DesignLive an Innovative Startup for Squarespace Users

Alex Tapper (left) and David Head are the founders of DesignLive, a startup for Squarespace users.

Alex Tapper (left) and David Head are the founders of DesignLive, a startup for Squarespace users.

Many entrepreneurs owe their success to identifying problems and then solving them. That’s the case for David Head and Alex Tapper, in Nashville, Tennessee.

In 2015 Head was a college student who also ran a web development firm. Tapper worked for a creative communications agency.

The problem they identified was a lack of affordable development and creative help for Squarespace websites. Their solution, which they launched in November 2015, is DesignLive, a marketplace of on-demand web developers focused exclusively on Squarespace.

The process works like this. Clients book video screen share sessions with one of DesignLive’s contract developers. Sessions can be booked in increments of 15, 30, 60, and 120 minutes. Depending on the task, the cost ranges from $50 to 150 per hour. Most clients book for 30 or 60 minutes. A new Squarespace site, built from scratch, takes about four hours.

Head grew up traveling, living in five different states by the time he was 16, thanks to his father’s career in the corporate restaurant industry. As a boy, he had an extreme fascination with putting things together, often in marathon sessions.

“I would spend so much time putting together K’nex [a toy construction system] that my mom would bring food to my room for fear I’d starve,” Head said. “It’s no different today. I enjoy 16-hour programming binges that result in turning out a great product more than almost anything.”

Head earned a B.B.A. in Entrepreneurship earlier this year from Belmont University, in Nashville. While at Belmont, he was recognized as one of the top student entrepreneurs in the United States by the Global Student Entrepreneur Awards.

Co-founder Alex Tapper graduated from Vanderbilt University, also in Nashville, where he received a B.A. Literary and Musical Studies, in 2012.

“DesignLive is essentially Uber for a web designer. Clients [Squarespace users] can summon a designer to work with them live via screen-share within five minutes,” Head said.

Although Squarespace is a do-it-yourself platform for launching a website, there is still a learning curve, according to Head and Tapper. They say that DesignLive is the first and (currently) only company dedicated to designing and maintaining a Squarespace site.

DesignLive itself uses Squarespace. But Head attributes much of DesignLive’s success to the integration of third-party tools, including Zapier (task automation), Acuity Scheduling (appointment software), Stripe Connect (online payments), SheetsDB, or Google Sheets (data management), Intercom (live chat), Aircall (cloud-based phone system), and MailChimp (email marketing). All of these, according to Head, greatly reduce costs and development time.

DesignLive’s revenue, which has grown by roughly 40 percent month-over-month since launching a year ago, should come in at roughly $150,000 in 2016, Head estimated.

Shopping Carts

DesignLive does not sell physical items. Instead, its “product” is live, online meetings via screen sharing to help clients build Squarespace sites. Acuity Scheduling is the company’s shopping cart of sorts.

Acuity is a third-party scheduling tool that can be embedded into a website. DesignLive’s customers can schedule a session with a designer and see their availability, and then pay using Stripe. DesignLive pays $34 per month for the top Acuity plan.

“As a designer, I’ve always had a gripe that Acuity was not the prettiest tool out there,” says Head. “We could not find the right combo of features that were just right for us, other than Acuity. I tried at least 10 tools.”

Design and Development

Since DesignLive is a web design company, Head and Tapper have done most of their own creative work.

“We tried to outsource the building of our web app and it cost us about $10,000 and a month of productivity,” said Head.

Although DesignLive is a Squarespace site, it is not able to add, via Squarespace, a client login feature. Head and Tapper built a custom app for this. Thus the two components, the website and the app, are blended together into a seamless experience.

The founders take design inspiration — which they call “drafting” — from well-funded, venture-backed startups.

“These companies can afford to hire designers whose focus it is to make their website cutting edge,” Head says. “Since we can’t afford that same luxury presently, we have a select few companies that we repeatedly draw insights from.”

This allows DesignLive to stay cutting-edge in user experience and aesthetic without dedicating as many resources.

Home page,

Home page,

Credit Card Payments

DesignLive uses Stripe Connect for credit card payments.

“It’s great because it segments the proceeds from the customer into two separate payments — one that pays our designers and another that pays us,” Head says.

He adds that many people might have heard of basic Stripe, but Stripe Connect is used in many marketplaces, such as Lyft, the taxi-like service.


DesignLive is currently hosted on Squarespace. The domain name,, the founders purchased through Namecheap, a registrar.

“Squarespace is extremely reliable and has great customer service,” said Head.

Eventually, Head and Tapper are looking to move hosting to Heroku, the app-focused cloud platform.

Order Management

Whenever a client schedules a session with DesignLive, Acuity Scheduling drops all the relevant data into SheetsDB (Google Sheets) via Zapier.

“We do absolutely nothing to maintain it once it’s set, other than improvements,” said Head.

DesignLive uses Zapier to port appointment information from Acuity Scheduling to SheetsDB, the output of which is shown here.

DesignLive uses Zapier to port appointment information from Acuity Scheduling to SheetsDB, the output of which is shown here.


Head and Tapper run the business themselves, including managing the participating Squarespace developers.

Head did hire one employee early on, but it did not work out.

“I did a poor job at judging whether this individual would be able to make the insane commitment that is required of startups.” Head said.

“In retrospect, I realize the importance of finding those people who have such an extreme level of passion for their work, that they’re actually energized by the idea of being consumed by the project.”

Search Engine Optimization

The company’s primary search-engine-optimization tactic is blog posts that announce new features of the platform. Head and Tapper use these posts to inform clients and prospects, as well as search engines.

The posts have helped rank within the top five for key, relevant terms, such as “Squarespace designer.”

Accounting Software

Head uses QuickBooks for DesignLive’s accounting.

“This is a tool that I’m hoping will be disrupted,” Head said.

“QuickBooks gained its foothold years ago, but it has not innovated since. It’s the only tool I use that has not evolved in the past three years.”

Expense Control

To control costs, Tapper and Head use a common startup methodology: paying themselves nothing during their first year.

“It hasn’t been the most exciting part of the business, but it adds stability to the company’s cash flow,” Head said.

The company’s primary expenses are software subscriptions, training resources, and software development.

“The software development we can throttle back easily if we want to be more conservative,” Head notes.

Customer Service

Tapper handles all of the customer inquiries through Intercom, a live chat provider.

For phone calls, DesignLive uses Aircall, a cloud-based telephone service, due to its integration abilities. Head and Tapper connect Aircall, via Zapier, to Intercom and SheetsDB — the call data is ported into both tools.

“Integrating with SheetsDB is incredible for running a quick analysis on our data,” said Head. “We wouldn’t be able to do it with a two-person team if it weren’t for Aircall’s integrations.”

Biggest Successes

“Our biggest success has been our growth and the conversations with our users, who tell us how much they love what we’ve built,” said Head.

“Hearing that is really satisfying and reassuring when you have a business that, by choice, doesn’t pay off for a while.”

Biggest Mistakes

Head and Tapper’s biggest mistakes are common among startups.

Hiring the wrong person early on and having poor experiences subcontracting out development work have given them trouble during their first year.

DesignLive also implemented a feature wherein clients can book sessions as short as 15 minutes. This, according to Head, is both a success and a mistake.

“At first, [15-minute sessions] helped our growth in monthly session hours. Quickly, it started to really hinder our revenue, though,” Head said. “We prefer that clients book for longer than 15 minutes. Plus, designers were not likely to respond to our requests for just 15 minutes of work.”

“Alex [Tapper] and I have questioned whether we should have released this option so early on.”

Still, the co-founders are ambitious as ever.

“We’re not back-peddling,” Head said. “Our clients and designers love it. That’s the reason DesignLive exists.”

Nic Murdock
Nic Murdock
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