9 lessons from my 9 years at Pinterest
Choosing courage over comfort
When people ask me how I spent nearly a decade at Pinterest, the short answer is: the company kept evolving, and so did I.
But the real answer? I grew because I kept choosing courage over comfort.
During my nine years at Pinterest, I held six different roles, worked with twelve (all male) managers, and got promoted five times. I also got married and became a mom.
I started in Biz Ops and made the leap into product, where I led teams across growth, advertiser experience, and sales productivity. I worked on 0-to-1 initiatives, turned struggling teams around, and grew from an IC to a manager, eventually moving into a Director role.
But the biggest growth didn’t come from product launches or fancy titles. It came from the messy, real moments - the ones that stretched me, humbled me, and taught me how to lead.
Here are the nine defining moments that shaped my time at Pinterest, and the leadership lessons I’ll carry with me.
1. Sometimes you take a step back to move forward.
When I graduated from business school, I had my sights set on Biz Ops at a high-growth startup. I saw a posting for Pinterest, applied online (rookie mistake, always try to network in!), and to my surprise, got an offer.
But it came with a catch: it was for an entry-level role.
I didn’t know how leveling worked in tech, but I knew I had four years of experience in finance and an MBA from Harvard. I almost turned it down. Taking a pay cut and a step back felt counterintuitive after everything I’d worked for.
Still, something about the company felt right. I believed in the mission, and I trusted that if I could just get my foot in the door, I could prove myself.
A few months in, after consistently delivering strong work, my manager and skip-level realized I’d been under-leveled. They corrected it, and I was promoted to the level I should have started at.
💡Lesson: Sometimes the fastest way forward is a small, strategic step back. If the opportunity feels right, trust your instincts, not your resume.
2. You don’t need a title to lead.
Shortly after joining, I volunteered for the women@ employee resource group (ERG). When the chair went on maternity leave, she asked if I’d step in to lead the steering committee.
I was honored - and terrified. I wasn’t sure I was senior enough. I worried it would distract from my day job while I was still finding my footing. It was “non-promotable work”, but I also knew it mattered, so I said yes.
Over the next two years, I co-chaired women@, hosted panels, organized events, and built programming that amplified women’s voices across the company. I met inspiring leaders like Mary Barra and Tiffany Dufu, and I built relationships with executives that I otherwise wouldn’t have had access to (see Lesson #3!).
Most importantly, I found my own leadership voice. I learned how to rally people around a cause, how to navigate tough conversations, and how to advocate for more than just myself.
💡Lesson: Leadership isn’t about waiting for permission; it’s about stepping up when something needs to be done.
3. Failure is a catalyst, not a conclusion.
One of my Biz Ops projects involved exploring self-serve advertising as the company diversified beyond enterprise sales.
I pitched a new strategy to the executive team, got buy-in, and formed a tiger team to validate the idea. Resources were limited, so for 90 days, I acted as the PM - a huge opportunity that many dream about. I poured my heart into it.
At the end of the 90 days, the test was successful, and the initiative was greenlit. Everyone assumed I’d take the PM role permanently, including me. I just had to interview to make it official.
And then…I bombed the interviews.
I was embarrassed, discouraged, and full of self-doubt. I blamed my manager for not preparing me properly. I questioned my skills and whether I even belonged in product.
But a sponsor (the exec sponsor for women@!) believed in me and advocated for me to get the role anyway.
So I entered the role determined to prove I deserved it. I studied the PM craft obsessively, asked for feedback constantly, and pushed myself every day.
Failing those interviews stung, but it also became rocket fuel for my growth.
💡Lesson: Failure isn’t the end of the story. Sometimes it’s the start of your best chapter.
4. If something’s broken (or missing), fix it.
A few years into my product career, I noticed a gap: most of the PM leaders at Pinterest were men.
From my finance days, I was used to being a woman in a traditionally male-dominated field. But now, as I started thinking about starting a family soon, I wanted access to female role models for career advice and support.
There wasn’t a dedicated community for women in product at Pinterest. So I partnered with a colleague to build one.
Inspired by the broader Women in Product movement, we created our own internal version. We found a sponsor, secured budget, and started running events and mentorship programs.
At first, it was small. But it quickly grew into a thriving community where women could share advice, support each other, and see a future path to leadership.
Through that work, I met incredible female PMs and built relationships across teams. I also deepened my own leadership skills - creating, nurturing, and passing on a community that lived on even after we stepped down.
💡Lesson: Leadership is about seeing what could be better and doing something about it.
5. Trust is the foundation for real change.
At one point, I moved into a more technical product area to stretch myself. Not long after, the pandemic hit, and everything went remote.
I found myself leading a distributed team with low morale, messy processes, and a track record of missed deadlines. It was a turnaround situation, and it would either make me or break me.
There were real doubts about whether we could deliver value (and days I doubted myself too).
I knew the first step wasn’t overhauling the roadmap. It was rebuilding trust, starting with engineers, designers, and cross-functional partners.
So I spent time getting to know them outside formal meetings. I asked open-ended questions and listened, deeply.
Then I got my hands dirty: fixing processes, removing blockers, and showing that I was willing to do the hard work alongside them.
Once I earned credibility, I reshaped the roadmap and advocated for the resources we needed to execute at a higher level. We launched a major backend project, evolved our charter, and changed how the team was viewed across the company.
💡Lesson: You can't build real change without first building real trust.
6. Ask for what you want, even when it feels inconvenient.
I always knew I wanted to be a people manager.
When I felt solid in my PM skills, I started mentioning it during every career conversation, but there was no clear opportunity available.
Instead of waiting, I raised my hand to lead a critical workstream outside my job scope. It was a chance to show what I could do.
And it worked. I delivered, gained visibility, and got the confidence to know I could lead. When a manager role opened, I felt ready.
But life had other plans: I had just found out I was pregnant.
I was exhausted. I was scared. Could I really take on a new team right before maternity leave?
Part of me wanted to pass. But a bigger part of me knew I had to go for it. That if I said no out of fear, I’d regret it.
I said yes, and I got the job. And when I told my new manager about my pregnancy, he was 100% supportive.
💡Lesson: Opportunities don’t always come at the perfect time. Go for them anyway.
7. Resilience is the most underrated leadership skill.
My first day as a manager, one of my reports quit. Within a few months, the entire team turned over for a mix of performance and personal reasons.
There I was: a brand new manager, pregnant, and with no team to manage but still accountable for delivering results.
It was overwhelming. I wondered if the turnover was my fault and battled serious imposter syndrome.
But there was no time to wallow. I had to rebuild, fast, before going out on maternity leave.
I prioritized ruthlessly, focusing on hiring and onboarding as my number one job. I stepped in personally to cover critical projects to avoid business disruptions. And I leaned heavily on peers and cross-functional partners for everything else.
When I finally left for leave, I had a new team in place, a clear roadmap, and enough momentum to sustain progress.
It was a crash course in organizational design, hiring, and resilience.
💡Lesson: Teams are always in flux. Your job as a leader is to stay calm, adapt fast, and build systems that endure.
8. Maternity leave doesn’t stall your career, unless you let it.
After my first maternity leave, I came back with a lot to prove - to others, but mostly to myself.
I was hungry to reaccelerate my growth, and I also had a sense of urgency. I knew I wanted another baby soon, and I wanted to make my mark in the limited time I had.
The old version of me had climbed through working longer and harder. But now, success wasn’t about more hours. It was about better systems - at home and at work.
My husband and I divided chores fairly and equally, built a schedule that gave us both space, and treated my career as a shared priority.
Back at work, I pushed hard: proposed a reorg, grew my team, led a major revamp of our advertiser flows. That work drove real results and caught the attention of leadership.
In the 24 months after my first maternity leave, I earned two promotions, including the Director title I’d been working toward for years.
💡Lesson: Motherhood doesn’t have to hold you back. It can sharpen your focus and strengthen your leadership.
9. What breaks you open makes space for your next chapter.
When my first daughter was one, we started trying for a second child.
Luckily I got pregnant quickly, but the second pregnancy was much harder: nine months of nausea, exhaustion, and mental strain.
I was promoted to Director just before going out on my second maternity leave. This time, postpartum was rough. I struggled with postpartum depression, loneliness, and the pressure of returning to a bigger role.
What surprised me most was how many other moms were quietly struggling too.
So I started a pilot program for returning moms: a space for honest conversations, shared tips, and real support.
That experience lit a fire in me: I realized I wanted to spend more of my life helping ambitious women navigate big careers and full lives.
It was the moment I knew: it was time to build something of my own.
💡Lesson: When you follow your passion to build something bigger than yourself, you create true community and find yourself in the process.
Final Thoughts
Nine years at Pinterest taught me that growth doesn’t come from being ready. It comes from choosing courage, again and again.
Every step forward came from advocating for myself, stepping into uncertainty, and saying yes when it would have been easier to stay comfortable.
Self-advocacy isn’t just about asking for promotions or opportunities. It’s about trusting your own potential, even when others haven’t seen it yet.
If you're waiting for a sign, let this be it:
Raise your hand. Speak up. Say yes.
Even when it feels scary. Especially then.
Namaste,
Tamara
Loved this one ☝️