Alternative Ownership Financial Analyst & Project Manager

Written By Peter Koehler

Project-Based Independent Contractor

About Stronghold Ownership and Purpose Owned

Stronghold Ownership and Purpose Owned frequently collaborate to help business owners explore, design, and implement ownership transitions that benefit employees, protect company purpose, support people and planet (sometimes through associated philanthropic entities), and support long-term business independence and durability.

We advise privately held companies on Perpetual Purpose Trusts,  Employee Ownership Trusts (EOT), Employee Stock Ownership Plans (ESOP), Management Buyouts, hybrid ownership-structures that include non-profits, transaction financing, governance design, and related ownership structures.

We are seeking an experienced Employee Ownership Analyst / Project Manager to support client engagements on a project basis.

The Role

The Alternative Ownership Analyst & Project Manager will serve a dual role across client engagements: finance/deal analyst and project manager.

On the finance/deal side, this person will help evaluate transaction feasibility, compare structural alternatives, build and refine financial models, and translate complex ownership and financing issues into clear recommendations and decision points. This is the most important skillset for this person to possess.

On the project management side, this person will help keep engagements organized and moving. That includes tracking workstreams, coordinating deadlines, identifying open questions, following up on missing information, preparing for meetings, and helping ensure that clients and advisors understand what needs to happen next. Project management skill/experience is important, but not as important as the finance skillet.

This person will work closely with Stronghold Ownership and Purpose Owned’s senior advisors and will interact directly with clients, attorneys, tax advisors, valuation professionals, lenders, trustees, and other transaction participants.

This is a project-based independent contractor role. Hours will vary significantly from month to month based on project load, client timelines, and the nature of available assignments. There is no guaranteed minimum number of hours. Candidates must be comfortable with that variability.

Depending on experience, the contractor may support defined analytical and project management assignments or independently manage substantial portions of a client workstream.

Responsibilities

Deal Structuring and Financial Analysis

  • Help evaluate and compare potential transaction structures for ESOP, EOT, purpose trust, and other employee ownership transitions

  • Build and refine financial models for employee ownership transactions

  • Analyze historical financial statements, projections, normalized earnings, cash flow, debt capacity, valuation inputs, and transaction feasibility

  • Model alternative ownership transactions, financing arrangements, payment schedules, tax estimates, and operating scenarios

  • Evaluate the financial and structural effects of seller notes, senior debt, subordinated debt, earn-outs, warrants, dividends, redemptions, direct sales, partial sales, and related transaction components

  • Compare ESOPs, EOTs, purpose trusts, management buyouts, third-party sales, and other succession alternatives

  • Help identify and communicate structural tradeoffs, financing constraints, implementation risks, tax and legal questions, and areas requiring further diligence

  • Translate models and transaction alternatives into clear conclusions, recommendations, and decision points

  • Prepare polished client materials, presentations, memoranda, and financial exhibits

  • Help business owners and advisors understand the practical implications of different ownership transition paths

Project Management and Client Coordination

  • Help manage client engagement timelines, workplans, deliverables, and deadlines

  • Track open items, outstanding diligence requests, key decisions, and next steps

  • Coordinate information flow among Stronghold Ownership, Purpose Owned, clients, and external advisors

  • Prepare agendas, meeting materials, follow-up notes, and action item lists

  • Monitor progress across financial, legal, tax, valuation, governance, and financing workstreams

  • Help ensure that client engagements remain organized, focused, and on schedule

  • Flag delays, bottlenecks, missing information, or unresolved questions before they become larger problems

  • Support senior advisors in preparing for client meetings and advisor coordination calls

  • Participate in client-facing calls and confidently walk business owners and advisors through models, assumptions, sensitivities, transaction alternatives, conclusions, and next steps

  • Explain technical financial, structural, and ownership concepts in clear, practical language

Tools, Quality Control, and Confidentiality

  • Use AI tools responsibly to improve research, financial analysis, model development, documentation, quality control, project management, and overall efficiency

  • Independently verify AI-assisted work

  • Maintain strong internal organization across files, models, notes, workplans, diligence trackers, and client materials

  • Produce work that is accurate, clear, timely, and useful to both clients and senior advisors

  • Protect client confidentiality

Preferred Experience

We do not expect any candidate to have every qualification/experience criteria listed below. Strong candidates will bring a mix of employee ownership experience, financial modeling capability, deal judgment, project management ability, and client-facing communication skills.

Past Experience

  • Direct professional experience with Purpose Trusts, EOTs, ESOPs, employee ownership transactions, business succession, leveraged buyouts, or closely related transaction structures

  • Experience with an employee ownership advisory firm, ESOP trustee, valuation firm, investment bank, accounting firm, family office, transaction advisory practice, or similar professional services environment

  • Experience supporting transactions from initial feasibility analysis through implementation

  • Experience working directly with business owners, senior executives, and professional advisors

Financial and Analytical Skills

  • Strong financial modeling skills in Excel or Google Sheets, with the ability to use AI tools to improve modeling efficiency and accuracy

  • Ability to interpret financial statements and analyze operating and transaction cash flows

  • Familiarity with business valuation, debt capacity, transaction financing, and ownership transition mechanics

  • Experience with seller financing, senior debt, subordinated debt, earn-outs, warrants, and transaction capitalization

  • Strong attention to detail and a high standard for analytical accuracy

Deal Judgment

  • Ability to think through deal structure, not just financial outputs

  • Comfort comparing different transaction paths and explaining the tradeoffs clearly

  • Understanding of the tax, legal, fiduciary, and governance considerations associated with employee ownership transactions

Project Management

  • Strong project management skills, including comfort managing timelines, open items, follow-ups, and multi-party workstreams

  • Experience managing or coordinating transaction, consulting, advisory, or implementation projects

  • Familiarity with project management tools, shared workplans, diligence trackers, CRM systems, or similar workflow tools

  • Ability to work independently, manage deadlines, and produce polished work with limited oversight

Client-Facing Communication

  • Strong written and verbal communication skills

  • Professional presence and confidence in client-facing conversations

  • Ability to present financial models and transaction alternatives clearly and respond effectively to client questions

AI Fluency

  • Practical experience using AI tools to improve the quality and efficiency of professional work

  • Sound judgment regarding the limits, verification, security, and appropriate use of AI-generated work

Work Style

  • Comfort with an assignment-based workload that may fluctuate materially from month to month

What Success Looks Like

A strong contractor in this role can take imperfect financial information, develop a reliable and understandable model, identify the questions that matter, and explain the results clearly to a business owner.

They can also help think through the structure of a deal. They understand that the model is not the answer by itself. It is a tool for evaluating tradeoffs, pressure-testing assumptions, surfacing constraints, and helping clients make better decisions.

They can keep an engagement moving. They know what has been decided, what remains open, who owns each next step, and what needs to happen before the next meeting. They bring order to complex projects without adding unnecessary bureaucracy.

They maintain professional and timely communication with clients, advisors and project Leaders. Demonstrate willingness to be flexible and responsive to meet transaction deadlines.

They are analytically rigorous, organized, responsive, and comfortable with ambiguity. They can distinguish between what the numbers demonstrate and what still requires legal, tax, valuation, or strategic judgment.

They also know when to work independently, when to raise a concern, and when to bring in a senior advisor.

Engagement Structure

  • Independent contractor

  • Remote

  • Project-based assignments

  • No guaranteed minimum number of hours

  • Hours may vary significantly from month to month based on project load

  • Assignments may range from discrete modeling, deal analysis, or project management work to ongoing support across a broader client engagement

  • Contractors must communicate their availability and meet agreed-upon project deadlines

  • Compensation of $100 to $150 per hour, depending on relevant employee ownership experience, financial modeling capability, deal structuring capability, project management capability, and ability to independently manage client-facing work

 

To Apply

Please submit the following to hiring@strongholdownership.com by EOD Monday, August 17th, 2026.

  • A resume or LinkedIn profile

  • A cover letter including

    • Brief description of your experience with ESOPs, EOTs, PPTs, Management Buyouts, conventional M&A, or other ownership transactions

    • Brief description of your experience with deal structuring, financial modeling, and transaction analysis

    • Brief description of your experience managing or coordinating client engagements, transaction processes, or multi-party workstreams

    • Your desired hourly rate

    • Your general availability and capacity for variable project work

 

A Note on AI

We welcome thoughtful and responsible use of AI by contractors once they are working with Stronghold Ownership and Purpose Owned. However, please do not use AI to draft or revise your application materials. We want to hear your own voice and get a clear sense of how you think and communicate. Applications may be reviewed using AI-detection and screening tools.

Peter Koehler