Enterprise Account Executive

Overview

You sell Faire's B2B wholesale marketplace to enterprise retail brands - think regional chains, larger independent retailers, or brands with complex multi-channel distribution. You manage full sales cycles from first contact through close, navigating procurement, operations, buying teams, and finance. Deals involve getting brands to shift how they've done wholesale ordering for years.

Role Snapshot

Company Context

Stage: Late-stage venture-backed (likely Series D+)

Size: ~1,500 employees

Growth: Building out enterprise sales team specifically

Market Position: Leading B2B wholesale marketplace, disrupting traditional wholesale distribution and direct brand relationships

GTM Reality

Pipeline Sources:

• 60% Outbound - You prospect or SDR team generates intro meetings with enterprise targets
• 30% Inbound - Larger retailers discover Faire and request enterprise pricing/terms
• 10% Expansion - Existing mid-market accounts growing into enterprise tier

SDR/AE Structure: SDR team provides some meetings, but you're expected to self-source into named enterprise accounts

SE Support: Likely shared Solutions Engineer support for technical demos and integration discussions

Competitive Landscape

Main Competitors: Traditional wholesale distributors, direct sales reps from brands, legacy ordering systems, other wholesale platforms

How They Differentiate: Net 60-day terms for buyers, returns on unsold inventory, data on what's trending, consolidated ordering across brands

Common Objections: "Our current relationships work fine," "We can't change our procurement systems," "Our buyers like working with brand reps directly," "60-day terms hurt our cash flow"

Win Themes: Inventory risk reduction through returns, payment flexibility, access to emerging brands, streamlined operations, data-driven buying decisions

What You'll Actually Do

Time Breakdown

Prospecting (25%) | Active Deal Management (40%) | Internal Coordination (20%) | Demos/Meetings (15%)

Key Activities

• Navigate stakeholder silos: You're talking to procurement (who want cost savings), operations (who want easy ordering), buyers (who want unique products), and finance (who scrutinize payment terms). They often don't talk to each other. You're the connector.
• Send "trumpeting emails": Christopher's phrase for those check-in emails when deals stall. You're following up on the person who asked for ROI analysis three weeks ago, the ops person who wanted to see the integration docs, the buyer who said "circle back in Q2."
• Manage deals that won't die or close: Enterprise brands keep asking for more information, more demos, more case studies. They're interested but not moving. You're figuring out what's actually blocking them vs. what's a polite stall.
• Run discovery across departments: Enterprise deals require understanding their current wholesale process (how many suppliers, what systems, who places orders, what the workflow is) and building a business case for change.
• Build consensus when there isn't a single champion: You rarely get one decision-maker. You're assembling internal advocates, handling skeptics, creating materials for people to share internally.

The Honest Reality

What's Hard

• Stakeholders who won't move but keep engaging: The buying committee asks for another meeting, another demo for a different team, another reference call. They're not saying no, but they're not saying yes. You're stuck in limbo while your quota clock ticks.
• Complex distribution strategies: Enterprise brands have relationships with distributors, direct brand partnerships, regional suppliers, franchise requirements. Faire needs to fit into that complexity, which means custom terms, integrations, and selling change management.
• Long, unpredictable cycles: 4-8 months is the expectation, but enterprise deals slip quarters easily. Budget freezes happen. Priorities shift. Champions leave. You need the patience to stay with deals that might not close this year.
• You're selling process change, not just a product: These companies have procurement workflows built over decades. You're asking them to shift how they've always done business. That's organizational change, which is slow and political.
• Quota pressure with few at-bats: With 4-8 month cycles, you close maybe 6-10 deals per year. Each one matters a lot. You can't afford many losses.

What Success Looks Like

• You close $800K-1.2M in new ACV annually (2-3 large deals per quarter)
• Your pipeline is 4-5x quota because so many deals slip or stall
• You get good at diagnosing what's a real deal vs. what's just tire-kicking
• You build multi-threaded relationships so deals don't die when one person leaves or changes priorities
• You develop conviction and persistence - you stay with complex deals even when progress is slow

Who You're Selling To

Primary Buyers:

• VP/Director of Procurement at retail chains
• Head of Merchandising or Chief Buyer
• VP Operations (cares about ordering efficiency)
• CFO or Finance teams (scrutinize payment terms)

What They Care About:

• Procurement: Cost savings, supplier consolidation, streamlined processes
• Buyers: Access to unique/emerging brands, data on trends, reducing risk on untested products
• Operations: Easy ordering, system integrations, reducing admin overhead
• Finance: Payment terms impact on cash flow, fraud risk, credit exposure

Requirements

• Sold to enterprise accounts with 3+ stakeholders involved in decisions
• Managed complex sales cycles (4+ months) where deals stall and you had to diagnose blockers
• Don't need Databricks/Snowflake pedigree, but need rock-solid fundamentals - discovery, multi-threading, objection handling, business case building
• Know what to do when you're siloed with one stakeholder who keeps asking for info but won't bring in the broader team
• Gritty and persistent - comfortable staying with deals through slow periods and organizational politics
• Based in San Francisco for hybrid work