About you

You are an experienced sales leader energized by building—someone who sees opportunity in complexity and brings structure, clarity, and momentum to evolving environments. You have a deep understanding of enterprise SaaS and solution-based go-to-market strategies, along with a proven ability to build and scale revenue engines. You bring rigor to sales enablement, forecasting, and qualification, and have a track record of elevating and transforming sales organizations. You operate with executive presence and influence, aligning cross-functional teams to drive accountability and sustained growth.

About Us

Cornerstone is a highly respected B2B software company in the travel, expense and data management space – one of the largest and most vibrant sectors in the world. We’ve built a great reputation for delivering solid technology that scales globally, tailored to the needs of each customer. Our reputation is based on a deep understanding of the industry, our technology, our hands-on, approachable culture and the highest level of integrity.

This legacy is our launchpad to innovation. We are bringing a game-changing data management platform to market, we have recently re-branded and we’re expanding into new markets. Why? Data issues are the biggest obstacle facing our industry. And we’re the best ones to solve the problem because we live it side by side with our customers every day, at scale. So we’re taking on the challenge. It’s what we do.

Position Overview

The Chief Revenue Officer (CRO) serves as Cornerstone’s executive commercial and sales leader, accountable for transforming and scaling Cornerstone's end-to-end revenue engine. The CRO will lead the evolution from a relationship-driven, services-led revenue model into a disciplined, scalable, intelligence-powered sales and commercial organization.

Reporting to the Chief Operations Officer (COO) and partnering closely with the CEO, this role owns enterprise sales execution, revenue architecture, pipeline health and velocity, account management, renewals, channel partnerships, pricing strategy, and revenue operations. The CRO is responsible for building 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.

Key Responsibilities

Commercial Transformation:

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.

Data & Intelligence Monetization:

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.

Revenue Strategy & Architecture:

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.

Account Portfolio & Expansion Strategy:

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.

Channel & Partnership Leadership:

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.

Revenue Operations & CRM Governance:

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.

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.

Qualifications

Education and Experience

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.

Skills and Competencies

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.

Equal Opportunity Employer

Cornerstone Information Systems is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Cornerstone Information System

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Chief Revenue Officer