Founding Enterprise Account Executive

Careerscape; Arlington (VA); On-site; USD 200,000 - 220,000; Full time

Benefits offered by this job

Equity/Stock options

Ownership stake offered

Job summary

Careerscape is seeking an Enterprise Account Executive in Arlington, VA to lead the full sales cycle from prospecting to close. You will build a pipeline from a standing start and engage senior executives at large enterprise accounts to drive growth.

The role demands strategic storytelling, rigorous deal discipline, and the ability to craft compelling business cases in a fast-paced environment.

Qualifications

• Bachelor's degree required.
• Enterprise accounts experience.
• Strong stakeholder management.
• Ability to build compelling business cases and RFP responses.

Responsibilities

• Build a pipeline from a standing start.
• Open and manage complex enterprise accounts.
• Close deals with executive stakeholders.
• Develop and present business cases and RFP responses.

Skills

Enterprise sales

Account management

Pipeline development

Executive presentations

Education

Bachelor's degree

Job description

...inaccurate outputs, weak governance or exposed data are unacceptable. They are hiring their first dedicated enterprise Account Executive. Salary: $300k OTE+ Equity

Responsibilities Build pipeline from a standing start Open complex enterprise accounts Sell to...

Commission Structure

Not disclosed — ask in interview

Commission

Structure not specified

OTE

$220k (range: $200k–$220k)

Ramp Period

Not mentioned — clarify timeline

Selling Motion

Enterprise

Requirements at a Glance

Bachelor's Degree · Required

Typical Day — Account Executive

Stakeholder meetings 3–5/week

Executive presentations 2–3/week

Business cases & RFPs 1–2/week

Champion coaching Daily

Estimates based on role type and selling motion — actual may vary by company.

Role Signals

Green Flags

• Equity/Stock Options
• Ownership stake offered

Tags

Interview Questions 5 —

• Walk me through your discovery process.
• How do you handle a prospect who goes silent mid-deal?
• Tell me about your largest closed deal and the sales cycle.
• How do you build business cases for stakeholders?
• Describe a deal you lost and what you learned.

Research Careerscape's product, recent news, and key competitors

Prepare 2-3 specific deal stories with quantifiable outcomes

Review the job description and map your experience to each requirement

Role Insights

This Account Executive position at Careerscape involves managing the full sales cycle from prospecting through close.

With OTE potential exceeding $220k, this role sits in the top tier of sales compensation. Expect rigorous performance expectations and a proven track record requirement.