Upland Software Waives 4.5% Preferred Dividend, Lifts UPLD Common

Upland Software, Inc. (Nasdaq: UPLD) announced on 9 November 2026 that Ulysses Aggregator, LP, an affiliate of HGGC, LLC, has agreed to waive the accumulation and accrual of dividends on the company's Series A Convertible Preferred Stock for an indefinite period, effective 1 October 2026. The Series A Preferred currently accrues paid-in-kind dividends at 4.5% annually across 115,000 outstanding shares, and HGGC continues to hold all of them. The waiver is permanent for dividends forgone during the period and is not subject to future catch-up.

Context — Why the Dividend Waiver Matters Now

The waiver lands five days after Upland laid out a phased strategic plan alongside its third quarter 2026 results on 4 November 2026. That plan runs in three stages: Simplify and Delever through early 2027, Stabilize and Expand in 2027, and Grow in 2028 and beyond. The dividend waiver is the sponsor's financial endorsement of that sequence rather than a standalone capital-markets event.

The report gives no prior-period comparison for the accrual balance, no figure for the preferred stock's liquidation preference, and no conversion price. Readers looking for the dollar size of the dividend that will no longer accumulate will not find it in the announcement. Upland said additional information will be included in a Current Report on Form 8-K filed with the Securities and Exchange Commission.

What changed is the direction of accrual. Under the prior terms, the 4.5% rate was paid in kind, meaning dividends were added to the preferred stock's liquidation preference rather than settled in cash. That mechanism quietly increased the claim sitting ahead of common equity each quarter and raised the number of common shares issuable on conversion. The waiver stops both effects at the source.

HGGC framed the decision as long-term sponsorship. The private investment firm, which manages over $10 billion in assets under management as of 30 June 2026, said the waiver reflects its support for where the company is headed, moving from simplifying the business to driving growth through its AI-powered intelligence layer. That statement carries weight because HGGC is the counterparty giving up the accrual, not a third party commenting on it.

Upland's own framing ties the waiver to debt reduction. Chief Executive Officer Sean Nathaniel said the waiver further supports the Simplify and Delever strategy as the company continues to reduce debt and positions the business for sustainable growth. The report does not quantify Upland's debt balance or any repayment schedule.

Data — What the Numbers Show

The headline figures are small in absolute terms and structural in effect. The Series A Preferred carries a 4.5% annual paid-in-kind rate on 115,000 shares. HGGC holds 100% of that class. The waiver took effect 1 October 2026, so Upland expects the full quarterly benefit to begin in the fourth quarter of 2026.

The benefit is defined in accounting terms, not cash terms. Upland expects improved net income (loss) attributable to common stockholders and related per-share results. That is the same line item that preferred dividends reduce under standard presentation, so removing the accrual lifts the residual attributed to common holders without any change in operating performance.

Before the waiver, each quarter added 4.5% annualized to the preferred liquidation preference and increased the common share count issuable on conversion. After the waiver, the liquidation preference holds at its current level and the number of common shares issuable on conversion is limited. The table below sets the two states against each other.

Item	Before waiver	After waiver (from 1 Oct 2026)
4.5% PIK accrual	Accrues quarterly	Does not accrue
Liquidation preference	Rises with accrual	Held at current level
Common shares on conversion	Increases with accrual	Limited
Net income to common	Reduced by accrual	Improved

All other terms of the Series A Preferred Stock remain unchanged. The report gives no peer comparison, no sector benchmark and no market-cap figure for Upland, so no like-for-like valuation contrast can be drawn from the disclosure.

Analysis — What It Means for UPLD and Software Peers

The mechanical read is that Upland has converted a recurring drag on common earnings into a one-time structural improvement, funded entirely by its largest preferred holder. Because the waived dividends are permanently forgiven with no catch-up, the benefit compounds: each quarter that passes without accrual is a quarter of dilution and preference build-up that never happens.

Second-order effects run through the capital structure rather than the income statement. A static liquidation preference means the preferred claim does not creep closer to the common equity's residual value, and a capped conversion share count means future dilution from the Series A is bounded while the waiver holds. For anyone modelling UPLD's fully diluted share count, the input just became less path-dependent.

The counter-argument is that a dividend waiver is a signal about the holder's priorities, not about the business. HGGC gives up accrual only when the accrual is worth less to it than the strategic optionality of a healthier common equity — or when the accrual is unlikely to be paid in cash anyway, since the 4.5% was never a cash obligation. A sponsor can waive a non-cash accrual at low economic cost while retaining the full 115,000-share position and every other term of the instrument.

The waiver is also revocable prospectively. Upland stated it remains in effect until revoked in accordance with the waiver agreement, and that revocation would not trigger catch-up on forgiven amounts. That structure protects the company from a retroactive claim but leaves the forward accrual subject to HGGC's discretion.

Positioning follows the same logic. The waiver removes a known quarterly headwind for common holders, which is the kind of change income- and value-oriented holders of the common track. Preferred holders of the Series A are unaffected in coupon terms because there was no cash coupon to receive, and HGGC's economic exposure is unchanged at 115,000 shares.

Outlook — What to Watch Next

Three items sit on the calendar. The Form 8-K referenced in the announcement will carry the additional disclosure Upland promised, and it is the first place the waiver agreement's terms will be documented in a filing. Fourth quarter 2026 results are the first reporting period that captures the full quarterly benefit, and the company said it expects that benefit to show up in net income (loss) attributable to common stockholders and per-share results.

Execution against the three-phase plan is the longer arc. Simplify and Delever runs through early 2027, Stabilize and Expand covers 2027, and Grow begins in 2028 and beyond. Management tied the waiver directly to the deleveraging phase, so any update on debt reduction is the natural next checkpoint for the same thesis.

On the instrument itself, the only level the report names is the 4.5% annual accrual rate, now suspended. There is no conversion price, no liquidation preference figure and no revocation trigger disclosed, so there is nothing further to watch on the preferred until the 8-K lands. The report gives no dates for the fourth quarter earnings release or the filing.

Frequently Asked Questions

What does the Upland Software dividend waiver mean for retail investors holding UPLD?

For holders of the common stock, the waiver removes a quarterly accrual that previously reduced net income attributable to common stockholders. Upland said it expects improved net income (loss) attributable to common stockholders and related per-share results, with the full quarterly benefit starting in the fourth quarter of 2026. It is an accounting-level improvement, not a cash distribution, and the company is not paying a dividend to common holders.