Pale orange pencils with bold slogans, symbolizing the creative and strategic planning in SmallBiz Sidekick's website design and development for solopreneurs.

Meet your tech-decoding website designer for small businesses & brands with personality.

about smallbiz sidekick

Carolyn Leasure, website designer for small businesses, stands in front of a row of trees smiling at the camera while thinking about all of the brands with personality she is going to help launch
image of the letter k in vesterbro poster font

Finding one studio who can build a strategic website, craft branding & messaging, streamline your small business tech - & really get you - is nearly impossible.

We’ve found each other!

a black and white photo of Carolyn Leasure, a white woman, seated and holding a Ruth Bader Ginsburg mug, discussing design strategies, highlighting her focus on brands with personality in Squarespace website development

I’m here to help your business grow & thrive while finally feeling like all the pieces click.

The vibrant hummingbird from the SmallBiz Sidekick logo, a beacon of innovative and tailored website design solutions for the bustling entrepreneur

My mission is to help free up your time through functional design and easy tech solutions that you can rely on.

I want you to feel confident in your solid foundation. Experience consistent business growth of ideal clients and a life-first business.

  • I work with 1-2 clients at a time, so each project gets my full attention.

  • You’ll have someone to guide you: a listener, a leader, an ally, a partner.

Let’s redefine what’s possible for the next stage of your business.

Headshot of Sally Hayes of Women in Self Healing in Los Angeles California

“No matter who you’re hiring, they have to understand your business and your vision. Carolyn gave me a lot of homework, but once we were done she understood exactly what I wanted - and even I was surprised at the direction the process took me.

For a long time, I didn’t think what I do could be translated online. I didn’t think you could look at a website and get the feel - and you helped me do it. I’m obsessed.”

Sally Hayes // Women in Self Healing

What I CARE about

Running a solopreneur business means I get to put my “why” into everything I do, and let go of the bullsh*t.

Here’s a sneak peak into what drives the work:

Carolyn Leasure of SmallBiz Sidekick, smiling, seated and talking with her hands. She demonstrates her expertise as a website designer and Squarespace conversion specialist, ready to enhance the online presence of small businesses

How that shows up in our work together

Featured
No false promises, no forced signups, no fake countdown timers.

When you work with me, we won’t employ any pressured marketing tactics.

Your clients will connect with the authentic you and what you are offering.

If we speak to your potential clients in a way that feels legit, you naturally connect with those who are the best fit!

You get to focus on your zone of genius

What got you into your business and career is your purposeful passion. Keep doing that and it will magnetically attract your perfect-fit clients.

Leave the things that you can do (but don’t like) or the things that are super-challenging to the experts.

And I’ll do the same!

Offer meaningful value (yes, sometimes for free!)

Did you know that most people need 5-7 touches with a business before they’re ready to get on board?

Let’s find ways to keep people in your ecosystem so they can see the value in your offers and just how damn good you are at what you do.

Then they’ll purchase when they are ready - rather than get pressured into a sale when they’re not.

Anti-hustle culture

My inbox is always open, but I’ll only respond during working hours (and I hope you will too!).

Hustle culture can lead to burnout, illness, and disconnection. True connection and purposeful passion creates balance and growth.

For me, this means:

  • Treating others with respect and empathy.

  • Spending time with family.

  • Meditating every day (and by “every day” I mean when I drag my bottom to do it, and then remember how good it is).

  • Getting outside as often as possible.

  • Being able to take on a pro bono project annually.

  • Showing up as my true self (hello, awkward) both in person and online.


Ultimately, being balanced between my online life and still deepening my offline world with friends, family and community.

Growth from knowledge

I make decisions based on gathering as much information as possible.

We determine strategy based on analytics, your goals, and what works for you in your day-to-day.

I don’t skip the first steps – no matter how challenging – for quick fixes that don’t allow for growth in the long term.

Instead, I make them as simple as possible and guide you through the process.

Always learning, always growing

The one truly limited resource we have is time.

I use design and tech innovation to gain the highest ROI in connecting with your ideal audience.

Because who has time to spend spinning wheels trying to just keep up with trends and shouting into the void?

Consistently innovating means consistently finding new ways to engage with potential clients.

And while some marketing bros are thinking about today’s one sale, working with me means creating long-term relationships with your audience. This builds a solid client base that will come back to you time and time again.

A subtle yet elegant divider, because in web design, even the smallest details matter, just like in our tailored Squarespace website solutions

A few of my MAJOR achievements

One time I made it in and out of Ikea in less than an hour and spent less than $100.

I had a mini burlesque career from age 29-32.

(Sign up for my emails & get the full story)

Carolyn Leasure of SmallBiz Sidekick laughing with a client, showcasing the friendly and collaborative approach in Squarespace website design for small businesses, emphasizing personalized client relationships

I also had a short-lived one-season rollerderby run that ended with a concussion.

String lights casting a warm, inviting glow, symbolizing SmallBiz Sidekick's approach to creating welcoming and engaging Squarespace websites for small businesses and entrepreneurs

My first word was cheese (and I opened an artisanal cheese shop & wine bar in 2012).

I can drive stick shift.

A black and white photo of Carolyn Leasure of SmallBiz Sidekick, based in Charlottesville, Virginia, smiling in a polka dot dress, exemplifying professional Squarespace website design expertise, dedicated to empowering small businesses
Serene dock at a lake, reflecting the calm and focused approach of SmallBiz Sidekick in Squarespace website design for small businesses, embodying tranquility and clarity in the creative process
Another stylish divider, because who says you can't mix business with pleasure? Certainly not us at SmallBiz Sidekick, where we blend functionality with flair.

js-hero-timeline My JOURNEY to SmallBiz Sidekick

  • Born a strategist in Buffalo, NY

    Entrepreneurship & strategy have always been my calling.

    Starting at age 5, selling painted pet rocks with my big sister on the side of the road.

    And even during my off-hours these days, at my tactics-fueled board game nights with family & friends.

    Carolyn Leasure of SmallBiz Sidekick, as a 5 year old, sitting under an umbrella in the yard with her sister

  • Hustling for Cheddar in Washington DC

    I spent my late 20’s and 30’s establishing a national reputation as a fromager/wine wiz and building my brick-and-mortar artisanal cheese shop & wine bar in Washington DC.

    I had no idea what I was doing – but it was a wild ride.

    I was working 7 days a week, growing my business every year, doing everything myself. And everything was absolutely fab.

    Or so it seemed.

    3 polaroid images of Carolyn Leasure starting and running her first business, Righteous Cheese, a cheese shop and wine bar in Washington DC

  • Successful but overwhelmed

    Then in 2018, I popped my head up to realize I was barely keeping above the quicksand.

    Solopreneur life with a staff of 9, managing manual systems, worsening chronic health issues, and figuring out how to be a new mom?

    I was no longer doing the work that I loved – my purposeful passion.

    Two polaroid images of the burnout days of Carolyn Leasure's first career, which prepared her to help other solopreneurs and small business owners with streamlining systems

  • A life-first career change

    So we moved to the beautiful, chilled-out mountain town of Charlottesville, Virginia. Now I gaze out on the mountains over my morning pour-over coffee. And can float down the Rivanna River on an inner tube with my family on the weekends if we want.

    Ironically, I leaned hard into some of my biggest stressors and I started helping solopreneur friends of mine that were struggling.

    I put my creative writing degree to use and started copywriting.

    I learned coding, brand strategy, email marketing best practices, web design UX, and SEO techniques to become an expert and help other burned-out small business owners.

    3 polaroid images of Carolyn Leasure's life in Charlottesville Virginia: drinking coffee next to the mountains, river rafting, and hiking

  • SmallBiz Sidekick: growth, connection, and purposeful passion

    In 2019, I started SmallBiz Sidekick and became obsessed with helping service providers and coaches nix that same feeling of overwhelm that comes with small business DIY design platforms and manual systems.

    At the SmallBiz Sidekick studio, I apply the combo superpowers of brand & web design, copywriting, systems, and interactive lead generation at once.

    This magnetically attracts right-fit clients to your biz and creates long-term relationships with them - all in ways that let you breathe easier instead of getting wound tighter.

    Carolyn Leasure of SmallBiz Sidekick, sitting at a cafe table, meeting with a client to craft small business strategy
Another stylish divider, because who says you can't mix business with pleasure? Certainly not us at SmallBiz Sidekick, where we blend functionality with flair.

Will we be a GOOD FIT?

Will I be the right web designer and strategist for you? I hope so!

I love working with solopreneurs, small business service providers, coaches, and health & wellness professionals that are aligned with what I offer. If not, I’m happy to make a recommendation for someone else. Take a look and see if I’m the right choice for you:

  • Caucasian wellness entrepreneur client of SmallBiz Sidekick, viewed from the back. Working from home, on the couch, with a small potted tree in from of her, she exemplifies the successful implementation of Squarespace website solutions

    • You are excited and passionate about your project.

    • You are ready to delve into what it takes to show up as as your authentic brand – rather than what you think it should be.

    • You want to build long-term relationships with clients rather than ones built on pressure.

    • You are willing to gather all of your details and have your content ready to go 1 week before your start date.

    • You are systems- and process-oriented. You can make the time commitment to ensure the project keeps moving and deadlines are met.

    • You understand this is a business investment that will lead to long-term growth for your brand.

    • You are ready to trust a professional with design, rather than try to dictate each element.

    Let's do this!
  • A potted plant in front of a round mirror on a wooden dresser, symbolizing the organic approach of SmallBiz Sidekick in Squarespace website design for small businesses, reflecting a commitment to nurturing and sustainable web solutions

    • You are not sure where you want your business to go or what content you need to start.

    • You don’t have a sound starting knowledge of your ideal audience or your brand identity.

    • You don't find value in brand or marketing strategy, or why it is a key starting point.

    • You prefer a pressured marketing technique rather than building long-term trust with clients.

    • You are not open to new design ideas and layouts, particularly that prioritize functionality and accessibility.

    • You prefer to dictate every design detail.

    • You want a website on Wix, Wordpress, Webflow, Kajabi, or Showit.

    • Process and systems are a waste of time - only the end result matters.

    No judgement here, it just means we might not be the ideal fit.

How I’ve helped other small businesses LIKE YOURS:

Sprints • Custom Projects • Strategy

Creative workspace with yellow background, scissors, and purple pencils, representing the innovative and artistic design process at SmallBiz Sidekick for Squarespace websites, embodying creativity and precision in small business web solutions
A subtle yet elegant divider, because in web design, even the smallest details matter, just like in our tailored Squarespace website solutions

Section Styles quote

Kind Words

···

Kind Words ···

Headshot of Neil Runyon of Carnegie Hill Massage in Manhattan. NY leading to a video testimonial

Carolyn had my back, & understood the nature of my business and where I wanted to go with it. Carolyn is a partner.

— Neil Runyon / Carnegie Hill Massage

Another stylish divider, because who says you can't mix business with pleasure? Certainly not us at SmallBiz Sidekick, where we blend functionality with flair.
graphic - layered sections in a circle shape: green, grey and white.