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

Cornerstone

Open Positions (1)

Marketing

Chief Revenue Officer