Startup Option-Plan Repricing-and-Retention Director

The mandate

A developer-platform startup completed a down round that left most employee options underwater. Managers made inconsistent refresh promises during fundraising, newer hires hold lower strike prices than longer-serving peers and headline ownership ignores preference overhang. The board needs a retention response that employees can understand and that differentiates lost incentive from guaranteed value without rewarding negotiation volume or resetting every historical outcome.

The eight-week deliverable is an option population reconciliation, employee-outcome model, design alternatives and implementation decision pack. Milestone one establishes grants, holders and promises in week two; milestone two models value and retention cohorts in week four; milestone three tests repricing, exchange, cancellation and refresh options in week six; milestone four delivers accepted design, communication principles, controls and employee casebook.

The client will provide cap tables, plan rules, grant and vesting files, exercise history, valuation inputs approved for use, preference summaries from counsel, employee populations, performance and criticality evidence, manager promises, attrition data and vendor constraints. Acceptance requires every in-scope grant to reconcile, scenarios to reproduce by cohort and internal reward staff to process six employee cases through the chosen rules.

Consultants will not issue legal, tax, accounting or valuation opinions; set company value; amend grants; choose individual recipients; communicate offers; negotiate with employees; or administer the plan. Counsel and the board own rights and approvals. The project may illustrate outcomes under supplied values and terms, but cannot promise future liquidity or personal tax consequences.

Outputs will separate vested and unvested position, exercise price, time, dilution, preference effect, role critical retention need and manager commitment. Broad fairness, long-service recognition and critical-skill intervention must remain distinct. Grant execution, tax filings, employee negotiation and post-design administration after week eight are outside the engagement.

Why this is external work

Founders, investors and employees experienced the down round differently, and internal reward staff must administer whichever solution is chosen. Specialist independence is needed to expose cohort effects and inconsistent promises under intense retention pressure. External option-design expertise can build choices without valuing the company or deciding individual grants.

What you will own

• Reconcile holder, grant, vesting, exercise price, expiration, cancellation, promise and employment-status populations.
• Model employee outcomes under current value, dilution, preference, exit timing and future financing scenarios.
• Compare repricing, option exchange, cancellation and regrant, incremental refresh and targeted cash alternatives.
• Test fairness across tenure, grant vintage, performance, criticality, geography, leave and recent-hire cohorts.
• Quantify share-pool use, incentive leverage, retention reach, windfall and likely misunderstanding under each design.
• Create manager promise treatment, exception governance, employee examples and communication boundaries for board approval.
• Deliver reconciled grant data, scenario engine, design paper, employee casebook, control matrix and board-approved implementation requirements.

Candidate qualifications

• Led employee option repricing or exchange after a down round in a venture-backed technology company.
• Reconciled cap-table, plan, grant, vesting, employment and manager-promise evidence before design.
• Modelled employee value across strike price, preference overhang, dilution, time and uncertain exit scenarios.
• Balanced retention, fairness, tenure and critical-skill needs without promising liquidity or personal tax outcomes.
• Worked with boards and counsel while avoiding valuation, legal, tax and grant authority.
• Left reward teams able to administer chosen rules consistently across difficult global employee cohorts.

Non-negotiables

• Can complete four Tel Aviv-led employee and investor workshops within the eight-week engagement.
• Will disclose startup, investor, founder, option-vendor, law-firm and prospective employee relationships.
• Brings executed option repricing after a down round; ordinary equity benchmarking is insufficient.
• Accepts no authority over valuation, legal rights, individual grants, employee negotiation or plan administration.

1. 49 words maximum. Describe a down-round option redesign where repricing alone would have produced unfair employee outcomes.
2. 49 words maximum. Which source records must reconcile before modelling an option exchange?
3. 49 words maximum. How would you address informal refresh promises made during fundraising?