Josh Gordon

Head of Sales (Partnerships)

AI Marketplace (Stealth via JAC Recruiting)

sales_managerOutbound HeavyStrategicOn-site📍 San Francisco, CA
Deal Size: $50K-$500K+ ACV (varies by partner tier)
Sales Cycle: 2-4 months
Posted by Josh Gordon

Overview

You're running sales and partnerships for one side of a two-sided AI marketplace that went from stealth to 8x revenue growth in a year. You'll inherit an AE team, raise their performance, and personally close key partnership deals while simultaneously building the entire operating system (territories, comp plans, metrics, playbooks) that lets them scale. The tension: move fast and sign partners vs. protect marketplace quality—you're measured on both.


Role Snapshot

AspectDetails
Role TypeHead of Sales - Player-Coach
Sales MotionOutbound-heavy partnerships, high-trust consultative
Deal ComplexityStrategic partnerships (multi-stakeholder, long-term agreements)
Sales Cycle2-4 months (partner vetting, integration planning, legal)
Deal SizeVaries by partner tier - likely $50K-$500K+ ACV in platform fees/rev share
Quota (est.)Team quota likely $3-5M ARR; personally carrying 30-40% of that

Company Context

Stage: Series A/B (~$25M raised from top-tier investors)

Size: 60 employees

Growth: 8x revenue growth last year, now scaling the team and formalizing GTM

Market Position: Early mover in AI marketplace space—building two-sided network effects before competition catches up


GTM Reality

Pipeline Sources:

  • 70% Outbound - Your team is cold calling, emailing, and LinkedIn-ing potential partners. This is founder-led sales transitioning to repeatable process.
  • 20% Inbound - Some word-of-mouth and demo requests from marketplace visibility, but not reliable volume yet
  • 10% Referrals - Existing partners introducing you to their networks

SDR/AE Structure: AE team owns full cycle (prospecting + closing). No dedicated SDRs yet—that's something you might build.

SE Support: Likely shared technical resources for complex integrations, but AEs need to be technical enough to handle most partner questions.


Competitive Landscape

Main Competitors: Other AI marketplaces (likely competing on supply quality, platform features, and rev share terms)

How They Differentiate: Unknown specifics, but at Series A with this growth, they likely have a quality/curation angle or unique AI capability

Common Objections: "Why not build this ourselves?" / "Your marketplace doesn't have enough supply/demand yet" / "Rev share terms" / "Integration effort"

Win Themes: Network effects kicking in, quality of existing partners, speed to market vs. building internally


What You'll Actually Do

Time Breakdown

Active Deals (30%) | Team Coaching (25%) | System Building (20%) | Recruiting/Hiring (15%) | Internal (10%)

Key Activities

  • Closing Strategic Partnerships Yourself: You're carrying 3-5 active deals at any time. These are high-stakes conversations with potential partners who can bring significant supply or demand. Expect multi-threading (legal, product, finance stakeholders), negotiating rev shares, and working through integration timelines.
  • Raising Team Performance: Your AE team exists but needs leveling up. You're in deal reviews, listening to calls, fixing their pitch, teaching them to qualify harder, and pushing back on deals that would hurt marketplace quality. Some might not make it.
  • Building the Operating System: You're creating territories (vertical? geographic? partner tier?), defining what a "qualified partner" means, setting activity metrics, building comp plans, and writing the first real playbooks. This is strategy work, not just management.
  • Protecting Marketplace Quality: Every partnership affects both sides of the marketplace. You're balancing "hit the number" pressure with "don't sign shitty partners who churn or hurt the product." This means saying no to revenue sometimes.
  • Hiring: You'll likely need to add 2-3 more AEs and maybe an SDR or ops person. You're writing job descriptions, interviewing, and selling candidates on joining.

The Honest Reality

What's Hard

  • Player-coach tension is real: You're trying to close your own deals while unblocking your team's deals while building systems while hiring. Most days feel like you're doing three jobs poorly instead of one well.
  • No playbook exists: Founder-led sales worked at 8x, but what they did won't scale. You're figuring out what's repeatable, which means lots of experiments fail and you're always behind on documentation.
  • Marketplace quality vs. quota: Your comp is probably tied to revenue, but your job security depends on partner quality. When you're at 80% of quota in Q4, signing a mediocre partner is tempting—but it'll bite you in six months.
  • Partner sales is slow and political: These aren't transactional deals. You're waiting on legal for four weeks. Product needs to prioritize their integration. Their executive sponsor goes dark for a month. Deals slip constantly.
  • Talent bar is high: At a 60-person Series A, every hire matters. You're competing with bigger names for talent, and your equity story only works if people believe in the vision.

What Success Looks Like

  • Team hits $3-5M ARR with 90%+ partner retention: You scaled revenue without breaking quality
  • 3-5 "lighthouse" partnerships: You landed marquee partners that attract other partners (network effects)
  • Repeatable process exists: A new AE can ramp in 60 days using your playbook; quota attainment across the team is 70%+
  • You're not the bottleneck: The team is closing deals without you in every call; you're coaching, not doing

Who You're Selling To

Primary Buyers:

  • VP/Director of Partnerships or BD at potential supply-side partners (if selling to AI service providers, agencies, etc.)
  • VP Product or Head of AI at demand-side partners (if selling to companies who need AI capabilities)

What They Care About:

  • ROI and effort: How much revenue/value does this partnership generate vs. how much work is it to integrate and maintain?
  • Marketplace liquidity: Is there enough supply/demand on the other side to make this worth it, or are they building your marketplace for you?
  • Platform risk: Are they betting on your startup staying alive? What happens to their integration if you get acquired or shut down?
  • Competitive dynamics: If they join, are their competitors also on the platform? Does that help or hurt them?

Requirements

  • 7+ years in sales or partnerships with at least 3 years leading a team (player-coach experience preferred)
  • Track record of personally closing strategic partnerships or enterprise deals—not just managing from the sidelines
  • Experience building sales process from scratch (playbooks, comp plans, territories) in a 20-100 person startup
  • Marketplace or platform sales background is a major plus (understanding two-sided dynamics)
  • Comfortable in ambiguity—Series A/B means things change weekly and you're often making it up as you go
  • Based in San Francisco and willing to be in-office (this is an onsite role)
  • Can coach and fire—you'll need to upgrade the team, which means hard conversations