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Posted October 5, 2026, closed October 24, 2026. Check out similar open roles below.

Senior Account Executive

Clera
Chicago, IL
RemoteCareer-pivot friendly

Who this role is best for

Strong fit for B2B sales professionals who have sold AI data products to AI labs and can thrive in a lean, founder-led environment.

Best fit for

  • B2B sales professionals with a history of closing deals in AI data solutions
    — “Direct experience selling AI data products, such as annotation, evaluation, reinforcement learning, or expert talent solutions, to frontier or emerging AI labs.”
  • Candidates who have worked at AI data vendors and can navigate technical sales challenges
    — “Experience at an AI data vendor is required; familiarity with healthcare or clinical data and enterprise AI sales is a plus.”

Things to consider

  • Visa sponsorship is limited to candidates with at least 24 months of work authorization remaining in the US
    — “Visa sponsorship is available for eligible candidates with at least 24 months of work authorization remaining.”
  • Remote work is possible but the primary location is Chicago, requiring potential travel or relocation
    — “Remote within the United States. Primary location: Chicago, Illinois.”

How to stand out

  • Highlight your ability to structure and negotiate deals across varying contract sizes and customer needs
    — “Structure and negotiate deals suited to a range of customer needs and contract sizes.”
  • Demonstrate adaptability and ownership in ambiguous environments, especially with founder-led teams
    — “Comfort working with ambiguity and taking ownership in a founder-led, early-stage company.”
Pace · Fast PacedCollaboration · MediumAutonomy · MediumDecision Impact · Individual

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • built relationships with AI labs
  • structured and negotiated deals
  • closed new business
Typical background
2 to 10 years of B2B sales experienceExperience selling AI data products

Skills & requirements

Required

B2B SalesAI Data Products SalesCustomer Relationship ManagementNegotiationDeal StructuringClosing Deals

Preferred

Healthcare Data SalesEnterprise AI Sales

Stack & domain

AI Data ProductsSalesNegotiationContract StructuringAIHealthcareClinical DataEnterprise AI Sales

About the role

Original posting from Clera via Ashby

ABOUT THE ROLE

Join the early sales team at an early-stage AI data solutions company. You will own customer relationships with frontier and emerging AI labs, helping them source specialized data and expertise for model training and evaluation.

WHAT YOU'LL DO

  • Build relationships with research, post-training, and data teams at AI labs.
  • Understand customer needs across expert annotation, reinforcement learning environments, model evaluations, and expert talent.
  • Structure and negotiate deals suited to a range of customer needs and contract sizes.
  • Close new business and grow customer relationships over time.
  • Work directly with the founder in a lean, early-stage environment.

WHAT WE'RE LOOKING FOR

  • Approximately 2 to 10 or more years of relevant experience, including quota-carrying B2B sales and a record of closing deals.
  • Direct experience selling AI data products, such as annotation, evaluation, reinforcement learning, or expert talent solutions, to frontier or emerging AI labs.
  • Existing relationships with AI lab research, post-training, or data teams.
  • Experience at an AI data vendor is required; familiarity with healthcare or clinical data and enterprise AI sales is a plus.
  • Comfort working with ambiguity and taking ownership in a founder-led, early-stage company.

COMPENSATION & BENEFITS

Base salary is $160,000 to $200,000 annually, with $320,000 to $400,000 OTE (on-target earnings, base plus variable). Visa sponsorship is available for eligible candidates with at least 24 months of work authorization remaining. TN, F-1 OPT, STEM OPT, and H-1B transfers may be considered; new H-1B petitions are not available.

LOCATION

Remote within the United States. Primary location: Chicago, Illinois.

Source: Clera careers (Ashby)

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