Enterprise Account Executive

Job Title

This is a hybrid sales and consulting role with a delivery mindset.

Responsibilities:

Create real, meaningful relationships with customers and partners.

Own pipeline, deals, and P&L for a set of enterprise accounts you are accountable for the number.

Lead client-facing teams through discovery, solutioning, delivery, and renewal.

Navigate the full enterprise deal lifecycle, including security reviews, procurement, legal, and contract execution.

Design solutions and write proposals and SOWs that are technically credible and commercially sound.

Advise clients on enterprise AI adoption with honesty about where initiatives typically fail and how to avoid it.

Serve as the connective tissue between clients, product, engineering, and marketing synthesizing field insights into actionable feedback.

Lead client engagements with a delivery orientation, not just a sales orientation.

Operate with radical candor internally and externally sharing real opinions and surfacing problems early.

Qualifications:

Real experience inside large enterprise organizations you understand how decisions get made, who the actual stakeholders are, and why initiatives stall.

Firsthand exposure to enterprise procurement complexity: security reviews, legal cycles, IT architecture approval, budget sign-off.

Demonstrated ability to wear multiple hats without needing a clear lane you figure out what needs doing and do it.

Track record of being part of teams that have delivered meaningful outcomes for clients, not just sold them.

Direct, honest communication style with the confidence to share real opinions with clients and leadership.

Solutions orientation you bring options and answers, not just problem descriptions.

Enough technical curiosity to hold your own with engineering teams and ask the right questions.

Genuine hunger this role will expand quickly for the right person.

Preferred Skills:

Thieves in expectation management and turning challenges or failure into opportunities.

Background in management consulting, systems integration, or professional services.

Experience with AI, data, or enterprise software platforms.

Familiarity with sovereign, private, or air-gapped deployment environments.

Technical background or engineering-adjacent experience.

Industry depth in aviation, manufacturing, logistics, or other regulated sectors.

Experience in a growth-stage or startup environment.

We at webAI are committed to living out the core values we have put in place as the foundation on which we operate as a team. We seek individuals who exemplify the following:

Truth - Emphasizing transparency and honesty in every interaction and decision.

Ownership - Taking full responsibility for one's actions and decisions, demonstrating commitment to the success of our clients.

Tenacity - Persisting in the face of challenges and setbacks, continually striving for excellence and improvement.

Humility - Maintaining a respectful and learning-oriented mindset, acknowledging the strengths and contributions of others.

Benefits:

We strive to provide competitive benefits to all employees. The benefits listed in this posting generally apply to U.S.-based employees. For employees hired outside the United States, benefits may vary based on local law, country-specific requirements, and the employment platform or entity through which the employee is hired.

Competitive salary

Comprehensive health, dental, and vision benefits package

401(k) match

Equity options

$200/month Health & Wellness stipend

Continuing Education support

$500/year Function Health subscription

Free parking for in-office employees

Flexible Time Off (FTO)

Parental leave for eligible employees

Supplemental life insurance

webAI is an Equal Opportunity Employer and does not discriminate against any employee or applicant on the basis of age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances. We adhere to these principles in all aspects of employment, including recruitment, hiring, training, compensation, promotion, benefits, social and recreational programs, and discipline. In addition, it is the policy of webAI to provide reasonable accommodation to qualified employees who have protected disabilities to the extent required by applicable laws, regulations and ordinances where a particular employee works.