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 45 companies with combined revenues of $1.5B.

Together, Chicago SaaS companies employ over 8K employees, have raised $249.4M capital, and serve over 31K customers around the world.

$0 - $1M ARR
  1. BenchPrep $1.0M
  2. Integrify $1.0M
  3. Membrain $1.0M
$1M - $5M ARR
  1. Shotfarm $1.4M
  2. Visible $1.1M
  3. Enodo $1.1M
$5M - $10M ARR
  1. project44 $10.0M
  2. iManage $10.0M
  3. Revenew $10.0M
$10M+ ARR
  1. Flexport $861.0M
  2. Centro $142.8M
  3. Uptake $100.0M
  4. Relativity $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.

    $861.0M

    $1.3B

    10K

    2K

    2013

    Chicago

  2. 02
    Centro

    Centro

    Digital Advertising Platforms

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

    $142.8M

    $52.8M

    2K

    921

    2001

    Chicago

  3. 03
    ActiveCampaign

    ActiveCampaign

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

    $100.0M

    712

    2003

    Chicago

  4. 04
    Uptake

    Uptake

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

    $100.0M

    251

    2014

    Chicago

  5. 05
    Relativity

    Relativity

    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...

    $100.0M

    1K

    2001

    Chicago

  6. 06
    Dialogtech

    Dialogtech

    CRM and Related Software|Call Tracking Software

    DialogTech’s AI call tracking and conversation analytics helps digital marketers and agencies track ROI, drive sales, and personalize experiences.

    $40.0M

    $76.1M

    3K

    206

    2007

    Chicago

  7. 07
    Yello

    Yello

    HR Software

    talent acquisition software

    $30.0M

    $46.0M

    600

    216

    2008

    Chicago

  8. 08
    MediaFly

    MediaFly

    Sales Software

    Sales Enablement & Content Management Platform

    $18.7M

    $28.0M

    260

    120

    2006

    Chicago

  9. 09
    Hireology

    Hireology

    Talent Management Software

    The all-in-one hiring and talent management platform for businesses of all sizes. Centralize your hiring process to save time and build your best team.

    $14.4M

    $67.3M

    4K

    235

    2010

    Chicago

  10. 10
    project44

    project44

    project44 is the world’s leading advanced visibility platform for shippers and third-party logistics firms. project44 connects, automates and provides visibility into key transportation processes to accelerate insights and shorten the time it takes to tu

    $10.0M

    $90.5M

    100

    2014

    Chicago

1-10 of 45

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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.

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