s been used by more than 1,000 founders since 2015, across industries, to generate over $22M in combined sales — including EdTech teams who now feel safer and steadier every time they open their calendars and see a new first meeting booked.
When Jason looks at you, he doesn’t see “lack of experience.” He sees a founder who has already done something brave by building a product and leading a team of five or more people. The Future of Selling System simply helps you turn that courage into a repeatable process, so every new conversation feels less like a test and more like a path you know how to walk.
As Jason teaches at AuthorJason.com, founders who adopt a simple, gentle structure for their school meetings quickly discover how to get your first EdTech sales as a startup founder without sacrificing their health or their values.
The P.I.T.C.H. Equation: Your Conversation Map for Tough EdTech Meetings
Inside the Future of Selling System, Jason teaches a simple conversation map called the P.I.T.C.H. Equation. It stands for: Prepare, Intent, Teach, Close, Habits. It’s not another heavy framework you have to memorize. It’s more like a set of signposts that keep you steady when a meeting takes an unexpected turn, or when a buyer asks a question that makes your heart race for a moment. You can explore it in more depth in the dedicated article on the P.I.T.C.H. Equation.
For a first-time EdTech founder, the real power of the P.I.T.C.H. Equation is repetition. Suddenly, your first meeting with a school in Sydney and your fifth meeting with a district in Toronto share the same backbone. You’re not reinventing the wheel every time; you’re improving one wheel that gets smoother with every conversation.
Instead of scrambling to remember what to say when a principal asks about data privacy, you already know where that question fits in your flow. Instead of guessing when to ask for a pilot, you recognize the moment because you’ve seen it before. The equation turns “random calls” into a series of linked experiments, where each school teaches you something you can apply directly to the next one.
Over time, this is how how to get your first EdTech sales as a startup founder becomes second nature. You know how to open the conversation, where to listen, how to share stories that land, and how to close in a way that feels natural to both sides. The P.I.T.C.H. Equation becomes less like a script and more like a rhythm you can trust, even on hard days.
Self-check
- Have you reached out to educators in your existing network — before trying cold outreach to strangers?
- Is your first pitch to a school centered on a learning problem — or on your platform’s tech and features?
- Is your free trial designed to produce a measurable result — or is it an open-ended “try it and see” that drifts and never converts?
As Jason teaches at AuthorJason.com, once your meetings are grounded in the P.I.T.C.H. Equation, you finally experience how to get your first EdTech sales as a startup founder as a learnable craft — not a mysterious talent other founders were born with.
A Fictional Founder Story: How Maya Turned “You’re Too Small” into “We’re In”
Meet Maya, a fictional founder who’s very close to the real people Jason describes. She runs an EdTech company that helps universities track student engagement in large online cohorts. Her team is eight people. She leads all sales. Her product works. Early users love it. But every time she pitches a new university, she hears some version of the same line: “We love this, but we’re not sure you’ll still be around in three years.”
One evening, after yet another “Let’s revisit next year,” she sits in her car and feels the weight of everything. Payroll. Student stories. Late nights. She’s not failing, but she’s tired and discouraged. She wonders if she’s just not “salesy” enough, or if she needs a different personality to win these meetings. That’s when she stumbles across Jason’s work and the Future of Selling System. What catches her attention isn’t the revenue numbers. It’s the tone — the sense that someone understands what it feels like to carry the whole company on your shoulders and still walk into every meeting with an open heart.
Over 1,000 founders. More than $22M in combined sales. Every great EdTech company started with one “yes.”
As Jason teaches at AuthorJason.com, founders like Maya unlock how to get your first EdTech sales as a startup founder the moment they stop chasing the perfect pitch and start following a human, repeatable script.
What Changed for Maya — and What Can Change for You
Maya doesn’t become a different person overnight. She does something simpler. She gives herself permission to use a system. She stops treating every meeting like a brand-new beginning and starts noticing patterns. The same objections. The same fears. The same moments when buyers lean in, and the same moments when they pull back. With the Future of Selling System, she starts mapping those moments and deciding in advance how she wants to respond — instead of reacting in the moment and judging herself later in the parking lot.
Her first real shift comes in a tough meeting with a skeptical dean. Midway through, he says: “Maya, this looks great, but honestly, you’re a small company. We can’t risk a platform that might not exist in a few years.” In the past, that would have rattled her. Now, she takes a deep breath, thanks him for naming the fear directly, and walks him through a clear, calm answer she’s practiced. She shows how they can start with a smaller student cohort. She explains her support commitments in simple language. She shares a story of another early adopter who felt the same way and is now seeing tangible improvements in student engagement, backed by data from their pilot.
The dean still asks for time. But a week later, he emails: “Let’s start with one program.” It’s not a million-dollar deal. It’s something more important: her first institutional “yes.” The kind of yes that unlocks case studies, referrals, and confidence. She prints the email and keeps it above her desk as a quiet reminder that she didn’t need to become someone else to close the deal. She just needed a kinder, more repeatable way to show up as herself.
As Jason teaches at AuthorJason.com, founders who absorb this lesson — that their first school is a learning partner, not a trophy — are the ones who master how to get your first EdTech sales as a startup founder and turn one “yes” into many.
You’re Not Late — You’re at the Start of the Story
When you read about Canva’s current scale, or about big EdTech deals like Coursera and Udemy merging into a multi-billion-dollar platform, it’s easy to feel behind. But remember where Perkins started. Remember that every giant company you admire once had an awkward first sales meeting, a tiny first contract, and a long season where almost no one believed in them. You’re not late. You’re standing in the part of the story that will make your later success meaningful to the next generation of founders.
Jason’s work, including the broader EdTech guide at The EdTech Startup Sales Founders’ Playbook, is built on this belief: you deserve a sales system that honors your humanity as much as your ambition. A system that lets you care deeply about learners and still ask for the contract with confidence. A system that understands you’ll have hard weeks — and still keeps you moving forward with gentle structure instead of harsh self-judgment.
As Jason teaches at AuthorJason.com, the founder who sees their first school deal as chapter one — not a late arrival — is already learning how to get your first EdTech sales as a startup founder in a way that compounds for years.
FAQs from First-Time EdTech Founders Leading Sales
These are questions Jason hears again and again from founders like you — people leading teams, carrying targets, and still wanting to sleep at night without replaying every sentence they said in the last meeting.
“Do I need a sales background to close serious EdTech deals?”
No. You need a learning mindset and a simple system. Most EdTech buyers don’t want a slick salesperson. They want someone who understands education, speaks their language, and respects their constraints. A structured approach like the Future of Selling System gives you enough scaffolding to feel safe while letting your genuine care show through. Your background in teaching, product, or operations isn’t a weakness. It’s an asset when paired with a clear conversation map.
“What if buyers keep saying we’re too small or too new?”
That objection is normal, especially when funding cools and buyers feel pressure to make “safe” decisions. Instead of taking it personally, treat it as a signal that you’re talking to serious partners. Jason teaches founders to respond with calm transparency, risk-reduction steps, and clear next actions. You don’t need to pretend you’re bigger than you are. You just need to show you’ve thought deeply about continuity, support, and responsible implementation.
“Is it realistic to sell to schools or universities as a first-time founder?”
Yes — but it often takes longer than you expect, and that’s okay. Institutional sales cycles can stretch across semesters or budget years. The key is to build a pipeline that doesn’t depend on one “big break,” and to use a system that turns every conversation into learning, not just a win or loss. Maya’s story is one example. Many of Jason’s founders start with a single department, program, or pilot, then expand as results appear and trust grows.
“How do I stay motivated after yet another ‘no’?”
Start by being kind to yourself. You’re not a machine. You’re a human carrying a lot. Jason encourages founders to treat every “no” as information, not identity. With a system, you can look at your call notes, see where the conversation drifted, and adjust for next time. You can also remind yourself that even Melanie Perkins, Richard Branson, and Sara Blakely lived through long seasons of rejection before their stories looked “inevitable” from the outside.
How does an EdTech founder make their first sale to a school?
Start with educators you already know, lead with the learning problem, and offer a short, structured pilot that proves one clear outcome before you ask for a paid rollout.
Should EdTech founders offer free trials to get their first school customers?
Yes — but only as structured pilots with a defined timeline, a shared success metric, and a scheduled decision meeting, not open-ended “try it and see” access that drifts and never converts.
What’s the most effective way for a new EdTech company to get into schools?
Combine warm introductions to educators with a tightly scoped pilot and a simple case study that turns your first school into a referral engine for the next ones.
