Enterprise Account Executive

About Digital.ai

At Digital.ai, we are revolutionizing enterprise software delivery. A 9-time leader in the Gartner Magic Quadrant for Enterprise Agile Planning, we enable large-scale organizations to drive digital transformation through AI-powered DevSecOps. Our products empower over 50% of the Fortune 100 and market leaders across industries like financial services, retail, technology, manufacturing, and government. By unlocking the power of predictive insights and secure software delivery, we help our clients accelerate their innovation and stay ahead of the digital curve.

About the Role

This is a strategic new business sales role focused on acquiring and expanding relationships with large enterprise organizations across North America. You will represent Digital.ai's full portfolio of DevSecOps, Application Security, and Continuous Testing solutions, selling into complex environments and engaging senior technology and business leaders.

You will own the entire sales cycle, from prospecting and opportunity creation through executive alignment, negotiation, and close. Success in this role requires the ability to navigate sophisticated buying processes, build consensus across multiple stakeholders, and drive transformational initiatives within Global 2000 organizations.

You'll be joining a high-performing team with deep technical expertise, strong leadership support, and significant investment in growth across the Americas. This is an opportunity to help shape our enterprise go-to-market strategy while influencing how the world's largest organizations modernize software delivery in the age of AI.

What You'll Do

• Drive new logo acquisition and strategic growth across Digital.ai's enterprise software portfolio.


• Develop and execute territory and account plans focused on Global 2000 and large enterprise organizations.


• Engage C-level executives, VP-level technology leaders, and key business stakeholders to identify transformational opportunities.


• Manage complex, multi-stakeholder sales cycles from initial engagement through contract execution.


• Build and maintain a robust pipeline through proactive outbound prospecting, networking, and partner engagement.


• Lead value-based and consultative sales conversations focused on business outcomes and ROI.


• Utilize MEDDPICC methodology to qualify opportunities and drive forecast accuracy.


• Partner closely with Sales Engineering, Product Management, Customer Success, and Marketing to deliver compelling customer solutions.


• Successfully displace incumbent vendors and position Digital.ai as a strategic technology partner.


• Consistently achieve and exceed annual revenue targets.

What You Bring

• 7+ years of enterprise software sales experience, with a proven track record of exceeding quota in complex new business environments.


• Demonstrated success selling into large enterprise and Global 2000 accounts with deal sizes ranging from mid-six figures to multi-million dollars.


• Experience engaging executive stakeholders, including CIOs, CTOs, CISOs, Heads of Engineering, and Digital Transformation leaders.


• Strong background selling DevOps, DevSecOps, Application Security, Software Development Lifecycle, Testing, Infrastructure, Cloud, or related technology solutions.


• Expertise in navigating complex procurement cycles and managing large buying committees.


• Deep understanding of MEDDPICC, Command of the Message, or comparable enterprise sales methodologies.


• Strong executive presence, business acumen, and consultative selling skills.


• Proven ability to build pipeline independently and create opportunities within named enterprise accounts.


• Willingness to travel as needed to support customer engagements and strategic account development.

Why Digital.ai?

At Digital.ai, we’re more than just a software company — we’re a team of innovators, thinkers, and problem-solvers. By joining our sales organization, you’ll be part of a dynamic, collaborative environment that encourages professional growth and values diverse perspectives. You’ll work with some of the brightest minds in the industry, all while having the opportunity to shape the future of AI-enabled enterprise software development.

If you're ready to take your sales career to the next level and make a real impact with a leading tech company, we want to hear from you.

Digital.ai offers phenomenal benefits such as:

• Comprehensive medical, dental, and vision plans


• Paid parental leave


• Long Term Cash Incentive Programs


• Unlimited access to continuous learning and professional development with Udemy


• Flexible working arrangements


• Opportunity to work with a diverse, globally distributed team

All are welcome to apply.  We maintain compliance with federal, state, and local laws that prohibit employment discrimination on the basis of age, race, color, gender, identity, gender expression, sex, pregnancy, national origin, ancestry, religion, physical or mental ability, medical condition, sexual orientation, marital status, citizenship status, protected military or veteran status, and all other protected classifications. We welcome everyone and believe that diversity is the foundation of innovation.

For individuals with disabilities who would like to request accommodation, please advise us within your job application or cover letter.

FRAUD PREVENTION ALERT: please note that Digital.ai does not use third party recruiters. In our efforts to protect you against impersonation please check the email address or if you are contacted by an unfamiliar/third party requesting please reach out directly to Digital.ai.