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Cayuse

Director of Sales

RemoteUnited States only
Published
Role
Sales
Experience
Senior
Salary not disclosed
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Open to US only. Set where you work from to check your eligibility.

No BS summary

Experienced enterprise software sales leader (12+ years) to lead and scale a commercial sales team while also carrying an individual quota. Must have formal management experience and strong command of sales methodologies like MEDDPICC. Remote role.

Core skills

MEDDPICCEnterprise Sales

Required skills

ChallengerGAP SellingCRMForecastingPipeline ManagementRFPNegotiationExecutive Engagement

Optional skills

Experience operating in a player/coach capacityExperience selling into higher education, healthcare, research organizations, or similarly complex enterprise environments

What you'll do

  • Directly manage and coach a team of Account Executives
  • 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
  • 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
  • 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
  • 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 they require

  • 12+ years of B2B SaaS or enterprise software sales experience
  • 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
  • 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

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

Cayuse is a provider of cloud-based eRA (electronic Research Administration) solutions for research institutions.

EdTech
Salary not disclosed