Document type: Guide Practice area: Corporate — Executive Compensation Jurisdiction: United States (federal and Delaware) Last reviewed: 5 September 2026
Step 1: Get separate counsel, before the term sheet
Company counsel represents the company. The sponsor's counsel represents the sponsor. A management team without its own lawyer is negotiating the most consequential set of documents of its members' careers with nobody on its side of the table.
Engage early. The terms that move — the rollover instrument, the cause definition, the treatment of rollover equity on departure, the performance vesting mechanics — move when raised at the term sheet stage and calcify afterward. A specialist raising them in week two gets them; the same specialist raising them in week ten does not.
Who pays. Sponsors routinely agree to reimburse management's counsel up to a capped amount, and it is a normal ask. Where the company pays, confirm the engagement is with the management team, not the company.
Whether the team shares counsel. One lawyer for the whole team is efficient and creates conflicts where members' interests diverge — the CEO rolling forty percent and a divisional VP rolling nothing are not similarly situated. Common representation with an express conflict waiver works for a team with aligned interests; it does not work when the packages differ materially.
Step 2: Model the deal before negotiating it
Do not negotiate terms whose value you have not computed.
Build a three-scenario model at exit values of roughly flat, moderate appreciation, and strong appreciation — five years out, with the actual capital structure.
For each scenario, compute the waterfall: debt repaid; sponsor preference and accrued preferred return; sponsor capital returned; residual split; and what each of your positions receives — cash at closing, rollover equity, time-vested incentive, and performance-vested incentive.
The output that matters is a table showing, for each exit value, what the rollover is worth and what the incentive pool is worth. A manager who has seen that table negotiates completely differently from one who has not.
Run the flat case honestly. Rollover equity behind a large preference and a large debt stack can be worth zero at an exit value equal to the purchase price. If the flat case shows zero, that is the single most important fact in the negotiation, and it is the fact that justifies changing the rollover instrument.
Model the after-tax outcome too. Capital gain on rollover and properly structured profits interests; ordinary income on non-qualified spreads and phantom payments; and the three-year holding period of 26 U.S.C. § 1061 applied to profits interests.
Do not rely on the sponsor's model. It was prepared by people whose interest is in your rolling, it reflects their base case, and it carries disclaimers. Use their assumptions if you like; build the model yourself.
Step 3: Fix the rollover instrument
This is the highest-value item in the negotiation.
Ask the question directly: what security does my rollover buy, and how does it rank against the sponsor's security?
The three answers.
The same instrument as the sponsor, at the same price. Full alignment. The rolled capital enjoys the same preference and preferred return as the sponsor's. This is the position to negotiate for, and it is conceded more often than managers expect.
A strip — some preferred, some common, in the same ratio as the sponsor. The middle position, and entirely defensible. Management participates in the same blend of downside protection and upside leverage.
Common only, behind the sponsor's preferred. Maximum leverage in a strong outcome, and complete wipeout at a flat or modest exit. Sponsors propose this because it is cheap for them and because managers do not always model it.
How to make the ask. Not as a demand but as a modeling question: "at an exit at the purchase price, the common receives nothing and my rollover is gone — is that the alignment you intend?" Framed that way, it is a conversation about incentives rather than a fight about value, and it usually resolves in favor of a strip or of pari passu treatment.
Also negotiate. The rollover percentage itself, which is a function of what the manager can afford to have at risk. Whether the rollover is calculated pre- or post-tax — rolling a percentage of gross proceeds means paying tax on the cash portion with a smaller cash portion. And whether any portion of the rollover receives a guaranteed return or a preference of its own.
Step 4: Confirm the tax structure
The rollover must be non-recognition, or the manager pays tax on money they did not receive.
If the acquisition vehicle is a partnership or LLC, a contribution of property in exchange for a partnership interest is generally non-recognition under 26 U.S.C. § 721. This is the cleaner path and the reason most sponsor vehicles are LLCs.
If the vehicle is a corporation, 26 U.S.C. § 351 requires that the transferors, as a group, control the corporation immediately after the exchange. The structure must be built so management and the sponsor are part of the same transferor group, and a technical failure here is expensive and irreversible.
Where the target's own equity is contributed rather than proceeds, confirm the mechanics: a direct contribution of target shares versus a sale followed by a purchase produces different answers, and the documents must reflect the intended one.
Reorganization treatment under 26 U.S.C. § 368 applies in some structures, less commonly in sponsor buyouts.
Get a tax opinion or at least a written analysis, and confirm the reporting position both parties will take. A structure the parties describe differently on their returns is a problem waiting for an examination.
Step 5: Negotiate the incentive pool
Size. Eight to fifteen percent fully diluted is the usual range, driven by company size, team size, and sponsor practice. Ask what percentage is granted at closing and what is reserved — a fully allocated pool leaves nothing for future hires, which means dilution later or an unhappy new CFO.
Anti-dilution. Negotiate an obligation to increase the pool proportionately on future equity issuances so the intended percentage is preserved. Without it, an add-on acquisition strategy funded with sponsor equity dilutes the team continuously.
Instrument. In an LLC, profits interests are the most tax-efficient instrument available: no tax at grant when properly structured, and capital gain on appreciation. In a corporation, options under 26 U.S.C. § 422 or non-qualified options; restricted stock taxed under 26 U.S.C. § 83; or phantom equity, which is simple and produces ordinary income and § 409A exposure.
Threshold or strike. Set at transaction value. Confirm the valuation supporting it, because a strike below fair market value makes the option deferred compensation under 26 U.S.C. § 409a with a twenty percent additional tax on the holder.
Participation point. Does the pool share from the first dollar of appreciation, or only after the sponsor receives its capital and preferred return? The difference is large and it is often buried in the waterfall rather than stated.
Distributions before exit. Whether incentive equity participates in interim distributions, and whether tax distributions are made to cover phantom income on allocated but undistributed profits — which for profits interest holders is a genuine cash flow problem if not addressed.
Step 6: Negotiate vesting
Time vesting. Five years is standard. Negotiate: whether there is a cliff; the vesting frequency; and acceleration.
Acceleration. Full single-trigger acceleration on a change of control is management-favorable and resisted. Double trigger — change of control plus termination without cause or resignation for good reason within a window — is the balanced position and is widely accepted.
Performance vesting. Negotiate the hurdles and, more importantly, the mechanics:
- Linear interpolation between hurdles, not cliffs. Removes the distortion at the margin and removes the worst arguments at exit.
- Interim distributions count toward the multiple and the return. Otherwise a dividend recapitalization delivers return to the sponsor and nothing to vesting.
- Follow-on sponsor capital added to invested capital at cost only, with the resulting earnings counted. Otherwise the hurdle moves away from management every time the sponsor invests.
- Vesting to the extent hurdles are met by the exit transaction itself, computed on the transaction's own consideration.
- Measurement definitions — what counts as invested capital, what counts as proceeds, how in-kind consideration and escrows are valued, and who computes it.
And ask for a worked example. A schedule showing vesting at three exit values, appended to the award agreement, surfaces every ambiguity in the formula before it matters.
Step 7: Negotiate the leaver provisions
This is where the value is kept or lost, and it is the section managers most often skim.
Narrow "cause." The target definition: conviction of (or plea to) a felony or a crime of moral turpitude; fraud, embezzlement, or theft against the company; willful misconduct or gross negligence causing material injury to the company; and material breach of a written agreement that remains uncured for thirty days after written notice. Determined by the board, with the manager given written notice specifying the conduct and an opportunity to be heard with counsel.
Resist: "failure to meet performance objectives"; "violation of any company policy"; "conduct detrimental to the company"; and any determination "in the Board's sole discretion" without process.
Insist on "good reason." Material diminution of duties, authority, title, or reporting line; material reduction in base salary or target bonus; relocation beyond fifty miles; and material breach by the company — each with notice within a window, a company cure period, and a resignation window. Without good reason, constructive termination costs the manager everything.
Separate rollover equity from incentive equity. Rollover was purchased with after-tax money; incentive equity was granted for services. A bad leaver discount on purchased equity is a forfeiture of the manager's own capital, and naming that distinction usually wins the point.
Negotiate the middle category. Voluntary resignation without good reason: press for good leaver treatment after a cliff (three years is common), or at minimum for a defined discount rather than a repurchase at cost.
Valuation mechanism. Board determination of fair market value, subject to the manager's right to require an independent appraisal by a firm selected from an agreed list, with cost borne by the company if the appraisal exceeds the board's figure by a stated margin.
Payment terms. Cash at closing where possible. Where a note is required, negotiate market interest, a maximum term, and acceleration on a change of control or a dividend recapitalization.
And remember what the law will not do for you. Nemec v. Shrader, 991 A.2d 1120 (Del. 2010) confirms that the implied covenant of good faith cannot override an express contractual redemption right, even when exercised at a moment that is very good for the company and very bad for the departing holder. The terms you sign are the terms you get.
Step 8: The employment agreement
Negotiated in parallel and read together with the equity documents, because the definitions interlock.
Match the definitions. "Cause," "good reason," and "change of control" must be identical across the employment agreement, the equity plan, and the award agreements. A manager who is a good leaver under one document and a bad leaver under another has a drafting failure that costs real money, and it is extremely common.
Compensation. Base salary with a review mechanism. Target bonus stated as a percentage, with the metrics and who sets them specified. Resist a purely discretionary bonus — in a sponsor-owned company, a discretionary bonus is a bonus the sponsor may decide not to pay. Ask for a formula, a floor, or at minimum a good-faith standard.
Severance. A multiple of base plus target bonus, benefit continuation, pro rata bonus for the year of termination, and outplacement. Confirm that a termination triggering severance also triggers good leaver treatment under the equity documents.
Restrictive covenants. Non-compete scope, duration, and geography; non-solicitation of employees and customers; confidentiality; and inventions assignment. Enforceability varies by state and several states restrict or prohibit employee non-competes. Note that a covenant given in connection with the sale of a business is treated more favorably than one in an employment agreement in most jurisdictions — which is why sponsors often place them in the purchase agreement. Negotiate the duration, the definition of the restricted business, and a carve-out permitting passive investment.
The forfeiture linkage. Many packages convert a good leaver into a bad leaver retroactively on breach of a covenant, with a clawback. Negotiate: material breach only; notice and cure; a determination by a court or arbitrator rather than the board; and a defined clawback period.
Indemnification. Charter and bylaw indemnification to the fullest extent permitted, an indemnification agreement with advancement of expenses, and D&O coverage including a tail on exit.
Section 409A compliance. Severance, deferred bonus, and any promise to pay in a later year are within 26 U.S.C. § 409a unless exempt. The failure penalty falls on the employee: immediate inclusion, a twenty percent additional tax, and a premium interest charge. Confirm the agreement uses the standard exemptions and specified-employee delay provisions correctly.
Step 9: The deadlines that cannot be missed
The 83(b) election: thirty days. Under 26 U.S.C. § 83, the election must be filed within thirty days of the transfer of the property. There is no extension and no relief.
Practical protocol. On the grant date, calendar the deadline for day twenty. Prepare the form the same week. File by a method that produces proof of mailing, and retain the proof permanently. File a protective election for profits interests even though a properly structured profits interest has no value at grant — the cost is a stamp and the downside of being wrong about valuation is total.
Who files. The individual, not the company. Companies routinely assume someone else is handling it, and the manager is the one who bears the consequence.
The 280G shareholder vote: before the change of control. For a private corporation, 26 U.S.C. § 280G disallows deductions and 26 U.S.C. § 4999 imposes a twenty percent excise tax on the individual where change-of-control payments to a disqualified individual reach three times the base amount.
The exception requires: identification of disqualified individuals and computation of base amounts; determination of the parachute payments including equity acceleration; written waivers from each individual of the amounts exceeding the threshold, conditioned on approval; adequate disclosure to shareholders of all material facts; and approval by more than seventy-five percent of the voting power entitled to vote, excluding shares held by disqualified individuals.
Timing. Start six weeks before closing. The computation requires valuation work, the waivers require individual sign-off, and the vote requires a shareholder base that can actually be assembled. This is the deadline most often discovered too late.
Blue sky and Rule 701 disclosure. Where the compensatory plan exemption under 17 C.F.R. Part 230 is used and aggregate sales exceed the threshold in a twelve-month period, financial statements and risk factors must be delivered to participants before sale. Confirm the exemption relied on and the disclosure obligation before grants are made.
Vesting commencement and grant dates. Confirm they are documented contemporaneously with board or manager approval. Backdated grant documentation is a serious problem and an entirely avoidable one.
Step 10: The documents to read and what to look for
| Document | What it does | What to look for |
|---|---|---|
| Rollover agreement / contribution agreement | Effects the rollover | The class of security received; per-unit price; non-recognition mechanics; representations given |
| LLC agreement / stockholders agreement | Governs the equity | Waterfall; preference and preferred return; leaver provisions and call rights; transfer restrictions; drag and tag; preemptive rights; information rights; board composition |
| Equity incentive plan | Framework for awards | Pool size; anti-dilution; administration and discretion; amendment rights; the definition of "cause" |
| Award agreement | The individual grant | Number and class; threshold or strike; vesting, time and performance; acceleration; forfeiture; the worked example if you obtained one |
| Employment agreement | Employment terms | Term; compensation; severance; "cause" and "good reason" matching the equity documents; restrictive covenants; 409A compliance |
| Restrictive covenant agreement | Post-employment limits | Scope, duration, geography; definition of the restricted business; passive investment carve-out; consideration |
| Indemnification agreement | Protection as a fiduciary | Advancement; scope; D&O coverage and tail |
| 280G waiver and disclosure | Parachute mitigation | The waiver's conditionality; the disclosure's completeness |
| 83(b) election | Tax election | Filed within 30 days; proof retained |
Read the LLC agreement's leaver and call provisions first. They are usually in the middle of a long document, they are the least discussed, and they determine more of the outcome than anything else in the package.
Step 11: Living with it
Keep the documents. All of them, with the 83(b) proof of filing, permanently. Managers routinely cannot locate their own award agreements five years later, at exactly the moment the terms matter.
Get the information rights used. Annual and quarterly financials, and an annual valuation. Ask for them; a right nobody exercises is a right the company stops honoring.
Track vesting. Time vesting on a calendar; performance vesting against the actual invested capital and distribution history. Ask the CFO annually for the invested capital figure and the distribution total, and keep your own running computation.
Watch for events that change the analysis. A dividend recapitalization (does it count toward hurdles?). A follow-on equity investment (added at what value?). An add-on acquisition (does the pool get topped up?). A refinancing. Each is a moment to check what your documents say and to raise it if the answer is unclear, rather than discovering the answer at exit.
Reassess before departing voluntarily. The leaver provisions determine the outcome, and the difference between resigning in month thirty-five and month thirty-seven can be the entire value of the position.
And before an exit, run the model again with the actual numbers: waterfall position, vesting, tax character including the three-year holding period of 26 U.S.C. § 1061, and drag-along obligations. Surprises at exit are almost always failures of tracking rather than failures of drafting.
Transfer restrictions, drag, tag, and information
These sit in the LLC agreement or stockholders agreement and are read last, which is the wrong order.
Transfer restrictions. Expect a general prohibition with carve-outs for estate planning transfers to permitted transferees, and a right of first refusal. Normal. Confirm the permitted transferee definition covers trusts and family entities used in the manager's own planning.
Drag-along. The sponsor can compel a sale. Negotiate:
- The same form and per-security amount of consideration the sponsor receives.
- Representations limited to title, authority, and no conflicts — no business representations, which belong to the company and the sponsor.
- Several, not joint, liability for any indemnity.
- A cap on indemnity exposure at the proceeds actually received, and no escrow exceeding a pro rata share.
- No obligation to enter into any new restrictive covenant, employment agreement, or non-compete with the buyer as a condition of the drag. This is imposed regularly and accepted regularly, and it should not be.
- A minimum price or minimum-return condition, if obtainable.
Tag-along. If the sponsor sells, management participates pro rata on the same terms. Confirm it applies to partial sales, that it covers incentive as well as rollover equity, and that transfers to sponsor affiliates are either excluded from the tag or subject to a continuing obligation.
Preemptive rights. Sponsors often exclude management, meaning every follow-on issuance dilutes the team. At minimum, obtain pool anti-dilution; ideally, obtain a participation right on the rollover equity.
Information rights. Annual audited (or reviewed) financial statements; quarterly unaudited statements; an annual determination of the fair market value of the equity; and notice of material events — a change of control, a dividend recapitalization, a material acquisition, or a refinancing.
Why the valuation right matters. A manager holding an illiquid position for six years with no idea what it is worth cannot plan, cannot evaluate an offer to depart, and cannot tell whether the performance hurdles are within reach. It is a cheap ask and it is routinely omitted.
Board and observer rights. The CEO usually sits on the board. Consider whether a second management seat or an observer right is obtainable, and confirm indemnification and D&O coverage extend to it.
Negotiating for the rest of the team
The CEO's package gets negotiated. The rest of the team's often does not, and the differences compound.
Map the team before anything is agreed. Who rolls, who does not, who receives incentive equity, and in what proportions. A CEO who negotiates only their own terms leaves the team worse off and will hear about it for five years.
The recurring divergences.
Rollover capacity. The founder may be rolling from a nine-figure outcome; a divisional president may be rolling from a two-hundred-thousand-dollar option gain they need for a down payment. Requiring rollover from executives who cannot afford it is a retention risk, not an alignment tool.
Allocation of the pool. Concentrated at the top or spread more broadly. There is no correct answer, and the decision should be made deliberately and communicated, because it will become known.
Leaver treatment. Junior executives are more likely to depart voluntarily before an exit, which makes the voluntary-resignation category matter more to them than to the CEO. The three-year cliff for good leaver treatment is worth more to a VP than to a founder.
Employment terms. Severance multiples, notice periods, and restrictive covenant scope should scale with seniority, and the "good reason" definition matters most to those most likely to be reorganized around.
The practical approach. Negotiate a common framework for the team — one cause definition, one good reason definition, one leaver structure, one valuation mechanism — and vary only the economics. A team on one set of definitions with different numbers is far better off than a team with individually negotiated documents, and it is easier for the sponsor to administer, which makes it an easier ask.
Communicate. Tell the team what they are getting, in writing, with a model. A team that discovers at exit that the vesting worked differently than they assumed is a team that will not roll into the next deal, and the sponsor will care about that.
Step 12: Governance, conflicts, and the process record
Management negotiating its own package while also selling the company creates a conflict the other stockholders are entitled to have managed.
When a special committee is needed. Where management is on both sides of a transaction — as sellers, as rollover investors, and as prospective incentive holders — a committee of disinterested directors with independent financial and legal advice is the conventional protection. In re Trados Inc. Shareholder Litigation, 73 A.3d 17 (Del. Ch. 2013) is the cautionary case: directors holding incentive awards approved a sale paying the preferred and the incentive plan and leaving the common with nothing, with no committee, no consideration of the common's interests, and no independent advice. Liability was avoided only because the common turned out to be worthless.
Sequencing. The cleaner order is price first, management package second. Where the sponsor insists on locking management early, the management terms should be disclosed in full to whoever approves the transaction — the board, the special committee, and the stockholders.
What to disclose. The rollover amount and instrument; the pool size and the individual's expected allocation; the employment terms; and the timing of when each was agreed. Partial disclosure is worse than none, because it invites the inference that the rest was concealed.
For the manager personally. Recuse from board votes on the transaction and on the management package. Have counsel present. Keep a record of what you told the board and when — the process record is the manager's protection as well as the company's.
And for minority stockholders' counsel on the other side. The questions worth asking are: when were the management terms first discussed; who negotiated them; was there a committee; did it have independent advice; and does the price reflect a market check conducted before management's own package was fixed.
Worked example: the nine days that mattered
Tomasz Bregović is selling Meridian Thermal to Calder Ridge Partners at a two hundred forty million enterprise value, rolling thirty percent, and taking five percent of a twelve percent pool. His own counsel is engaged the week the term sheet is circulated.
Day 1 — the model. Three scenarios. At a flat exit, Calder Ridge's eighty million of preferred plus an eight percent compounding return consumes roughly one hundred eighteen million, and the common — where Tomasz's thirty-nine million rollover sits — receives nothing. The table is one page.
Day 2 — the ask. Not "we want better terms" but the model, with the question: is a structure in which management's rolled capital is wiped out at a flat exit the alignment you intend? Calder Ridge agrees Tomasz rolls into the same units it holds, at the same price. Two days of work; the largest single value change in the negotiation.
Day 3 — tax. The vehicle is an LLC, so § 721 non-recognition applies to the rollover. Counsel confirms the reporting position in writing with the sponsor's tax adviser.
Days 4–5 — the pool and vesting. Anti-dilution added so the pool tops up on future issuances. Performance vesting mechanics negotiated: interim distributions count; follow-on capital added at cost with resulting earnings counted; linear interpolation between 2.0x and 3.0x; vesting to the extent hurdles are met by the exit itself. A worked vesting example is appended to the award agreement.
Days 6–7 — leaver provisions. The first draft's "cause" includes failure to meet board-set performance objectives, and there is no "good reason" at all. Both are rewritten. Rollover equity is carved out of bad leaver discounts entirely — the argument that purchased equity is not compensation is made once and accepted. A valuation challenge right with cost-shifting is added.
Day 8 — employment agreement. Definitions aligned across all documents. Bonus formula specified rather than discretionary. Severance linked to good leaver treatment. Restrictive covenants narrowed and moved partly into the purchase agreement, where they are more enforceable and where they were priced.
Day 9 — the deadlines. 280G analysis commissioned — five weeks before closing, and only just in time. The vote, waivers, and disclosure are completed eleven days before closing. The 83(b) filing protocol is set up with a calendar reminder for day twenty after grant.
The result. Nine days of specialist time. The rollover instrument change alone is worth tens of millions in the downside case. The leaver rewrite removes the possibility that a pretextual termination forfeits thirty-nine million of Tomasz's own money. And the 280G work, started five weeks out, avoided a twenty percent excise tax that nobody had mentioned.
The valuation question, in practice
Several provisions turn on "fair market value," and the word does more work than it can bear.
Where it appears. The strike or threshold on incentive awards at grant. The repurchase price on a leaver event. The annual valuation supporting information rights. And, for options, the § 409A requirement that the exercise price not be below fair market value at grant.
Who determines it. Board determination is the sponsor's default. An independent appraisal is management's preference and costs money. A formula — a multiple of trailing EBITDA less net debt — is cheap and predictable and can be badly wrong in either direction.
What to negotiate.
At grant. A contemporaneous valuation supporting the threshold or strike. For options this is not optional — a strike below fair market value converts the option into deferred compensation under 26 U.S.C. § 409a, with a twenty percent additional tax on the holder.
On repurchase. A board determination, delivered in writing with the methodology, subject to the manager's right to require an independent appraisal by a firm chosen from an agreed list, with the cost borne by the company if the appraisal exceeds the board's figure by more than a stated margin. That cost-shifting provision is what makes the challenge right real.
Annually. A valuation delivered to holders, so the position can be tracked and planned around.
Two recurring problems.
Marks that move in the company's favor at exactly the wrong moment. A repurchase valued at a trough is entirely lawful — Nemec makes that clear — and the protection is a mechanism agreed in advance, not an argument afterward.
Discount for lack of marketability and minority interest. A repurchase price computed with a thirty percent combined discount is a very different number from one computed without. Say whether discounts apply, and if they do, cap them.
Variations on the standard deal
A minority investment rather than a buyout. The sponsor takes a stake and management retains control. Rollover is not the frame; instead the existing equity is diluted and a new class is issued above it. The critical terms shift to protective provisions, board composition, and the exit rights the sponsor obtains — a put right, a redemption right, or a drag that management must eventually honor.
A management buyout with sponsor backing. Management is on the buy side, which sharpens the conflict enormously. A special committee and independent advice are not optional here, and the process should be documented as though it will be litigated, because it may be.
A second sponsor deal — the "second bite." Management rolls again into the next sponsor's structure. The team is more experienced, the negotiation is faster, and the recurring question is whether the incentive pool is reset at the new, higher valuation. It should be, and the argument that management "already made money" is not a reason for a smaller pool going forward.
A family or founder-owned business selling for the first time. The seller frequently has never seen these documents, is emotionally invested, and is negotiating with a counterparty who does this monthly. The single most valuable thing counsel does is slow the process down enough to model it.
A public-to-private. Adds proxy disclosure of the management arrangements, the Trados conflict analysis in its most visible form, appraisal exposure, and a special committee process that will be examined closely. Management's arrangements will be disclosed in full, which is itself a discipline.
A distressed or restructuring context. Incentive plans adopted around a restructuring face different constraints, existing equity is often wiped out, and rollover is rarely on the table. The relevant instrument is usually a post-emergence management incentive plan negotiated with the creditors who will own the company.
A carve-out from a larger corporate. Management's existing parent-company equity does not travel; it is cashed out, forfeited, or converted under the parent's plan. The new package starts from zero, and the value of the parent awards being given up should be part of the negotiation.
Practice pointers
Engage separate counsel before the term sheet. Every other item on this list depends on it.
Build the three-scenario model in week one and lead with it. The flat case is the argument.
Ask "into what?" before "how much?" The rollover instrument is worth more than the rollover percentage.
Confirm § 721 or § 351 non-recognition in writing, and agree the reporting position with the sponsor's tax adviser.
Calendar the 83(b) deadline on the grant date, file by day twenty, and keep the proof forever.
Commission the 280G analysis six weeks before closing. The waivers, the disclosure, and the seventy-five percent vote all take time.
Negotiate performance vesting mechanics, not just hurdles: interpolation, interim distributions, follow-on capital at cost, and vesting on the exit itself. Attach a worked example.
Rewrite "cause" and insist on "good reason" — and align them across all three documents.
Carve rollover equity out of bad leaver discounts. It is purchased capital, not compensation.
Get a valuation mechanism with a challenge right, and cash at closing for repurchases where possible.
Cap the drag-along: same consideration, title representations only, several liability, indemnity capped at proceeds, and no new restrictive covenants.
Obtain annual valuation and financial information rights, and use them.
Negotiate one framework for the whole team and vary only the economics.
Track vesting and invested capital yourself, annually. Surprises at exit are tracking failures, not drafting failures.
Common mistakes
Engaging counsel after the term sheet. Everything else follows from this.
Negotiating the percentage before the instrument. The class matters more.
Not modeling the flat case. It is the case that justifies every other ask.
Assuming the rollover is tax-free. Confirm § 721 or § 351 treatment in writing.
Missing the 83(b) deadline. Thirty days, no relief, and the manager bears it.
Discovering 280G five weeks out — or later. Start six weeks out.
Accepting a cause definition that reaches performance. It makes every award discretionary.
Accepting no good reason definition. Constructive termination then costs everything.
Letting rollover equity be treated as incentive equity on departure. It is the manager's own capital.
Performance hurdles with cliffs and no interim distribution credit. Both distort behavior and both are conceded when raised.
Definitions that differ across documents. Read the three definitions side by side before signing.
Never exercising information rights. A right nobody uses stops being honored.
Assuming fairness will fill the gaps. Nemec says otherwise.
Related documents
- Management Rollover and Incentive Equity in Sponsor Deals: What the Team Actually Gets
- Management Equity and Rollover Checklist: A Practical Checklist
- Management Equity Toolkit: Rollover Mechanics, Incentive Plans, and Employment Terms
- Equity Compensation: Stock Options, RSUs, Profits Interests, and Section 409A
- Choice of Entity and the Tax Consequences That Follow: LLC, S Corporation, C Corporation, and Partnership
- Restrictive Covenants in Business Sales, Franchises, and Partnerships
This guide is general information, not legal advice, and does not create an attorney-client relationship.