What Surprise Highway does

Surprise Highway is a privately held, Chicago-based web development and design agency founded in 2006, operating with a core team of four people (Owner Jason Siffring, Producer Katie Madden-Aker, Developer Mike Kroll, Studio Manager Shawn Campbell). The firm builds websites and web applications that solve specific business problems — ranging from product catalog systems and multi-site corporate networks to virtual event platforms and donation systems — for clients across medical devices, logistics, craft brewing, higher education, and nonprofit sectors. Its technical core is Craft CMS, on which it builds multi-site architectures with templated microsites, automated data synchronization via Google Sheets, and custom API integrations (notably a shipping tracking API for Radiant Global Logistics spanning 9 installations and 100+ locations). Notable products include Capstone Moment (a UC Berkeley virtual graduation platform) and the STEAM Punk Kids school fundraising platform.

The business operates as a professional services firm generating revenue through custom, quote-based project engagements covering strategy, design, development, and ongoing CMS support. Go-to-market is portfolio-driven: detailed case studies on the company website serve as the primary marketing channel, with bottom-of-funnel conversions driven by 'Request a Quote' CTAs and direct contact inquiries. Surprise Highway maintains a long-standing development partnership with creative agency Thinkso (since 2013), collaborates with Mighty Few on design-led projects, and contributes pro bono development to the Give a Brand! nonprofit rebranding initiative. The company is bootstrapped with no external funding, no parent company, and operates entirely in the United States with a single Chicago headquarters.

Name

Surprise Highway

Legal name

Surprise Highway

Website

https://surprisehighway.com

Company type

Private

Founded year

2006

Operating status

Operating

Headcount range

1–10 employees

Short description

Surprise Highway is a Chicago-based, four-person web development and design agency founded in 2006 that builds custom Craft CMS websites, multi-site networks, and specialized platforms for enterprise, education, and nonprofit clients through project-based engagements.

Ownership category

akta.pro rank

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Web Design & Development Services: Project-based professional services for website design, development, and support. Services include strategy, design, development, and ongoing CMS support. Revenue generated through custom project engagements with enterprise and mid-market clients.

Go-to-market motion1 record

Distribution channels1 record

Marketing channels2 records

Core offering

Surprise Highway is a Chicago-based web design and development agency that builds websites and web applications using the Craft CMS platform. The firm delivers strategy, design, development, and ongoing support services, specializing in multi-site CMS architectures, custom API integrations, and modular design systems for enterprise and mid-market clients across logistics, medical devices, brewing, education, and nonprofit sectors.

Product overview

Surprise Highway is a digital agency offering strategy, design, development, and support services. Their core product is a multi-site CMS platform built on Craft CMS that enables clients to manage networks of websites with shared architecture, templated microsites, and synchronized data. The company has built specialized platforms including Capstone Moment (virtual graduation/yearbook for UC Berkeley) and STEAM Punk Kids (school fundraising donation platform). Their project portfolio includes product catalog systems for medical device companies, e-commerce sites for breweries with automated inventory integration, and logistics platforms with API-based tracking. Services span from initial strategy and design through ongoing development and support.

Differentiator

Problem solved

Functional benefit

Products and services

• Web Development Services Digital agency services including strategy, design, development, and ongoing CMS support for websites and web applications, serving clients across industries such as logistics, healthcare, brewing, education, and nonprofits. Delivered by a core team of four dedicated professionals with deep Craft CMS expertise.

Quantifiable outcome

• 71 products organized and searchable for Sun Nuclear
• +2 more outcomes

Named customers6 records

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature4 records

Partnerships

Two partnerships are on record, tiered core and minor.

• ThinksocoreStrategic or Co-development Partner · 1 January 2013Long-term agency partnership since 2013. Thinkso provides design while Surprise Highway handles development. Collaborated on multiple digital projects as cohesive virtual team. Surprise Highway serves as primary development partner for Thinkso-designed websites. Also partners on Give a Brand! pro bono nonprofit rebranding event.
• Mighty FewminorStrategic or Co-development PartnerDesign partner for Black Market Brewing project. Mighty Few provided design while Surprise Highway handled development and CMS implementation.

Scale indicators6 records

Recent moves5 records

Expansion highlights4 records

Direct peers

• FreshySites: A web design and development agency specializing in WordPress-based enterprise websites. Comparable to Surprise Highway as a CMS-specialized digital agency serving multi-location and multi-brand enterprise clients.
• Huemor: A boutique web design and development agency serving enterprise and mid-market clients with custom website builds. Comparable to Surprise Highway as a similarly-positioned boutique digital agency competing for similar B2B project work.
• Lullabot: A digital agency with deep, recognized specialization in Drupal and CMS-driven web platforms, including complex multi-site architectures. Highly comparable to Surprise Highway's Craft CMS focus and enterprise-project orientation, although typically larger in scale.
• Thinkso: A creative agency and Surprise Highway's long-standing design partner since 2013. Comparable as a similarly-sized boutique creative/digital agency serving enterprise and nonprofit clients with brand-driven web engagements.
• Mighty Few: A boutique design partner that collaborated with Surprise Highway on the Black Market Brewing project. Comparable as a similarly-sized creative agency serving SMB and consumer-brand clients with web and brand work.
• Verbsz: A Craft CMS development agency serving enterprise clients. Direct platform-level peer to Surprise Highway in terms of CMS specialization, project-based professional services model, and multi-site architecture expertise.

Emerging players

• Pixelcabin: A boutique web development agency with Craft CMS expertise and a focus on bespoke CMS-driven builds. Comparable to Surprise Highway in technology focus and boutique positioning, though operating primarily in a different geography.

Broad incumbents

• WebFX: A large, established digital agency and web development firm with enterprise clients and a broad service portfolio including SEO, design, and development. Comparable as a scale player in the same horizontal web services market.
• Lounge Lizard: A larger digital agency offering web design, branding, and digital marketing. Comparable as an incumbent player in the web services space, with a wider service portfolio and larger team than Surprise Highway.
• Blue Fountain Media: A larger, established digital agency offering web design, development, and digital marketing across enterprise and mid-market clients. Comparable as a full-service web services competitor, though broader in scope and significantly larger in headcount.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/surprisehighway
• Facebookfacebook.com/SurpriseHighway
• LinkedInlinkedin.com/company/surprise-highway

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Surprise Highway