Director of Sales

Cayuse is seeking an experienced, hands-on Director of Sales to help lead and scale our commercial sales organization while continuing to directly drive new business.

Reporting to the Vice President of Sales, this role will operate as a true player/coach: owning a defined sales territory and individual revenue target while also leading, coaching, and developing a team of Account Executives.  The ideal candidate is an accomplished enterprise software seller who wants to remain close to customers and deals while expanding their impact as a sales leader. This individual will partner closely with the VP of Sales to drive execution against company revenue goals, improve sales consistency and discipline, develop talent, and create greater leverage across the sales organization.

Success in this role requires someone who can move seamlessly between leading the business and working the business- coaching an AE through a complex opportunity in one conversation and leading their own executive-level customer meeting in the next.

What You’ll Do

Lead and Develop the Sales Team

• Directly manage and coach a team of Account Executives responsible for new logo acquisition and strategic growth.
• Conduct regular 1:1s, pipeline reviews, deal strategy sessions, and performance conversations.
• Coach sellers on discovery, value articulation, executive engagement, competitive positioning, negotiation, and closing.
• Reinforce consistent use of Cayuse's sales methodology, including MEDDPICC and disciplined opportunity management.
• Develop individual coaching plans based on each seller's strengths, gaps, pipeline, and performance.
• Establish clear expectations and accountability while creating an environment where sellers can continuously improve.
• Identify performance risks early and partner with the VP of Sales on appropriate coaching and action plans.
• Support onboarding and ramping of new Account Executives as the organization grows.

Own and Close Strategic Business

• Carry an individual quota and manage a defined territory 
• Build and maintain a healthy pipeline sufficient to consistently achieve revenue targets.
• Lead complex enterprise sales cycles from initial discovery through evaluation, procurement, negotiation, and close.
• Engage senior and executive stakeholders across research, administration, compliance, IT, finance, and procurement.
• Develop strong business cases tied to institutional priorities, measurable outcomes, and the value of the Cayuse platform.
• Navigate complex buying committees, RFPs, competitive evaluations, and enterprise procurement processes.
• Model the sales behaviors, preparation, curiosity, and execution expected from the broader sales organization.

Drive Sales Execution

• Partner with the VP of Sales to inspect pipeline health, deal progression, forecast accuracy, and overall team performance.
• Maintain a clear understanding of what is required to achieve monthly, quarterly, and annual revenue targets.
• Identify pipeline gaps and work with Account Executives, BDRs, Marketing, and other teams to develop strategies to address them.
• Ensure opportunities have clearly identified business problems, measurable impact, decision criteria, decision processes, champions, economic buyers, competition, and next steps.
• Challenge assumptions and help sellers distinguish between activity and meaningful deal progression.
• Participate directly in strategic opportunities where leadership involvement can materially improve the likelihood of success.
• Maintain high standards for CRM hygiene, forecasting, opportunity management, and sales process adherence.

Partner Across the Organization

• Work closely with Solutions Consulting, Marketing, Customer Success, Strategic Account Management, Product, Professional Services, and Revenue Operations.
• Ensure resources are aligned appropriately to the highest-value opportunities.
• Bring market, customer, and competitive insights back into the organization to inform strategy and decision-making.
• Help identify opportunities to improve sales processes, tools, messaging, and organizational effectiveness.

• Provide visibility into team performance, pipeline health, deal risk, resource needs, and emerging issues.
• Step into leadership conversations, deal escalations, and cross-functional discussions when appropriate.
• Represent the sales organization professionally with customers, prospects, and internal leadership.

What We’re Looking For

• 12+ years of B2B SaaS or enterprise software sales experience, including demonstrated success closing complex, multi-stakeholder opportunities.
• Previous experience formally managing, coaching, or leading sales professionals.
• Demonstrated history of achieving or exceeding individual revenue targets.
• Experience operating in a player/coach capacity is strongly preferred.
• Strong understanding of enterprise sales methodologies such as MEDDPICC, Challenger, GAP Selling, or similar frameworks.
• Proven ability to inspect opportunities, identify gaps, and coach sellers toward concrete next actions.
• Experience navigating complex procurement processes, RFPs, negotiations, and executive-level buying committees.
• Strong forecasting, pipeline management, and business planning skills.
• Ability to coach with both empathy and accountability.
• Strong executive presence and communication skills.
• Comfortable operating in a fast-moving environment where priorities, opportunities, and resource requirements can shift.
• Experience selling into higher education, healthcare, research organizations, or similarly complex enterprise environments is strongly preferred.

What Success Looks Like

Success in this role is not measured solely by the performance of an individual territory or solely by team attainment. The Director of Sales will be expected to positively influence both.

Within the first year, this leader will have:

• Built credibility as both a successful seller and an effective sales coach.
• Established a consistent operating rhythm for their team around pipeline, forecasting, coaching, and deal strategy.
• Improved the quality and predictability of opportunities within their team's pipeline.
• Developed stronger sales discipline and greater consistency in how Account Executives execute complex opportunities.
• Personally built and converted a healthy pipeline within their assigned territory.
• Helped improve forecast accuracy and visibility into deal risk.
• Developed stronger sellers through regular, actionable coaching.
• Become a trusted extension of the VP of Sales who can independently lead important aspects of the sales organization.

Benefits

• Competitive Medical Benefits (PPO + HSA available)
• Vision, Dental, Short-Term Disability fully covered by Cayuse
• Unlimited PTO + Holidays + Flexible Work Schedule
• Remote Work Stipend
• Equal Paid Parental Leave
• 401k with Employer Matching
• Quarterly Wellness Reimbursement
• Remote Work Environment, supporting the Ultimate Employee Experience