Sales Director, Majors (TOLA)

About Us

At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of websites and other Internet properties for customers ranging from individual bloggers to SMBs to Fortune 500 companies. Cloudflare protects and accelerates any Internet application online without adding hardware, installing software, or changing a line of code. Internet properties powered by Cloudflare all have web traffic routed through its intelligent global network, which gets smarter with every request. As a result, they see significant improvement in performance and a decrease in spam and other attacks. Cloudflare was named to Entrepreneur Magazine’s Top Company Cultures list and ranked among the World’s Most Innovative Companies by Fast Company.

At Cloudflare, we’re not looking for people who wait for a polished roadmap; we’re looking for the builders who see the cracks in the Internet that everyone else has simply learned to live with. We value candidates who have the instinct to spot a "normalized" problem and the AI-native curiosity to create a solution using the latest tools. Our culture is built on iteration, leveraging AI to ship faster today to make it better tomorrow, while ensuring that every improvement, no matter how small, is shared across the team to lift everyone up. If you’re the type of person who values curiosity over bureaucracy, and that AI is a partner in solving tough problems to keep the Internet moving forward, you’ll fit right in.

Sales Director, US Majors (TOLA)

Location: Must live in Texas and willing to travel across Texas, Oklahoma, Louisiana, Arkansas (TOLA) Team Size: 6-8 Enterprise Account Executives Quota Responsibility: $15-20M annual recurring revenue Travel: Up to 50% within territory and to customer/company meetings

About the Role

Cloudflare seeks an experienced and dynamic First Line Sales Leader to drive and manage our US Enterprise Majors sales team covering the TOLA region. You will drive revenue across Fortune 500 accounts by combining modern value-selling with Cloudflare's AI-powered sales intelligence platform.

This role demands deep platform expertise in security, networking, and edge computing, exceptional executive relationship-building skills, and a proven track record of closing multi-million dollar deals in high-growth environments. You will develop top-tier sales talent, coach complex deals, forecast with precision, and deliver predictable revenue while maintaining Cloudflare's builder culture.

Additional Responsibilities

• Quota Ownership: Own a $15–20M annual quota across a team of 6–8 Enterprise Account Executives focused on the largest, most strategic accounts in TOLA.

• Forecast Precision: Maintain >90% forecast accuracy through disciplined weekly pipeline inspection using Salesforce, BoostUp, and Cloudflare's internal deal intelligence layers.

• Consistent Execution: Drive consistent quota attainment—meet or exceed quarterly and annual targets with predictable, repeatable execution.

• Modern GTM Strategy: Execute modern GTM strategies for Fortune 500 companies navigating digital transformation, security modernization, and AI infrastructure needs.

Key Responsibilities

Deal Leadership & Coaching

• Serve as a strategic deal coach and executive escalation point on complex, multi-million dollar platform deals.

• Guide reps through competitive displacement and large-scale platform adoption scenarios.

• Orchestrate cross-functional deal teams, partnering with Solutions Engineering, Customer Success, Product, and Legal to secure resources and drive technical wins.

• Navigate complex buying centers and coach reps on multi-threaded engagement across technical, economic, and executive stakeholders.

Team Development & Culture

• Recruit, onboard, and develop top-tier enterprise sales talent; build a high-performance, inclusive team culture.

• Mentor reps from ramp to top performer, providing hands-on coaching on discovery, value selling, executive engagement, and negotiation.

• Build bench strength by developing future leaders and promoting from within.

• Foster Cloudflare's unique culture—maintain our builder mentality, customer obsession, and collaborative approach even at scale.

Strategic Planning & Territory Management

• Develop territory plans that identify whitespace, prioritize accounts, and align resources for maximum impact.

• Leverage data-driven insights from Cloudflare's AI-assisted sales tools to optimize pipeline coverage, accelerate deal velocity, and improve win rates.

• Cultivate executive relationships at the CIO, CISO, and VP of Infrastructure levels across strategic accounts.

• Drive account expansion by building multi-year growth strategies that deepen platform adoption and increase customer lifetime value.

What You Bring

Required Experience

• 10+ years in B2B Enterprise SaaS/software sales, with deep expertise selling platform solutions to Fortune 500 companies.

• 3+ years as a First Line Sales Manager, building and leading top-performing enterprise teams (minimum 5 direct reports).

• Consistent 100%+ quota attainment with a proven track record as both an individual contributor and a team leader.

• Multi-million dollar deal experience, including a history of managing and closing $1M+ ARR contracts with Global 2000 organizations.

Domain Expertise

• Deep knowledge of security, networking, application delivery, or edge computing, with the ability to articulate complex platform value to technical and executive audiences.

• Experience selling to CIO, CISO, or VP of Infrastructure buyer personas; comfortable navigating both technical and economic buying centers.

• Solid understanding of modern enterprise infrastructure (e.g., cloud migration, Zero Trust security, SASE, application modernization, or edge computing).

Sales Excellence

• Expert-level proficiency in strategic sales methodologies such as MEDDPICC, Challenger, or similar value-selling frameworks with an emphasis on business outcomes and financial justification.

• Strong Salesforce.com competency; a daily user who leverages CRM data for pipeline management, forecasting, and rep coaching.

• Proficiency with a modern sales technology stack (e.g., Gong, Outreach, BoostUp, LinkedIn Sales Navigator).

• A data-driven mindset with the ability to analyze pipeline health metrics, conversion rates, deal velocity, and team performance indicators.

Leadership & Soft Skills

• Proven talent developer with a track record of coaching reps to promotion or top-performer status (including team members recruited into leadership roles elsewhere).

• Exceptional coaching and mentoring skills, with the ability to diagnose rep performance gaps and develop targeted improvement plans.

• High executive presence; comfortable engaging with C-level buyers and representing Cloudflare in high-stakes situations.

• Entrepreneurial spirit and a startup mentality; thrives in ambiguity, adapts quickly to change, and drives results in high-growth environments.

• Collaborative cross-functional leadership style that builds trust and partnership across sales, engineering, product, support, and finance teams.

What Success Looks Like

First 30 Days

• Complete team assessment and conduct 1:1s with all direct reports.

• Shadow 5+ customer calls and review the top 20 opportunities in the pipeline.

• Develop an initial territory plan with account prioritization and resource needs.

• Establish a consistent forecast cadence and pipeline inspection rhythm.

First 90 Days

• Achieve pipeline coverage of 3–4x quota across the team.

• Maintain a forecast accuracy of >85%.

• Complete at least one strategic hire or initiate recruitment for open headcount.

• Close or advance 3+ strategic deals valued at >$500K ARR.

First Year

• Achieve 100%+ of team quota with balanced contribution across all reps.

• Recruit and successfully ramp 2+ new Enterprise AEs.

• Develop and promote at least 1 team member.

• Maintain a >90% rep retention rate.

• Build 5+ referenceable customer relationships that provide case studies, references, or expand by >50%.

Compensation

Estimated annual salary of $380,000 - $480,000.

Equity

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

Benefits

Cloudflare offers a complete package of benefits and programs to support you and your family. Our benefits programs can help you pay health care expenses, support caregiving, build capital for the future and make life a little easier and fun! The below is a description of our benefits for employees in the United States, and benefits may vary for employees based outside the U.S.

Health & Welfare Benefits

• Medical/Rx Insurance

• Dental Insurance

• Vision Insurance

• Flexible Spending Accounts

• Commuter Spending Accounts

• Fertility & Family Forming Benefits

• On-demand mental health support and Employee Assistance Program

• Global Travel Medical Insurance

Financial Benefits

• Short and Long Term Disability Insurance

• Life & Accident Insurance

• 401(k) Retirement Savings Plan

• Employee Stock Participation Plan

Time Off

• Flexible paid time off covering vacation and sick leave

• Leave programs, including parental, pregnancy health, medical, and bereavement leave

What Makes Cloudflare Special?

We’re not just a highly ambitious, large-scale technology company. We’re a highly ambitious, large-scale technology company with a soul. Fundamental to our mission to help build a better Internet is protecting the free and open Internet.

Project Galileo : Since 2014, we've equipped more than 2,400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks that would otherwise censor their work, technology already used by Cloudflare’s enterprise customers--at no cost.

Athenian Project : In 2017, we created the Athenian Project to ensure that state and local governments have the highest level of protection and reliability for free, so that their constituents have access to election information and voter registration. Since the project, we've provided services to more than 425 local government election websites in 33 states.

1.1.1.1 : We released 1.1.1.1 to help fix the foundation of the Internet by building a faster, more secure and privacy-centric public DNS resolver. This is available publicly for everyone to use - it is the first consumer-focused service Cloudflare has ever released. Here’s the deal - we don’t store client IP addresses never, ever. We will continue to abide by our privacy commitment and ensure that no user data is sold to advertisers or used to target consumers.

Sound like something you’d like to be a part of? We’d love to hear from you!

Please note that applicants who progress to the offer stage of the interview process may be asked to attend an in-person interview within one of the Cloudflare Offices or Cloudflare Hubs. More details about this will be available at that stage of the interview process.

This position may require access to information protected under U.S. export control laws, including the U.S. Export Administration Regulations. Please note that any offer of employment may be conditioned on your authorization to receive software or technology controlled under these U.S. export laws without sponsorship for an export license.

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 hr@cloudflare.com or via mail at 101 Townsend St. San Francisco, CA 94107.