Secondary Sales, AI Comp, and Why Your Equity Plan Might Not Be Working

The Optio Team

May 21. 2026

In this article

Spela Prijon, co-founder of Equity People powered by Optio, recently joined Guy Hutchinson on the Startup CFO podcast to share what she is seeing on the ground: where compensation planning is breaking down, and why secondary share sales are one of the most underused tools in the equity toolkit.

 

The conversation covered two themes that keep coming up in client work: the compensation modelling problem created by the shift to AI roles, and the retention and culture case for employee secondaries. Both are worth understanding before your next headcount plan or equity review.

 

From Equity People to Optio

 

Equity People was built on a simple observation. When Spela was working in cap table software, she found herself in conversations with 50-person companies asking basic questions about new hire grants, while simultaneously speaking with 2,000-person companies that had already worked through the same problems. The knowledge existed. It just was not being shared in a stage-appropriate way. That gap became the consultancy, founded with co-founder Tamas.

 

Over time, the scope broadened from pure equity consulting into a full total rewards practice covering salary benchmarking, leveling, bonus design, and equity. VCs began coming to them for portfolio-wide insights alongside direct company clients, with relationships at funds including Sequoia, General Catalyst, and Balderton. The client list grew to include companies like Personio, Vinted, and Granola.

 

The acquisition by Optio Incentives was not a departure from that work. It was the logical next step. Because Equity People ran competitive RFPs on behalf of clients evaluating equity management platforms, they had a clear and unbiased view of the market. Optio was the platform they kept recommending. The acquisition joins that consulting practice with an equity management platform built to take companies from Series B through pre and post-IPO, anywhere in the world.

 

"We run a lot of RFPs for our clients. That gives us a clear view of the market. Optio is a platform that can take you from Series B through pre and post-IPO all over the world. Combined with the consulting practice, we are well positioned to offer full cycle equity management."

 

AI roles are breaking headcount models

 

Two years ago, a headcount plan with a 5 to 10 percent margin of error on compensation was workable. Role-to-role variability within a broad engineering function was small enough that minor inaccuracies didn't materially affect the budget. That is no longer true for companies introducing AI-specific roles.

 

Spela describes a pattern she now sees in the majority of new projects: companies arrive 30 percent into their planning process having modelled on software engineering benchmarks, only to discover they are actually hiring machine learning engineers, forward deployed engineers, or AI researchers. The compensation gap between those roles and the ones in the plan can be 50 to 100 percent on equity alone.

 

"It's not enough anymore. We need to separate out those AI roles because the premium is so much larger. The model doesn't work anymore with the margin of error we were hoping for."

 

The problem is concentrated in one group: SaaS companies entering the AI race. AI-native companies calibrated their compensation early through direct market feedback. Non-AI businesses are unaffected. But the large middle group, established SaaS companies now introducing AI departments, is discovering mid-hiring-process that old benchmarks and old job families produce roles that sit unfilled for nine to twelve months.

 

The planning horizon question

 

Spela goes further than noting the benchmarking gap. She raises whether three-year planning still functions the way it used to. The question is worth sitting with rather than assuming the old cadence applies. What is more immediately actionable is the granularity problem: even within AI roles, the same title at different companies can span from $180,000 at a company just beginning its AI transition to $500,000 at the top end of the market. That is not a rounding error in a model.

 

What good looks like

 

Her recommendation is that earlier-stage companies need to behave more like large enterprises, which maintain internal compensation data and analytics functions building proprietary benchmarks from live recruitment data. A $50 million company does not have that department, but that is the direction of travel.

 

In practice, that means moving from "we need an AI engineer" to knowing which segment of AI, which seniority level, and which specific talent pool you are competing in. The modelling accuracy comes from internal benchmarks fine-tuned to the exact roles being hired, not from broad market data applied uniformly across an engineering function.

 

Secondary share sales: the case for making equity real

 

A secondary transaction is when an existing shareholder sells shares they already hold to a third party, without the company issuing new shares. The company receives nothing; the individual receives cash. It converts paper wealth into real money before an exit event.

 

The traditional timing framework placed founder liquidity at Series B and broader employee participation at Series C, which historically corresponded to companies generating meaningful revenue at roughly a $500 million valuation. AI has broken that mapping. Companies are now reaching billion-dollar valuations at seed stage. Spela now evaluates readiness differently: Has the company generated revenue? Is it on a credible path to justify its valuation? How much work remains? Is capital deployed on secondaries the best use of the remuneration budget given competition with public companies?

 

The incentive and educational effect

 

The strongest argument Spela makes for secondaries is not financial. It is cultural and educational.

 

When a secondary closes and colleagues see someone convert paper equity into real money, something shifts across the entire employee population. People who previously showed no interest in equity start asking how to earn more. That effect, she argues, exceeds anything achievable through communication programmes, onboarding explainers, or equity education sessions.

 

"A company has invested $100 million into an incentive plan with uncertain ROI. Secondaries are one of the best ways to turn that into a positive ROI the minute after it closes. All of a sudden, everyone actually believes that 10 percent is $100 million. Before it was 100 pieces of paper."

 

There is also a retention effect that precedes the transaction itself. Announcing that you are exploring a secondary, with eligibility tied to being a current employee, functions as a retention tool before a single share changes hands. It adds a layer to the incentive structure that sits alongside grants, refreshers, and bonuses.

 

The Revolut example and why discounts exist

 

Spela points to Revolut's secondary as a strong example of what good looks like. They included not just leadership but employees and alumni, and even at a reported 30 percent discount, the transaction had a powerful incentive effect across the business.

 

The discount question comes up often. Her answer is structural, not a signal about valuation. Employees typically hold common shares. Investors hold preferred shares, which carry additional rights including liquidation preferences. The discount on a secondary reflects that difference in rights between share classes, not a view that the company is approaching peak value. Some companies take an alternative route entirely, buying back common shares and reissuing preferred, though the mechanics vary.

 

The human psychology of secondaries

 

The motivational impact of a secondary is not uniform, and the right approach depends on the individual. For some people, a $5 million payout is actually disincentivising. They believe those shares will be worth $50 million in five years, and converting them to cash feels like leaving value behind. For others, five years of being unable to buy a house or access any liquidity is itself the disincentivising factor, and a secondary is what keeps them engaged. The same transaction produces opposite effects depending on who is holding the equity and what they need from it. That is why participation design cannot be one-size-fits-all, and why the decision to offer a secondary has to be grounded in an honest read of your specific team.

 

The founder rationale

 

CFOs sometimes worry that permitting insider sales while simultaneously raising at a given valuation sends contradictory signals. Spela's view is that in most cases, founders seeking partial liquidity are doing a straightforward calculation: years of below-market cash salary, four or five years of 80-hour weeks at $100,000 when the market rate was $350,000, and a secondary that bridges that gap. That rationale naturally caps how much someone would rationally seek to capture.

 

A complete exit through a secondary is a different and more meaningful signal. Partial liquidity from a long-tenured founder is usually something else entirely: a hedging exercise for someone with concentrated risk in a single asset, rather than a view on where the valuation is headed.

 

The downstream effects on strike price

 

One consequence that is easy to overlook: a secondary creates a new proof point for the value of common shares. For companies running tax-advantaged schemes like EMI, this can push future strike prices higher, reducing the in-the-money value of subsequent grants. That is not a reason to avoid secondaries, but it is a parameter to model before proceeding, and potentially a reason to review whether tax-optimised vehicles remain the right choice for future grants.

 

How to structure participation

 

The guardrails Spela recommends are practical and worth having defined before any secondary is announced:

 

  • Current employees versus alumni. The most common approach allows both groups to participate, but at different caps. Alumni participation is often justified by cap table cleanup, but their cap should be materially lower, something like 5 percent of vested holdings versus 10 percent for current employees.
  • Eligibility thresholds. Tenure requirements (commonly two years), performance floors, and in some cases an inverse seniority model where more senior employees can sell a smaller percentage of their vested equity.
  • Dollar caps at the top end. Almost universally applied. If someone is sitting on $5 million in vested equity, allowing full liquidation creates an obvious flight risk after the payout.
  • Refresher alignment. A secondary should be a milestone in someone's equity journey, not the finish line. Top performers should always have something meaningful still vesting after a secondary closes. Using the transaction as a prompt to review refresher grant adequacy is good practice.

 

What this means in practice

 

The two topics Spela covers connect to the same underlying problem: equity and compensation only work as retention and incentive tools when they feel real to the people holding them. Benchmarks that do not reflect the actual talent market, and equity that never converts to liquidity, both fail to produce the behaviour they were designed to produce.

 

Getting the modelling right on AI roles is a planning discipline. Getting secondaries right is a cultural one. Both require more intentionality than most companies apply to them, and both pay off in ways that are measurable if you are tracking the right signals.

 


 

From a conversation on the Startup CFO podcast with host Guy Hutchinson, recorded April 2026.

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Author image The Optio Team
The Optio Team
The Optio Team is your go-to crew for all things employee ownership and equity compensation. We're here to share practical tips, industry insights, and lessons learned from helping companies get equity right.

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