How will the additional $100 million buyback affect UPWK's earnings per share and valuation multiples?

Impact on EPS – The $100 million repurchase will shrink Upwork’s share count by roughly 1–1.2 % (≈ 5 – 6 M shares at the current‑≈ $18‑$19 price). Because net income is unchanged in the short run, earnings per share rise proportionally – roughly a 1 %‑‑1.2 % uplift to “historical” EPS. In practice the market will begin to price‑in a higher forward‑EPS, nudging consensus forecasts a little higher once the reduced‑share base is reflected in analysts’ models.

Effect on valuation multiples – With a modestly higher EPS and the same headline earnings, the P/E (or forward‑PE) will initially contract if the stock price stays flat, making the shares look cheaper on a earnings basis. However, a $100 M buyback is a strong “confidence” signal; investors typically bid the stock up on the expectation that management is returning excess cash rather than churning growth‑capital. As the price appreciation materialises, the P/E will likely stay roughly level, while the price‑to‑sales and price‑to‑EBITDA multiples may edge higher, reflecting a premium on perceived “share‑holder friendliness”.

Trading takeaway – The buyback acts as a short‑term catalyst: expect bullish momentum on the chart, with the stock testing the recent $20‑$22 resistance zone on the upside. A pull‑back to the $18–$19 range could offer a low‑risk entry for “buy‑the‑dip” traders, targeting a breakout above $22‑$23 on the next earnings window. Keep an eye on cash‑flow health—if Upwork starts to fund repurchases while trimming its R&D or sales spend, the upside could be capped. Conversely, a sustained price lift with a stable or rising EPS will justify a higher valuation multiple, making the stock attractive for both growth‑ and yield‑inclined investors.