Strategic Enterprise Account Executive


Chicago, IL, USA

Account Executive

Oct 29

Are you a full-cycle sales professional driven by an innate desire to help clients find solutions to real problems?

Do you proudly "geek out" on the latest disruptive recruiting and HR technology?

Are you someone with the unique blend of grit, patience, and compassion it takes to sell into Fortune 500 enterprise companies? (and a track record of success to prove it!)

At Paradox, we believe when you get the people thing right you can build teams that can change the world. We’re a high-performance culture with a laser focus on building world-class products and a team that our clients love. Our flagship product, Olivia, is the AI assistant helping companies around the world reimagine the way they hire: conversations instead of job applications, automatic interview scheduling, and so much more.

Recently named one of Forbes’ Top 500 Startup Employers, we’re looking for top performers who have a track record of success and want to build a company together as we continue our triple-digit growth.

Selling disruptive, first-of-its-kind software to Fortune 500 companies is hard work, and the Enterprise Sales team at Paradox lives for that challenge. We’re searching for an ambitious full-cycle sales professional who, like us, is motivated by the opportunity to drive meaningful, positive change among the world’s biggest enterprise organizations. You’ll help us transform the entire industry of recruiting and hiring by building relationships, serving as a trusted advisor, and introducing our conversational AI software to the most beloved brands around the world.

Sound like your dream job? We want to hear from you!

As An Enterprise Account Executive, You Will

  • Leverage your extensive SaaS sales and HR tech industry experience to drive new business opportunities with global enterprise organizations and Fortune 500 companies
  • Manage the full sales cycle with enterprise clients using a consultative, relationship-driven approach
  • Navigate complex org structures and tech stacks across the business as you lead discovery conversations, product demos and solution discussions
  • Listen and ask questions to gain a deep understanding of clients’ recruiting and hiring challenges
  • Present creative solutions through storytelling and consultative conversations
  • Educate potential clients and their teams on the transformative power of our AI products, building a coalition of Paradox enthusiasts throughout the organization

Experience & Skills Required

  • 7+ years in full-cycle SaaS/B2B sales roles, with experience selling software solutions to large enterprise and Fortune 500 companies
  • 7+ years of experience selling disruptive recruiting software and deep knowledge of the enterprise HR tech landscape (e.g. ATS, HCM, and CRM platforms)
  • A consultative, relationship-driven sales philosophy and an innate desire to help clients
  • Ability to navigate complex organizational structures, long sales cycles, and multiple decision-makers
  • Track record of long-term success and upward mobility in previous roles
  • Ability to travel to clients (post-COVID)

Why You Should Work At Paradox

  • Work side by side with passionate, purposeful people - Talent is our DNA and we pride ourselves on having the best!
  • Ability to make a big impact on a growing organization and drive your own growth
  • The opportunity to build the next big thing in recruiting technology
  • Internal and external professional development, coaching, and continuous education opportunities

You must be logged in to to apply to this job.


Your application has been successfully submitted.

Please fix the errors below and resubmit.

Something went wrong. Please try again later or contact us.

Personal Information


View resume



We are Paradox, the AI company that believes recruiting is a people game.