Director of Sales, AI Enterprise

Stitch Talent; New York (NY); Hybrid; USD 324,000 - 396,000; Full time

Benefits offered by this job

Equity

Guaranteed draw (first 3 months)

Uncapped commissions

Job summary

Stitch Talent is partnering with a high-growth AI company to hire a frontline sales leader to build and ramp a team of enterprise AEs. You will own the playbook, close multi-stakeholder deals, and drive the sales motion from first contact to production scale.

The role requires 8+ years in B2B software sales, 3+ years of frontline management, and a track record in fast-growing startups selling technical AI products to technical buyers. NY hybrid work is required.

Qualifications

• 8+ years of B2B software sales experience including complex enterprise deals.
• 3+ years of frontline management experience directly managing Account Executives.
• Track record at a high-growth startup (Series A+) where you built or scaled a team.
• Experience selling technical products (AI, APIs, infrastructure, or data platforms) to technical buyers.
• A true player-coach with low ego, high ownership, and comfort with ambiguity and fast pace.

Responsibilities

• Hire, ramp, and lead a team of enterprise AEs.
• Carry territory and close complex, multi-stakeholder deals with your team.
• Coach AEs to conduct credible technical conversations and close late-stage deals.
• Build the sales motion end-to-end from first contact to production-scale expansion.
• Partner with product, engineering, and marketing to unblock adoption and feed roadmap.
• Own forecasting and pipeline discipline and scale the team and playbook.

Skills

B2B software sales

Team leadership

Strategic selling

Executive engagement

Job description

Director of Sales, AI Enterprise (Head of Sales)

The opportunity

Stitch Talent is partnering with a high-growth AI company to hire a frontline sales leader. This is a build-from-scratch role: you will recruit and ramp a team of enterprise Account Executives, build the playbook, and close business alongside your team while the company scales through its next stages of growth. If you have led sellers at a fast-moving startup and want to build the team rather than inherit one, this is that seat.

Compensation

$360K+ OTE on a 50/50 base and commission split. Uncapped commission, with a guaranteed draw for the first 3 months, plus competitive equity.

What you will do

• Hire, ramp, and lead a team of enterprise AEs, recruiting top performers from your own network and holding a high bar from day one
• Carry territory and close complex, multi-stakeholder deals alongside your team, selling to technical and business buyers alike (CIOs, engineering leaders, founders)
• Coach AEs to run credible technical conversations, and step into late-stage deals to help get them across the line
• Build the sales motion end to end: first conversation, evaluation, proof of concept, negotiation, and production-scale expansion
• Partner with product, engineering, and marketing to unblock adoption and feed field patterns back into the roadmap
• Own forecasting and pipeline discipline, and scale the team, process, and playbook as the company grows through its next funding stages

What we are looking for

• 8+ years of B2B software sales experience, including complex enterprise deals
• 3+ years of frontline management experience, directly managing Account Executives
• A track record at a high-growth startup (Series A and beyond) where you built or scaled a team through rapid growth
• Experience selling technical products (AI, APIs, infrastructure, or data platforms) to technical buyers
• A true player-coach: low ego, high ownership, comfortable with ambiguity and a fast pace
• Based in New York able to work hybrid in-office

About Stitch Talent

Stitch Talent is a boutique recruiting firm that partners with high-growth technology companies on their most important go-to-market hires.