Mentorship Jobs in Chicago, IL

4,721 open positions · Updated daily

Looking for Mentorship jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Mentorship position in the Chicago, IL area.

Senior Enterprise Sales Trainer

Company: Upwork

Location: Chicago, IL

Posted Apr 06, 2023

Upwork is seeking a Sr. Enterprise Sales Trainer to develop and facilitate a world-class new hire training program for their sales organization. The role requires expertise in sales training methodologies, deep knowledge of executive-level buyer personas, and experience with all aspects of training. The annual base salary ranges from $107,000 - $154,000 and the position is eligible for bonuses and long-term equity incentives.

Senior Engineer, Backend (Drivers League)

Company: SpotHero

Location: Chicago, IL

Posted Mar 29, 2023

SpotHero is looking for Senior Backend Engineers to join the Drivers League. The role involves contributing to the codebase, working on multiple environments, and having the opportunity to work on implementation independently. The team uses a monolithic architecture with Django/Python/PostgreSQL and is moving towards a modular monolith with Domain Driven Design. They use Docker, Kubernetes, Kafka, and gRPC for service-to-service communication. The front-end stack is React/Redux, Sass, Jest/React Testing Library/Cypress, and Webpack. They use AWS+Kubernetes for hosting, Terraform+Helm Charts for IaaS/Deployment, ConcourseCI for CI/CD, Prometheus/Alertmanager/VictorOps for team alerting. The company offers excellent benefits, flexible PTO policy, and a workplace recognized for its culture and work environment.

Social Content and Community Intern

Company: Grubhub

Location: Chicago, IL

Posted Apr 05, 2023

Grubhub is looking for a dynamic, creative, and social savvy Content and Community Intern to assist in handling communication with their diners across various social media platforms and work on 360 content initiatives. The ideal candidate should be obsessed with social media, understand branding, and can create engaging content quickly. The role involves managing social media and community management, content creation, scheduling, analytics, and collaboration with the influencer marketing team. The candidate should be comfortable with being on Grubhub's TikTok page, have a strong interest in social media and influencer marketing, and be able to adapt to changing timelines and objectives.

Sales Operations Analyst - Expansion Sales

Company: Upwork

Location: Chicago, IL

Posted Apr 07, 2023

Upwork is a remote-first organization that offers remote work opportunities for a global community of professionals. They are committed to recruiting and retaining a diverse and inclusive workforce. The company provides a vibrant culture, development opportunities, mentorship, and employee resource groups. Upwork also offers amazing benefits. They are proudly committed to recruiting and retaining a diverse and inclusive workforce.

Sales Operations Manager

Company: Upwork

Location: Chicago, IL

Posted Apr 01, 2023

Upwork is a global work marketplace that serves businesses and professionals. They offer a trust-driven platform for companies and talent to work together. The Sales Operations team aims to be a trusted partner to enterprise teams, providing tools, learning, and operational processes. The Sales Operations Manager role involves partnering with various teams to grow and retain Upwork Enterprise clients. The ideal candidate has project management experience, proficiency in Salesforce, and familiarity with data visualization tools.

Sr. Sales Operations Analyst

Company: Upwork

Location: Chicago, IL

Posted Apr 08, 2023

Upwork is a global work marketplace that serves businesses and talent from startups to Fortune 100 companies. They offer a trust-driven platform for companies and talent to work together, with a focus on enabling innovation in careers. The company is looking for a Sr. Sales Operations Analyst to lead the creation and maintenance of data pipelines and ETL processes within the Sales organization.

Director, Offline Media

Company: GoHealth

Location: Chicago, IL

Posted Apr 12, 2023

GoHealth, a leading health insurance marketplace, is seeking a Director of Offline Media to oversee and optimize its multi-million-dollar advertising programs. The role involves managing Direct Mail, DRTV, Radio, Print, Outdoor, and other offline campaigns, developing a 12-month offline media plan, and collaborating with various teams to maximize ROI/CPA goals. The ideal candidate should have 5-10 years of experience in offline media management, proven campaign and lead generation experience, and SQL, Python, AWS, and Sagemaker experience. GoHealth offers a fast-paced, entrepreneurial environment with opportunities for career growth, open vacation policy, and comprehensive benefits.

Sales Associate/Stylist

Company: gorjana

Location: Chicago, IL

Posted Apr 08, 2023

The role of a sales associate/stylist at Gorjana involves creating an exceptional shopping experience for customers, driving sales through styling and relationship building, and providing customer service. The ideal candidate is a positive, energetic individual with previous retail, sales, or customer service experience, a confident and enthusiastic attitude, and a passion for building brand loyalty. The role offers medical, vision, and dental benefits, a generous employee discount program, and opportunities for growth and development.

Enterprise Account Manager

Company: Upwork

Location: Chicago, IL

Posted Mar 30, 2023

Upwork is a global work marketplace that connects businesses and professionals. They offer a platform for companies and talent to work together, with a focus on enabling innovation and growth. The Sales team is responsible for managing customer relationships, meeting sales goals, and providing thought leadership. To be considered for a role, candidates should have a proven track record of hitting over 100% of their quota, industry expertise, and the ability to analyze problems and identify solutions.

Sales Operations Analyst

Company: Upwork

Location: Chicago, IL

Posted Apr 08, 2023

Upwork is a remote-first organization that provides a platform for companies and talent to work together. They are looking for a Sales Operations Analyst to support their Land partners by developing, tracking, and refining forecasting models and pipeline movement.

Business Development Representative - Inbound

Company: Upwork

Location: Chicago, IL

Posted Apr 06, 2023

Upwork is a global work marketplace that connects businesses and talent. They offer a platform for companies and professionals to work together, with a focus on flexibility and innovation. The Sales team brings their flexible workforce solutions to mid-market and large enterprises. The role of Business Development Representative involves prospecting, qualifying leads, and booking sales meetings. The company values a growth mindset, attention to detail, and collaboration. They offer remote work opportunities and a vibrant culture with shared values and a mission to create economic opportunities.

Associate Consultant

Company: Premier International

Location: Chicago, IL

Posted Apr 11, 2023

Premier International is hiring entry-level Data and Technology consultants to join their growing consulting staff in Chicago. The company is a privately held software and technology consulting firm that has been awarded one of Crain's 2021 Best Places to Work in Chicago. The ideal candidate will have experience working with data and using technology to address clients' needs.

Frequently Asked Questions

What are typical salary ranges by seniority in mentorship roles?
Entry‑level Mentor Coaches earn $50k–$70k; mid‑level coaches $70k–$100k; senior mentors or Program Managers range $100k–$150k, with bonuses tied to mentee success metrics.
What skills and certifications are required for a mentorship career?
Certifications such as ICF‑P, ATD’s Certified Learning Professional, or SHRM‑CP are highly valued. Core skills include active listening, empathy, data‑driven coaching, LMS proficiency, and remote facilitation using Zoom, Slack, or Microsoft Teams.
Is remote work common for mentorship positions?
Yes—70%+ of mentorship roles offer fully remote or hybrid options, supported by digital platforms like Mentorloop, Chai, and AdvisoryCloud, allowing coaches to engage mentees worldwide.
What career progression paths exist within mentorship?
Coaches can advance to Senior Mentor, Program Manager, Learning & Development Director, or Talent Development Lead. Some transition to entrepreneurship, launching coaching startups or consulting firms.
What industry trends are shaping mentorship today?
AI‑driven mentor matching, analytics dashboards tracking mentee outcomes, microlearning modules, and a growing emphasis on soft‑skill development are reshaping how companies structure and assess mentorship programs.

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