Enterprise Account Executive
Tools for this application (partners): Resume Corner (opens in new tab) (resume) · JobCopilot (opens in new tab) (tracking) · Frontline Coach (opens in new tab) (interview practice) · Prospeo (opens in new tab) (hiring manager's email) · Secta Labs (opens in new tab) (headshot) · Terac (opens in new tab) (side work) what each does
SalesJobs.Now is free for job seekers. Some links here pay us: a job ad network pays for a click on one of its sponsored jobs, a recruiting firm pays a referral fee when someone who came from here is hired, and a career tool pays a commission when you buy it. That costs you nothing and never lowers what you are paid. Roles whose links pay us can be placed higher in a list. "Featured roles" are openings an employer picked during a free trial with us; no employer can pay for that spot.
The posting
About the job
An early-stage AI company is automating the insurance industry's most tedious paperwork: organizing documents, reading policies and loss runs, and catching issues that would take hours to find manually. Reporting to the CEO, you will own the full enterprise sales cycle, from executive prospecting and multi-stakeholder discovery through tailored demos, procurement and close, and help build the enterprise motion from the ground up.
One of the first four Enterprise AEs at a top-tier-VC-backed insurance AI startup. $250K+ ARR deals, OTE $300K–$400K, remote US.
About the company
Early-stage AI company for the insurance industry, backed by top-tier VCs, automating the most tedious paperwork across a $1T+ industry.
Location and employment
Remote · Remote – US (near a major city; travel every 2 weeks) · Full-time
Compensation and work policy
Base salary: $150K–$200K
OTE: $300K–$400K (50/50 split)
Equity: Competitive
Work policy: Remote (US), preferably near a major city; travel every 2 weeks and as needed for customers
Work authorization: US citizens / green card holders only (no visa sponsorship)
- Base $150K–$200K
- OTE $300K–$400K (50/50)
- Competitive equity
Key responsibilities
- Own the end-to-end enterprise cycle: executive discovery, tailored demos, legal and procurement negotiation
- Build relationships across C-suite, operations, finance and IT in large accounts
- Close large, multi-stakeholder deals and hit or exceed revenue targets
- Develop account plans for strategic targets with Product, Engineering and Leadership
- Help define ICPs, sales stages and commercial frameworks
- Surface customer insights that shape the product roadmap
Must-haves
- Proven quota outperformance at a fast-scaling B2B SaaS startup with a strong sales program
- Strong tenure: average 2.5+ years per company
Requirements and qualifications
- 7+ years as an Enterprise AE at fast-scaling B2B SaaS startups
- Closed complex, multi-stakeholder $250K+ ARR deals with long cycles
- Rapid progression at the same company (e.g. SDR to Commercial to Mid-Market to Enterprise)
- Not mainly healthcare-vertical experience; not too senior (e.g. Sales Director)
- Nice to have: selling into commercial insurance or brokerage firms
- 7+ years of enterprise SaaS closing at fast-scaling startups
- History of high ACVs ($250K+) and long sales cycles
- Long tenures with steady promotions
- Comfortable with early-stage ambiguity and frequent travel
Why join
- Be one of the first four Enterprise AEs and shape the GTM playbook
- Sell a product that saves people hours of work every day
- Own complex $250K+ ARR deals with C-suite buyers
- Backed by top-tier VCs
- Be one of the first four Enterprise AEs and shape the GTM playbook
- Sell a product that saves people hours of work every day
- Own complex $250K+ ARR deals with C-suite buyers
- Backed by top-tier VCs
Interview process
- Hiring manager screen
- Hiring manager interview: enterprise deal methodology
- Sales presentation / role play
- Final round: culture and GTM strategy
Where you can sell from
Fully remote, for people based in United States.
Taken from AlwaysHired's own posting, last seen live on 14 Nov 2026.
AlwaysHired sales openings in your inbox
We look at AlwaysHired's careers page every 10 hours. Once a week you get its newest sales openings, plus close matches at other companies. Free, and one click stops it.
Sponsored jobs from job networks, which pay SalesJobs.Now when you click one.
About AlwaysHired
A recruiting firm that fills SDR, BDR and account executive seats at venture-backed US software startups, posting each role with its base and OTE but without the client's name.
Pay schedule: Salaried employment with the client company, base plus commission toward the stated OTE and usually equity; a Residency role is paid a monthly stipend through its training period first.
Carrying a quota today?
Hiring managers ask us for sellers with a certain segment, territory or track record. Fill in one profile, and when a seat matches it we make the introduction, never without your yes. It costs you nothing.