Director, Enterprise Sales (AI & Digital Natives)

WinsAbove; San Francisco (CA); On-site; USD 415,000 - 496,000; Full time

Benefits offered by this job

Equity plan

Incentive compensation

Job summary

Cloudflare is seeking an entrepreneurial Sales Director for the SF Bay Area, leading a high‑performing team to win and expand strategic accounts within the Digital Native and AI native landscape. You’ll guide senior technical buyers, architect modern network and AI solutions, and partner with Product, CS, Solutions Engineering, and Field Marketing to drive growth.

You will recruit and mentor top talent, manage a data‑driven pipeline, and personally close complex deals while aligning with

Qualifications

• 10+ years of direct B2B sales experience.
• 5+ years leading high‑performing field sales teams.
• Proven track record selling to CTOs, VPs of Engineering, and other technical buyers.

Responsibilities

• Achieve and exceed regional revenue targets for SF Bay Area Digital Native ecosystem.
• Recruit, coach, and develop a field sales team.
• Act as trusted advisor to CTOs and Engineering leaders on modern architectures and AI platforms.

Skills

B2B sales leadership

Executive coaching

Value selling to C-suite

Job description

Available Locations: SF Bay Area

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.

We are seeking an entrepreneurial Sales Director to lead this cornerstone segment, focusing on both the strategic acquisition and expansion of our highest impact accounts. In this role, you will scale and mentor a high performing team tasked with embedding Cloudflare as the core infrastructure layer for the world’s most innovative companies. This is a defining leadership opportunity to operate at the intersection of the AI landscape and cloud infrastructure, driving critical revenue growth for the company.

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.

You might be a good fit if you have:

• 10+ years of direct B2B sales experience, with 5+ years leading high‑performing teams deeply embedded in the Digital Native and AI‑native landscapes. You have 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.

Compensation

Compensation may be adjusted depending on work location.

• For Bay Area based hires: Estimated annual salary of $415,000–$496,000

This role is eligible to earn incentive compensation under Cloudflare’s Sales Compensation Plan. The estimated annual salary range includes the on‑target incentive compensation that may be attained in this role under the Sales Compensation Plan.

Equity

This role is eligible to participate in Cloudflare’s equity plan.

Cloudflare is proud to be an equal opportunity employer. We are committed to providing equal employment opportunity for all people and place great value in both diversity and inclusiveness. All qualified applicants will be considered for employment without regard to their, or any other person's, perceived or actual race, color, religion, sex, gender, gender identity, gender expression, sexual orientation, national origin, ancestry, citizenship, age, physical or mental disability, medical condition, family care status, or any other basis protected by law. We are an AA/Veterans/Disabled Employer.

Cloudflare provides reasonable accommodations to qualified individuals with disabilities. Please tell us if you require a reasonable accommodation to apply for a job. Examples of reasonable accommodations include, but are not limited to, changing the application process, providing documents in an alternate format, using a sign language interpreter, or using specialized equipment. If you require a reasonable accommodation to apply for a job, please contact us via e-mail at [e-mail] or via mail at 101 Townsend St. San Francisco, CA 94107.