Regional Sales Director

Cognition.AI; New York (NY); On-site; USD 250,000 - 450,000; Full time

Job summary

Cognition.AI is seeking a Regional Sales Director to lead a team of Account Executives driving net-new and expansion revenue across Fortune 500 accounts. This is a player‑coach role reporting to the VP of Sales, in the field, not dashboards.

You will set strategy, close large deals, recruit 3–6 AEs, and collaborate with Deployed Engineering, post‑sales, and executives to win in AI.

Qualifications

• 7+ years of enterprise software sales experience.
• 2+ years of experience managing a team of Account Executives.
• Proven track record closing $1M+ ARR deals with Fortune 500 accounts.
• Experience selling to CIO/CTO/SVP‑VP Engineering.
• Proficiency in MEDDIC or similar enterprise sales methodology.
• History of overachievement against quota as IC and manager.
• Ability to recruit and close top sales talent.

Responsibilities

• Own quarterly and annual bookings quota for your territory across new logo and expansion.
• Manage a pipeline of $5M–$20M+ ARR opportunities with average deal sizes of $1M+.
• Forecast using MEDDIC and maintain deal hygiene and stage discipline.
• Lead and coach a team of 3–6 Enterprise AEs; run weekly 1:1s and deal reviews.
• Define territory segmentation and account prioritization; build vertical messaging.
• Develop executive relationships within key accounts and align with Marketing, Product, and post‑sales teams.

Skills

Enterprise software sales

Team leadership

F500 selling

MEDDIC

Deal closing

Executive relationships

Recruitment

Job description

We are an applied AI lab building end-to-end software agents.

We're the makers of Devin, the first AI software engineer, and Windsurf, the AI-native IDE. Together, they represent our vision for collaborative AI teammates that enable engineers to focus on more interesting problems and empower teams to strive for more ambitious goals.

Our team is small and talent-dense. Among our founding team, we have world‑class competitive programmers, former founders, and leaders from companies at the cutting edge of AI including Scale AI, Palantir, Cursor, Waymo, Tesla, Lunchclub, Modal, Google DeepMind, and Nuro.

Building Devin is just the first step—our hardest challenges still lie ahead. If you’re excited to solve some of the world’s biggest problems and build AI that can reason on real‑world tasks, apply to join us.

The Role:

We're looking for a Regional Sales Director to lead a team of Account Executives driving net‑new and expansion revenue across Fortune 500 accounts.

This is a player‑coach role in a high‑ownership environment. You will set strategy, close alongside your team on the largest deals, and build one of the most consequential enterprise sales teams in AI. You will report directly to the VP of Sales and work in close partnership with Deployed Engineering, post‑sales, and executive leadership.

This is not a role for someone who manages from a dashboard. The right person is in the field, knows every major deal, and has a point of view on how to win.

What You’ll Own:

Revenue Execution

• Own quarterly and annual bookings quota for your territory across new logo acquisition and expansion
• Manage a pipeline of $5M–$20M+ ARR opportunities with average deal sizes of $1M+
• Forecast accurately using MEDDIC; maintain deal hygiene and stage discipline
• Be in the rooms that matter -- EBCs, executive dinners, key negotiations -- alongside your AEs

Team Leadership

• Recruit, hire, and develop a team of 3-6 Enterprise AEs
• Run rigorous weekly 1:1s and deal reviews focused on qualification, strategy, and close plans
• Build a team culture of accountability, intellectual curiosity, and competitive drive
• Identify performance gaps early and coach or make personnel changes decisively

Territory and GTM Strategy

• Define territory segmentation and account prioritization within your vertical
• Build vertical‑specific messaging and competitive positioning in partnership with Marketing and Product
• Partner with post‑sales to expand the installed base and protect renewals
• Develop executive relationships within key accounts that extend beyond the AE layer

Cross‑functional Influence

• Serve as the voice of the field – surface product gaps, competitive intelligence, and customer insights to leadership
• Collaborate with Deployed Engineering to scope and deliver compelling POCs and technical evaluations
• Work with Legal and Finance on complex contract structures, MSAs, and non‑standard terms

What We’re Looking For:

Required

• 7+ years of enterprise software sales experience, including at least 2 years managing a team of high‑level AEs
• 2+ years of experience successfully selling into F500 companies
• Demonstrated track record closing $1M+ ARR deals with F500 accounts in a complex, multi‑stakeholder sales motion
• Experience selling to CIO, CTO, SVP/VP Engineering, or equivalent technical executive buyers
• Proficiency in MEDDIC or a comparable enterprise sales methodology
• History of overachievement against quota as both an IC and a manager
• Ability to recruit and close top‑tier sales talent in a competitive market

Strongly Preferred

• Vertical‑relevant domain expertise – working knowledge of buyer personas, budget cycles, and procurement dynamics in the vertical
• Prior experience selling developer tools, AI/ML platforms, cloud infrastructure, or adjacent technical products
• Track record at a high‑growth startup or scale‑up (Series B through IPO stage)
• Familiarity with the competitive landscape in AI coding, including GitHub Copilot, Cursor, Windsurf, and emerging agentic tools

What This Is Not:

• A role where you manage by report and review dashboards. You will know every deal.
• A role with an established, fully staffed team. You will hire some of your AEs.
• A role where the product sells itself. Devin is a paradigm shift – you will need to sell the vision before the prospect fully understands the category.
• A slow‑moving environment. We move fast, change direction when we learn something, and expect the same from leadership.

Equal Opportunity

Cognition is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic under applicable law. We are committed to providing reasonable accommodations for candidates with disabilities throughout the hiring process - please let us know if you need any.