Sr. Director, Enterprise & Partner Sales

About You

You are an experienced enterprise sales professional who knows how to build lasting relationships, develop new business, and navigate complex sales cycles. You are equally comfortable cultivating strategic partner relationships and working directly with enterprise buyers to understand their needs, build a compelling business case, and move opportunities from initial conversation through close.

You bring a consultative approach to selling and are skilled at engaging senior leaders and cross-functional buying committees across Finance, IT, Procurement, and other functions. You understand that successful enterprise sales requires more than a strong pitch—it requires thoughtful discovery, disciplined follow-through, and the ability to connect technical capabilities to meaningful business outcomes.

You take ownership of your pipeline, forecasting, and sales process. You are comfortable managing both a high-velocity partner motion and longer, more strategic enterprise opportunities, and you bring the organization, urgency, and accountability needed to successfully manage both.

Above all, you operate with integrity. You build trust with customers, partners, and internal teams by communicating clearly, following through on commitments, and approaching every relationship with a long-term mindset.

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 Senior Director, Enterprise & Partner Sales is a senior, quota-carrying individual contributor responsible for driving revenue through two coordinated sales motions: building and scaling a repeatable, partner-led wholesale channel for ApexConnect and developing and closing consultative Upstream Data Management, Reporting and Analytics opportunities with large enterprise customers.

This role owns the full sales lifecycle—from prospecting and qualification through discovery, demonstrations, solution scoping, business-case development, proposals, negotiation, procurement, close, and implementation handoff. The Senior Director will work closely with Marketing, Account Management, Product, Solutions, Finance, and Commercial teams to develop opportunities, structure commercially sound solutions, and ensure a seamless transition from sale to implementation.

This is a full-time, remote position based in the United States, with approximately 25–30% travel for partner development, enterprise client meetings, conferences, and internal planning.

Key Responsibilities

• Build and manage a repeatable partner channel for ApexConnect, including recruiting, enabling, and co-selling with SAP Concur, Emburse, Cytric, Microsoft, and other ERP, HCM, payroll, and payment integration partners.
• Prospect, develop, and close enterprise opportunities for Upstream Data Management, Reporting & Analytics, Spend Reporting, reconciliation, and benchmarking solutions.
• Navigate complex, multi-stakeholder buying groups across Finance, IT, Procurement, and executive leadership.
• Own the full sales cycle for both partner and enterprise opportunities, including qualification, discovery, demonstrations, solution scoping, business-case development, proposals, negotiation, procurement, and close.
• Lead consultative, ROI-driven discovery and develop business cases that translate technical capabilities into measurable customer value.
• Partner with Account Management on qualified opportunities and introductions from Cornerstone’s installed customer base while retaining full seller accountability throughout the sales cycle.
• Maintain accurate and disciplined Salesforce records, including pipeline, forecasts, opportunity stages, next actions, and separately measurable ApexConnect and Upstream funnels.
• Collaborate with Marketing, Product, Solutions, Finance, and Legal to confirm scope, pricing, margin, implementation requirements, and delivery capacity prior to customer commitment.
• Prepare complete, well-documented post-sale handoffs to support successful implementation and customer transition.
• Represent Cornerstone in partner meetings, enterprise client engagements, industry events, conferences, and commercial negotiations.

Qualifications

Education & Experience

• Bachelor’s degree or an equivalent combination of education and relevant professional experience.
• Minimum of 7 years’ experience in both partner/channel development and complex, direct enterprise selling.

Skills and Competencies

• Experience managing high-velocity and consultative sales motions simultaneously.
• Working knowledge of travel & expense, ERP/accounting, HCM/HRIS, payroll, payment, or related enterprise-system ecosystems; SAP Concur experience strongly preferred.
• Experience leading technical and business discovery involving APIs, file/SFTP workflows, data mapping, security requirements, and implementation dependencies.
• Strong executive-level communication, presentation, demonstration, negotiation, and contracting skills.
• Ability to conduct effective consultative discovery and engage senior executives and cross-functional buying groups.
• Demonstrated ability to build compelling business cases and translate technical capabilities into measurable business value without overpromising.
• Disciplined Salesforce opportunity management, pipeline development, forecasting, and stage governance.
• Strong organizational and prioritization skills, with the ability to manage two distinct and separately measured sales motions simultaneously.
• Collaborative, cross-functional approach with the ability to work effectively across Marketing, Account Management, Product, Solutions, Finance, Legal, and external partners.
• Strong personal accountability and sound commercial judgment, with the ability to communicate risk early and operate within approved product, pricing, and delivery parameters.
• Ability to operate with urgency, integrity, and a high degree of ownership throughout the sales process.

Equal Opportunity Employer Statement

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.