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Senior Account Executive - Chicago

Teamtailor

Location: Chicago, US

Posted: 2026-07-22 (employer's date)

First seen by DirectJobSource: 2026-08-20

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#### Join us to shape the future!

Teamtailor is a global Employer Branding and ATS SaaS platform used by over 13,000 companies, 250,000 users, and available in 90 countries worldwide. 🌍 We are looking for a Senior Account Executive to join our Chicago team

Working at Teamtailor means joining a dynamic, fast-paced tech company where impact isn't just a buzzword — it's how we operate. Everyone here has real ownership over the outcomes they drive, and real say in how we grow. 🎉🥳

We've built a team full of different backgrounds, experiences, and perspectives, because that's what makes us better — not despite our differences, but because of them. If you want in on helping companies and people make life-changing decisions together, we want to hear from you. 👫

#### Why SaaS AEs love it here:

You know the drill — you've sold SaaS before, you're really good at it, and you're tired of environments that feel like a grind. Here's what's different at Teamtailor Chicago:

  • A full sales cycle you actually own - You prospect, run the demo, negotiate, and close. Full autonomy, full commission credit.
  • Real hybrid, not fake flexible - In office Tuesday–Thursday at our Chicago flagship HQ, work from home Monday and Friday. You get face time with a genuinely fun team and two days a week to lock in and sell without commute drag.
  • Uncapped earnings, no ceiling games - Competitive base + uncapped commission.
  • A market leader, not a "maybe it'll work out" startup - 13,000+ customers, 200,000+ users, 90 countries. You're selling something companies already trust, which means shorter sales cycles and warmer conversations.
  • A team that celebrates wins loudly - Our guiding stars are to be different, personal, and kind — and that shows up in how we hit quota together, not against each other. Deal closed? Bell rings, team cheers, coffee's on us. ☕️

#### What you'll be doing:

  • Owning the full sales cycle from prospecting to close — sourcing leads via cold outreach, LinkedIn, and social selling, then running meetings, negotiating, and signing new business.
  • Consistently hitting (and beating) monthly sales targets.
  • Teaming up with Marketing, Partnerships, and Customer Success to keep deals moving and customers thrilled.
  • Staying sharp — leveling up on product knowledge, industry trends, and your own sales craft.
  • Bringing your energy and ideas to the team, because we build this culture together.

#### What you bring:

  • 5+ years of B2B SaaS sales experience (HR tech/ATS experience is a big plus, but not required).
  • A track record of managing pipelines with real discipline — you forecast accurately and don't let deals go cold.
  • Solid experience with sales tools (Salesforce, SalesLoft, LinkedIn Sales Navigator, Cognism, Apollo, Slack, Notion).
  • A genuine drive to hunt for new business and close it — you like the chase as much as the win.
  • The relationship-building instincts to turn a first call into a long-term customer.

#### What we offer:

  • Competitive salary + uncapped commission. 💵
  • The chance to sell a category-leading employer branding and recruitment platform. 🥰
  • Real career growth in a fast-scaling company, with training and support that actually helps. 🎗️
  • A talented, supportive team that has each other's back. 🎤
  • A true hybrid setup at our flagship North America HQ in Chicago Downtown — in office Tue/Wed/Thu. 🏙️
  • A culture built on being different, personal, and kind — with genuinely good vibes, not just a ping-pong table. 🎉

If this opportunity excites you, we look forward to receiving your application!

![](https://images.teamtailor-cdn.com/images/s3/teamtailor-production/original-v3/image_uploads/81b6be3d-cbde-4b48-988b-d73b3695efa9/original.jpeg)