Director, Enterprise Sales (AI & Digital Natives)

About the role

The Enterprise AI and Digital Natives segment is Cloudflare's fastest growing and highest visibility market. This segment is dedicated exclusively to the largest organizations in the modern tech economy including premier SaaS platforms, hyperscale digital marketplaces, and leading AI labs. This is a deep infrastructure, developer centric play where technical alignment and deep engineering partnerships are our most critical currencies, resulting in Cloudflare’s largest and most complex enterprise agreements.

Responsibilities

• Own and exceed regional revenue targets, driving both high-velocity new logo acquisition and strategic account expansion within the SF Bay Area Digital Native ecosystem.
• Recruit, coach, and develop a world-class field sales team, driving the local hiring needs and instilling a high-tempo culture tailored to technical buyers and engineering leaders.
• Act as a hands-on trusted advisor to CTOs and Engineering leaders, guiding them on setting up modern, secure network architectures and AI platforms utilizing Workers AI and R2 storage.
• Effectively articulate Cloudflare’s value proposition across our entire portfolio, including Workers AI, R2 storage, advanced network security, and developer platforms.
• Partner closely with global functional leadership across Product, Customer Success, Solutions Engineering, and Field Marketing to design and execute regional go-to-market strategies.
• Act as a key executive sponsor for high-growth accounts, maintaining a tight business cadence for forecast calls, deal reviews, and customer account audits while personally helping close complex deals.

Requirements

• 10+ years of direct B2B sales experience, with 5+ years leading high-performing teams deeply embedded in the Digital Native and AI-native landscapes.
• A proven track record of managing field sales organizations through complex, technical sales cycles with hyper-growth startups and disruptive tech giants.
• A proven track record of mentoring teams in value selling to the C-suite, CTOs, VPs of Engineering, and technical buyers within the IaaS, computer networking, or developer platform space.
• A deep understanding of modern application architecture, serverless computing, network security services, and how AI companies utilize compute, data storage, and edge infrastructure.
• Strong leadership and interpersonal communication skills, with a history of driving innovation, managing pipeline health, and mentoring teams in fast-paced, dynamic environments.
• Hands-on experience navigating hybrid sales motions that blend product-led growth and developer adoption with top-down enterprise execution.
• A history of thriving in rapidly evolving markets where you can maintain an entrepreneurial spirit, turn ambiguity into clear strategies, and act as both a strategic influencer and operational leader.

Qualifications

• BS/BA degree in Computer Science, Business Administration, or related field.
• Experience with AI and machine learning technologies.
• Experience working with SaaS platforms and digital marketplaces.
• Experience in enterprise-level sales and account management.
• Experience in developing and executing go-to-market strategies.

Skills

• Strategic thinking and ability to drive complex, multi-year initiatives.
• Excellent communication and presentation skills, with the ability to effectively communicate technical concepts to non-technical audiences.
• Ability to build and manage strong relationships with key stakeholders, including C-level executives and engineering leaders.
• Experience with sales enablement and training programs.
• Experience with Salesforce or similar CRM systems.

Benefits

Cloudflare offers a competitive benefits package including:

• Health, dental, and vision insurance
• Flexible spending accounts for healthcare and dependent care expenses
• 401(k) retirement savings plan with company match
• Comprehensive paid time off policy
• Employee assistance program
• Parental leave
• Flexible work arrangements
• Professional development opportunities
• Regular team-building activities and events

Pay

Estimated annual salary of $415,000-$496,000, depending on work location. For Bay Area based hires.

Schedule

Full-time, Monday-Friday, 8am-5pm.