Sales Director, Majors (TOLA)

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