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Enterprise Account Executive

CRA | Admired Leadership
Chicago, IL Full Time
POSTED ON 12/10/2025
AVAILABLE BEFORE 6/30/2026

Enterprise Account Executive


CRA| Admired Leadership is a trusted consulting firm that advises clients in the areas of strategic communication, leadership development, organizational research, executive presentations, and talent assessment CRA| Admired Leadership has been serving as advisors to senior leaders in Fortune 100 companies since 1986. For over three decades, we have built long-term relationships with hundreds of clients. We take pride in identifying and cultivating leaders, both inside and outside of our organization.


We are seeking a Enterprise Account Executive who will lead the sales efforts for ALEX, our AI Leadership Coach. You’ll be selling ALEX, the world’s first AI leadership coach built on 35 years of proprietary leadership research and practice. First, when advising clients on matters of leadership, ALEX first relies on proprietary leadership data provided by Admired Leadership, drawing on a dataset of over 1,000,000 words of best practice content. As a result, the advice and recommendations ALEX offers are more specific and nuanced than those of other AI tools relying on a model’s general training corpus. Second, ALEX operates from a set of unique heuristics that allow it to engage leaders in thoughtful, authentic conversations. ALEX assesses a leader’s needs and responds in a conversational way, providing advice, reading context, making suggestions, or even playing devil’s advocate, depending on the coaching situation. ALEX can recommend best practices, design and engage in role-play, create practice situations, assist in writing performance reviews, design agendas, create development plans, and much more. ALEX stands ready to engage leaders 24/7 and speaks in over 80 languages and dialects. It is the most advanced AI leadership coach in the world.


The successful candidate will bring a hunter’s mindset—building new client relationships, expanding market presence, and partnering with internal and external stakeholders to deliver measurable results. Our ideal candidate is someone who inspires loyalty, can self-manage goals and objectives and is dedicated to teamwork/collaboration, and is eager and ready to scale the Leadership Development practice. This role offers the chance to scale a category-defining product, make a measurable impact on how enterprises develop leaders, and work directly with thought leaders shaping the future of leadership in the age of AI. Enterprises everywhere are racing to understand how AI will transform their organization—this role gives you the chance to be on the front edge of that transformation with a product that is genuinely differentiated in the market.


How you will make an impact:

  • Develop a plan and strategy for growing new business.
  • Communicating and establishing expectations for weekly activities, pipelines, and forecasts.
  • Develop best-of-breed practices to ensure sales goals and productivity targets are met/exceeded.
  • Tell the story of how AI decades of leadership expertise create measurable business impact in leadership development.
  • Effectively communicate value proposition through proposals and presentations.
  • Build and maintain strong, long-lasting client relationships.
  • Facilitate deal creation and oversight of all business development efforts.
  • Own and hit/exceed annual sales targets.



What makes you a great candidate:

  • Consistently exceeds new business targets, demonstrating a strong track record of driving revenue growth.
  • 7 years of business development experience, with a proven ability to win new logos and penetrate untapped markets.
  • Skilled in consultative SaaS/fintech sales, solution design, and full-cycle deal management, with a strong plus in AI-focused technologies.
  • Hunter mindset: self-starter who thrives on opening doors and creating new opportunities.
  • Lead by example with personal discipline and continuous improvement.
  • Strong emotional intelligence and able to relay demonstrable experiences.
  • Be a creative thinker, confident, and able to express complex ideas in an articulate, concise manner.
  • Ability to communicate, present, and influence all levels of the organization, including executive and C-level.
  • Proven ability to drive the sales process from plan to close.
  • Passion for artificial intelligence and its business applications, with the ability to translate complex concepts into clear value for clients.
  • Excellent listening, negotiation, and presentation skills.


What we offer:

  • Competitive Compensation: Base salary plus performance bonuses and an uncapped commission plan tied to new business acquisition, rewarding your success as a hunter.
  • Comprehensive Benefits: Health, dental, and vision insurance, 401(k), and generous paid time off.
  • Cutting-Edge Opportunity: Be at the forefront of AI in the leadership development space, selling the world’s first AI Leadership Coach built on 35 years of proprietary research.
  • Learning Culture: Join a team that values continuous growth and curiosity:
  • Encourages professional development, mentoring, and skill-building opportunities.
  • Fosters experimentation and innovation, where new ideas are welcomed and tested.
  • Supports knowledge-sharing across teams to enhance collective expertise.
  • Rewards curiosity and a growth mindset, helping you expand your impact and career trajectory.

Salary.com Estimation for Enterprise Account Executive in Chicago, IL
$74,636 to $101,609
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