These 2 CEOs Are Buying the Dip in Their Own Stocks — Here’s What Analysts Expect Next

Whether you’re a seasoned trader or just dipping your toes into the stock market, one piece of wisdom has stood the test of time: buy low, sell high. Of course, the tricky part is figuring out exactly when a stock is genuinely undervalued, or when it’s time to cash out before things head south.

That’s where insider activity can come into play. Corporate insiders – senior executives and board members – are not just passive observers. They’re the ones steering the ship, setting strategy, and overseeing performance. Their unique vantage point often gives them early insight into how their company is really doing beneath the surface.

Because of that, insider buying can speak volumes. While executives may sell shares for any number of reasons – tax planning, diversification, or personal expenses – they typically only buy when they believe the stock is set to rise. It’s a signal worth watching.

Fortunately, investors don’t have to guess. Regulatory rules require insiders to disclose their trades, and those filings are publicly available. We’ve used TipRanks’ Insiders’ Hot Stocks tool to pull up two beat-down stocks that have recently seen insider buying from the CEOs themselves. Analysts are watching closely too, and both stocks currently carry Buy ratings. Let’s break down the names that have insiders – and Wall Street – leaning bullish.

Charter Communications (CHTR)

We’ll get started today with Charter Communications, a Connecticut-based telecom company with operations in 41 states that provide a wide range of services to more than 57 million residential and business customers. These services include internet, mobile broadband, video streaming, and voice communications, along with 24/7 US-based customer support. Charter bills itself as a fast-growing service provider in the rural internet sector.

Overall, Charter boasts that there are some 500 million IP devices connected to its network. The company states that it has 29.9 million broadband internet customers, 12.6 million video customers, 10.9 million mobile lines, and 6.4 million voice customers. This network is supported by Charter’s workforce, some 95,000 strong, and an infrastructure network exceeding 950,000 miles. Charter Communications’ telecom services are offered to its customers through the Spectrum brand.

Charter got its start in 1993, and while it’s not in the same tier as the industry’s giants – T-Mobile, AT&T, Verizon – Charter’s $36 billion market cap ranks the company at a respectable 7th place among US telecom firms. Charter ranks higher among its peers by annual revenue; in the four quarters through 1Q25, the company generated over $55 billion at the top line, and placed 5th among its US peers.

Despite Charter’s large network and strong revenues, and its solid prospects for expansion, the company’s stock is down 23% for the year-to-date. That drop reflects steep share losses after the July 25 release of the 2Q25 results. In the quarterly report, Charter noted a decline of 117,000 in total internet customers – the 29.9 million internet customers noted above were the Q2-end total – and missed expectations on EPS. The company’s bottom line, reported as $9.18 per share, was 48 cents per share less than had been anticipated. The company’s Q2 revenue of $13.77 billion was a modest half-percent above the forecast and in line with expectations.

We should note that, in May of this year, Charter announced its intention to conduct a merger agreement with Cox Communications, another large cable company in the US market. At the end of July, Charter followed up by announcing that the transaction had received approval from its stockholders, and that the merger deal is expected to close in the middle of next year. The transaction is expected to be conducted in both cash and stock.

For those of us who like to follow insider trades, it’s interesting to note that Charter’s President and CEO, Christopher Winfrey, made a million-dollar purchase of CHTR just a few days after the earnings report. On July 31, the same day that the Cox transaction received its stockholder approval from Charter, Winfrey bought 3,670 shares, paying just over $1 million for the stock.

For analyst Jessica Reif Ehrlich, who covers this telecom for Bank of America, the key point here is that Charter has a clear path to expand its business. She writes, “While the environment remains fiercely competitive, we believe broadband trends will improve Y/Y in 2H25 and 2026. Further, video sub results have inflected, and Charter will likely remain the fastest growing mobile provider in the US. Capex is set to peak in ‘25, and cash tax benefits will help drive FCF growth for next several years. The merger with Cox (mid-26 close) should accelerate revenue growth (Cox is underpenetrated in video and mobile), elevate margins, be accretive to FCF and reduce leverage.”

Following from this, Ehrlich rates CHTR shares as a Buy, with a $440 price target that points toward a one-year upside potential of 66%. (To watch Ehrlich’s track record, click here)

Right now, Charter’s stock holds a Moderate Buy consensus rating from the Street’s experts, based on 15 recent reviews that include 7 to Buy, 6 to Hold, and 2 to Sell. The stock is priced at $264.69 and its $415.23 average price target implies an upside of ~57% by this time next year. (See CHTR stock forecast)

United Parcel Service (UPS)

Next on our list of insider buys is UPS, one of the most recognizable brands in the US. UPS first entered the package delivery business in 1907 and now we all know the company’s brown delivery trucks. Those vans with the distinctive bubble-nosed design were first introduced in 1965 and are a common sight across the country. Today, UPS is a $71 billion company, and has its headquarters in Atlanta, Georgia, one of the nation’s major air transport hubs.

UPS’s market cap makes it the world’s largest publicly traded courier company, by a wide margin – second-place DHL clocks in with a market cap of $51 billion. By annual revenues, UPS ranks second, having brought in $90.9 billion for the 12-month period ending with 1Q25.

UPS boasts that it delivers 22.4 million packages every day, for a total of more than 5.7 billion parcels last year. The company operates in more than 200 countries and territories around the world, where customers can use the website to calculate shipping costs, choose shipping options, arrange pickup and delivery, and even return misdelivered parcels. UPS claims that it has more than 1.6 million shipping customers, and more than 10.1 million delivery customers.

In addition to being among the world’s leading package delivery services, UPS is also known as a ‘dividend champion.’ The company has a reliable dividend payment history stretching back to 1999. It sent out its last payment this past June 5, for $1.64 per common share. At that rate, the dividend annualizes to $6.56 per share and gives a forward yield of 7.76%.

In its last earnings report, covering 2Q25, UPS reported a quarterly top line of $21.2 billion. This was down almost 3% year-over-year, but beat the forecast by $367 million. At the bottom line, the company’s non-GAAP earnings of $1.55 per share missed the forecast, coming in 2 cents lower than expected.

What really shook investors, however, was UPS’s refusal to provide guidance on revenue or operating profit for 2025, citing ‘current macro-economic uncertainty.’ In more specific terms, the company is struggling with the impact of President Trump’s tariff and trade policies on some of its best revenue generators, including the China-US trade and its US-based small- to mid-sized business customers. Shares in UPS have taken several hits this year, and the stock is down 33% for the year-to-date.

Looking at the insiders, we see that UPS’s CEO Carol Tome picked up 11,682 shares of the stock on August 1, a buy that cost her a shade over $1 million.

UPS has caught the attention of Stifel analyst J. Bruce Chan, who believes that the worst is past for this international package carrier. Chan says of the company, “We believe we’re now passing peak margin pressure. Execution on structural capacity cuts are complete and savings goals have been reiterated for perhaps the most aggressive network restructuring in the company’s history; additional cost pressures this quarter were more a function of timing, in our view. We’re in the ‘believer’ camp, but stakes are high on incremental execution. We think the hardest work is largely complete, pricing is moving in the right direction in a difficult demand environment, the market is rational (especially in priority), and while volumes have been slow, if one expects even a modest firming in demand later this year, we see meaningful leverage.”

These comments support Chan’s Buy rating on UPS, while his $120 price target suggests that the stock may gain 42% in the year ahead. (To watch Chan’s track record, click here)

This is another company that holds a Moderate Buy consensus rating from the Street. The 19 recent analyst reviews here break down to 9 Buys, 8 Holds, and 2 Sells. The shares have a trading price of $84.50 and the $106.32 average target price indicates room for a 26% one-year upside. (See UPS stock forecast)

To find good ideas for stocks trading at attractive valuations, visit TipRanks’ Best Stocks to Buy, a tool that unites all of TipRanks’ equity insights.

Disclaimer: The opinions expressed in this article are solely those of the featured analysts. The content is intended to be used for informational purposes only. It is very important to do your own analysis before making any investment.