Top SaaS Companies in Chicago

List of the largest SaaS companies in Chicago, United States (Click to apply)

These are the top SaaS companies in Chicago, United States. In todays day and age its possible to launch a company from anywhere. We wanted to show some love for Chicago by featuring these 161 companies with combined revenues of $2.2B.

Together, Chicago SaaS companies employ over 27K employees, have raised $249.4M capital, and serve over 177K customers around the world.

$0 - $1M ARR
  1. Fippex $1.0M
  2. Nimbulis $1.0M
  3. ADSHIFT $1.0M
$5M - $10M ARR
  1. Revenew $9.4M
  2. Adeptia $9.0M
  3. Ycharts $8.4M
  4. Vibes $7.5M
  5. dscout $6.8M
$10M+ ARR
  1. Flexport $861.0M
  2. Centro $142.8M
  3. SAI Global $106.0M
  4. Uptake $100.0M
  1. 01
    Flexport

    Flexport

    Supply Chain & Logistics Software

    Flexport is a licensed customs brokerage and freight forwarder built around a modern web application. Its freight service includes an online dashboard for businesses to easily understand, purchase, manage, and track the services required for global trade.

    $861M

    $1B

    10K

    2K

    2013

    Chicago

  2. 02
    ActiveCampaign

    ActiveCampaign

    Email Marketing Software

    Integrated email marketing, marketing automation, and small business CRM. Save time while growing your business with sales automation.

    $165M

    $360M

    145K

    842

    2003

    Chicago

  3. 03
    Centro

    Centro

    Digital Advertising Platforms

    Created the most comprehensive, automated and intelligent software platform for the digital media industry.

    $143M

    $53M

    2K

    921

    2001

    Chicago

  4. 04
    SAI Global

    SAI Global

    Governance|Risk & Compliance Software

    Provider of compliance and risk management software. The company offers a software that allows companies to manage their compliance obligations and risk mitigation in the areas of safety, health and the environment. It offers its services to utilities, oil

    $106M

    2K

    2012

    Chicago

  5. 05
    Uptake

    Uptake

    Digital Analytics Software

    Uptake is the industrial analytics platform that delivers products to major industries to increase productivity, security, safety and reliability.

    $100M

    $218M

    251

    2014

    Chicago

  6. 06
    Relativity

    Relativity

    Legal Software

    Relativity provides eDiscovery software solutions that give corporations, governments, & law firms tools to manage litigation, investigations & FOIA requests. Learn about Relativity's eDiscovery solutions to aid legal review, litigation support, docume...

    $100M

    $125M

    1K

    2001

    Chicago

  7. 07
    FanSided Inc

    FanSided Inc

    Digital Advertising Platforms

    Operator of sports and entertainment network on the internet. The company has unique sports and entertainment sites dedicated to team-specific, sport-specific, genre-specific and fanbase-specific coverage.

    $82M

    1K

    2007

    Chicago

  8. 08
    OneSpan

    OneSpan

    Accounting And Finance Software

    Vasco Data Security International designs, develops and markets digital services for identity, security and business productivity that protect and facilitate transactions online, via mobile devices and in-person. The company provides anti-fraud and digital

    $56M

    764

    1991

    Chicago

  9. 09
    Sphera

    Sphera

    Enterprise Software

    Sphera Solutions is a provider of software and information services intended to help customers advance operational excellence to create sustainable value. The company's SaaS-based platform offers software information services in the operational risk, envir

    $51M

    804

    2016

    Chicago

  10. 10
    Miller Heiman Group

    Miller Heiman Group

    Sales Software

    Provider of sales performance software. The company provides a framework for sales leaders to understand their performance gaps and prioritize initiatives. It provides sales performance improvement services that enable its clients to fundamentally improve

    $43M

    513

    1978

    Chicago

1-10 of 168

Next

What are the fastest growing companies doing?

83 of the fastest growing companies that also have the most revenue have a clear expansion revenue strategy. On average, sales reps are selling plans where starting contract value is $4,606.

Those same companies employ 1,678 sales reps that carry a quota. The most common compensation plan used by these companies is a 1:5 ratio of sales rep on target earnings (OTE) to quota. Meaning if a rep can earn $200k in base and commissions, quota target for that year is set at 5x, or $1m in new ARR closed.

If you’re going to build a high growth SaaS company, you need to figure out how to scale with quota carrying sales reps.

Which CEO’s are the most efficient capital allocators?

We can measure this a variety of ways. Which company has the most revenue per employee? What about dollars in revenue compared to dollars raised? What about time, which founder went from $0 to $10m the fastest?

Looking deeper at dollars in revenue compared to dollars raised, bootstrappers take the cake because they self fund (denominator zero). When we look at companies that have raised at least $1m, Actito is the clear winner generating $21m in revenue, growing 100% yoy, on just 1m raised ($.05 dollars raised for every $1 of revenue).

Omnisend comes in a close second with $.08 dollars raised for every dollar of revenue. Doing $19m as of December 2020. Proposify gets honorable mention with $0.46 dollars raised (3.25m) for every dollar of revenue ($7m).

The worst performers here are companies like YayPay with $3.68 dollars raised ($14m) per dollar of revenue ($3.8m). Many of the worst performers just did a round of funding and haven’t had a chance to deploy to drive growth yet. That makes this data less valuable but still illustrative.