twentyAI
Compensation:
Up to $185,000 base + commission
About the Company TwentyAI has partnered with an early-stage, venture-backed e-commerce startup building a new category that helps brands sell earlier - even before inventory arrives. By giving brands more control over when they sell, we increase sell-through, reduce waste, and unlock new revenue. Our ~20-person, globally distributed team is led by repeat founders and operates with high ownership in a true build-from-scratch startup environment.
The Role: Head of Sales This is a hands-on, startup-first player-coach role for a sales leader who thrives in ambiguity and wants to build, not inherit, a sales function.
You’ll own new revenue growth end-to-end: defining the sales motion, generating demand, closing deals, and building a scalable, repeatable engine. You’ll lead a small but growing team of AEs and SDRs, manage a growth marketer and marketing budget, and partner closely with founders and product leadership.
This role is ideal for someone who has helped take a company from early traction through scale and is excited by the Series A → Series B journey.
What You’ll Do
Build and scale the sales motion from mid-market to enterprise
Lead, coach, and hire AEs and SDRs
Carry a quota and close deals while coaching the team
Partner with a growth marketer to launch new lead channels
Own forecasting, pipeline rigor, and KPIs
Present sales strategy and performance to the board
Attend industry events to build pipeline
Act as the voice of the prospect with Product and Founders
Refine messaging, positioning, and pricing based on feedback
What You’ll Bring
6+ years of sales experience (SaaS or Fintech preferred)
Early-stage or high-growth startup experience
2+ years of people management experience
Proven player-coach leadership style
A clear sales methodology (MEDDICC/MEDDIC, Challenger, or similar)
Ability to build lightweight process from scratch
Strong communication skills and ownership mindset
Experience in e-commerce (required)
Excitement to build and own a sales function from Series A to Series B
If this sounds like an interesting opportunity and a role where you can make a meaningful impact, we’d love to hear from you - apply to start the conversation.
#J-18808-Ljbffr
Up to $185,000 base + commission
About the Company TwentyAI has partnered with an early-stage, venture-backed e-commerce startup building a new category that helps brands sell earlier - even before inventory arrives. By giving brands more control over when they sell, we increase sell-through, reduce waste, and unlock new revenue. Our ~20-person, globally distributed team is led by repeat founders and operates with high ownership in a true build-from-scratch startup environment.
The Role: Head of Sales This is a hands-on, startup-first player-coach role for a sales leader who thrives in ambiguity and wants to build, not inherit, a sales function.
You’ll own new revenue growth end-to-end: defining the sales motion, generating demand, closing deals, and building a scalable, repeatable engine. You’ll lead a small but growing team of AEs and SDRs, manage a growth marketer and marketing budget, and partner closely with founders and product leadership.
This role is ideal for someone who has helped take a company from early traction through scale and is excited by the Series A → Series B journey.
What You’ll Do
Build and scale the sales motion from mid-market to enterprise
Lead, coach, and hire AEs and SDRs
Carry a quota and close deals while coaching the team
Partner with a growth marketer to launch new lead channels
Own forecasting, pipeline rigor, and KPIs
Present sales strategy and performance to the board
Attend industry events to build pipeline
Act as the voice of the prospect with Product and Founders
Refine messaging, positioning, and pricing based on feedback
What You’ll Bring
6+ years of sales experience (SaaS or Fintech preferred)
Early-stage or high-growth startup experience
2+ years of people management experience
Proven player-coach leadership style
A clear sales methodology (MEDDICC/MEDDIC, Challenger, or similar)
Ability to build lightweight process from scratch
Strong communication skills and ownership mindset
Experience in e-commerce (required)
Excitement to build and own a sales function from Series A to Series B
If this sounds like an interesting opportunity and a role where you can make a meaningful impact, we’d love to hear from you - apply to start the conversation.
#J-18808-Ljbffr