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106 startups and scale-ups in Chicago are hiring salespeople right now, with 189 live roles between them, 86 of them opened in the last 30 days. Pick the ones you want and Haystack's AI agent fills in each employer's application for you.

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84% of candidates get an interview within 14 days568,056 candidatesRated 4.8/5 on G2
Chicago · SalesLive roles today
  • FIFilevine logo
    FilevineScale-up · 501-1,000 staff8 roles
  • AVAvePoint logo
    AvePointScale-up · 1,001-5,000 staff8 roles
  • ENEngine logo
    EngineScale-up · Remote-first7 roles
  • HOHorizon3ai logo
    Horizon3aiScale-up · 51-200 staff5 roles
  • NENexHealth logo
    NexHealthScale-up · 201-500 staff5 roles
  • ECEnergy CX logo
    Energy CXScale-up · Hybrid4 roles

and 100 more companies on the list

106 companies hiring now

Ranked by live roles (account executives, SDRs and BDRs, account managers, sales engineers and partnership managers). Every company is a startup or scale-up; recruitment agencies are left out. Press Auto apply on any role and Haystack's AI agent fills in that employer's form for you.

The top 40 of 106 companies, most live roles first.

  1. FIFilevine logo

    Filevine

    Scale-up501-1,000 staffTechnology & SoftwareOffice-first

    8roles8 opened this month

    Filevine provides legal practice management software and AI solutions to streamline law firm operations and enhance efficiency.

    All 8 roles at Filevine

  2. AVAvePoint logo

    AvePoint

    Scale-up1,001-5,000 staffTechnology & SoftwareHybrid

    8roles3 opened this month

    AvePoint provides data management solutions for Microsoft 365, helping organisations protect, manage, and mobilise their data for security, compliance, and efficiency.

    Replied to 50% of the applications Haystack's agent sentAll 8 roles at AvePoint

  3. ENEngine logo

    Engine

    Scale-upRemote-first

    7roles4 opened this month

    Engine is a creative engine for growth, offering integrated marketing and communications services to help businesses transform and achieve measurable results.

    Replied to 58% of the applications Haystack's agent sentAll 7 roles at Engine

  4. HOHorizon3ai logo

    Horizon3ai

    Scale-up51-200 staffTechnology & SoftwareRemote-first

    5roles1 opened this month

    Horizon3.ai provides autonomous penetration testing solutions to help organisations identify and fix security vulnerabilities and improve cyber resilience.

    All 5 roles at Horizon3ai

  5. NENexHealth logo

    NexHealth

    Scale-up201-500 staffHealthcare

    5roles

    NexHealth aims to accelerate innovation in healthcare by building tools and infrastructure that support doctors and developers in delivering exceptional patient experiences.

    All 5 roles at NexHealth

  6. ECEnergy CX logo

    Energy CX

    Scale-upHybrid

    4roles4 opened this month

    Energy CX aims to redefine the energy brokerage sector through cutting-edge technology, advanced analytics, and innovative solutions.

    All 4 roles at Energy CX

  7. SSSprout Social logo

    Sprout Social

    Scale-up1,001-5,000 staffRemote-first

    4roles4 opened this month

    Sprout Social transforms how businesses and organisations use social media and social intelligence to connect with their customers.

    All 4 roles at Sprout Social

  8. FIFin logo

    Fin

    Scale-up1,001-5,000 staffOffice-first

    4roles2 opened this month

    Fin aims to deliver perfect customer experiences by providing an AI-powered customer agent across the entire customer journey.

    Replied to 100% of the applications Haystack's agent sentAll 4 roles at Fin

  9. HAHarvey logo

    Harvey

    Scale-up

    4roles2 opened this month

    Harvey builds AI-powered solutions for legal professionals to boost efficiency and accuracy and help shape the future of professional services.

    All 4 roles at Harvey

  10. SASV Academy logo

    SV Academy

    Startup51-200 staffEducationHybrid

    4roles2 opened this month

    SV Academy trains job seekers for sales development roles in the technology industry and provides job placement assistance after program completion.

    All 4 roles at SV Academy

  11. GOGong.io logo

    Gong.io

    Scale-up1,001-5,000 staffTechnology & SoftwareOffice-first

    4roles1 opened this month

    Gong.io provides a revenue intelligence platform that uses AI to analyse customer interactions, helping sales teams gain insights and improve performance.

    All 4 roles at Gong.io

  12. BMBlufox Mobile logo

    Blufox Mobile

    Scale-upOffice-first

    4roles

    Blufox Mobile specialises in mobile application development and digital transformation solutions, creating user-centric mobile experiences and helping businesses leverage technology.

    All 4 roles at Blufox Mobile

  13. DGDouble Good logo

    Double Good

    Scale-upHybrid

    3roles3 opened this month

    Double Good is a technology company that provides an online fundraising platform for youth organisations, also supporting a foundation for children with special needs.

  14. LSLife Space Digital logo

    Life Space Digital

    StartupHybrid

    3roles3 opened this month

    Life Space Digital deploys digital screens in offices, multi-family residences, and retail environments to deliver content and targeted advertising.

  15. LOLoadsmart logo

    Loadsmart

    Scale-up

    3roles3 opened this month

    Reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.

  16. VEVerkada logo

    Verkada

    Scale-up1,001-5,000 staffTechnology & SoftwareOffice-first

    3roles1 opened this month

    Verkada provides an integrated cloud-based security platform that combines physical security and operational insights for organisations.

  17. FIFinout logo

    Finout

    Startup51-200 staffTechnology & SoftwareHybrid

    3roles

    Finout provides a FinOps platform that unifies cloud and SaaS costs, helping companies manage and optimise their cloud and AI spend.

  18. INInstawork logo

    Instawork

    Scale-up501-1,000 staffRecruitment & Staffing

    3roles

    Instawork connects businesses with qualified hourly workers, creating economic opportunities and helping businesses fill staffing gaps.

  19. MPMirum Pharmaceuticals logo

    Mirum Pharmaceuticals

    Scale-up201-500 staffPharmaceuticals & BiotechRemote-first

    3roles

    Mirum Pharmaceuticals is a biopharmaceutical company focused on developing and commercialising treatments for rare liver diseases.

  20. OPOpply logo

    Opply

    Scale-upHybrid

    3roles

    Opply aims to modernise how scaling food and consumer goods brands buy ingredients, solving market inefficiency for SMB brands.

Every startup has its own application form.

Applying to ten of these companies means ten careers sites and ten forms, each asking the same things in a different order. Haystack's AI agent fills them in from your CV and your answers, and asks you when a question needs you.

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Let the agent apply
Ashby application · Account ExecutiveApplying as Sarah · example
Full name
Sarah Okonkwo
Email
sarah.okonkwo@myapplications.to
Resume
Sarah_Okonkwo_Resume.pdf · tailored to this role
Are you legally authorized to work in the United States?
Yes
Will you now or in the future require visa sponsorship?
No
What are your salary expectations?
$120,000 a year
Application sent. 0 fields typed by Sarah. The reply lands in her Haystack inbox.
Haystack agent
  • Reading the job description
  • Tailoring your resume to the role
  • Filling in the Ashby form
  • Answering the employer's questions
  • Checking the employer accepts automated applications
  • Submitted. The reply will land in your inbox

Interviews landed at leading employers

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The agent applies. You interview.

84%get an interview within 14 days

of candidates who let the agent apply for them are invited to interview within two weeks.

12form fields answered

per application, from your resume and your answers. You type none of them.

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50 applications a month on Haystack Pro, at 15 minutes each, done for you.

Interview rate: candidates invited to interview within 14 days of their first application. Fields measured across applications the agent sent in the last 30 days. Hours back assume 15 minutes an application by hand.

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A woman taking an interview call at her laptop
sarah.okonkwo@myapplications.to
Reddit
Interview: Customer Success Manager
Now
Thu, Oct 30 · 2:00–2:45 PM · Google Meet
AcceptedMaybeDecline
Added to your calendar
Figma
Thanks for applying to Figma
Tue
Notion
We've received your application
Mon

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Which startups are hiring salespeople in Chicago?

As of October 2026, 106 startups and scale-ups in Chicago are hiring salespeople, with 189 live roles between them. The most are at Filevine, AvePoint, Engine, Horizon3ai, NexHealth. The full list on this page is rebuilt every day from the employers' own careers sites.

How is this list made?

Haystack reads the careers sites of more than 30,000 employers every day. This list takes the live roles in Chicago for account executives, SDRs and BDRs, account managers, sales engineers and partnership managers at companies recorded as startups or scale-ups, leaves out recruitment agencies, and ranks the companies by how many of those roles they have open.

Can I apply to all of these at once?

Not in one click, and you wouldn't want to. With Haystack Auto Apply you upload your resume once and pick the roles you want; Haystack's AI agent then fills in and submits each employer's own application form, asks you when a question needs your answer, and every reply lands in your Haystack inbox. Nothing is sent without your say-so.

Your resume once.
Then every role that fits.

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