Enterprise Account Executive

Overview

You'll sell recruiting services to startups in the AI/data/ML space that need to build technical teams in the US. Your buyers are founders, VPs of Engineering, and Head of People at companies that are either struggling to hire or scaling quickly. You're positioning flat-fee headhunting against contingency recruiters (20-30% per hire) and broken internal recruiting efforts.

Role Snapshot

Company Context

Stage: Bootstrap/Self-funded

Size: 3 employees

Growth: Early-stage agency building client base

Market Position: Small player in crowded recruiting space, differentiation on flat-fee model and cultural fit focus

GTM Reality

Pipeline Sources:

• 70% Outbound - cold LinkedIn outreach to founders/hiring managers at AI/data startups, email campaigns to HR leaders
• 20% Referrals - existing clients introducing you to other portfolio companies
• 10% Inbound - word of mouth, LinkedIn content from founder

SDR/AE Structure: Self-source everything. No SDR support.

SE Support: None. You handle all discovery, scoping, and proposal work yourself.

Competitive Landscape

Main Competitors: Contingency recruiting agencies (Hired, Terminal, specialized tech recruiters), internal recruiters, other flat-fee models

How They Differentiate: Flat-fee vs percentage-based pricing, focus on cultural fit and retention, woman-owned business

Common Objections: "We already have internal recruiting", "Why not just pay contingency on results?", "Can you really find technical talent?", "Your agency is too small"

Win Themes: Cost predictability, retention focus over volume placement, startup experience understanding, hands-on founder involvement

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (30%) | Proposals/Scoping (20%) | Internal (10%)

Key Activities

• Cold Outreach: You spend mornings on LinkedIn finding startups that recently raised funding or posted engineering jobs, then sending personalized connection requests and messages. You're targeting 30-50 new contacts per day.
• Discovery Calls: When someone bites, you run 30-45 minute calls to understand their hiring pain, how many roles they need filled, timeline urgency, and what they've tried before. You're qualifying whether they have budget and authority to sign.
• Proposal Work: You scope each search (role requirements, salary band, timeline), price it out (flat fee model), and send detailed proposals. This takes 2-3 hours per opportunity. You're competing against 2-3 other firms most of the time.
• Deal Nurturing: Following up with prospects who went dark, checking in on hiring urgency changes, sending case studies. Most deals don't close first conversation—they need to feel the hiring pain worsen.

The Honest Reality

What's Hard

• Most startups default to contingency recruiters because they don't pay unless there's a hire, making flat-fee a harder sell even if it's cheaper long-term
• You're competing against established brands and larger agencies with more placement track records
• Small team means no brand recognition—you're selling yourself and the founder's reputation
• Hiring needs are lumpy and urgent—feast or famine pipeline where companies either need 5 roles filled yesterday or nothing for months
• You'll hear a lot of "we'll handle this internally" then watch them post the same job for 6 months

What Success Looks Like

• Closing 3-5 new search contracts per quarter
• 60%+ of deals converting to repeat clients (multiple searches)
• Building referral network where portfolio companies introduce you to peer startups

Who You're Selling To

Primary Buyers:

• Founders/CEOs (Seed to Series B stage)
• VPs of Engineering or CTOs
• Heads of People/Talent at 20-100 person startups

What They Care About:

• Speed to hire (they have open reqs slowing product development)
• Quality over quantity (tired of reviewing bad contingency recruiter submissions)
• Cost predictability (flat fee vs 25% of salary)
• Cultural fit and retention (their last 2 hires didn't work out)
• US hiring expertise (they're international companies unfamiliar with US talent market)

Requirements

• 5+ years selling to startups (you understand founder mindset and how early-stage companies buy)
• Experience selling B2B SaaS, professional services, or recruiting solutions
• Knowledge of AI/data/ML space (you can speak credibly about technical roles and startup needs)
• Comfortable with 100% self-sourced pipeline and no inbound leads
• Track record closing $25K-100K deals with 4-8 week sales cycles
• Experience selling against established competitors as the smaller/newer player