Chief Revenue Officer

Role Overview

• Serve as Cornerstone’s executive commercial and sales leader
• Lead the evolution from a relationship-driven, services-led revenue model into a disciplined, scalable, intelligence-powered sales and commercial organization
• Own enterprise sales execution, revenue architecture, pipeline health and velocity, account management, renewals, channel partnerships, pricing strategy, and revenue operations
• Build a high-performing commercial organization capable of increasing revenue from $17M to $25–30M within three years while increasing the proportion of data and business intelligence revenue
• Transition the organization from founder-led and relationship-based selling to structured, process-driven enterprise sales execution
• Recruit, coach, and develop sales execution teams
• Institutionalize repeatable sales systems to reduce reliance on opportunistic selling
• Lead commercialization of Cornerstone’s business intelligence and data platform capabilities
• Increase BI/Data revenue mix from 40% to 50%
• Drive value-based messaging focused on customer outcomes rather than technology features
• Establish pricing and packaging discipline that reflects platform economics and eliminates low-margin custom engagements
• Partner with Marketing, Product, and Executive team to design and implement a scalable go-to-market model aligned with Cornerstone’s growth objectives
• Define and refine Ideal Customer Profiles (ICP), market segmentation, and Total Addressable Market (TAM)
• Establish disciplined qualification frameworks and standardized sales stages
• Build forecasting rigor and provide decision-ready revenue insights to executive leadership
• Protect and strategically expand top 5–10 enterprise accounts
• Reduce revenue concentration risk through new logo acquisition
• Work with teams to implement structured account management, cross-sell, and upsell programs
• Ensure long-term contract stability and customer retention
• Own and expand channel strategy beyond existing anchor partners
• Develop structured co-selling and embedded distribution partnerships
• Drive channel enablement programs that align partner success with Cornerstone growth
• Own CRM discipline, pipeline management, and revenue operations
• Implement scalable sales processes aligned with EOS operating rhythms
• Establish performance metrics and accountability standards across sales and account management
• Deliver accurate revenue forecasting and performance reporting to executive leadership
• Serve as a peer member of the executive team alongside the CEO, COO, CTO, EVP, Finance, and SVP, Marketing & Product Management
• Collaborate cross-functionally to align sales, marketing, product, and delivery
• Constructively challenge strategic assumptions while maintaining alignment with company vision and EOS structure
• Represent Cornerstone externally as a commercial leader within the enterprise travel and data intelligence ecosystem.

Requirements

• Bachelor’s degree in business, Marketing, Economics, Information Systems, or related field required
• MBA or advanced degree preferred
• Minimum 12 years of progressive sales leadership experience
• Demonstrated success scaling revenue from approximately $10M to $40M+
• Experience commercializing SaaS, data, analytics, or enterprise solution-based platforms
• Proven track record in building revenue operations and professionalizing pipeline management
• Experience operating in founder-led or growth-stage environments
• Experience balancing growth acceleration with margin discipline
• Ability to translate complex data and automation capabilities into differentiated customer value
• Comfort operating within EOS and accountability-driven cultures
• High tolerance for constructive tension and strategic challenge
• Proven accountability for multi-million-dollar revenue targets.

Benefits

• Equal Opportunity Employer
• Committed to creating a diverse environment
• Proud to be an equal opportunity employer