Enterprise Account Executive

Overview

You're a full-cycle Account Executive selling an AI product to enterprise companies (1000+ employees). You'll manage strategic deals from initial contact through close, typically working 8-15 active opportunities with 6-12 month sales cycles. Reporting to the Director of Sales in SF or NY, you're joining a team where every rep hit quota last year with 200%+ average attainment.

Role Snapshot

Company Context

Stage: Series B (just raised $55M, $75M total funding)

Size: ~50-100 employees (typical for this stage/ARR)

Growth: $10M+ ARR, actively hiring 4 AEs across two markets, just announced major funding round

Market Position: Fast-growing AI company moving upmarket - adding enterprise motion to proven mid-market success (200%+ attainment, zero missed quotas suggests strong product)

GTM Reality

Pipeline Sources:

• 60-70% Self-sourced outbound: You're hunting named accounts, building relationships over months, working referrals and warm intros
• 20-30% SDR support: Some SDRs booking intro meetings at target accounts, but enterprise deals require your own relationship building
• 10% Inbound: Occasional hand-raisers from large companies who found them through press, funding announcements, or product-led growth motion

SDR/AE Structure: Minimal SDR support for enterprise - you're mostly hunting your own accounts and building multi-year relationships

SE Support: Shared SE pool, probably 1-2 SEs supporting 4-6 enterprise AEs. You'll need to be strategic about when to bring them in.

Competitive Landscape

Main Competitors: Unknown without company specifics, but likely competing against established enterprise platforms plus well-funded AI startups

How They Differentiate: Strong product (evidenced by 200%+ MM attainment) but enterprise buyers will want deeper proof - more case studies, security reviews, enterprise SLAs

Common Objections: "You're too early for our enterprise standards", "Need more Fortune 500 references", "Procurement requires features you don't have yet", "We have an incumbent relationship", "Budget cycle doesn't open until Q3"

Win Themes: Likely winning on innovation and ROI vs legacy solutions, but will need to overcome Series B maturity concerns

What You'll Actually Do

Time Breakdown

Active Deals (40%) | Strategic Prospecting (35%) | Internal (25%)

Key Activities

• Strategic account planning: Researching target accounts, mapping org charts, identifying champions, building multi-quarter engagement strategies. 10-12 hours/week on outbound to 50-100 named accounts.
• Running complex deal cycles: Managing 8-15 active deals with 5-10 stakeholders each. You're coordinating executive briefings, technical deep-dives, security reviews, legal negotiations, and procurement processes. Most deals have 8-15 touchpoints before close.
• Executive relationship building: Taking calls with VPs and C-suite to understand strategic priorities. You're positioning the AI solution as strategic initiative, not just a tool. This means understanding their business deeply and speaking their language.
• Internal coordination: Weekly pipeline reviews with Director, quarterly business reviews with executives, working with CS on expansion opportunities, collaborating with product on feature requests from enterprise prospects, coordinating SE and executive resources for key meetings.

The Honest Reality

What's Hard

• Long, unpredictable cycles: You'll think a deal is closing in Q2, then it slips to Q4. Champions leave. Budgets freeze. Priorities shift. You need 3-4x pipeline coverage because most deals take 2-3 quarters longer than you expect.
• Series B challenges in enterprise: You'll hit "too early for us" objections. Procurement will ask for features they don't have yet. Security reviews will surface gaps. IT will want references from 3+ Fortune 500 companies they don't have.
• Smaller team, fewer resources: You don't have the army of SEs, customer success managers, and executive sponsors that established enterprise vendors have. You'll need to be scrappy and creative.
• 200%+ bar: You're joining a team with exceptional performance. The expectation is you'll match it in enterprise, which is harder and less predictable than mid-market.

What Success Looks Like

• Closing $300-400K per quarter in new enterprise ACV (hitting 200%+ attainment in year 2; year 1 may be ramping)
• Building pipeline of $4-6M with 10-15 qualified Stage 3+ opportunities
• Winning 2-3 deals per quarter at average deal size of $150-250K

Who You're Selling To

Primary Buyers:

• C-suite or SVP level for strategic initiative approval and budget
• VP/Director level champion who owns the problem and will drive internal adoption
• IT/Security for technical validation and compliance
• Procurement for contract negotiation and vendor management

What They Care About:

• Strategic value and ROI: Enterprise buyers want to see how this AI initiative ties to company-wide goals, not just departmental efficiency
• Risk mitigation: Security, compliance, data privacy, vendor stability (Series B concerns), implementation risk, what happens if you get acquired
• Proof at scale: Case studies from companies their size, references from similar industries, evidence the tech works at their volume/complexity
• Total cost and commitment: Not just software cost but professional services, change management, training, integration costs, multi-year commitment

Requirements

• 5-7+ years enterprise software sales experience with track record of $1M+ annual quota attainment
• History of closing deals $150K+ with 6+ month sales cycles
• Experience navigating complex enterprise organizations with C-suite engagement
• Comfortable selling for Series B company into Fortune 1000 accounts (you'll face "too early" objections)
• Strong business acumen - can speak to strategic initiatives, not just features
• Based in or willing to relocate to San Francisco or New York