The $1 Trillion Question

In June 2024, Sarah Friar walked into OpenAI's San Francisco headquarters facing a financial puzzle unlike any in tech history. As the newly appointed Chief Financial Officer, she inherited a company generating $10 billion in annual recurring revenue—doubling every six months—yet operating under a nonprofit corporate structure that prohibited traditional equity ownership and investor returns.

The challenge was extraordinary: How do you transform a nonprofit research lab into a for-profit corporation capable of raising hundreds of billions in capital, satisfy existing investors who had poured in $13 billion under unusual terms, navigate conflicting stakeholder interests across employees and the original mission, and prepare for what could become the largest IPO in history—all while the company's CEO had been fired and rehired just seven months earlier in a boardroom coup that exposed deep governance fractures?

For Friar, a 52-year-old Irish-American executive who had taken Square public at a $3 billion valuation in 2015 and watched it grow to $30 billion, the OpenAI assignment represented both vindication and risk. Her six-year tenure at Nextdoor as CEO had ended with the company's stock price collapsing from its $13 SPAC debut to under $2—a humbling experience that taught her painful lessons about growth-at-any-cost cultures, public market scrutiny, and the perils of overvaluation.

Now, CFO Sarah Friar has reportedly told associates that OpenAI is targeting a 2027 public listing at a potential $1 trillion valuation. If successful, it would validate her as one of tech's premier financial architects. If it fails, it could cement the Nextdoor struggles as a pattern rather than an anomaly.

The Northern Ireland Foundation

Sarah Jane Friar was born on December 24, 1972, in Sion Mills, a small town in Northern Ireland with a population of around 2,000. She attended Strabane Grammar School during a period when Northern Ireland was still experiencing significant sectarian conflict and economic challenges.

The young Friar showed exceptional academic talent, particularly in mathematics and sciences. She entered a national competition sponsored by the accounting firm Arthur Andersen and won a scholarship—a pivotal moment that would shape her career trajectory. The scholarship required her to work at Arthur Andersen for a year before pursuing university studies.

"I come from a very small town in Northern Ireland," Friar said in a 2019 Stanford interview. "The idea that I would end up in Silicon Valley was not part of any plan. But I was always curious about how things worked—systems, numbers, patterns."

That year at Arthur Andersen exposed Friar to corporate finance and business operations, providing practical grounding that would complement her subsequent academic training. She then pursued engineering studies at the University of Oxford, earning a Master of Engineering degree in Metallurgy, Economics, and Management—an unusual combination that reflected her interest in both technical systems and business applications.

The McKinsey and Goldman Sachs Training Ground

After Oxford, Friar joined McKinsey & Company, the elite management consulting firm. She worked in both the London and South Africa offices, gaining exposure to global business strategy and corporate transformation projects. McKinsey's rigorous analytical culture and focus on data-driven decision-making would become hallmarks of Friar's leadership style.

McKinsey sponsored Friar's application to Stanford Graduate School of Business, where she earned her MBA as an Arjay Miller Scholar—an honor given to the top 10 percent of each Stanford MBA class based on academic performance and leadership potential. The Stanford network would prove crucial throughout her career, connecting her to Silicon Valley's tech ecosystem.

After Stanford, Friar joined Goldman Sachs, where she would spend over a decade. She started in corporate finance and mergers and acquisitions, then moved into equity research. Her big break came when she was appointed lead software analyst and Business Unit Leader for Goldman Sachs' Technology Research Group.

In this role during the mid-2000s, Friar covered major software companies and developed expertise in how technology firms created value, structured their businesses, and navigated public markets. She learned to evaluate business models, assess management teams, and understand what institutional investors valued in tech companies—skills that would prove essential in her CFO roles.

"Goldman was where I learned to think like an investor," Friar told CNBC in 2024. "You're constantly asking: What drives sustainable value creation? What are the unit economics? How does management allocate capital? Those questions never leave you."

Friar also held a brief stint as senior vice president of finance and strategy at Salesforce, where she gained operational experience inside a fast-growing SaaS company. This combination—consulting strategy at McKinsey, investor perspective at Goldman, and operational execution at Salesforce—created a unique skillset rare among tech CFOs.

Square: The Breakout Success

In 2012, Sarah Friar joined Square as Chief Financial Officer. The company, co-founded by Jack Dorsey and Jim McKelvey in 2009, had created a small white square device that attached to smartphones and allowed anyone to accept credit card payments. But by 2012, Square was struggling to find a sustainable business model and faced skepticism about whether it could ever be profitable.

Friar's mandate was clear: professionalize Square's financial operations, build the infrastructure for sustainable growth, and prepare the company for an eventual public offering. She brought immediate credibility—a Goldman Sachs pedigree and Stanford MBA signaled to investors that Square was serious about becoming a real business.

Her first priority was understanding Square's unit economics. The company was processing payments and collecting small fees, but losing money on customer acquisition and support. Friar implemented rigorous financial analytics to measure every aspect of the business: customer acquisition cost, lifetime value, retention rates, and gross margins on different product lines.

"When I arrived, we didn't have good visibility into profitability by cohort or product," a former Square finance executive told The Wall Street Journal in 2015. "Sarah built the systems to measure everything. It changed how we made decisions."

Beyond the credit card reader, Friar championed expansion into adjacent services that could increase revenue per customer. Under her financial leadership, Square launched Cash App (a peer-to-peer payments application), Square Capital (small business loans), instant deposit services, and point-of-sale software for restaurants and retailers. The strategy was to become an integrated ecosystem for small businesses rather than just a payments processor.

The diversification proved critical. By 2015, Square was processing $70 billion in annual payment volume and had expanded from a hardware company into a comprehensive financial services platform for small businesses.

The High-Stakes IPO

Taking Square public in 2015 was Sarah Friar's defining achievement—and a masterclass in navigating adverse market conditions.

In October 2015, global markets were experiencing significant volatility. The VIX (volatility index) was elevated, tech IPOs had stalled, and investor appetite for unprofitable growth companies was weak. Square had filed its S-1 registration statement revealing losses of $154 million on revenues of $850 million—not the profile that excited public market investors in that environment.

Making matters worse, Square faced questions about competition from established payment processors, its business model sustainability, and whether CEO Jack Dorsey could effectively run two public companies simultaneously (he had just returned as Twitter CEO months earlier).

"Everyone told us to wait," Friar said in a 2018 interview. "The window wasn't great. But we felt ready as a company, and sometimes you have to take the market you're given rather than waiting for perfect conditions."

Square priced its IPO at $9 per share on November 19, 2015—well below the $11-13 range initially discussed, and significantly below the $15.46 per share valuation from its last private funding round. The company raised $243 million, valuing Square at approximately $2.9 billion. It was seen as a disappointing outcome compared to the valuations of other fintech companies at the time.

But Friar played the long game. She had structured Square's financials to demonstrate a path to profitability, emphasized diversified revenue streams beyond payments processing, and positioned the company as a platform rather than a single-product business. The IPO gave Square permanent capital and public market discipline.

The strategy worked. Square's stock price, which closed at $13.07 on its first day of trading, would grow to over $250 by 2021—a 25x increase from the IPO price. The company's market capitalization expanded from $2.9 billion at IPO to over $100 billion at its peak, and Square (later renamed Block) became one of the decade's great fintech success stories.

"Sarah was the architect of that transformation," Jack Dorsey said when Friar announced her departure in 2018. "She steered us through an IPO that many questioned, helped build an ecosystem that far exceeded the initial payment reader, and established Square as a public company that investors believed in."

During Friar's tenure, Square's annual revenue grew from $850 million to over $3 billion, and the company achieved profitability. She oversaw the launch and scaling of Cash App, which would become one of Square's most valuable assets, and developed Square Capital into a significant small business lending platform.

Friar held 1.3 percent of Square at the IPO, while Dorsey owned 24.4 percent. Her equity stake, initially worth around $40 million, would eventually be valued at over $100 million as the stock appreciated.

The Nextdoor Gamble

In October 2018, Sarah Friar made a decision that surprised Silicon Valley: she left Square at the peak of its success to become CEO of Nextdoor, a neighborhood social network with 200,000 active neighborhoods but persistent questions about its business model and content moderation challenges.

The move represented a significant career pivot. Friar was leaving a CFO role at a successful $30 billion public company to become CEO of a private company valued at approximately $2.1 billion—and one with complex challenges around community dynamics, monetization, and user growth.

"I realized I wanted to run my own thing," Friar told Fortune in 2021. "Square was an incredible experience, but I felt ready to be a CEO. Nextdoor represented an opportunity to build something that could strengthen communities and create meaningful social connection—not just financial transactions."

Jack Dorsey publicly supported the move, though he was reportedly disappointed to lose his key financial partner. "I was unrealistically expecting to work with Sarah well into our 90s," Dorsey tweeted when announcing her departure.

Friar took over as Nextdoor CEO in December 2018 with an ambitious vision: transform Nextdoor from a local bulletin board into an essential utility for neighborhood life, build a sustainable advertising business model, and establish the company as the "kinder" alternative to toxic social media platforms like Facebook and Twitter.

The Content Moderation Challenge

One of Friar's first priorities was addressing Nextdoor's reputation for racial profiling and divisive neighborhood conflicts. The platform had been criticized for enabling racist commentary disguised as "safety concerns" and for amplifying neighborhood disputes rather than fostering genuine community connection.

"Some of the toughest discussions have been the tradeoff between engagement and growth versus slowing people down," Friar acknowledged in a 2021 interview. "A growth-at-any-cost mentality is what is really damaging us in terms of areas like social media. We needed to be willing to sacrifice some engagement to build healthier communities."

Under Friar's leadership, Nextdoor implemented new anti-racism policies, added content warnings and moderation tools, and created programs to encourage positive community behavior. The company banned forward-to-police features in some contexts and implemented algorithmic interventions to slow down potentially inflammatory posts.

The initiatives received positive press coverage and positioned Nextdoor as more thoughtful about content moderation than larger social platforms. But they also created tension with growth metrics—precisely the tradeoff Friar had identified.

The SPAC Decision

In July 2021, Sarah Friar announced that Nextdoor would go public through a SPAC merger with Khosla Ventures Acquisition Co. II, valuing the company at $4.3 billion. The deal was expected to provide Nextdoor with approximately $686 million in proceeds to fund expansion and product development.

The SPAC route was increasingly popular in 2021, offering companies a faster path to public markets with less regulatory scrutiny than traditional IPOs. For Nextdoor, which had been private for nine years, the SPAC provided liquidity for early investors and employees while giving the company access to public capital.

Friar positioned the public offering as validation of Nextdoor's business model and growth potential. The company reported 280 million members across 290,000 neighborhoods in 11 countries, with 37 million weekly active users. Revenue had reached $123 million in 2020 and was projected to grow 47 percent in 2021 and 40 percent in 2022.

But the financial details revealed troubling underlying metrics. Nextdoor was projecting a $101 million net loss for 2021. Average revenue per user (ARPU) was just $1.65—far below established social media platforms. Customer acquisition costs were high, and the monetization strategy remained unproven.

Nextdoor began trading in November 2021 under the ticker symbol "KIND" (Khosla Ventures Acquisition Co. II). The stock closed its first day at $13—a 17 percent increase from the SPAC merger price of approximately $11.11—generating optimistic headlines about the company's public market debut.

But the optimism proved short-lived.

The Public Market Reality

Within months, Nextdoor's stock price began a brutal decline that would define the final years of Friar's tenure as CEO.

By early 2022, Nextdoor shares had fallen below $7. By mid-2022, they had dropped to $4. By 2023, the stock was trading below $2—an 85 percent decline from the SPAC merger valuation and a devastating loss for investors who had participated in the transaction.

The collapse reflected multiple factors. First, the SPAC market overall experienced a severe correction as investor enthusiasm waned and many SPAC mergers proved to be overvalued. Companies that went public via SPAC in 2020-2021 saw their share prices decline an average of 50-60 percent.

Second, Nextdoor's business fundamentals disappointed public market investors. Revenue growth decelerated to 20-30 percent rather than the projected 40-47 percent. ARPU growth slowed by 26 percent as the U.S. market showed signs of saturation. User engagement metrics failed to reach the levels needed to attract premium advertising rates.

Third, Nextdoor faced intensifying competition from Facebook Groups, Nextdoor clones in international markets, and the challenge of monetizing a platform where users primarily sought local information rather than the kind of engagement that drove advertising revenue on platforms like Instagram and TikTok.

A securities lawsuit filed in 2024 alleged that Nextdoor had misrepresented its growth prospects and failed to disclose that the U.S. market was already substantially saturated, impairing the company's ability to monetize at projected levels.

"The gap between the SPAC presentation and the actual business performance was significant," one institutional investor told The Information in 2023. "Nextdoor positioned itself as early innings when it was actually much more mature and facing real monetization headwinds."

The Lessons of Failure

In mid-2024, Sarah Friar announced she was stepping down as Nextdoor CEO after nearly six years in the role. The company's stock price was under $2, its market capitalization had fallen below $500 million (from the $4.3 billion SPAC valuation), and the business had failed to achieve the financial performance or strategic positioning Friar had envisioned.

It was a humbling end to what had been presented as Friar's ascent from CFO to CEO, from finance leader to operating executive. The Nextdoor experience taught her costly lessons about:

Valuation Discipline: The $4.3 billion SPAC valuation had priced in aggressive growth assumptions that proved unrealistic. Friar later acknowledged that public market discipline provides important checks on private market exuberance.

Monetization Timelines: Building a sustainable advertising business on a neighborhood social network proved far more difficult than anticipated. User engagement didn't translate into advertising revenue at the rates Nextdoor projected.

Market Saturation: Nextdoor's U.S. growth had plateaued earlier than disclosed, creating challenges for the revenue projections presented to SPAC investors.

CEO vs. CFO Skills: Friar's strengths as a financial strategist and capital markets expert didn't fully transfer to the operational challenges of scaling a consumer social network, managing product development, and competing with platforms like Facebook.

"I learned more from Nextdoor than any other experience in my career," Friar said in announcing her OpenAI appointment. "Not everything works. Markets change. Assumptions prove wrong. The question is whether you learn from those experiences."

The OpenAI Opportunity

When OpenAI came calling in early 2024, Sarah Friar faced a critical decision: return to a CFO role after having been a CEO, or pursue other CEO opportunities where she could apply the Nextdoor lessons to a fresh start.

She chose OpenAI—and the CFO role—for several compelling reasons.

First, OpenAI represented the most significant financial and organizational challenge in tech. The company was generating over $10 billion in annual recurring revenue—10x what Nextdoor ever achieved—yet operated under a nonprofit structure incompatible with that scale. Restructuring OpenAI would be the ultimate test of Friar's financial architecture skills.

Second, OpenAI's trajectory was the opposite of Nextdoor's. While Nextdoor had struggled to accelerate growth and monetize users, OpenAI's challenge was managing explosive revenue growth (doubling every six months), unprecedented investor demand (raising tens of billions at escalating valuations), and the operational complexity of becoming one of the world's most valuable companies in record time.

Third, Friar would be working with Sam Altman, who had been reinstated as CEO in November 2023 after a brief firing. The board crisis had exposed governance weaknesses and stakeholder conflicts—exactly the kind of complex corporate restructuring that required Friar's skillset.

Finally, OpenAI offered redemption. A successful IPO at a $1 trillion valuation would cement Friar as one of tech's premier financial leaders, erasing the Nextdoor disappointment and validating her track record from Square.

OpenAI announced Friar's appointment as CFO in June 2024, along with Kevin Weil as Chief Product Officer (later reassigned to VP of Science). In the announcement, CEO Sam Altman emphasized that Friar would "lead a finance team that supports OpenAI's mission by providing continued investment in core research capabilities, and ensuring that the company can scale to meet the needs of its growing customer base and the complex and global environment in which they are operating."

The Financial Puzzle

When Sarah Friar joined OpenAI in June 2024, she inherited a financial structure that defied conventional corporate logic.

OpenAI had been founded in 2015 as a nonprofit AI research laboratory, with the stated mission of ensuring that artificial general intelligence (AGI) benefits all of humanity. The nonprofit structure meant no shareholders, no equity ownership, and a governance board focused on the mission rather than profit maximization.

But by 2019, OpenAI's leadership recognized that developing cutting-edge AI required vastly more capital than nonprofit donations could provide. The company created a "capped-profit" for-profit subsidiary, allowing it to raise investment capital while promising investors capped returns (originally 100x their investment). Microsoft invested $1 billion in 2019, then $2 billion more in 2021, and eventually over $13 billion total.

By 2024, this hybrid structure had become untenable. OpenAI was generating approximately $10 billion in annual revenue, growing at extraordinary rates (doubling every six months), and valued by investors at $157 billion in its most recent funding round. Yet it remained controlled by a nonprofit board with unusual governance powers—the same board that had fired and rehired Sam Altman in November 2023.

Friar's challenge was transforming this structure into something that could support OpenAI's ambitions:

Investor Returns: Early investors like Microsoft and Khosla Ventures had invested under the capped-profit structure, but newer investors expected traditional equity stakes. Reconciling these different investor classes required complex financial engineering.

Employee Equity: OpenAI employees held profit participation units rather than traditional stock options. Converting to a standard equity structure while maintaining employee ownership was critical for retention and morale.

Mission Alignment: The nonprofit's mission to ensure AGI benefits humanity couldn't simply be abandoned. Any restructuring needed to preserve mission commitments while enabling profit-seeking operations.

Regulatory Approval: Restructuring from nonprofit to for-profit required approval from regulators in California and Delaware, and any appearance of nonprofit assets being diverted to private gain would trigger legal challenges.

Stakeholder Conflicts: Former employees like Elon Musk had filed lawsuits challenging OpenAI's for-profit shift. Managing these conflicts while executing the restructuring required careful legal and financial strategy.

The Restructuring Solution

Over six months from June to October 2024, Sarah Friar led the most complex corporate restructuring in AI history.

The solution she architected involved creating a two-tier structure: a new OpenAI Foundation (nonprofit) that would control a separate OpenAI Group PBC (public benefit corporation). The PBC structure allowed for profit-seeking operations while maintaining a stated public benefit mission.

Under the restructuring announced in October 2024:

The OpenAI Foundation received a 26 percent equity stake in the for-profit PBC, valued at approximately $130 billion based on the $500 billion total valuation being discussed for employee stock sales. This massive endowment ensured the nonprofit could fund AI safety research, philanthropic initiatives, and mission-aligned projects independent of the for-profit business.

The OpenAI Group PBC became the operating entity, with 47 percent owned by current and former employees and investors. Microsoft's $13 billion investment was converted into approximately 27 percent ownership of the PBC (valued at $135 billion), making it the largest single shareholder.

Governance was restructured to give the PBC operating independence while preserving the Foundation's oversight authority on existential AI safety questions.

The restructuring closed with approval from California and Delaware attorneys general, who determined that the nonprofit Foundation was receiving fair value for the assets being transferred to the for-profit entity.

"This restructuring took six months of intensive work involving lawyers, accountants, regulators, investors, and multiple stakeholder groups," one person close to the process told Bloomberg. "Sarah led every aspect—the financial modeling, stakeholder negotiations, regulatory strategy, and communication. It was a masterclass in complex corporate reorganizations."

The $130 billion nonprofit endowment was unprecedented—larger than the endowments of Harvard, Yale, Princeton, Stanford, and MIT combined. It addressed concerns that OpenAI was abandoning its mission by creating the world's richest charitable foundation focused on AI safety and beneficial AI deployment.

The Revenue Explosion

While executing the nonprofit-to-for-profit restructuring, Sarah Friar was simultaneously managing OpenAI's explosive revenue growth—perhaps the fastest revenue scaling in tech history.

ChatGPT, launched in November 2022, had reached 100 million weekly active users within two months. By 2024, it had become one of the world's most-used software applications, with paying subscribers, enterprise customers, and API developers all contributing to OpenAI's revenue.

The numbers were staggering:

2023: OpenAI generated approximately $2 billion in revenue.

2024: Revenue reached $5.5 billion in annual recurring revenue.

January 2025: Annualized revenue hit $6 billion.

June 2025: OpenAI reported $10 billion in annual recurring revenue.

October 2025: Sarah Friar told CNBC that OpenAI expected roughly $13 billion in revenue for 2025.

November 2025: Sam Altman stated on a podcast that revenue was "well more" than $13 billion.

The company was doubling its revenue approximately every six months—a growth rate that exceeded even the fastest-growing consumer internet companies at their peak. For comparison, Facebook took three years to go from $5 billion to $10 billion in revenue. OpenAI did it in six months.

Weekly active users grew to 800 million in October 2025, up from 500 million in March. Paying business customers surpassed 5 million, up from 3 million in June. The ChatGPT consumer subscription service ($20 per month) alone was generating billions in annual recurring revenue.

Managing this growth strained OpenAI's finance organization. Friar had to build financial forecasting systems capable of modeling exponential growth, develop scalable billing and collections infrastructure for millions of customers, and create financial controls appropriate for a company growing from $5 billion to potentially $15 billion in revenue in a single year.

"Most CFOs spend their careers trying to accelerate growth from 20 percent to 30 percent," a Silicon Valley CFO told The Information. "Sarah's challenge is the opposite—managing 200 percent growth without the business breaking. That's equally hard but in totally different ways."

The Infrastructure Challenge

OpenAI's revenue growth created an immediate problem: the company was spending enormous sums on compute infrastructure to train and run its AI models, and those costs were growing even faster than revenue.

In 2024, OpenAI spent an estimated $7 billion on compute infrastructure, including GPUs from NVIDIA, cloud services from Microsoft Azure, and custom chips. For 2025, infrastructure spending was projected to exceed $10 billion and could reach $15 billion depending on model training schedules and user growth.

These capital requirements far exceeded what OpenAI's current revenue and profitability could support through traditional financing. The company needed access to tens of billions in capital to fund its infrastructure buildout—capital that would need to come from investors, debt markets, or government partnerships.

In September 2025, Friar sparked controversy when she suggested at a conference that OpenAI was looking to create an ecosystem of banks, private equity, and a federal "backstop" or "guarantee" that could help finance its investments in cutting-edge chips and data center infrastructure.

The comment ignited immediate backlash. Critics accused OpenAI of seeking taxpayer subsidies to fund a private company's capital expenditures. Tech competitors questioned why OpenAI would need government backing if its business model was truly viable. Policy analysts worried about the precedent of the federal government providing financial guarantees to AI companies.

Within 48 hours, Friar issued a clarification: "OpenAI is not seeking a government backstop for our infrastructure commitments. My comments were about the importance of government-industry partnership on AI infrastructure more broadly, not a request for specific financial support."

The episode demonstrated the intense scrutiny Friar faced as OpenAI's CFO. Every public statement about financing, valuation, or strategy would be analyzed, criticized, and potentially misinterpreted. Managing communications while navigating complex infrastructure financing would require diplomatic precision.

The IPO Preparation

With the nonprofit-to-for-profit restructuring complete and revenue growth continuing to accelerate, Sarah Friar turned her attention to OpenAI's eventual IPO.

According to reports in October 2025, Friar has told associates that OpenAI is targeting a 2027 public listing, though some advisers believe it could come as early as late 2026. The company is in preliminary discussions to raise $60 billion or more in a pre-IPO funding round, which could value OpenAI at up to $1 trillion.

A $1 trillion IPO valuation would be unprecedented—more than double Saudi Aramco's $29.4 billion IPO (the largest in history) and far exceeding recent mega-IPOs like Meta's $104 billion valuation and Alibaba's $231 billion.

For Friar, the OpenAI IPO would be career-defining. She took Square public at $2.9 billion and watched it grow to $100 billion. An OpenAI IPO at $1 trillion would dwarf that achievement and establish her as perhaps the premier CFO in tech history.

But the path is fraught with challenges:

Valuation Justification: A $1 trillion valuation would value OpenAI at approximately 77x forward revenue (assuming $13 billion in 2025 revenue). Public market investors typically value software companies at 5-15x revenue. OpenAI would need to demonstrate sustainable competitive advantages, durable revenue streams, and a clear path to profitability to justify such a premium.

Profitability Timeline: Despite $13 billion in revenue, OpenAI is believed to be unprofitable or barely profitable due to massive infrastructure spending. Public companies are expected to demonstrate earnings growth. Friar will need to show a credible path to generating substantial profits.

Competition: By 2027, OpenAI will face intensifying competition from Anthropic (valued at $183 billion in September 2025), Google DeepMind, Meta AI, xAI (Elon Musk's company), and potentially new entrants. Maintaining market leadership will be critical to IPO success.

Regulatory Environment: AI regulation is evolving rapidly. New laws governing AI model training, data usage, copyright, and safety could materially impact OpenAI's business model and growth prospects.

Mission Credibility: OpenAI will need to convince public investors that its public benefit mission is compatible with profit maximization, or risk being seen as either disingenuous about the mission or compromised in its business execution.

Friar has reportedly begun meeting with investment banks to discuss IPO timing, valuation strategies, and investor positioning. Goldman Sachs and Morgan Stanley are expected to lead the offering, with Friar's Goldman Sachs background providing valuable relationships.

The Stakeholder Balancing Act

Perhaps Sarah Friar's most difficult challenge is balancing the competing interests of OpenAI's diverse stakeholders—each with different priorities and expectations.

Sam Altman and Leadership: Altman is focused on building AGI as quickly as possible and maintaining OpenAI's position as the industry leader. This requires massive capital investment, aggressive hiring, and tolerance for short-term losses to achieve long-term dominance. Friar must enable this ambition while imposing financial discipline.

Microsoft: As the largest shareholder and primary infrastructure provider, Microsoft wants maximum return on its $13 billion investment. But Microsoft also competes with OpenAI through its own AI products and has complex incentives around whether OpenAI should remain dependent on Azure or diversify its infrastructure.

Employees: OpenAI's 3,500+ employees (as of late 2024) have seen the company's valuation skyrocket and expect their equity stakes to generate life-changing wealth through an eventual IPO. Managing these expectations while maintaining motivation through 2027 requires careful communication and equity management.

The OpenAI Foundation: The nonprofit board still has oversight authority and remains committed to the mission of ensuring AGI benefits humanity. Any decisions perceived as prioritizing profit over safety or broad access could trigger governance conflicts.

Regulators: Government officials in the U.S., EU, and other jurisdictions are developing AI regulations that could constrain OpenAI's operations or impose new compliance costs. Friar must maintain productive relationships with regulators while advocating for policies favorable to OpenAI's business model.

Public Market Investors: Future shareholders in an OpenAI IPO will expect transparent financial reporting, consistent earnings growth, and governance structures that protect shareholder rights—all of which may conflict with other stakeholders' priorities.

Navigating these competing interests requires Friar to be simultaneously a diplomat, negotiator, strategist, and enforcer—roles that go far beyond traditional CFO responsibilities.

The Comparison to Square

Sarah Friar's time at Square provides a useful benchmark for evaluating her OpenAI tenure.

At Square, Friar had several advantages: a co-founder CEO in Jack Dorsey who trusted her completely and gave her wide latitude; a relatively straightforward business model (payments processing with adjacent services); clear metrics for success (payment volume, transaction fees, customer retention); and a path to profitability that could be modeled and executed systematically.

The Square IPO in 2015, while initially seen as disappointing, proved to be brilliantly timed in retrospect. Friar got the company public when it was ready operationally, even though market conditions weren't perfect. The stock's subsequent 25x appreciation validated her judgment.

At OpenAI, Friar faces far greater complexity: a business model that is still evolving (subscriptions, API access, enterprise licenses, and potentially new revenue streams); competition from companies with far greater resources (Google, Microsoft, Meta); technological uncertainty about whether OpenAI can maintain its lead as models commoditize; and a corporate structure with unusual governance and mission constraints.

The revenue numbers are far larger—$13 billion at OpenAI versus $3 billion when Friar left Square. But so are the challenges: OpenAI must justify a $1 trillion valuation in public markets, manage infrastructure spending in the tens of billions, and navigate existential questions about AI safety and governance.

"Square was a fintech company with a clear business model at the end of the day," one former Square executive said. "OpenAI is building something that could be as foundational as the internet itself, or could be obsoleted by next year's breakthrough. The uncertainty is orders of magnitude higher."

The Lessons Applied

Sarah Friar has stated that her Nextdoor experience taught her critical lessons she's applying at OpenAI:

Valuation Discipline: The $4.3 billion SPAC valuation for Nextdoor proved unsustainable. At OpenAI, Friar is reportedly being more conservative in valuation discussions, pushing back against aggressive investor pricing while ensuring the company doesn't overpromise on growth projections.

Profitability Focus: Nextdoor's inability to achieve profitability eroded investor confidence. Friar is emphasizing unit economics, gross margins, and a clear path to sustainable earnings at OpenAI—even while managing explosive growth.

Communication Clarity: The gap between Nextdoor's SPAC presentation and actual results damaged credibility. Friar is being more measured in her public statements about OpenAI's financial performance and prospects, avoiding overpromising.

Stakeholder Management: Nextdoor's challenges included conflicts between growth and content moderation, short-term metrics and long-term community health. At OpenAI, Friar is navigating similar tensions between commercial goals and mission commitments.

"I learned that you can't build a sustainable business on hopes and projections," Friar told Fortune in 2024. "You need actual unit economics, proven business models, and realistic assumptions. At OpenAI, we're maniacal about understanding our costs, margins, and what drives sustainable value."

The Personal Stakes

For Sarah Friar, the OpenAI assignment is deeply personal.

At 52, she is at the peak of her career with a track record that includes both triumph (Square) and failure (Nextdoor). The OpenAI outcome will likely define her professional legacy—either cementing her as one of the greatest CFOs in tech history or raising questions about whether Square was an anomaly.

Friar was awarded the Order of the British Empire (OBE) in 2019 for her contributions to entrepreneurship and financial services—a recognition of her impact beyond Silicon Valley. She serves on the boards of Walmart and several other companies, is co-chair of Stanford's Digital Economy Lab Advisory Group, and is involved in numerous philanthropic initiatives.

But she has also experienced the personal costs of executive leadership. The stress of taking companies public, managing through crises, and navigating stakeholder conflicts takes a toll. Friar has spoken openly about the challenges of work-life balance, the isolation that comes with senior leadership roles, and the importance of resilience.

"There are days when you question everything," Friar said in a 2022 interview during her Nextdoor tenure. "You're responsible for thousands of employees, billions in shareholder value, and decisions that affect millions of users. The weight of that can be crushing. You have to develop mechanisms to cope with the pressure."

At OpenAI, the pressure is magnified. The company is building technology that could transform civilization or create existential risks. The financial stakes are unprecedented—a potential $1 trillion valuation. The scrutiny from media, regulators, competitors, and the public is intense.

Friar's ability to manage this pressure while executing on OpenAI's ambitious financial strategy will be tested daily between now and the eventual IPO.

The Unanswered Questions

As Sarah Friar approaches the end of her first year as OpenAI's CFO, several critical questions remain unanswered:

Can OpenAI sustain its growth rate? Doubling revenue every six months is extraordinary, but all growth curves eventually plateau. Will OpenAI be a $20 billion revenue company by late 2026? Or will growth decelerate as markets saturate and competition intensifies?

Can the company achieve profitability? With infrastructure spending potentially exceeding $15 billion annually, OpenAI needs to generate substantial gross margins and operate efficiently to reach profitability. Can Friar demonstrate a clear path to earnings that justifies public market expectations?

Will the corporate structure hold? The nonprofit-to-PBC restructuring is complete, but tensions between mission and profit remain. Will the OpenAI Foundation's 26 percent ownership and governance authority create conflicts with majority shareholders as the business scales?

Can a $1 trillion valuation be justified? Public market investors are skeptical of extreme valuations. Friar will need to demonstrate that OpenAI's business is durably defensible, has decades of growth ahead, and can generate returns that justify a $1 trillion price tag.

What happens if AI progress stalls? OpenAI's valuation assumes continued rapid advancement in AI capabilities. If progress toward AGI slows, if competing models catch up and commoditize the technology, or if regulatory constraints limit deployment, the company's growth story could unravel.

Can Friar avoid the Nextdoor pattern? The SPAC collapse at Nextdoor raised questions about Friar's judgment on valuations, business models, and market timing. If OpenAI's IPO disappoints—whether due to market conditions, execution issues, or unrealistic expectations—it could confirm Nextdoor as a pattern rather than an isolated setback.

Conclusion: The Ultimate Test

Sarah Friar's journey from a small town in Northern Ireland to the CFO chair at the world's most valuable AI company is remarkable. She has demonstrated extraordinary financial acumen at Goldman Sachs, architected one of the decade's great fintech success stories at Square, endured the humbling failure of Nextdoor's public market collapse, and now faces the most complex corporate financial challenge in technology history.

The OpenAI assignment will test every skill Friar has developed: her analytical rigor from McKinsey, her investor perspective from Goldman Sachs, her capital markets expertise from the Square IPO, her operational learnings from Nextdoor, and her resilience through crises and setbacks.

If she succeeds in taking OpenAI public at or near a $1 trillion valuation while maintaining financial health, stakeholder alignment, and mission integrity, Friar will have accomplished something unprecedented. She will have transformed a nonprofit research lab into one of the world's most valuable companies, navigated one of the most complex corporate restructurings ever executed, and established a new model for how mission-driven AI companies can access public capital markets.

If she fails—whether through an IPO that disappoints, a restructuring that fractures, or financial performance that doesn't justify the valuation—the questions about her judgment, timing, and ability to distinguish sustainable businesses from overhyped visions will intensify.

The answer will likely come in 2027, when OpenAI is expected to go public. Until then, Sarah Friar is managing the most high-stakes financial transformation in Silicon Valley—with billions in investor capital, thousands of employees, and perhaps the future of artificial intelligence hanging in the balance.

Sometimes the greatest opportunities come with the greatest risks. For Sarah Friar, OpenAI represents both—the chance to cement her legacy as one of tech's greatest financial leaders, and the risk of being defined by falling short of an impossible standard.

The outcome is still being written.