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 35 companies with combined revenues of $1.5B.

Together, Chicago SaaS companies employ over 8K employees, have raised $249.4M capital, and serve over 121K customers around the world.

$0 - $1M ARR
  1. Fippex $1.0M
  2. Nimbulis $1.0M
  3. ADSHIFT $1.0M
  4. BenchPrep $1.0M
$1M - $5M ARR
  1. Shotfarm $1.4M
  2. Visible $1.1M
  3. Enodo $1.1M
$5M - $10M ARR
  1. Revenew $9.4M
  2. Ycharts $8.4M
$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.

    $861M

    $1B

    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.

    $143M

    $53M

    2K

    921

    2001

    Chicago

  3. 03
    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

  4. 04
    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

  5. 05
    ActiveCampaign

    ActiveCampaign

    Marketing Automation Software

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

    $100M

    $120M

    90K

    712

    2003

    Chicago

  6. 06
    Dialogtech

    Dialogtech

    CRM and Related Software

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

    $40M

    $76M

    3K

    206

    2007

    Chicago

  7. 07
    Yello

    Yello

    HR Software

    talent acquisition software

    $30M

    $46M

    600

    216

    2008

    Chicago

  8. 08
    ShowingTime

    ShowingTime

    Real Estate Software

    ShowingTime is the real estate industry’s leading showing management and market stats technology provider, serving more than 950,000 agents and more than 250 MLSs.

    $25M

    $2M

    278

    1999

    Chicago

  9. 09
    project44

    project44

    Supply Chain & Logistics Software

    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

    $23M

    $91M

    254

    2014

    Chicago

  10. 10
    iManage

    iManage

    Enterprise Software

    Get more from your firm's data with iManage's leading edge document management, data security, and AI solutions. Let us transform how your team works.

    $23M

    800

    2015

    Chicago

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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.