Mid-Market Account Executive - Chicago Sales · Chicago

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.

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.

You know the drill — you've sold SaaS before, you're 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.

• Owning the full sales cycle from prospecting to close — sourcing leads via cold outreach, Linked In, 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.

• 3+ 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.
• Comfortable with sales tools (Salesforce, Sales Loft, Linked In 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.

• The chance to sell a category-leading employer branding and recruitment platform.
• Competitive salary + uncapped commission.
• 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 you're a SaaS AE who wants uncapped earning potential, a team that has fun and hits numbers, and a hybrid setup that respects your time — we'd love to hear from you.

Apply today and let's build something great, together.