Executive Leadership & Entrepreneurship Fellow
A highly specialized track designed for personnel with an explicit goal of starting or acquiring a small business. All candidates will begin at Tier I to establish a baseline understanding of our specific entity structures and financial reporting before advancing to strategic functions. Advancement velocity is determined by the trainee's comprehension of applied business analytics.
Tier I: Business Analyst (Financial Literacy & Structure Focus)Target Profile: All incoming candidates.Training Focus: Entity structuring, P&L management, and capitalization.Responsibilities:-Review and analyze corporate entity structures (e.g., LLC vs. S-Corp).-Shadow the Owner in reviewing QuickBooks Online (QBO) to understand P&L statements, balance sheets, and cash flow.-Learn the mechanics of commercial capitalization, including SBA loan management and debt servicing.-Track basic Key Performance Indicators (KPIs) utilizing our operational tech stack.Tier II: Strategy & Growth Associate (Market Expansion Focus)Target Profile: Candidates demonstrating mastery of Tier I protocols.Training Focus: Market analysis, vendor negotiations, and asset acquisition diligence.Responsibilities:-Conduct due diligence on potential asset purchases utilizing data analytics (e.g., analyzing target companies' client lists).-Assist in negotiating terms with enterprise-level vendors and commercial insurance providers.-Draft internal growth initiatives and AI-assisted marketing strategies for existing operational units.-Evaluate local market trends to identify new service offerings or market expansions.Tier III: Executive Co-Pilot (Leadership & Execution Focus)Target Profile: Candidates demonstrating mastery of Tier II competencies.Training Focus: Total business management, executive decision-making, and entrepreneurial resilience.Responsibilities:-Operate directly alongside the CEO as a sounding board for high-level strategic pivots.-Take the lead on a specific, 30-day corporate initiative (e.g., launching a new marketing channel).-Experience the day-to-day realities of total business ownership, balancing field-level emergencies with high-level financial planning.-Finalize a comprehensive business plan for the trainee’s own future venture, peer-reviewed by the CEO.
Winfield, IL - This position requires frequent traveling to job-sites, HQ Office, partner locations, and commerce and networking events as necessary.
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Interview prep for this program▸
- ▸ "How many of your past SkillBridge interns received full-time offers?" — a serious program knows the number.
- ▸ "Who will my day-to-day mentor be, and what does week one look like?"
- ▸ "The listing says 151 - 180 days — can that flex to my approved window if my command shortens it?"
- ▸ "Is relocation expected for a full-time offer, or can I convert where I am?"
- ✓ Your projected start window and separation date (from your profile)
- ✓ Your command's approval status — even "packet drafted" signals you're serious
- ✓ Your civilian-translated resume bullets (generate them here)
- ✓ A written training-plan ask — you'll need it for your packet anyway
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