Paystack has confirmed it terminated the employment of its co-founder and former CTO, Ezra Olubi, citing “significant negative reputational damage” caused by resurfaced decade-old tweets; a move that is now drawing scrutiny from legal experts who say the company may have stretched its contractual powers.
The development comes after Paystack suspended and subsequently fired Olubi following a storm of sexual misconduct allegations and the circulation of archived posts from his X (formerly Twitter) account, some of which contained explicit and objectionable content, referencing pedophilia, voyeurism, bestiality, and sexual harassment.
The suspension triggered an independent investigation into workplace misconduct claims (still ongoing, according to the company), but Paystack now says Olubi’s firing is separate from that process.
In a written statement to WT, Paystack said it exercised its contractual right to terminate Olubi on 22 November 2025, arguing that the resurfaced content caused “significant negative reputational damage” inconsistent with company values and expectations of leadership.
However, for the broader industry, the episode also raises questions of how far back a company can reach when deciding what constitutes a reputational risk, and who gets to decide when the past becomes grounds for dismissal.
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Paystack, now owned by US payment giant Stripe, declined to offer further clarification on whether reputational clauses in its employment agreements allow retroactive application, and whether its internal processes include auditing historic public posts by senior executives. “We’re currently unable to comment beyond the statement,” said a company rep in an emailed response.
Olubi’s exit has triggered a wider debate across Nigeria’s tech community, partly because the posts cited by Paystack were more than a decade old and had been publicly accessible throughout the company’s growth, Stripe’s due diligence process, and the 2020 acquisition. While the specific tweets have not been detailed by Paystack, the company determined that their resurfacing created a reputational risk under the terms of Olubi’s contract.
But that interpretation is being questioned by legal practitioners, including savvy corporate lawyer A.O. Akinyemi, who argues that using historic, previously public material to trigger a reputational-risk clause stretches the intent of such provisions. Akinyemi asserted that reputational clauses in employment and executive contracts are typically forward-looking and tied to new behaviour, not archived posts predating the contract itself.
“The key phrase in these clauses is always ‘does,’ not ‘did,’” he said, noting that most agreements restrict conduct that occurs during the term of the contract. Retroactively applying them to past behaviour, he added, contradicts contract principles that require both parties to agree on what is being regulated. “You cannot punish conduct that was public, discoverable, and never hidden long before the contract existed.”
Akinyemi also points to the acquisition process as a complicating factor. Olubi’s years-old tweets were available on the open internet at the time Stripe acquired Paystack for USD 200 M in 2020, and nothing prevented the acquirer—or Paystack itself—from reviewing his online footprint.
“If the conduct was public at the time of contracting, it can be strongly argued that the company is deemed to have accepted it,” he said. “You cannot accept a fact when it benefits you and reject it later when it becomes inconvenient.”
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Another question is whether resurfacing by third parties constitutes new conduct by the executive. Olubi did not post anything new before the controversy reignited; his old tweets were circulated by others. Akinyemi argues that reputational clauses generally require an action or omission directly attributable to the employee. “The employee did nothing new. The causal link between conduct and reputational impact is broken,” he said.
The case has generated broader concern among executives, founders, and lawyers about what a retroactive interpretation of reputational-risk clauses could mean for employment law and due diligence norms if left unchallenged. “If an employer fails to do it[due diligence], they can later weaponise their own negligence against the employee,” he argued.
Akinyemi argues that a precedent allowing historic behaviour to trigger termination at any time would undermine contractual certainty.
“A Facebook post from 2009 could become a basis for termination in 2040. It destabilises the value of due diligence and creates a dangerous grey zone,” he opined.
“If the court allows retroactive interpretation of these clauses, no one is safe, and the corporate scene becomes a joke.”
For now, neither Paystack nor Stripe has addressed the legal debate. Internally, a separate workplace-related grievance remains under investigation, but the company maintains that Olubi’s removal is entirely because “his recently resurfaced public tweets have caused significant negative reputational damage to the company.”
Olubi has not issued a detailed public statement beyond confirming his exit, saying in his Sunday blog post that he was informed of his termination before the independent investigation wrapped up and without a meeting or opportunity to respond, an action he says contradicts Paystack’s own suspension terms.
He maintains the resurfaced posts “do not reflect” his conduct and has instructed his legal team to review the process and its alignment with internal policy.
The unresolved legal questions around reputational clauses, prior knowledge, and retroactive enforcement have ensured the controversy around Paystack, a prominent fintech player, continues to ripple across the African tech ecosystem.
Several lawyers say the matter may ultimately require judicial interpretation if it ever moves to litigation, though some expect both sides to resolve it privately. But the company’s attempt to draw a clear line between the old tweets and the still-ongoing internal case has not ended the scrutiny.
