The Pinterest Paradox: Cupcakes and Toxicity

Francoise Brougher
Aug 11 · 17 min read

Pinterest has always been about aspiration. It is a platform for sharing beautiful images, curating galleries of an idealized world. Users can reimagine their home, their garden, their meals, their clothes, their hair, even their cupcakes. In reality, Pinterest’s workplace is far from perfect.

Although 70 percent of Pinterest’s users are women, the company is steered by men with little input from female executives. Pinterest’s female executives, even at the highest levels, are marginalized, excluded, and silenced. I know because until my firing in April, I was Pinterest’s chief operating officer.

I started at Pinterest in March 2018. In less than two years, I grew Pinterest’s revenue from $500 million to $1.1 billion, increased the advertiser base from 10,000 to 80,000, and expanded operations to 20 countries. Half the company’s 1,500 employees reported to me.

According to Pinterest, I was fired not for the results I achieved, but for not being “collaborative.” I believe that I was fired for speaking out about the rampant discrimination, hostile work environment, and misogyny that permeates Pinterest.

What happened to me at Pinterest reflects a pattern of discrimination and exclusion that many female executives experience, not only in the tech industry but throughout corporate America. I have always been a private person, but I am opening up about my experience because if someone of my privilege and seniority is fired for speaking out about these issues, the situation is likely far worse for people earlier in their careers.

Pinterest’s flaws exist in many organizations. I hope that by sharing my story, I can contribute to dismantling the system of gender bias that persists despite the progress made exposing misconduct within companies like Pinterest. It is time to eliminate the “boys clubs” that dominate far too many companies and make room for more women leaders and their ideas.

The Opportunity

In the fall of 2017, a friend called with an exciting opportunity. Pinterest Co-Founder and CEO Ben Silbermann wanted to hire the company’s first ever COO. He was looking for a seasoned executive who understood online advertising and could help him prepare to take Pinterest public. It sounded like a job that played to my strengths. At Google, I had run a $16 billion ad sales business and managed thousands of people. At Square, I had successfully ramped up revenues and been involved in the IPO process.

Pinterest had been around for over a decade but had not yet realized its full potential. The platform had over 200 million users, yet its ad product was still in its infancy. Its advertiser base was dominated by a few large retail customers. Resources were misallocated and there was little process. There were no solid mechanisms for teams to communicate and few significant marketing or business development activities.

These are typical problems that fast-growing tech companies face and I had solved similar issues at Google and Square. I felt uniquely qualified and saw the role as an opportunity to help a promising, dynamic tech company reach the next level.

The Reality

Immediately I recognized problems.

First, important decisions were often made in sidebar conversations between Ben and two or three of his lieutenants, invariably men, who often did not have complete information. These decisions were difficult to track and their illogic was often demoralizing to the people who understood the issues better.

Ben appeared to listen to only a few people and sealed himself off from opposing viewpoints. Ben’s “in group,” the men invited to the “meeting after the meeting,” held all the power and influence. This structure was detrimental to Pinterest’s culture, velocity, and results. The senior management team was riven by backstabbing and gossip as executives competed for Ben’s attention. A colleague once remarked, “the only way we get things done here is hiding things.”

Day-to-day operations were marked by secretiveness. Executive meetings were brisk, formal, and did not confront critical issues the company faced. There was both no collegial banter and no debate. This made it difficult for me to create the culture I believe is most effective. Several times in my career, I have been told that I am excessively transparent. When everything is out in the open, it makes workplaces fairer, happier, and more effective.

I knew that I could not foster a better culture unless our people could get to know and trust one another, so I organized off-sites, mixing hiking, drawing, and cooking with serious topics. In a short time, we achieved a sense of trust and clarity. My team told me they enjoyed my direct style and bad grammar. (I am French and English is my second language.) I loved working with them.

I put in place a series of processes designed to foster communication and cooperation, including Objectives and Key Results, a popular goal-setting strategy in Silicon Valley. I asked each of my direct reports to send me a summary of their highlights and lowlights from the week, as well as their plan for the next week. I read them all and sent summaries to the entire organization so everyone knew everyone else’s priorities and challenges.

Soon Pinterest started making decisions faster. We launched our product in international markets and opened sales offices across Europe. Our sales process, customer segmentation, and overall pipeline metrics became more disciplined. I brought in phenomenal talent in marketing and business development. Our communications team focused more on external rather than internal audiences, defining Pinterest and telling our story to the world. We were on the path to an IPO.

When the founders redrafted Pinterest’s mission in early 2019, one of the five values was “care with candor.” I interpreted this initiative as a commitment to changing the culture. Team members would now be encouraged to share their ideas directly and respectfully. Employees who had been excluded would finally have a voice.

Ben asked me to be the company spokesperson for the “care with candor” value. I did not seem to understand what everyone else knew intuitively: saying what you really thought was still dangerous at Pinterest. I was naively proud.

On the morning Pinterest announced this new mission, the entire workforce gathered in San Francisco’s Orpheum Theater. I stood onstage and explained how important it was for Pinterest to foster transparency and direct feedback. My message echoed around the grand theater but fell on deaf ears.

The First Public Exclusion

Analysts Day is an early milestone in the IPO process. It precedes the roadshow, where executives travel across the country to meet investors. Analysts Day is important because it gives executives a chance to hone their pitch in front of a friendly audience. Ben asked me to take a leading role in the presentation. Afterward I only heard positive feedback from the advisors and investors in the room.

Soon after, Ben said I would not be joining the other executives on the roadshow. When I asked why, he told me someone needed to stay behind because we had failed to meet our Q1 revenue targets. I was the only executive on the team who had taken a company public before and already had relationships with some of the investors the team would be meeting. When I pressed Ben and explained why I felt the decision to leave me behind was irrational, he never replied. I was later told that the team used my slides for their presentation.

The Discovery

The first step of an IPO process is the publication of an S1 filing that discloses the main facts about the company, including compensation of the highest-paid executives.

When I was hired, I was told that all Pinterest executives had the same backloaded vesting schedule. Our equity portion vested 10 percent the first year, 20 percent the second, 30 percent the third, and 40 percent the fourth. I had accepted this schedule because I was planning to be at Pinterest for the long run.

With the S1 filing, I realized that I was the only executive on the leadership team given this backloaded deal. In my first year, I vested 37 percent of what my closest peer, Chief Financial Officer Todd Morgenfeld, vested in his first year. I would catch up to him eventually, but only if I was not fired first.

Discovering that I was given a less favorable vesting schedule was upsetting, but what really bothered me was that I had been misled. I raised the issue with Ben. I was, after all, responsible for enforcing Pinterest’s “culture of candor.” And I was not just fighting for myself. I had hired another senior female executive and offered her the same vesting deal I had received. Following Ben’s advice, I spoke with HR. Pinterest fixed the issue by issuing a new grant, but only after I presented a spreadsheet illustrating the inequity and fought for my fair share.

There is a reason that women do not negotiate as hard as men for higher pay. It is not because we are not good negotiators. As I would learn at Pinterest, it is because we get punished when we do.

More Exclusions

In April 2019, Pinterest held its initial stock offering. Even though the IPO was a success, I felt something changed for me in its wake.

Shortly after the IPO, I stopped being invited to board meetings. No one told me why.

When I first joined Pinterest, I attended all board meetings. It was my responsibility as the number two executive at the company to come prepared with ideas for increasing revenue and diversifying our customer base. Invariably, the board would be cordial, nodding their heads at my proposals and rarely asking difficult questions. This was not something I was used to. At Square, the board would drill down on any new proposals and ask probing questions. It could be nerve-wracking, but when I walked out of those meetings, I felt invigorated. When I asked Ben why the board did not challenge us, he answered, “I chose them.”

Revenue projections the quarter following our IPO were not looking good. I dug in to understand why our revenue was not growing as expected. When my team finally untangled the issue, we discovered the problem was a subtle but consequential change the engineering team had made to the ad targeting system. Their changes were good ones which allowed us to add more value to advertisers, but my team had not been told about them. Had the engineering team looped us in, we could have made adjustments to avoid the revenue shortfall. I had been pushing the product and engineering teams for better communication, but discussions around the issue had taken place in ad hoc meetings I had been excluded from.

There was another reason why our revenue was hurting. Our advertisers found our tools difficult to use and lacking the basic features of our competitors’ ad systems. I sounded the alarm because it was my job to raise these issues. I was blunt and did not hold back. I told the team that we were making a critical mistake by ignoring the concerns of our advertisers. Ben, in addition to being CEO, was also head of product. Now suddenly I was disinvited from all the product team meetings.

It was impossible to do my job if I was excluded from meetings where important decisions were made. I had to waste time and energy just determining what was happening at a company where I was supposed to be a leader. When Ben tried to catch me up on critical decisions after the fact, I was unable to advise him, the reason he had hired me in the first place.

The Review

My performance review came a few months later. In earlier reviews, I had been praised for championing the “care with candor” value. Now I was being told that I was “not collaborative.”

The two-page document cherry-picked the critical feedback and ignored the positive. I was criticized for my communication style and challenging my peers, asserting that I needed to “understand that blanket statements like “we have basically not improved X” land especially heavy from someone in your position.” If I were a man, I would have been considered bold and thoughtful. As a woman, I was “misusing my energy and work ethic.”

I pride myself on taking feedback to heart, so I vowed to take a hard look at my behavior. Maybe the hard-driving instincts that brought me success at Google and Square were not suited to Pinterest? I tried to change my style, but it just did not feel right in my heart.

My review was a textbook case of the “abrasiveness trap,” a concept Kieran Snyder, a female tech executive whose writing I admire, coined. “Men are given constructive suggestions,” she writes. “Women are given constructive suggestions — and told to pipe down.” One peer reviewer suggested I “spend time listening and ensuring your understanding of a challenge. Avoid interrupting people or misunderstanding intent.” In other words, I should pipe down.

The “Champion for Diversity Issues”

Over time, other women at Pinterest reached out to me because they were struggling to be successful in this environment too. Most wanted advice on dealing with being excluded or undervalued. I heard stories of blatant gender discrimination. Certain teams could not retain women because the workplace was so toxic. Some women were offered spot bonuses not just to stay at the company, but to stick it out in certain departments that were particularly fraught. Women were pushed out for being too candid, others for being too caring. Many women felt they had been under-leveled when they were hired and could not get promoted.

I listened to the issues the women raised and worked to improve the situation where and how I could. I had already endangered my standing at the company for advocating on behalf of our advertisers. I was not sure I could be an effective spokesperson for women. I thought the best thing I could do for women at Pinterest was deliver excellent business results.

In November 2019, I was diagnosed with a serious illness that required surgery. When I returned to work in January 2020, I was proud of the work my team had accomplished while I was out. After a Q3 revenue stumble, we had come back roaring in Q4. There are few things more gratifying for a leader than building a team strong enough to thrive in your absence.

Around the time I returned, Todd had been tasked with building out a series of long-term goals for the business and assessing the resources needed to achieve them. In one of the first executive meetings of the year, he asked me to help with this project, which was proving to be challenging. He insinuated that I had nothing more significant to work on, shouting at me, “what is your job anyway?”

In January, I received another performance review. Todd had been asked to provide feedback on me, although I was not asked to provide feedback on Todd. Todd’s assessment of my 2019 performance did not follow the process of balancing positive and negative feedback or assessing my achievements in my role. All he wrote in the positive section was, “she seems to be a champion for diversity issues.”

Reducing a female executive’s achievements to “diversity” is a common form of gender discrimination. Being a woman at Pinterest was not my only accomplishment. What about the problems I solved, the revenue I drove, the processes I put in place, the experience I brought to the IPO process, and the talent I recruited and nurtured? By my own assessment, I did not do enough to help women at Pinterest. I was not connected to a single diversity initiative while at the company.

Following Ben’s advice, I called Todd to discuss his feedback and clear the air so that we could work more effectively together. It quickly went off the rails. He was defensive and questioned the value I brought to Pinterest. He yelled at me, interrupted me, called me a liar, and eventually hung up on me.

I scheduled another meeting with Ben. I explained that I wanted to resolve things with Todd but no longer felt comfortable being alone in a room with him. I needed help. Ben trivialized my concerns, saying that Todd and I were like “an old married couple bickering over how to make coffee.”

At this point, Todd had stopped speaking to me entirely, did not acknowledge me in meetings, and went behind my back to reach out to my team members. HR promised to bring the two of us together, but that meeting never happened. At the end of March, Jo Dennis, the chief human resources officer, sent me a note that the investigation into Todd’s behavior was closed and that Todd was found to have done nothing wrong. I had never asked for an investigation. I wrote to Jo that Todd’s behavior was offensive and that I needed help to repair our working relationship in order to perform my job. She never answered.

The Retaliation

Exactly a week later, Ben fired me during a 10-minute video call. He said he was “sad to do something like this to someone so logical.” Two days later, he called to ask that I tell my team that leaving Pinterest was my decision and that I would be staying on for a month to ease the transition for my successor, Todd. While my arrival at Pinterest was highly publicized, my departure was buried in one line at the end of a revenue guidance revision due to the COVID-19 pandemic.

I was not going to lie to my team and did not sign the NDA presented to me. I realized it was more important to finally be an advocate for women at Pinterest, and for anyone else experiencing the pernicious effects of sexism, bias, and retaliation. It was time for a company that caters to women to respect their own.

The Glass Ceiling

I worked long and hard to become COO of a company like Pinterest and am proud of my career and accomplishments. At the same time, I recognize my privilege, which has only compounded over the course of my career.

I naively thought that I had broken the glass ceiling. But even as the COO of a major Silicon Valley company, I was expected to act a certain way and be deferential to men because I am a woman. The discrimination I experienced at Pinterest was different from the “bro culture” so many other tech companies are notorious for. It was more subtle, but it was no less insidious and devastating.

I now realize that the glass ceiling persists in many forms we cannot see with our eyes but can feel in our work lives. By definition, the glass ceiling is hidden until you run into it. Some women hit it in their 20s, I encountered it in my 50s. It will continue to hold women and the organizations they serve back unless there is real change, not empty presentations, initiatives, and promises.

Notably, when I was fired, not one board member called me to hear my side of the story or discuss what had happened. On every board I have served on or under, when someone at the executive-level leaves, it is discussed and board members reach out to that person. I considered one of Pinterest’s board members to be a personal friend. Even he did not call, and we have not spoken since.

My Recommendations

An unjust workplace starts from the top. Few executives ask themselves, “what can I do to make this an unfair and unpleasant place for underrepresented groups?” I doubt Ben and Todd intentionally foster an unjust workplace. But too few leaders ask themselves how they can proactively design their organizations to be truly equitable and make a practice of confronting bias, prejudice, and bullying. They do not put checks and balances in place, so discrimination and harassment are hard to recognize or report. Instead, they seek control. They make decisions behind closed doors, consciously and unconsciously excluding those who do not look, sound, or behave like them.

I realize, with the benefit of three months hindsight, the role I played in Pinterest’s toxic culture. I did not answer the few requests I did receive from women to be a more vocal champion. Sometimes I even made excuses for the men they confided in me about. I apologize for that and am hoping that this piece will correct some of my complicity.

It is important to understand that it is not just about having more women. It is about changing the culture regarding how women leaders are viewed and treated. This requires the hard work of recognizing stereotypes and training ourselves and our organizations to hold men and women to the same standards.

Below are simple steps Pinterest, or any organization, can take to improve its culture and create an equitable and effective working environment for all.

1: Stop making grandiose statements without taking meaningful action.

A company’s culture springs from what it does, not what it says. Every year, Pinterest has days to celebrate Black history, Latinx heritage, LGBTQ+ rights, and women’s issues. When I was COO, we even had our own women’s conference, hosted by a white man. Stop promoting self-declared “allies” and instead promote deserving, underrepresented employees.

Like many companies, Pinterest makes grand statements on how in the future, Pinterest will be a more equal workplace. Everyone feels good because we are going to appoint an underrepresented person to the board or we are going to improve diversity in hiring. But these ideas never became a reality. Pinterest could not retain its employees from underrepresented groups, despite all the grand statements the executive leadership made.

While metrics on hiring goals are highly publicized, data on retention and promotion are not shared. As a result, institutional change is not measured. Start measuring.

2: Recognize and dismantle the system of gender bias.

We have to stop punishing women for the type of strong leadership that is rewarded in men, and root out the microaggressions that impede female leaders’ ability to be successful.

When a woman leader is accused of not being collaborative or not having strong cross-functional relationships, but her male counterpart is rewarded with a promotion, that is gender discrimination in the executive ranks. When she is recognized for bringing diversity, while her male peer is commended for his operational achievements, that again is gender discrimination. When she is told not to challenge men, that is sexism. And when she calls out demeaning and sexist behaviors and gets fired, that is retaliation.

To debunk this pattern, the first step is to recognize it. See them for who they are, not the token you hired them to be.

3: Take effective, proactive steps to root out discrimination.

Companies should not wait for someone to report a discrepancy then, resentfully, react to that specific complaint. Instead analyze pay, promotion, retention, and firing by gender, race, and other areas of underrepresentation. Where there are discrepancies, investigate and repair them. Companies should be able to publicly share their data on promotion and compensation by gender and race.

One obstacle that executives face when confronting workplace injustice is that lawyers, PR executives, and HR departments will warn them about the risks of taking action, but not the danger of inaction. If you are an executive, you need to know the risks so that you can navigate around them. More importantly, you are the one accountable for creating an equitable work environment, not your lawyers and handlers.

4: Focus on retention, not just hiring.

If companies do not understand the reasons why they are having trouble retaining the people they have hired, they are just pouring water into a leaky bucket. Eliminating discrimination and the pay gap will go a long way to helping retention efforts, but companies also need to take steps to create an inclusive culture. Do not demand culture “fit” but encourage “culture adds.” Make sure you are not just mentoring people who “look like you.” Use Harvard Business School Professor Amy Edmondson’s survey to measure psychological safety of underrepresented versus overrepresented populations, and figure out what you need to do to move the needle.

5: Stop making decisions in ad-hoc, opaque ways.

When decisions are made in the “meeting after the meeting,” either people tell leadership what they want to hear or manage around them, reinforcing the culture of secrecy. A distant, disengaged style of leadership creates an environment where underrepresented people do not have the social handshakes that their mostly male, mostly white counterparts have. Underrepresented people will get marginalized, people closest to the facts will be excluded, and the quality of decisions will be harmed, along with the sense of justice. Over time, people who are underrepresented will be fired or quit, leading to a homogeneous team. When leaders seek to avoid conflict by making decisions in private, it only exacerbates problems and often leads to much greater conflict and inequity.

6: Embrace candor and compassionate leadership.

Listening to different points of view will build a more trusting culture. This is true even when it is uncomfortable, especially when it is uncomfortable. When only the dominant voice is heard, important perspectives get lost.

But even when leaders are willing to listen, it can be hard for people to speak up when they fear retaliation. That is why it is so important to build a culture where people are not afraid to show their humanity and be candid, and not worry about the consequences of saying how they feel. Leaders should look at their own behavior, and what they did to create that culture. While cliche, culture starts at the top. Sharing personal stories and being vulnerable helps. Get to know people personally.

7: Hold the board of directors accountable.

The Sarbanes-Oxley Act requires that publicly held companies maintain a system for employees to report matters that might have a material impact to the audit committee of the board of directors. Most public companies rely on a third-party system that provides an anonymous reporting hotline for this purpose. These systems, however, are not designed with workplace injustices like discrimination in mind. Companies should be investing in more sensitive systems to improve their access to information about this kind of misconduct, which helps them manage the risk of undetected discrimination in the workplace, rather than relying solely on HR. Board members, please hold yourself accountable.

8: Don’t use NDA’s to buy silence.

This recommendation speaks for itself.

Follow me on Twitter at @FrancoiseBr

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Francoise Brougher

Written by

Former Pinterest COO and Executive at Square and Google. French American, from Marseille to the Bay Area. Mom of Three

Digital Diplomacy

Technology, digital, and innovation, at the intersection with government and foreign policy

Francoise Brougher

Written by

Former Pinterest COO and Executive at Square and Google. French American, from Marseille to the Bay Area. Mom of Three

Digital Diplomacy

Technology, digital, and innovation, at the intersection with government and foreign policy

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