Chief Revenue Officer

Cornerstone Information Systems•Bloomington, IN

About The Position

Cornerstone is a highly respected B2B software company specializing in travel, expense, and data management. They are known for delivering scalable, tailored technology globally, built on a deep understanding of the industry, advanced technology, a hands-on culture, and high integrity. The company is currently innovating by launching a new data management platform, has recently rebranded, and is expanding into new markets to address critical data issues within the industry. The Chief Revenue Officer (CRO) will serve as Cornerstone’s executive commercial and sales leader, responsible for transforming and scaling the company's entire revenue engine. This role involves transitioning the organization from a relationship-driven, services-led model to a disciplined, scalable, and intelligence-powered sales and commercial operation. Reporting to the Chief Operations Officer (COO) and collaborating closely with the CEO, the CRO will oversee enterprise sales execution, revenue architecture, pipeline health and velocity, account management, renewals, channel partnerships, pricing strategy, and revenue operations. A key objective for the CRO is to build a high-performing commercial organization capable of increasing revenue from $17M to $25–30M within three years, while also boosting the proportion of data and business intelligence revenue.

Requirements

Bachelor’s degree in business, Marketing, Economics, Information Systems, or related field required.
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.

Nice To Haves

MBA or advanced degree preferred.

Responsibilities

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.