Insider Trading April 2, 2026

Amwell Product Executive Sells Shares to Cover Taxes; Company Reports Mixed Financial Signals

Chief Product & Technology Officer Dmitry Zamansky completed an automatic sell-to-cover on April 1, 2026, as the telehealth firm grapples with losses and declining revenue despite a solid cash balance.

By Leila Farooq AMWL
Amwell Product Executive Sells Shares to Cover Taxes; Company Reports Mixed Financial Signals
AMWL

Dmitry Zamansky, Amwell's Chief Product & Technology Officer, sold 5,575 Class A shares on April 1, 2026, in an automatic sell-to-cover tied to restricted stock unit vesting. The transaction raised $29,547 at $5.30 per share. The firm reported a 22.1% year-over-year revenue decline in Q4 2025, a loss of $5.96 per share over the trailing twelve months and negative free cash flow of $65.97 million, but finished the year with $182 million in cash and no debt. Amwell's stock rose 2.55% amid investor interest in its technology and AI initiatives.

Key Points

  • Zamansky sold 5,575 Class A shares on April 1, 2026, at $5.30 each, totaling $29,547; the sale was an automatic sell-to-cover tied to RSU vesting.
  • Amwell reported a 22.1% year-over-year revenue decline in Q4 2025, a trailing twelve-month loss per share of $5.96 and negative free cash flow of $65.97 million.
  • The company ended the year with $182 million in cash and no debt; investor interest in its technology and AI efforts coincided with a 2.55% stock increase.

Dmitry Zamansky, who serves as Chief Product & Technology Officer at American Well Corp (NYSE: AMWL), sold 5,575 shares of the company’s Class A common stock on April 1, 2026, according to a Form 4 filing with the Securities and Exchange Commission. The shares traded at $5.30 apiece, producing proceeds of $29,547.

Following the transaction, Zamansky’s direct holdings total 241,080 shares. The filing specifies the sale was executed to satisfy the tax withholding obligation that arose when restricted stock units vested and were settled on April 1, 2026. The trade was carried out automatically as a "sell to cover" and was not a discretionary sale initiated by Zamansky.

Financial metrics disclosed by the company underscore ongoing headwinds. Over the last twelve months Amwell reported a loss per share of $5.96 and recorded negative free cash flow of $65.97 million. Separately, the company reported a 22.1% year-over-year drop in revenue for the fourth quarter of 2025.

Despite those pressures, Amwell ended the reporting period with $182 million in cash and no debt on the balance sheet. The company’s emphasis on technology and integration of artificial intelligence into its offerings has been noted as a factor supporting investor sentiment, and the stock registered a 2.55% gain following the recent updates.

Additional analysis and tips on the company’s financial health and outlook are available via InvestingPro, which lists five supplementary items related to AMWL’s position.


What happened

  • An automatic sell-to-cover on April 1, 2026, saw 5,575 shares sold at $5.30 for $29,547.
  • The sale covered tax liabilities tied to RSU vesting and settlement on the same date and was non-discretionary.

Where the company stands

  • Amwell reported a 22.1% revenue decline in Q4 2025 and a trailing twelve-month loss per share of $5.96.
  • Free cash flow was negative $65.97 million, while year-end cash totaled $182 million with no outstanding debt.
  • The stock moved up 2.55% amid investor attention to the company’s technology and AI integration.

These items together outline the immediate context for the insider transaction and the broader financial snapshot disclosed by the company.

Risks

  • Sustained losses and a trailing twelve-month loss per share of $5.96 create profitability risk for shareholders - impacts the digital healthcare and broader healthcare technology sectors.
  • Negative free cash flow of $65.97 million indicates cash burn that could constrain operations or investment plans - relevant to markets assessing capital allocation and telecom/tech spending.
  • A 22.1% revenue decline in Q4 2025 highlights near-term revenue risk and demand pressure in the telehealth segment.

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