Most entrepreneurs dream about the day they can finally stop undercharging, break free from the feast-or-famine cycle, and confidently sell high-ticket packages that actually reflect the value of their work. Rachel’s story is proof that it’s possible. She started out selling $800 websites, hustling across multiple platforms, and patching together income with whatever projects she could get her hands on. Today, she’s booked months in advance and just closed the biggest project of her career — a five-figure package.
In this post, I’ll walk you through Rachel’s evolution: how she went from cobbling together work to building a streamlined, profitable business that no longer lives at the mercy of unpredictable client flow. Along the way, you’ll see the exact shifts she made in pricing, sales, and positioning — and how you can apply those lessons to your own business to escape the rollercoaster of uncertainty.
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What you’ll hear inside:
- The disconnect Rachel noticed between “cool” brands and her nonprofit events, and what it revealed about marketing strategy
- The unusual thing that gave Rachel a sharper edge in web design than a traditional marketing degree ever could
- The messy first years of taking “any project under the sun” and the moment she realized it wasn’t sustainable
- The accidental $8,700 project that taught her to expand her perception of what clients were willing to pay
- How motherhood forced a dramatic overnight price increase — and how she was able to support selling at such higher rates
- The difference between selling $800 and $3,600 websites and $10,000+ websites — and how she changed her entire sales process to match
- Why Rachel starts every call with a visual presentation — and how customizing slides with tiny personal details helps her close
- The four “alities” Rachel uses to design sites that actually convert — that you can use to get your site to convert better
Quick side note for transparency: Rachel is my client, and I’ve had the privilege of working with her for the past two years!
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Getting Started in Web Design
Rachel didn’t set out to be a web designer. In fact, she majored in religion in college — studying how people think, how culture shapes their decisions, and how entire societies process information. After graduating in 2012, she struggled to land a job and quickly realized a pattern: she was “too driven, too passionate, too loud” to fit neatly into someone else’s box. As she put it, she couldn’t settle for mediocrity or people not keeping up with her, which ultimately nudged her toward entrepreneurship.
Her first full-time roles were in the nonprofit world, where she was tasked with hosting and marketing events. That’s when she noticed something was off. The people she met in her personal life were cool, engaged, exactly the kinds of young professionals the organization was trying to reach. But the people actually attending the events? Not even close.
She remembers the disconnect vividly: parents and grandparents would call her office asking her to recruit their kids and grandkids to come. But as she quickly realized, “if your grandson is only coming because you told him to, we can’t win.” The marketing wasn’t resonating. The brand looked outdated, and the events felt misaligned with the very audience they were supposed to attract.
That disconnect sparked Rachel’s first foray into branding and digital marketing. She dove into research, studying how companies like Nike and Lululemon attracted their communities. Eventually, the organization launched a rebrand and a new website — and Rachel was hands-on through the entire process. It was like an apprenticeship with the consulting firm: she participated in focus groups, brand strategy sessions, and the nitty-gritty of designing assets and pulling together a site that actually worked.
At the same time, she earned a certification in web design and interned with a mentor who ran her own marketing firm. By the time the rebrand launched, Rachel had more than textbook knowledge — she had practical experience in branding, marketing strategy, and the tech side of building websites. She stayed on to run the organization’s marketing for another year, but when she realized she had learned all she could there, she made the leap.
Her first client wasn’t a big pitch or a strategic funnel — it was someone she met by chance who needed help managing a blog. That side gig became her anchor client and gave her the stability she needed to start her own business. At first, she said yes to everything: email marketing, blog management, WordPress, Wix, Weebly, Squarespace. But over time, the pattern became clear — Squarespace was the platform where she was fastest, most skilled, and able to deliver the highest value.
And that’s where the next chapter of her business really begins.
Early Pricing and the Evolution of Her Packages
Like so many service-based entrepreneurs, Rachel started out charging far less than her work was worth. Her first websites were $800 projects — and as she admits, clients got exactly $800 worth of work. The sites looked nice enough, but they weren’t fully functional, and she often had to lean on a developer friend to patch together problems she couldn’t solve yet.
In the early years, Rachel spread herself thin across every platform and tool imaginable: WordPress, Wix, Weebly, Squarespace, plus email marketing setups on MailChimp and Constant Contact. Each project required her to flip her brain into a new system, which meant constant context-switching, wasted hours, and very little efficiency.
Eventually, she realized Squarespace was where she was fastest, strongest, and able to create the most value for clients. That’s when she pivoted into her first real “package”: a two-week Squarespace website for $1,800. Soon after, she doubled her rate to $3,600.
It wasn’t until Rachel became a mom that she made her boldest move yet. Suddenly, the math no longer worked. Two projects a month at $3,600 wasn’t enough to cover her family’s expenses, let alone give her the freedom she wanted. So she did what most business owners are terrified to do — she tripled her prices overnight.
That decision was both a breakthrough and a breaking point. On one hand, her packages were finally priced at a level that reflected the true scope of her work. On the other, her entire business infrastructure — from client acquisition to systems — had been built for a smaller engine. She had to re-engineer her marketing, streamline her processes, and rebuild the way she sold in order to match the new level she was stepping into.
The lesson here is one every entrepreneur eventually faces: raising prices isn’t just about the number on the invoice. It requires upgrading how you deliver, how you position yourself, and how you present your value.
The Hard Lessons of Scaling
Tripling her rates overnight was both liberating and destabilizing. On paper, Rachel’s work was finally priced in a way that matched the quality she was delivering. In practice, the shift exposed every weak spot in her business.
Her systems were built for smaller projects — the $3,600 websites that came together casually over coffee chats and friendly referrals. But when she started pitching $8,500, $10,000, even five-figure packages, the old way of working couldn’t keep up. Acquisition felt clunky. Her marketing wasn’t set up to consistently attract the level of client she now needed. Even the way she delivered projects had to change.
One of the biggest realizations was how underpaid she had been for years. At first glance, $3,600 for a two-week website sounded solid. But when she factored in all the unpaid hours — the time spent on sales calls, networking coffees, posting on LinkedIn, and tinkering with code problems — the math didn’t work. She was earning far less per hour than she imagined, often dipping into feast-or-famine cycles where the workload was heavy but the income uneven.
To break that cycle, she streamlined relentlessly. She built a personal code bank so she no longer had to reinvent solutions from scratch or hunt through old client sites. She got faster, more confident, and more strategic in how she used her time. And she began shifting her mindset from charging by the hour to charging for the value and outcomes she created.
It wasn’t a smooth transition — few scaling moments are — but it forced her to grow into the kind of entrepreneur who could sell and deliver at a higher level.
Selling at a Higher Level
One of the biggest shifts Rachel had to make after raising her rates was in how she sold. The casual approach that worked when she was charging $3,600 — hopping on a friendly call, chatting through needs, and soft-closing based on a personal connection — simply didn’t translate to five-figure projects.
She realized quickly that clients willing to invest $8,500, $10,000, or more weren’t just buying a website. They were buying an experience. They wanted to feel confident they were hiring someone with a process, a proven framework, and the professionalism to match the price tag.
So Rachel transformed her sales process. Instead of showing up to calls empty-handed, she began using a structured, visual presentation. From the first minute of a call, she set the tone: “I have a little agenda, so I’m going to steer this conversation.” That simple shift told prospects immediately that she was the expert in the room.
The presentation itself wasn’t flashy — it was strategic. She walked potential clients through her process, showed them how she works, and paired every explanation with visuals that made the concepts concrete. When she reached the part of the call where most people stumble — justifying their pricing — her slides did the heavy lifting.
And then came the personalization. Rachel started weaving in what I’d call “relevancy triggers” — small, customized touches that made each presentation feel built just for that client. If someone mentioned loving sailing, she’d include an image of a sailboat when explaining the “sit back and relax” part of her process. If another client was a Swiftie, she’d drop in a playful photo of Taylor Swift kicking her feet up. These little cues showed she was listening, that she cared, and that she was building a process around them, not just for them .
This shift alone changed the game. Instead of competing with “the neighbor’s kid who just learned Squarespace,” Rachel positioned herself as the obvious choice for clients ready to invest at a higher level. And often, by the time she finished her presentation, they told her exactly that: “Now I see why you’re worth so much more.”
Why Rachel’s Marketing Works
What made Rachel’s sales process stronger wasn’t just the visual presentation she started bringing to calls — it was the way her design work itself embodied smart marketing. She wasn’t just handing over a polished site. She was translating human behavior into design choices that made clients easier to sell, easier to book, and ultimately more profitable.
Selling vs. Marketing
At the core, she sees a clear difference between selling and marketing. Selling is about understanding what someone wants. Marketing is about putting feeling behind it . That simple distinction shaped the way she designs websites. Instead of only laying out information, she asks: what should someone feel as they scroll? Excited? Reassured? Curious? That emotional response is the thing that converts visitors into clients.
The Power of Imagery
Imagery is one of the most overlooked aspects of marketing, and Rachel leans into it heavily. Too often, clients come in with a folder of stiff headshots or overly branded photos and assume that will be enough. But, as we talked about, no one cares about you just standing in front of a camera — they care about what working with you will do for them. The photos that actually move people are the ones that show outcomes and capture feelings. A confident business owner mid-presentation. A client celebrating a milestone. A team in motion. Those images do more than decorate a site — they sell the transformation.
Reverse Engineering Human Behavior
Rachel also thinks about something most designers miss: how to reverse engineer human behavior. As she put it, “tech is so dry” — so her job is to make it engaging enough that people want to keep scrolling . Sometimes that means balancing a page visually so it feels easy on the eyes. Other times it’s introducing subtle movement — a hover effect, an image that fades in — to keep attention flowing. Even if clients later veto those touches, she builds them in first because she knows they’re what keep users engaged.
Creative Direction as Strategy
And then there’s creative direction. Many clients don’t even realize they need it until she points it out. She’ll step in to guide a photoshoot, make suggestions about props or backgrounds, or even coach someone on how to show up in front of the camera. It’s time-intensive work, but it’s also what sets her apart. As Rachel told me, she can guarantee that your neighbor’s cousin who just learned Squarespace isn’t doing that . That’s why her packages command higher prices — because she’s selling more than a site. She’s selling the strategy that makes marketing actually work.
Rachel’s Frameworks: The 4 “Alities” of Web Design
When Rachel explains her approach to clients, she doesn’t just talk about “making a site pretty.” She uses a framework she calls the 4 “Alities” — visuality, functionality, personality, and propositionally. It gives structure to what can otherwise feel abstract, and it helps clients understand exactly why her work commands premium pricing.
Visuality in Web Design
Visuality is the part most people think of first: what the site looks like. Fonts, colors, layouts, and images. But Rachel is quick to point out that this is only the tip of the iceberg. A beautiful site that doesn’t engage or convert is just decoration. Visuality matters because it creates the first impression — the thing that keeps someone scrolling long enough to even consider what you’re offering.
Functionality in Website Development
Functionality is what happens beneath the surface. Can users navigate easily? Does the site work on mobile? Is it set up to support the business owner long-term without constant tweaks and fixes? Rachel has seen too many sites that look great but frustrate visitors — or worse, frustrate the business owner who can’t update anything without calling a developer. Functionality ensures the site actually works for everyone involved.
Personality in Brand Design
A truly effective site isn’t generic — it reflects the person or brand behind it. Personality is where Rachel brings in details about tone, imagery, and story so that the site feels like an extension of the business owner. For coaches, that might mean weaving in quirks or passion points. For creative brands, it might be bold visuals or playful copy. Personality makes the site memorable and creates trust, because people are buying into a real human, not just a service.
Propositionally: Clarifying Your Unique Value
The final piece is propositionally — how the site communicates what makes you different. This is where Rachel’s marketing insights show up most clearly. It’s not enough to have a list of services. Your site has to clearly articulate why someone should choose you over the dozens of other options out there. That clarity of proposition is what elevates a website from a digital brochure into a sales engine.
Together, these four “Alities” transform a website into something far more powerful: a marketing tool that’s rooted in psychology, storytelling, and strategy. It’s how Rachel helps her clients stop competing on price and start competing on value.
Takeaways for Entrepreneurs
Rachel’s journey isn’t just inspiring — it’s instructive. The shifts she made in pricing, systems, and marketing carry lessons for every entrepreneur who wants to build a sustainable, profitable business.
Adaptability Is the Foundation of Sustainable Business
Rachel’s definition of sustainability is simple: adaptability and flexibility. Every pivot she’s made — from shifting platforms to raising prices to restructuring her offers — has been driven by life circumstances and bigger “whys.” Entrepreneurs who thrive long term are the ones willing to adjust their business models as their lives and markets evolve.
Anchor Clients Create Safety — and Limit Growth
For years, Rachel relied on an anchor client to stabilize her income. It gave her peace of mind, but it also capped how far she could grow. Letting go of that safety net exposed her to her first real feast-or-famine cycle, but it also freed her up to take bigger risks that paid off . The lesson: stability matters, but don’t let it hold you back from scaling.
Pricing Reflects Value, Not Hours
Charging $800 or even $3,600 for a website seemed fine until Rachel realized how many unpaid hours were baked into each project. Once she started pricing based on outcomes and value rather than time, her business model finally made sense. If you’re undercharging, it’s usually because you’re calculating hours instead of positioning results.
High-Ticket Sales Require High-Ticket Systems
When Rachel tripled her rates overnight, she quickly saw that five-figure packages required more polished systems: structured sales calls, personalized proposals, and a client experience that matched the price point. The same is true for any entrepreneur — if you want to sell at a higher level, you need the infrastructure to back it up.
Frameworks Make Expertise Tangible
The 4 “Alities” framework — visuality, functionality, personality, and propositionally — gives Rachel’s work structure clients can instantly understand. Frameworks turn intuition and expertise into something concrete, which makes it easier for prospects to see the value and say yes.
Wrapping it up
Today, Rachel’s business looks completely different from where she started. She’s booked months in advance, she just closed the biggest project of her career, and she’s running her company in a way that actually supports her life rather than draining it. None of that happened overnight. It came through cycles of growth, recalibration, and sometimes hard pivots — from losing her anchor client to raising her prices to re-engineering every system behind the scenes.
Her story is a reminder that building a sustainable business isn’t about getting it “right” the first time. It’s about continually reshaping your work to match both your vision and your reality. The feast-or-famine cycles, the messy middle years, the bold price jumps — they’re all part of the process.
And for anyone reading this, Rachel’s evolution proves one thing: the moment you start treating your business as a living system that adapts with you, you unlock the path to growth that lasts.
Rachel Seid is a Squarespace web designer and Head Honcho at Bright Seid Design. She is obsessed with creating beautiful, functional websites that are easy for business owners and small teams to manage themselves. Her web design process establishes genuine personal connections with her clients that enable her to build personality-packed websites that feel as authentic as they do professional. Today she helps solopreneurs, small businesses, and non-profits build simple, easy-to-use websites that become powerful marketing tools to attract and convert dream clients.
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