AI Sales Coach

Requisition Number: 103719

AI Sales Coach

Location: This is a hybrid work opportunity in our Chicago office (1 day/week in office)

Salary: 52 ,000-60,000 annually + bonus and other incentives available.

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Insight at a Glance

• 14,000+ engaged teammate s globally
• #20 on Fortune’s World's Best Workplaces ™ list
• $9.2 billion in revenue
• Received 35+ industry and partner awards in the past year
• $1.4M+ total charitable contributions in 2023 by Insight globally

Now is the time to bring your expertise to Insight. We are not just a tech company; we are a people-first company. We believe that by unlocking the power of people and technology, we can accelerate transformation and achieve extraordinary results. As a Fortune 500 Solutions Integrator with deep expertise in cloud, data, AI, cybersecurity, and intelligent edge, we guide organisations through complex digital decisions.

About the role

The AI Sales Coach is responsible for accelerating the adoption, proficiency, and impact of Artificial Intelligence (AI) tools and methodologies across the sales organization. This role focuses on translating AI capabilities into measurable sales outcomes by providing hands-on coaching, developing specialized training, and ensuring the seamless integration of AI-driven workflows into the daily life of a salesperson. You will be the bridge between our AI center of excellence and the frontline sales teammates, ensuring maximum sales team effectiveness in the age of AI. As an AI Sales Coach , you will be:

Coach: AI Proficiency and Application

• Provide hands-on coaching, advisement, and training to sales teammates on the effective and ethical use of AI tools in all stages of the sales cycle, from prospecting and lead qualification to presentation and closing.

• Empower the team to develop the skills, mindsets, and mastery of AI toolsets that will help achieve sales goals and business objectives by providing a balance between tactical and strategic approaches.

• Analyze user engagement and performance data of AI tools to identify coaching opportunities and inform the development of targeted enablement programs.

Communicate: Adoption and Feedback

• Cultivate and maintain open communication channels with sales leadership and individual contributors to ensure a clear understanding of AI initiatives, gather feedback, and address concerns regarding AI implementation.

• Facilitate group discussions that effectively deliver a message about new AI features, best practices, and solicit appropriate engagement from the sales audience.

• Ensure that business units, stakeholders, and leaders have a clear understanding of the strategic value, measurable impact, and return on investment (ROI) derived from the adoption of AI-enabled sales practices and the support provided by the AI Sales Coach team.

Collaborate: Integration and Strategy

• Work jointly with relevant stakeholders, including Sales Enablement, Sales Operations, and Data Science/IT teams, to generate ideas, find solutions, and achieve common goals.

• Ensure all strategic and tactical approaches for AI tool use connect to the overall business ambitions and maintain holistic alignment with the company's sales methodology.

• Maintain effective communications with leaders across the organization to determine resource requirements and coordinate collaboration efforts across teams to leverage capabilities.

Be AmbITious: This opportunity is not just about what you do today but also about where you can go tomorrow. When you bring your hunger, heart, and harmony to Insight, your potential will be met with continuous opportunities to upskill, earn promotions, and elevate your career.

What we’re looking for

• 3+ years in sales enablement, sales coaching, or quota-carrying B2B sales experience.

• Practical experience using and coaching others on AI tools in a professional sales context is highly preferred.

• A proven track record of success in B2B sales with experience managing accounts or leading/supporting those who do.

• Demonstrated ability to quickly learn, master, and articulate the value of emerging AI technologies and translate technical concepts into simple, actionable sales strategies.

• Possess a strong leadership orientation, a commitment to teamwork, a growth mindset and motivated by results and excellence.

What you can expect We’re legendary for taking care of you, your family and to help you engage with your local community. We want you to enjoy a full, meaningful life and own your career at Insight. Some of our benefits include: 

• Freedom to work from another location—even an international destination—for up to 30 consecutive calendar days per year.
• Access to 11 thriving and diverse Teammate Resource Groups

But what really sets us apart are our core values of Hunger, Heart, and Harmony, which guide everything we do, from building relationships with teammates, partners, and clients to making a positive impact in our communities.

Join us today, your ambITious journey starts here.

Insight is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.

When you apply, please tell us the pronouns you use and any reasonable adjustments you may need during the interview process.

Insight does not accept unsolicited resumes from recruiters or employment agencies. Unsolicited resumes will be treated as direct applications from the candidate, and recruiters or agencies who submit candidates for this position without a prior, written vendor agreement will not be eligible for any form of compensation, even if the candidate is hired.

The position described above provides a summary of some the job duties required and what it would be like to work at Insight. For a comprehensive list of physical demands and work environment for this position, click here .

Insight is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.

Posting Notes: Chicago || Illinois (US-IL) || United States (US) || Sales/Business Development || None || US - Chicago, IL ||