Director of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead and mentor a team of Account Executives focused on acquiring new clients and driving strategic growth.

• Conduct regular one-on-one meetings, pipeline assessments, deal strategy discussions, and performance evaluations.

• Provide coaching to team members on discovery techniques, value presentation, executive engagement, competitive analysis, negotiation, and closing strategies.

• Strengthen Cayuse’s sales methodology, including MEDDPICC and disciplined opportunity management practices.

• Create coaching strategies, set accountability measures, identify performance risks, and assist in onboarding and ramping processes.

• Carry an individual sales quota while managing a specified territory.

• Develop and sustain a robust sales pipeline to meet revenue objectives.

• Oversee intricate enterprise sales cycles from initial discovery through to evaluation, procurement, negotiation, and closure.

• Engage with senior and executive stakeholders across various functions, including research, administration, compliance, IT, finance, and procurement.

• Navigate buying committees, respond to RFPs, conduct competitive evaluations, and manage enterprise procurement processes.

• Collaborate with the VP of Sales to monitor pipeline health, deal progression, forecast accuracy, and team performance.

• Identify gaps in the pipeline and work with Account Executives, BDRs, Marketing, and other teams to coordinate strategies.

• Ensure CRM accuracy, manage forecasting, oversee opportunity management, and adhere to sales processes.

• Work closely with Solutions Consulting, Marketing, Customer Success, Strategic Account Management, Product, Professional Services, and Revenue Operations.

• Provide insights into team performance, pipeline status, deal risks, resource needs, and emerging challenges.

• Act as a representative of the sales organization to customers, prospects, and internal leadership.

⛳️ Requirements

• Minimum of 12 years of experience in B2B SaaS or enterprise software sales, particularly in complex, multi-stakeholder scenarios.

• Prior experience in managing, coaching, or leading sales professionals is essential.

• Proven track record of meeting or exceeding individual revenue goals.

• Player/coach experience is highly preferred.

• Strong knowledge of MEDDPICC, Challenger, GAP Selling, or similar sales methodologies.

• Capability to analyze opportunities, identify gaps, and guide sellers towards actionable next steps.

• Familiarity with complex procurement processes, RFPs, negotiations, and executive-level buying committees.

• Excellent forecasting, pipeline management, and business planning abilities.

• Capacity to coach with empathy and accountability.

• Strong executive presence coupled with effective communication skills.

• Comfortable working in a fast-paced environment with changing priorities and resource needs.

• Experience in selling to higher education, healthcare, research organizations, or similarly complex enterprise settings is strongly preferred.

🏝️ Benefits

• Competitive Medical Benefits (PPO + HSA options available).

• Vision, Dental, and Short-Term Disability fully covered by Cayuse.

• Unlimited PTO along with Holidays and a Flexible Work Schedule.

• Remote Work Stipend provided.

• Equal Paid Parental Leave offered.

• 401k plan with Employer Matching contributions.

• Quarterly Wellness Reimbursement available.

• Supportive Remote Work Environment aimed at providing the Ultimate Employee Experience.