Data and AI Customer Solutions at Chicago, Illinois

AI Sales Leader

Why you'll love Softchoice: We are a software-focused IT solutions and services provider that equips organizations to be agile and innovative, and for their people to be engaged, connected, and creative at work. That means moving them to the cloud, helping them build the workplace of tomorrow, and enabling them to make smarter decisions about their technology. By doing these things we help them create success for their customers and their people. We stand proudly for our people and support their success through career development and advancement. We are recognized and respected for our culture of inclusion and belonging, continuously striving to do what's good for our people and communities.

The impact you will have: Are you ready to be at the forefront of the AI revolution, shaping the future of how organizations harness cutting-edge technology to drive real, measurable results? As a pivotal member of our team, you won't just be selling solutions-you'll be empowering our customers to unlock the full potential of workplace AI, intelligent agents, and robust data platforms, regardless of the cloud ecosystem they prefer. At Softchoice, your influence will reach far beyond pilots and proofs of concept. You'll have the unique opportunity to architect and deliver AI strategies that become the backbone of our customers' success, transforming how they work, innovate, and compete. Through our integrated consulting and engineering approach-leveraging deep alliances with Microsoft, AWS, and Google Cloud-you'll help organizations move from vision to execution, making AI practical, durable, and truly impactful. Imagine being the trusted advisor who brings clarity to complex challenges, guiding senior executives to align on a transformative AI roadmap. You'll be instrumental in shaping business cases that deliver productivity gains, reduce operational costs, and strengthen compliance-while mapping out the tangible ROI that drives executive buy-in and long-term adoption. In this role, you'll quarterback a high-performing team of account executives, solution architects, and technical experts, orchestrating seamless collaboration to deliver AI solutions tailored precisely to each customer's unique needs. You'll facilitate boardroom-level discussions, influence strategic decision-making, and see your recommendations come to life in ways that redefine what's possible for your clients. If you're passionate about making a lasting impact, eager to champion responsible AI adoption, and thrive on building relationships that fuel innovation-this is your chance to be the catalyst for real change, helping organizations across industries shape their futures with confidence and clarity.

Who you will be working with:

• This role will report to the regional leader of technical sales and be part of a "technical sales" organization.
• You will work with our most strategic customers looking to guide their AI journey leading to a transformation of their business.
• You and your team will be directly supported by technical solution architects and engineers, bringing technical acumen early in the sales cycle to ensure our customers find fast value in their discussions with you.
• You will collaborate with account executives, sales leadership and GTM team members, in partnership to ensure we grow our AI business together.

What you will do:

• Own the executive sales cycle from discovery to close: map business problems to offers, orchestrate virtual teams (pre-sales architects, delivery, partners), shape proposals/SOWs, and negotiate to signature.
• Lead with value/ROI: build business cases (productivity, cost to serve, compliance/risk), success metrics, and adoption plans for measurable impact.
• Facilitate C-level conversations to enhance understanding of AI and bring alignment at customers to specific AI initiatives
• Partner co-sell & funding: align with Microsoft (and other hyperscalers) to unlock workshops, AMMP/MDF, and POC funding motions that accelerate deals.
• Pipeline discipline: maintain accurate Salesforce hygiene and weekly cadence on funnel adds and sufficiency; leverage Sales Ops dashboards.
• Evangelize responsibly: position governance, identity, Purview, DLP, and COE patterns to reduce risk while scaling value.

What you bring to the table:

Professional Experience

• The ideal candidate will bring 5 to 10 or more years of demonstrated success in solutions sales, specifically focused on data platforms, analytics, or artificial intelligence. This experience should include a proven track record in selling multi-workload programs and professional services.

Cloud and Platform Expertise

• Microsoft: Proficiency with Microsoft Fabric, Azure AI, M365 Copilot, and Copilot Studio/Agents.
• AWS: Familiarity with Bedrock, SageMaker, and a range of data analytics services, including an understanding of patterns for Amazon Q and related guardrails.
• Google Cloud: Experience with Vertex AI, Dialogflow/CCAI, and BigQuery analytics patterns.
• Ecosystem: Awareness of Databricks and Snowflake lakehouse patterns, as well as business intelligence platforms such as Power BI, Looker, or QuickSight, as applicable.

Business Acumen

• The candidate should possess the ability to translate executive-level objectives-such as growth, margin, risk, and customer/employee experience-into a well-structured AI roadmap and adoption plan. They must be able to present a clear narrative connecting agents, data, and governance to desired business outcomes.

Team Leadership and Orchestration

• Proven capability in leading virtual pursuit teams and coordinating partner co-selling and funding efforts is essential.

Technical Familiarity

• The candidate should be familiar with agentic patterns, including Retrieval-Augmented Generation (RAG), tool use, and orchestration, and understand how these patterns intersect with line-of-business applications and data estates.
• Willingness and ability to travel frequently within a designated Sales District, up to 25% of the time.

Pay Range:

The typical pay range for this role is $106,000 - $150,000. Note: the pay range represents the full pay range for this position. Each individual offer will take into consideration a range of factors, including prior experience and geographic location. In addition to the base salary, this role is eligible for additional elements of compensation including (cell allowances, annual bonus, or commissions etc.), as well as a comprehensive benefits plan.

Not sure if you qualify? Think about applying anyway:

We understand that not everyone brings 100% of the skills and experience for the role. At Softchoice, we offer opportunities to a diverse group including those with a variety of workplace experiences and backgrounds. Whether you are new to corporate tech, returning to work after a gap in employment, or looking to transition and take the next step in your career, we are excited to learn more about you and encourage you to apply.

Why You'll Love Working Here:

• The People: You'll thrive in our collaborative environment, surrounded by incredible colleagues who foster support and innovation, driving our collective success
• High-Performing Culture: At Softchoice, we are dedicated to achieving our goals and committed to success for our customers and each other
• Flexibility: Plan your workdays in a way that suits you best
• Award-Winning Workplace: Proudly recognized as a Great Place to Work for 20 consecutive years
• Inclusive Culture: We are committed to an inclusive culture where every team member can be their authentic self
• Competitive Benefits: Benefit from competitive perks that start on day one

Inclusion & Equal opportunity employment:

We are an equal opportunity employer committed to diversity, inclusion & belonging. People seeking employment at Softchoice are considered without regard to any protected category including but not limited to, race, color, religion, national origin, age, sex, marital status, ancestry, disability, veteran status, gender identity, or sexual orientation.

Require accommodation? We are ready to help:

We are proud to provide interview & employment accommodation during the recruitment and hiring process. If you require any accommodation to apply or interview for a position, please reach out directly to View email address on click.appcast.io. We are committed to working with you to best meet your needs.

Our commitment to your experience:

We are committed to the safety of all applicants and team members. With that in mind, we have implemented digital interviewing for everyone. We understand that you may need to interview with distractions around you (such as children or furry friends) and we will be doing the same. Before you start with us, we will