In January 2026, Clay, the AI-powered sales automation startup, announced its second employee tender offer in nine months. The valuation: $5 billion. Nine months earlier, Clay had run the same exercise at $1.5 billion. In less than a year, employees who sold shares in the first round more than tripled their paper gains, and those who held could now cash out at an even higher price.
Clay is not an outlier. ElevenLabs authorized $100 million in employee share sales at a $6.6 billion valuation. Linear completed a tender offer at $1.25 billion. Across the startup ecosystem, secondary sales have exploded from a niche financial tool into a standard operating procedure, and founders are rewriting the rules of when and how they get paid.
Why Founders Are Taking Chips Off the Table Before an IPO
The old playbook was simple: raise money, build the company, and wait for an IPO or acquisition to cash out. In practice, that meant founders spent five to ten years living on below-market salaries while their net worth existed entirely on paper. If the exit never came, neither did the payday.
In 2026, that model is breaking down. Secondary transactions, where existing shareholders sell their stock to new buyers in private deals, ballooned to approximately $160 billion in 2024 and are projected to exceed $210 billion in 2025. The trend shows no signs of slowing as record venture fundraising from 2025 gets deployed into the market.
Investors are not just tolerating this shift. They are encouraging it. The logic is straightforward: a founder with some financial security takes bigger swings. As venture capital firms now openly acknowledge, a starving founder is a risk-averse founder. By letting founders and early employees take chips off the table at Series B or even late Series A, VCs are betting that financial breathing room leads to more ambitious, moonshot-level thinking.
How the New Secondary Sales Actually Work
A tender offer is the most common mechanism. The company, often with support from its lead investor, invites existing shareholders to sell a portion of their stock at a set price. Unlike selling on a secondary marketplace, tender offers are structured, company-sanctioned events with clear terms.
Clay’s January 2026 tender offer illustrates the model. The company invited employees who had been with the startup for a set period to sell a portion of their vested shares at the $5 billion valuation. The offer was not limited to founders or executives. Engineers, product managers, and early hires could all participate, turning years of accumulated equity into actual cash.
ElevenLabs took a similar approach at its $6.6 billion valuation, allowing employees who had worked at the company for at least a year to sell up to $100 million in stock combined. The company framed the offer explicitly as a retention tool, giving employees a reason to stay by proving their equity was not just theoretical.
The Shift From Founder Windfalls to Employee Retention
The biggest change in 2026 is who benefits from secondary sales. During the 2021 boom, large founder payouts were common and often controversial. Investors frowned on founders pulling millions out of companies that had not yet proven sustainable unit economics.
The current wave looks different. According to TechCrunch’s reporting on the trend, recent transactions from Clay, Linear, and ElevenLabs are structured as company-wide tender offers that include employees at all levels. The framing has shifted from “founder liquidity event” to “employee retention strategy.”
This distinction matters for founders thinking about how to structure their fundraising. Building a secondary sale into your Series B or C negotiation is no longer unusual. It is becoming expected, and founders who do not offer some form of employee liquidity risk losing talent to competitors who do.
What Founders Need to Know Before Selling Shares
Secondary sales come with real considerations. Selling too early at too low a valuation means leaving money on the table if the company grows significantly. Selling too much can signal a lack of confidence to investors and the team. Most advisors recommend selling no more than 10 to 20% of vested shares in any single tender offer.
Tax implications also matter. Secondary sales of private company stock are typically taxed as capital gains, but the rate depends on how long you have held the shares and your total income. Founders should work with a tax advisor before any transaction.
Cap table cleanup is another benefit. A well-structured secondary sale can remove tired early-stage investors who may be blocking decisions or pushing for premature exits. Replacing them with later-stage investors who are aligned with the company’s current trajectory can be just as valuable as the cash.
The window for secondary sales is also narrowing in some sectors. As Capital Founders OS noted in their 2026 analysis, every path to liquidity is getting more competitive. IPO timelines are stretching, acquisition multiples are compressing in non-AI sectors, and private markets are increasingly the only game in town. Founders who want liquidity need to plan for it proactively, not wait for the market to deliver it.
The bottom line: if you are a founder sitting on paper wealth and waiting for the “right time” to cash out, 2026 is making a strong case that the right time is now, or at least soon. Secondary sales are no longer a sign of giving up. They are a sign of building smart.
