[Hiring] Head of Sales @Modern AI

Role Description

You are the first dedicated seller at Modern. Not the first sales leader managing an existing team, the first person whose job is to figure out how this product gets sold, then prove it by selling it.

• Walking into real momentum with warm inbound and a customer base that loves the product.
• Building a repeatable playbook: who buys, why, how fast, at what price, and through which channel.
• Player role first: carry the number, run the deals, and write the playbook out of your own wins.
• Team comes later, hired alongside growth rather than ahead of it.

What You'll Own

• Pipeline generation and strategy: decide where the next hundred customers come from.
• Selling across four motions:
  • Self-serve / product-led: converting and expanding signups who found us on their own.
  • Mid-market brands: demo-led sales cycles with $5M–$50M+ commerce operators.
  • Enterprise and strategic accounts: longer cycles, multiple stakeholders, custom scope.
  • Agencies and partners: selling Modern as infrastructure other operators build on.
• Expert-level product fluency: trained on the full platform and expected to know its entirety.
• Pricing and packaging feedback: closest person to how buyers react to our pricing.
• Product feedback loop: bring reasons for lost deals to the product team with specificity.
• Building the team: hire and lead the reps who scale the proven motion.

What Success Looks Like

• First 30 days: Know the platform as well as anyone at the company; understand client usage.
• First 90 days: Define the ICP with evidence; document sales process and build a pipeline.
• First 6 months: Establish a repeatable motion with predictable conversion rates.
• First 12 months: Achieve consistent quota attainment and prepare a hiring plan.

Qualifications

• 5+ years of B2B SaaS sales experience with a specific track record.
• Genuinely technical: able to discuss APIs, data integrations, and attribution methodology.
• Familiar with the AI landscape and its implications for businesses.
• Experience selling in ambiguity and understanding the difference from established products.
• Understanding of commerce metrics like CAC, MER, LTV, and contribution margin.
• A builder mindset: prefer writing the first version over optimizing existing systems.

Bonus Points

• Experience as an early or first sales hire with insights on improvements.
• Experience selling both self-serve/PLG and enterprise motions at the same company.
• Experience selling into agencies or working at one.
• Background in martech, analytics, attribution, or commerce infrastructure.
• Used AI tooling to build prospecting or research workflows.

Why This Role

• A product with proof: selling a platform used by a portfolio of brands.
• Real ownership: defining the go-to-market strategy.
• Direct access to leadership: work closely with decision-makers.
• Honest about the stage: early-stage environment with potential messiness.

Benefits

• Competitive salary.
• Competitive health benefits.
• Unlimited PTO.
• Health and wellness credit.
• Fully remote work.
• A front-row seat at an AI-native company building the future of brand and creator collaboration.