AI Sales Specialist

AHEAD; Chicago (IL); Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Medical, Dental, and Vision Insurance

401(k)

Paid company holidays

Paid time off

Paid parental and caregiver leave

Job summary

AHEAD is seeking a results-driven AI Enterprise Sales Specialist to lead services-led engagements for enterprise clients. You will translate complex AI solutions into business outcomes, work with consulting, delivery, presales, and marketing, and drive adoption of AI-enabled services.

Located in MST/PST, you will build strategic relationships, manage multi-year engagements, and influence C-level stakeholders while collaborating with cross-functional teams to deliver measurable business impact.

Qualifications

• 5+ years in enterprise sales focusing on professional services or managed services.
• Experience selling complex services engagements (multi-phase transformations).
• Excellent communication, negotiation, and presentation skills.

Responsibilities

• Develop and execute sales strategies to hit revenue targets and grow market share.
• Engage enterprise clients, understand challenges, and propose AI-based solutions.
• Collaborate with Consulting, Delivery, Presales to design tailored AI solutions.
• Negotiate and close enterprise contracts, aligning with client goals.

Skills

Enterprise sales

Communication

Negotiation

Presentation skills

Entrepreneurial mindset

Stakeholder management

Education

Bachelor's degree in business/tech

Tools

Salesforce

Sales analytics platforms

Job description

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. Note: Candidate must be located in MST/PST.

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 for additional details.

Use of AI:

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, assessing responses, or to capture recordings and create transcriptions or summaries during interviews. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please refer to the Candidate Privacy Notice or contact us at . You may opt-out of the review or analysis of your application and resume by AI tools by using the General Application. You may also choose to opt-out of recording and transcription at any time, including after joining an interview. Candidates will not be penalized for choosing to opt-out.