Jobs in Chicago, IL

AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.

At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.

We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.

We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD.

We are seeking a results-driven AI Enterprise Sales Specialist to join our team and drive the adoption of cutting-edge services-led solutions AI solutions for enterprise clients. The ideal candidate will have a strong background in enterprise professional and managed services sales with experience structuring complex services engagements that may include supporting product components. This role requires the ability to translate complex AI solutions into tangible business outcomes and to lead with services value—strategy, implementation, integration, and ongoing optimization.

Key Responsibilities

Sales Strategy and Execution:
Develop and execute sales strategies to achieve revenue targets and market growth.
Identify and pursue new business opportunities with enterprise clients in targeted industries.
Build and maintain a robust sales pipeline, ensuring a consistent flow of qualified leads and opportunities.
Client Engagement and Relationship Management:
Act as a trusted advisor to clients, understanding their business challenges and recommending tailored AI solutions.
Build and nurture long-term relationships with key stakeholders, including C-level executives and decision-makers.
Deliver compelling presentations and product demonstrations, highlighting the value of AI in driving business outcomes.
Solution Selling:
Collaborate with Consulting, Delivery, Presales teams to design customized AI solutions that address client needs.
Translate complex technical concepts into clear and actionable business benefits for non-technical stakeholders.
Negotiate and close enterprise-level contracts, ensuring alignment with client goals and organizational objectives.
Market Insights and Thought Leadership:
Stay informed about the latest trends and developments in AI and machine learning technologies.
Provide market feedback to internal teams on services offerings, packaging, and pricing to refine product offerings and strategy.
Represent the company at industry events, conferences, and webinars, positioning the organization as a leader in AI solutions.
Collaboration and Teamwork:
Work closely with Core Sales, Marketing, Presales, Engineering and Customer Success teams to ensure seamless client onboarding and support.
Share best practices on services-led selling, SOW structuring, and value realization, and contribute to the development of sales tools, playbooks, and enablement assets.

Qualifications

Bachelor’s degree in business, technology, or a related field; advanced degree preferred.
5+ years of experience in enterprise sales with a primary focus on professional services, consulting, and/or managed services, ideally in data, cloud, or AI domains.
Demonstrated success selling and closing complex services engagements (e.g., multi-phase transformations, multi-year managed services, or large consulting programs).
Exceptional communication, negotiation, and presentation skills.
Ability to manage complex sales cycles and navigate organizational hierarchies.
Entrepreneurial mindset with a passion for technology and innovation.

Preferred Qualifications

Experience selling consulting and managed services focused on AI, data, or other technology-based solutions to enterprise clients.
Industry expertise in sectors such as finance, healthcare, retail, or manufacturing.
Familiarity with CRM tools (e.g., Salesforce) and sales analytics platforms.

Key Attributes

Results-driven with a proactive approach to problem-solving.
Adaptable and capable of thriving in a fast-paced, dynamic environment.
Consultative and strategic, capable of elevating conversations from products and features to business outcomes, operating models, and change management.
Collaborative and influential, able to work across sales, delivery, product, and executive stakeholders to shape and close complex services deals.
Strong interpersonal skills with the ability to inspire confidence and trust in clients.

The compensation range indicated in this posting reflects the On-Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.

Why AHEAD:

Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.

We fuel growth by stacking our office with top-notch technologies in a multi-million-dollar lab, by encouraging cross department training and development, sponsoring certifications and credentials for continued learning.

USA Employment Benefits include:

- Medical, Dental, and Vision Insurance

- 401(k)

- Paid company holidays

- Paid time off

- Paid parental and caregiver leave

- Plus more! See benefits https://www.aheadbenefits.com/ for additional details.

$360,000 - $400,000 a year

AI Sales Specialist

Assistant Director of Talent

Patient Care Technician medical Stabilization Unit

Staff Nurse/Med Surg

Staff Nurse/ICU

Account Manager - Bound Tree Medical - Milwaukee, WI

Stormtrooper

Inclusion & Disabilities Specialist

Mid-Market Account Manager

Hiring Event

Assistant Store Manager

Store Manager in Training (MIT)

Store Manager in Training

Store Manager in Training

Staff Geologist / Scientist I

OR Tech

Staff Nurse/L&D

AI Sales Specialist at AHEAD – Chicago, Illinois

Explore Related Opportunities

About This Position

Scan to Apply

Job Location

Frequently asked questions about this position