Hybrid Skilled Entrepreneur Jobs in Chicago IL

Entrepreneurial Account Executive: Build Your Market

North Bridge Staffing Group • Chicago (IL)

Hybrid

USD 90,000 - 120,000

Entrepreneurial Liability Underwriter & P&L Owner

Private Client Select • Schaumburg (IL)

Hybrid

USD 150,000 - 230,000

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Skilled Entrepreneur

Chicago IL

Hybrid

Strategic Exit Advisor & Growth Consultant (1099)

Exit Factor • Elgin (IL)

Hybrid

USD 50,000 - 100,000

Uncapped commission-based compensation

High income potential

Flexible schedule

Startup Sales Leader: Scale New Business & Lead AEs

Nubeero Limited • Chicago (IL)

Hybrid

USD 150,000 - 230,000

Business Consultant Exit Advisor IL

Exit Factor • Wheaton (IL)

Hybrid

USD 60,000 - 100,000

Training and onboarding

Flexibility to build a book of business

Proven consulting frameworks

Business Consultant Exit Advisor IL

Exit Factor • Elgin (IL)

Hybrid

USD 50,000 - 100,000

Uncapped commission-based compensation

High income potential

Flexible schedule

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Business Consultant Exit Advisor IL

Exit Factor • Schaumburg (IL)

Hybrid

USD 60,000 - 100,000

Flexible schedule

Uncapped commission

Training and ongoing support

Exit Strategy & Growth Advisor (Remote/Hybrid, 1099)

Exit Factor • St. Charles (IL)

Hybrid

USD 100,000 - 150,000

Flexible schedule

Training and onboarding

Ongoing coaching

Business Consultant Exit Advisor IL

Exit Factor • Naperville (IL)

Hybrid

USD 60,000 - 120,000

Flexible schedule

Commission-based compensation

Training and ongoing support

Business Consultant Exit Advisor IL

Exit Factor • St. Charles (IL)

Hybrid

USD 100,000 - 150,000

Flexible schedule

Training and onboarding

Ongoing coaching

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Business Development Sales Representative

Millennium Millionaire Investors • Chicago (IL)

Hybrid

USD 180,000 - 220,000

Enterprise Sales Leader - Scale Revenue & Growth

Nubeero Limited • Chicago (IL)

Hybrid

USD 130,000 - 210,000

Enterprise Transformation Leader with Agentic AI

Nexwave • Chicago (IL)

Hybrid

USD 120,000 - 150,000

Partner Acquisition Lead - Enterprise SaaS (Remote, Equity)

Engine • Chicago (IL)

Hybrid

USD 220,000 - 250,000

Equity

Hybrid work model

Bonuses/commissions

Senior Business Immigration Attorney - Remote-First Leader

CIP PC. • Chicago (IL)

Hybrid

USD 120,000 - 180,000

Sales Manager, Startups - Hunter

WinsAbove • Chicago (IL)

Hybrid

USD 150,000 - 190,000

Exit Planning Consultant & Growth Advisor (1099)

Exit Factor • Wheaton (IL)

Hybrid

USD 60,000 - 100,000

Training and onboarding

Flexibility to build a book of business

Proven consulting frameworks

Tax Manager — Partner Track & Remote

Founder’s CPA, Inc. • Chicago (IL)

Hybrid

USD 110,000 - 140,000

Casual dress

Profit sharing bonuses

Work-life balance focus

Enterprise SaaS Sales Director - High Impact, Equity

Root • Chicago (IL)

Hybrid

USD 180,000 - 260,000

Top-tier pay

Equity

Education Market Growth Leader (Hybrid & ESOP)

Graef Anhalt Schloemer & Assoc • Chicago (IL)

Hybrid

USD 135,000 - 155,000

Hybrid schedule

ESOP

Training and leadership development

Sales Manager, Enterprise - Hunter

WinsAbove • Chicago (IL)

Hybrid

USD 180,000 - 280,000

Director of Growth Sales, Enterprise

Skai • Chicago (IL)

Hybrid

USD 130,000 - 150,000

Hybrid work model

Equity

Strong commission plan

Enterprise Sales Leader: Scale Revenue & Grow Teams

Nubeero Limited • Chicago (IL)

Hybrid

USD 120,000 - 200,000

New Leader – Pitch Us

SentiLink • Chicago (IL)

Hybrid

USD 180,000 - 250,000

Employer-paid health insurance

401(k) plan with employer match

Flexible paid time off

Private Tax Leader — Wealth & Family Governance (Hybrid)

EY • Chicago (IL)

Hybrid

USD 106,500 - 195,100

Comprehensive compensation package

Medical and dental coverage

401(k) plans

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Hybrid Skilled Entrepreneur Jobs in Chicago IL

Entrepreneurial Account Executive: Build Your Market

Entrepreneurial Liability Underwriter & P&L Owner

Strategic Exit Advisor & Growth Consultant (1099)

Startup Sales Leader: Scale New Business & Lead AEs

Business Consultant Exit Advisor IL

Business Consultant Exit Advisor IL

Business Consultant Exit Advisor IL

Exit Strategy & Growth Advisor (Remote/Hybrid, 1099)

Business Consultant Exit Advisor IL

Business Consultant Exit Advisor IL

Business Development Sales Representative

Enterprise Sales Leader - Scale Revenue & Growth

Enterprise Transformation Leader with Agentic AI

Partner Acquisition Lead - Enterprise SaaS (Remote, Equity)

Senior Business Immigration Attorney - Remote-First Leader

Sales Manager, Startups - Hunter

Exit Planning Consultant & Growth Advisor (1099)

Tax Manager — Partner Track & Remote

Enterprise SaaS Sales Director - High Impact, Equity

Education Market Growth Leader (Hybrid & ESOP)

Sales Manager, Enterprise - Hunter

Director of Growth Sales, Enterprise

Enterprise Sales Leader: Scale Revenue & Grow Teams

New Leader – Pitch Us

Private Tax Leader — Wealth & Family Governance (Hybrid)

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