Account Executive (Mid-Market) AI Sales

Oscar; Austin (TX); Remote; USD 100,000 - 120,000; Full time

Job summary

Oscar, a fast-growing AI startup, seeks an experienced Account Executive to drive sales for mid-market companies. This remote role offers flexible work hours and the opportunity to sell innovative AI solutions. The ideal candidate has strong B2B SaaS sales experience and a proven track record of success.

Benefits

Equity in the startup

100% medical, dental, and vision coverage

$2K annual professional development stipend

Quarterly offsites and sales contests

Qualifications

• 3-6 years of B2B SaaS sales experience selling AI or related tech.
• Proven track record of exceeding sales quotas.
• Ability to influence senior-level stakeholders.

Responsibilities

• Manage the full sales cycle for mid-market companies.
• Exceed an annual quota of $1M+ in sales.
• Work closely with Solutions Engineers to demonstrate ROI.

Skills

B2B SaaS sales

Consultative sales

Engaging senior stakeholders

Articulating AI solutions

Job description

This range is provided by Oscar. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100,000.00/yr - $120,000.00/yr

Additional compensation types

Commission

Direct message the job poster from Oscar

Resource Consultant @ Oscar | BS in Advertising

Account Executive (Mid-Market) AI Sales | Remote & Flexible | Fast-Growing AI Startup

Ready to Sell the Future of AI?

Join a fast-growing, venture-backed AI startup helping mid-sized businesses unlock intelligent automation, predictive insights, and next-gen productivity. This is your chance to close high-value deals with a proven AI platform and make a real impact.

What You'll Do

• Own the full sales cycle for mid-market companies (200-1,000 employees) with typical deal sizes of $30K-$120K ACV
• Hit or exceed an annual quota of $1M+ with sales cycles averaging 60-90 days
• Partner closely with AI Solutions Engineers to build strong business cases demonstrating ROI within 3 months
• Lead discovery calls, deliver tailored demos, and close deals with VP and Director-level stakeholders
• Use top sales tools including Gong, Salesforce, and LinkedIn Sales Navigator
• Provide actionable feedback that helps shape product, marketing, and sales strategy

Why This Role Stands Out

• 100% remote + flexible hours, work where and when you perform best
• Immediate hiring, start making an impact this quarter
• Sell a proven AI platform with strong product-market fit and measurable client success
• Join a founder-led, high-velocity startup where your wins directly influence company growth

What We're Looking For

• 3-6 years of B2B SaaS sales experience, ideally selling AI, automation, analytics, or related technologies
• Proven track record of consistently meeting or exceeding quota in a consultative sales environment
• Experience engaging and influencing senior stakeholders (VP, Director-level and above)
• Ability to understand and articulate complex AI-driven solutions and their business value

Bonus: Experience in sales tech, Martech, analytics, or vertical SaaS

What You'll Get

• $100K-$120K base salary + uncapped commission with accelerators (OTE ~$200K+)
• Equity in a fast-growing AI startup
• 100% covered medical, dental, and vision for you and your dependents
• Remote-first culture with flexible and asynchronous work options
• $2K annual professional development stipend and ongoing AI sales enablement training
• Quarterly offsites, competitive sales contests, and a collaborative, team-driven environment
• Clear career path to Senior AE, Sales Manager, or Strategic Account roles

Apply Today

If you're a driven SaaS sales professional ready to close meaningful AI deals and accelerate your career, apply now. We review every qualified candidate carefully and reply promptly.

Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Business Development and Sales

• Industries

  Media and Telecommunications, Software Development, and Technology, Information and Internet

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Inferred from the description for this job

Medical insurance

Vision insurance

401(k)

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