Job Search and Career Advice Platform

Remote Skilled Entrepreneur Jobs in Chicago IL

Remote Growth Advisor for Early-Stage Startups

Remote Growth Advisor for Early-Stage Startups

TEEMA Solutions Group • Chicago (IL)

Remote
USD 50,000 - 85,000
Flexible working hours
Access to exclusive startups
Networking opportunities
+1
Senior Growth Strategist

Senior Growth Strategist

FlexUp • Chicago (IL)

Remote
USD 90,000 - 150,000
Remote schedule sovereignty
High-ticket earning potential
Turnkey enterprise infrastructure
+2
Founders’ Remote Chief of Staff

Founders’ Remote Chief of Staff

Overseas • Chicago (IL)

Remote
USD 120,000 - 180,000
100% remote setup
US business hours availability
Remote Business Growth Coach & Exit Strategy Consultant

Remote Business Growth Coach & Exit Strategy Consultant

Exit Factor • Oswego Township (IL)

Remote
USD 35,000 - 60,000
Remote work
Flexible schedule
Mentorship program
+1
Remote Growth Architect: Lead Global Impact & Mastery

Remote Growth Architect: Lead Global Impact & Mastery

Shine To Prosper • Chicago (IL)

Remote
USD 60,000 - 100,000
Schedule Autonomy
Location Independence
Mentorship & Development
+1
Internal General Manager (INS856)

Internal General Manager (INS856)

Overseas • Chicago (IL)

Remote
USD 90,000 - 150,000
100% remote
US business hours
Autonomy
+1
Remote Fintech Co-Founder & CTO — Scale to €100M+

Remote Fintech Co-Founder & CTO — Scale to €100M+

EWOR • Chicago (IL)

Remote
USD 139,000 - 289,000
Competitive salary during startup development
Up to €500k in funding
1:1 mentorship from unicorn founders
+2
Remote Business Strategist & Financial Modeling Expert

Remote Business Strategist & Financial Modeling Expert

EPAM Systems • Chicago (IL)

Remote
USD 110,000 - 170,000
Medical, dental and vision insurance (
Health savings account
401(k) with match
+6
Business Development Consultant, Exit Strategy (IL)

Business Development Consultant, Exit Strategy (IL)

Exit Factor • Aurora (IL)

Remote
USD 50,000 - 150,000
HubSpot CRM access
Marketing materials
Lead flow from multiple sources
+2
Internal Account Manager (INS852)

Internal Account Manager (INS852)

Overseas • Chicago (IL)

Remote
USD 70,000 - 110,000
Remote work
Direct exposure to founders
Investment Analyst

Investment Analyst

Trolley • Chicago (IL)

Remote
USD 536,000 - 670,000
Founder Relationships Architect — Chicago (Remote)

Founder Relationships Architect — Chicago (Remote)

Acquisition Network LLC • Chicago (IL)

Remote
USD 120,000 - 180,000
Independent Remote People & Culture Consultant

Independent Remote People & Culture Consultant

LifestyleBiz • Chicago (IL)

Remote
USD 90,000 - 150,000
Uncapped earning potential
Total autonomy over schedule
Access to advanced e-learning products
Expert Opportunity - Insolvency Practitioner ($100/hr, up to $2,000/week)

Expert Opportunity - Insolvency Practitioner ($100/hr, up to $2,000/week)

Ethos • Chicago (IL)

Remote
USD 114,000 - 162,000
Remote CEO: Scale a National Tax Franchise Network

Remote CEO: Scale a National Tax Franchise Network

Guaranteed Rate • Chicago (IL)

Remote
USD 210,000 - 320,000
Expert Opportunity - Corporate Strategy Consultant ($80/hr, up to $1,600/week)

Expert Opportunity - Corporate Strategy Consultant ($80/hr, up to $1,600/week)

Ethos • Chicago (IL)

Remote
USD 94,000 - 127,000
Expert Opportunity - Engagement Manager ($100/hr, up to $2,000/week)

Expert Opportunity - Engagement Manager ($100/hr, up to $2,000/week)

Ethos • Chicago (IL)

Remote
USD 124,000 - 165,000
Strategic Revenue & Growth Leader

Strategic Revenue & Growth Leader

Human Agency • Chicago (IL)

Remote
USD 180,000 - 320,000
Equity participation
Competitive compensation
Collaborative remote work environment
Expert Opportunity - Head of Financial Planning ($80/hr, up to $1,600/week)

Expert Opportunity - Head of Financial Planning ($80/hr, up to $1,600/week)

Ethos • Chicago (IL)

Remote
USD 83,000 - 138,000
Venture Partner - Chicago

Venture Partner - Chicago

Acquisition Network LLC • Chicago (IL)

Remote
USD 120,000 - 180,000
Enterprise AI & Software Advisor for Founders & Boards

Enterprise AI & Software Advisor for Founders & Boards

Graphora • Chicago (IL)

Remote
USD 120,000 - 230,000
Remote work
Expert Opportunity - Strategic Account Manager ($80/hr, up to $1,600/week)

Expert Opportunity - Strategic Account Manager ($80/hr, up to $1,600/week)

Ethos • Chicago (IL)

Remote
USD 94,000 - 127,000
Remote Senior Consultant: Transformation & ROI Leader

Remote Senior Consultant: Transformation & ROI Leader

Helix Workforce • Chicago (IL)

Remote
USD 78,120 - 111,600
Business Coach and Consultant, Exit Strategy (IL)

Business Coach and Consultant, Exit Strategy (IL)

Exit Factor • Oswego Township (IL)

Remote
USD 35,000 - 60,000
Remote work
Flexible schedule
Mentorship program
+1
SMB Exit Strategy Coach — Remote (Chicago Suburbs)

SMB Exit Strategy Coach — Remote (Chicago Suburbs)

Exit Factor • Aurora (IL)

Remote
USD 60,000 - 120,000
Flexible schedule
Remote work