Sales Director, Majors (TOLA)

Cloudflare•San Francisco, CA

2d•Remote

About The Position

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.

Requirements

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.
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).
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.
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.

Responsibilities

Own a $15–20M annual quota across a team of 6–8 Enterprise Account Executives focused on the largest, most strategic accounts in TOLA.
Maintain >90% forecast accuracy through disciplined weekly pipeline inspection using Salesforce, BoostUp, and Cloudflare's internal deal intelligence layers.
Drive consistent quota attainment—meet or exceed quarterly and annual targets with predictable, repeatable execution.
Execute modern GTM strategies for Fortune 500 companies navigating digital transformation, security modernization, and AI infrastructure needs.
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.
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.
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.

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
Short and Long Term Disability Insurance
Life & Accident Insurance
401(k) Retirement Savings Plan
Employee Stock Participation Plan
Flexible paid time off covering vacation and sick leave
Leave programs, including parental, pregnancy health, medical, and bereavement leave