Mentorship Jobs in Chicago, IL

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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 Copywriter

Company: GoHealth

Location: Chicago, IL

Posted Apr 12, 2023

GoHealth, a leading health insurance marketplace, is seeking a Senior Copywriter for its Chicago, IL office. The role involves managing direct to consumer, brand marketing, and lifecycle marketing messaging. The ideal candidate will have 5+ years of copywriting experience, a portfolio showcasing short-form and long-form copy, and a commitment to producing engaging content. The company offers a fast-paced, entrepreneurial environment, mentorship, open vacation policy, and comprehensive benefits.

Creative Director

Company: GoHealth

Location: Chicago, IL

Posted Apr 13, 2023

GoHealth is a leading health insurance marketplace that aims to improve access to healthcare in America. They offer a full-funnel marketing library to drive awareness, consideration, and conversions across various channels. The Creative Director role involves leading brand ethos, architecture, visual identity, and creative, as well as developing a library of creative assets to engage customers in their health insurance decisions.

Remote Contract Recruiter

Company: Veo

Location: Chicago, IL

Posted Apr 21, 2023

None Found

Senior Data & Technology Consultant

Company: Premier International

Location: Chicago, IL

Posted Apr 18, 2023

Premier International is seeking a Senior Data & Technology Consultant to join their growing consulting team in Chicago. The role involves working on diverse projects, using leading-edge technologies, and providing guidance to clients. The ideal candidate should have experience as a consultant, data analyst, or business analyst. The position offers competitive compensation, benefits, and the opportunity to work with clients across various industries.

Senior Salesforce Administrator

Company: SpotHero

Location: Chicago, IL

Posted Apr 12, 2023

SpotHero, a parking reservation service, is seeking a Senior Salesforce Administrator with 3-5 years of experience. The role involves managing Salesforce administration, development, and security, collaborating with various teams, and providing technical guidance. The ideal candidate is analytical, motivated, inquisitive, organized, a strong communicator, scalability-minded, adept with change management, collaborative, security-minded, and technically capable. SpotHero offers excellent benefits, flexible PTO, an annual parking stipend, and a collaborative atmosphere. The position is located in Chicago, IL or Toronto, ON.

Vice President, Performance Marketing

Company: GoHealth

Location: Chicago, IL

Posted Apr 12, 2023

GoHealth is a leading health insurance marketplace that aims to improve access to healthcare in America. The company is looking for employees who feel empowered, engaged, and inspired to contribute to its long-term health. The VP of Performance Marketing role is a hybrid/remote position based in Chicago, IL, responsible for leading the Performance Marketing Team and managing a significant marketing budget.

Associate Account Manager, Restaurant

Company: Grubhub

Location: Chicago, IL

Posted Apr 21, 2023

The text is about Grubhub's opportunity to connect diners with restaurants, their innovative technology, and the role of an Associate Account Advisor. The company values authentically fun culture, teamwork, and empowering people. The role involves building relationships, resolving issues, educating decision-makers, and helping restaurants attract new diners. The company offers benefits like PTO, health and wellness programs, competitive pay, learning and career growth opportunities, meal perks, and fun events. Grubhub is an equal opportunity employer.

Digital Marketing Manager

Company: GoHealth

Location: Chicago, IL

Posted Apr 17, 2023

GoHealth is a leading health insurance marketplace that aims to improve access to healthcare in America. They offer technology, agents, and expertise to help customers enroll in the right plan with the best coverage and benefits. The company values diversity and encourages women and underrepresented groups to apply. They are looking for builders who will contribute to the long-term health of the company. The role involves working with the VP of Growth Marketing to scale existing channels and expand into new ones. The successful candidate will drive optimizations, prepare volume forecasts, and be a subject matter expert for digital campaigns.

VP of Sales, Land

Company: Upwork

Location: Chicago, IL

Posted Apr 13, 2023

Upwork is seeking an experienced Vice President of Enterprise Sales to lead the Sales team and provide direct leadership to the Enterprise Land Sales teams. The role involves developing plans and strategies for acquiring business, creating a culture of continued success, creating and executing against a sales forecast, defining and overseeing sales staff compensation and incentive programs, defining and coordinating sales training programs, managing customer expectations, defining and deploying best practice prospecting methodologies, partnering with marketing for Sales Development/Lead Generation, monitoring and reporting on lead quota attainment, defining the characteristics of a successful sales team, rolling up sleeves to prospect and help close deals, and playing a critical role in ensuring tight coordination and collaboration across Sales, Solutions, and Services.

Manager, Training

Company: Grubhub

Location: Chicago, IL

Posted Apr 16, 2023

Grubhub is a company that values innovation, teamwork, and fun. They are looking for a Care Training Manager to lead a team of learning professionals and develop training curriculums. The company offers a range of benefits, including flexible PTO, health and wellness programs, and opportunities for career growth.

Senior Copywriter

Company: GoHealth

Location: Chicago, IL

Posted Apr 12, 2023

GoHealth is a leading health insurance marketplace with a mission to improve access to healthcare in America. They offer a performance marketing powerhouse approach, focusing on trusted relationships and personalized communication. The company values diversity and is looking for builders who can contribute to their long-term health. They are seeking a Senior Copywriter to manage their direct-to-consumer, brand marketing, and lifecycle marketing messaging.

Software Development Engineer - Mentor

Company: Idea Entity

Location: Peoria, IL

Posted Apr 16, 2023

Idea Entity, a Microsoft Gold Partner, is seeking a Software Development Engineer - Mentor with 5+ years of experience in full product cycle, strong understanding of Agile principles, and hands-on experience in managing software development teams. The role involves designing, developing, and delivering high-quality software, leading development builds, and managing project priorities. The ideal candidate should have a collaborative team player attitude, passion for software development, and results-oriented approach.

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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