Account Executive - Enterprise

CAI Software, LLC•Pittsburgh, VT

32d•Onsite

About The Position

CAI Software builds digital work execution platforms and software solutions that help manufacturing businesses operate with greater clarity and control. Our people bring structure to complexity by replacing fragmented, paper-based processes with connected digital workflows that improve visibility, compliance, and decision-making in real industrial environments. With 45+ years of experience and a presence across 10+ countries, CAI combines deep industry understanding with practical technology. Our teams work across 15 core industries and support 5,000+ customers, guided by sound judgment, long-term thinking, and outcomes that endure. CAI Software is seeking a driven and results-oriented Account Executive to lead new business development and revenue growth within the manufacturing industry. This role is responsible for managing the full enterprise sales cycle, developing strategic customer relationships, and positioning our software and services as mission-critical solutions for print organizations. The ideal candidate brings deep experience selling enterprise MIS/ERP/MES solutions, thrives in complex sales environments, and is energized by building long-term customer partnerships.

Requirements

5–10 years of enterprise software sales experience (MIS/ERP/MES preferred).
Minimum 5 years of field sales experience with a proven track record of quota achievement.
Demonstrated success selling to senior executives.
Strong understanding of commercial print operations and industry trends.
Experience managing complex, multi-stakeholder sales cycles.
Proven ability to convert cold prospects into long-term, revenue-generating accounts.
Strong business acumen and ability to articulate software ROI to executive buyers.
Excellent presentation, negotiation, verbal, and written communication skills.
Highly self-motivated and able to operate independently.
Proven ability to collaborate cross-functionally to drive results.
Ability to manage and grow a territory at a strategic level.
Applicants must be authorized to work in the United States.

Nice To Haves

Bachelor’s degree in Business Administration or related field.
Experience with MEDDPICC or MEDDICC sales methodology
Experience achieving President’s Club or similar top-performer recognition.
Knowledge of CAI Software Graphic Communication’s products.

Responsibilities

Own and execute the full sales cycle, from prospecting and discovery through proposal development, ROI presentations, negotiation, and close.
Develop and manage a strong pipeline using Salesforce, providing accurate forecasts and clear visibility to leadership.
Achieve monthly, quarterly, and annual revenue targets while managing discount levels and operating within budget guidelines.
Expand market share and strengthen CAI’s presence within the commercial print sector.
Navigate complex enterprise sales cycles involving internal cross-functional teams including Sales, Product Management, Professional Services, Finance, Legal, and Executive Leadership.
Position CAI solutions strategically to senior leadership teams within commercial print organizations.
Engage regularly with prospects and customers through onsite visits, virtual meetings, webinars, and industry events.
Collaborate with other CAI sales teams to drive cross-selling initiatives.
Partner with Product, Engineering, and Marketing teams to align solutions with market demands.
Attend and actively participate in trade shows, open houses, and company-sponsored events.
Maintain deep knowledge of CAI products, competitive positioning, and industry trends.
Act as a market ambassador, positioning CAI as a leader in the commercial print space.
Build, qualify, and maintain a robust, self-sourced pipeline aligned to enterprise growth targets
Forecast accurately and consistently, managing opportunities through defined MEDDPICC framework sales stages with disciplined deal inspection
Drive deal progression by establishing clear next steps, mutual action plans, and executive alignment
Confidently navigate complex, multi-stakeholder decision processes and remove blockers to close