From Executive to Beginner Again
I ain’t workin’ here* no more.
(*corporate America)
This is long AF and if you don’t want to read, I can’t blame you! Listen to me read it instead, you know I love to tell stories.
00:00 The moment it hit me.
Last week, I was genuinely excited to check out the NYC Small Business Month Expo. I wanted to learn more about winning government contracts, meet other entrepreneurs, maybe hand out a few business cards, you know the drill. Not to brag, but I’m great at conferences. In the tech and CX world, it’s rare for me to walk into a room and not know at least one person, or have someone know me.
The expo hall was packed: dozens of tables, swag, resources, and people to talk to. It was loud, echoey, and busy. I got overwhelmed, so I hopped into a learning session to catch a panel called “Leveraging Big Business for Your Small Business,” with speakers from Mastercard, the Tory Burch Foundation, and the NYC Department of Small Business Services.
And that’s when it hit me:
I’ve spent ten years on stages, leading international teams, consulting with tech giants. But in this room full of small business owners, I felt like a stranger… like I didn’t belong. I wished I had a buddy, or knew someone who could help break the ice. I realized I didn't know how to introduce myself. I didn’t know where I fit.
And the truth is I’m starting over. So yeah, I’m a little scared.
01:55 The rise: from entry-level to executive.
I’ve always been a go-getter. When I landed my first job, I got a second one. In high school and college, I couldn’t go long without being trusted with the keys to the retail stores I worked in. I wanted responsibility. I wanted to be in charge. I wasn’t a great student, so work became my way to shine.
In my final year in retail, I was 25 and managing a flagship Gap store in Manhattan, leading a team of 80 across operations roles. I was the only manager who came from a “core store,” where every employee had to know how to do everything: cashwrap, fitting rooms, stock, visuals, replenishment, opening, closing, cleaning, all of it. At the flagship, most people were only trained for one or two areas. So when a department was short, I was the first one they called no matter what else I needed to get done. I knew how it all worked so I had the keys to a $40M operation and nearly gave my life* for the privilege of saying I dressed the holiday windows on Fifth Avenue.
(*story for another time)
In 2014, I left for an IC support role at Paperless Post - finally, a desk job! I told myself, “You don’t need to be the boss. Just do the work.” A JOKE. LOL. Of course I wanted to be the boss.
We were a tiny team, each with our own specialties and ownership we took pride in. But it wasn’t long before we were split into Paper and Digital support. We got direct reports and became responsible for building remote team culture from the ground up.
We sacrificed a lot and got close in the process as an overworked, underpaid, out-of-sight group of advocates saving weddings, birthdays, and bar mitzvahs because that was our job. And not even a month after the CEO stood up in a town hall and said he looked forward to growing 5x… almost my entire team was laid off.
I got my Six Sigma Yellow Belt that summer and joined Shapeways, a Dutch 3D printing company, with a new title, a salary bump, and the challenge of managing the U.S. support team in Queens. I also took on building quality assurance programs to reduce production errors in the on-site manufacturing process. Across the pond, the Dutch team was led by a different manager, and this was my first real experience with international support operations.
Nine months in, layoffs hit. The Dutch office and Manhattan tech team were gutted. The support org shrank by 40%, but my direct reports doubled. I got promoted. And just like that I owned customer experience.
At Shapeways, I clawed my way into meetings uninvited, launched a Voice of Customer program no one asked for, and held the (possibly dubious) record for employee retention AND won the quarterly popularity contest award once. One year I had EIGHT different bosses. Eventually the work grew stale, and it was clear there was nowhere left to grow.
I left in 2019 after being headhunted for a Director role at TuneCore.
A few years later, Shapeways declared bankruptcy after some questionable moves from an American CEO tied to a SPAC IPO. No severance. No warning. Just wiped out. A year or so later, the OG Dutch team bought it back and reopened it in Eindhoven under the same name. Honestly? Kind of iconic. Rooting for you guys!
06:05 This is where things got interesting.
Over five years at TuneCore, I grew a scrappy team of ~10 into a global CX powerhouse of 150+, supporting customers in a dozen languages across six countries. I launched a Voice of Customer program, drove major product improvements, and ultimately oversaw over half the business’ headcount. I ran a tight budget, brought my teams along through massive change, and made it my mission to teach clients and peers what excellent customer experience could really look like, and more importantly what advocacy looked like.
For a few years, I was a corporate darling. Recruiters sent offers for easier jobs with better pay, but I turned them down because I liked the challenges I already had. I was getting wined and dined, invited to speak, tapped for advisory boards, going to awards shows and other events. I lost myself in it. My bosses were demanding and I was eager to deliver. I traveled, I was first in, last out, I loved my team, I loved the mission, and I wanted to show up as the leader they deserved, even as I moved further from the entry-level roles I came from.
I kept climbing. One more promotion, one more team, one bigger problem to solve. I built a name in the CX world and in the music biz, and I built a quiet, steady burnout right alongside it.
On my five-year anniversary, I was told, “due to a restructure,” I was being let go. Just like that. The work, the wins, the routine, the people I spent ten hours a day with... gone. Like an NPC in a game, I was out of sight and out of mind. They were ready to move on without me.
Oh, and this happened on my first business day back after the U.S. election. One day after I flew home from speaking at a CX conference in London. So yeah... I already wasn’t at 100%.
What I wouldn’t give for 30 minutes in my old GDrive to recover my work history, performance reviews, to remember which KPIs I crushed, and when (for my resume). But what are you gonna do? I have to let go of that, that was hard.
08:42 Nobody use the tech! The tech has gone bad!
There’s never a great time to lose your job, but I was lucky to lose mine at the start of Suneet Bhatt’s “Find and Evolve your Purpose: A Course for Professionals.” I was skeptical about a lot of the concepts presented in the second half of the coursework, in particular exercises that centered on letting go and forgiveness. I was acting like I wasn’t mad about getting fired and had everyone fooled, but inside I definitely was. Super bitter, actually. I was burning through my deductible in therapy talking about it multiple times a week.
My therapist calls this an “occupational hazard,” that I can easily present shitty situations to people in ways that don’t make them sound so bad. It’s not denial, it’s a result of a working in retaliation and fear-based work environments for the last 2 decades.
In class, Suneet challenged me to think about my choices through a different lens, because it was a choice to remain angry about losing my job. And certainly a choice to pretend like I wasn’t. It wasn’t until months later that I started to understand how forgiveness could serve me. I’m still not totally bought in but I’m getting there.
In unemployment, I went looking for myself. I’d always been busy, just constantly in motion, and then suddenly I had nowhere to be and nothing to do. In the dead of winter. In New York City. I was depressed. I knew I was depressed, I just had to wait it out. I was waking up, vaping, staring at my phone for 15 hours, and going back to bed. It wasn’t great, I needed to rest and this wasn’t rest.
I took some interviews, but I couldn’t get interested in any of them. Every job felt meaningless, especially in tech. I can’t bring myself to care about another AI-enabled garbage tool designed to “revolutionize CX” but really just existed to chase a Series B round no one asked for.
One day, I took a phone screen for a Chief of Staff role at a pet insurance company. The recruiter asked me, “Tell me about a time you used data to make a decision,” and at that moment I thought I cannot go back to corporate America.
“Tell you about a time I used data to make a decision?” I’ve made every decision using data for the last 20 f*cking years. You’d know that if you read my resume.
Tell me about a time.
Tell me about a time.
Tell me about a time.
Tell me about a time you gave a shit about the people you’re hiring. About the culture you’re building. Because these prescriptive “tell me about a time” questions are not it, especially at the senior leader level. Have a real conversation with me, for f*ck’s sake.
My therapist also told me to try pilates. Said it might help channel the rage into something productive. She was right, I love it. Shout out to The Fit In in Bed-Stuy. (And note to self: pitch them on SunshineCX.)
Where do I go from here?
My best interviews were the ones that started with “What do you want to do here?” and not “How do you fit into our box?” But even then, nothing felt right. I couldn’t imagine signing back on for another company, making new work friends, learning new products, fighting the same uphill battles I’d fought in every role I’ve ever had… for what? For it to not matter again? For my commitment to CX to be undermined by execs who only see the bottom line? For more sleepless nights, 5am flights, and maybe a 4% raise?
No thanks.
In late February, I flew to Puerto Rico for one of my closest friend’s weddings. That trip changed me, quietly, but deeply. A week in the sun surrounded by love, laughter, and chosen family. The kind of beauty that lingers and reminds you what it feels like to be soft and open again. One of the brides wanted us all to experience the place that shaped her, and we did. I felt it in my bones: I wasn’t going back to who I was, not to how I worked, not to the version of success that wore me down. Over and over, friends said, “I’m glad you’re out of that last situation. Whatever you do next, it’ll be great.” I wanted to believe them, and for the first time in a long time, I almost did.
What I want now is new and scary. I’m networking without name recognition, I’m scared I won’t be accepted by peers in a world I’m just entering, and I don’t feel like a real small business owner. I’m just one girl! With a computer and an LLC.
I don’t want to just be a consultant. I want to serve my neighbors, my community, my peers in tech. I want to help small businesses compete with the big guys through smart, approachable, people-first operations.
And I don’t want to market to my neighbors, I really don’t want to sell to them, that doesn’t feel right. I want them to know I’m here to help, genuinely. I bring a ton of knowledge and skills that can help them run their businesses smarter, leaner, and with more peace of mind. That’s it.
It sounds weird to say out loud, but to serve is my purpose in life. I’ve spent years helping billion-dollar companies optimize their CX and now I just want to help my neighbor’s bodega build a website that brings in foot traffic because their chop cheese is eliiiiiiiiiiite.
14:38 This is my sweet spot.
I’m new here, small business owners. Hello. But I’m not new to operational efficiency, and I know how the big businesses are doing it.
At the “Leveraging Big Business for Your Small Business” panel, Ginger Siegel (North America SMB Lead at Mastercard) listed the three biggest challenges small businesses are facing:
Access to capital (Can’t help with that sorry!)
Operational efficiency (HELLO, yes, me!)
Digital security (Not my lane, but I know people…)
When she said “operational efficiency,” I had to sit on my hands. And then Dynishal Gross, Commissioner of NYC’s Department of Small Business Services, talked about how, during COVID, the city scrambled to help small businesses build websites because soooo many didn’t have one. Too many people still think building a website or managing digital tools requires deep technical expertise. That’s just not true anymore.
“I CAN BUILD YOU A WEBSITE!” I wanted to shout.
“I CAN BUILD YOU AN INVENTORY MANAGER. A CRM. A VIRTUAL BUDTENDER FOR YOUR CANNABIS CUSTOMERS!”
If that room had known what I could do, affordably, I would’ve run out of business cards.
I can build SEO-friendly FAQs.
I can set up your CRM.
I can create customer surveys and build dashboards.
I can optimize your help desk or ticketing system.
I can setup your newsletter.
I can help you hire smarter, serve better, and compete with giants without losing your soul (or your budget).
I can, I can, I can!
And I want to, because I want your small business to succeed. Because I don’t want to see my neighbors struggle when big businesses creep into our neighborhoods. According to the U.S. Department of Treasury, small businesses created over 70% of new jobs in America since 2019, and 46% of the American workforce is currently employed by small businesses. We have a lot to lose by not supporting each other.
On the other hand, 72% small businesses in NYC aren’t able to cross that $1m in revenue milestone, according to the New York State’s 2020 Annual Report on the State of Small Business* and that means we also have a lot to gain by actively supporting each other, too.
(*2020 is the most recent year that specific stat is published, though the report is updated through 2024. The 72% stat was a conversation topic by panelists at the Small Biz Expo, so I’d imagine not much has changed.)
I’ve helped big companies get this stuff right. Let me help you win. Nothing (other than cats) would bring me more joy than helping regular people outshine the executive class I used to be part of.
The means of production belong to the proletariat… something something.
17:39 The emotional reality of starting over.
It’s hard to let go of who I was, but I don’t want my identity to be work anymore. And I’m not going to pretend I’ve got it all figured out. Sure, one life-changing trip to Puerto Rico inspired me to start a business, but let’s be real: it’s only been a couple of months and I’m still me, still sorting it out. But one thing I can say, with full confidence, is that right now I’m happy and that was not the case a year ago.
I don’t have any paying clients for SunshineCX yet. But I’m working with local animal rescues pro bono, helping them update their websites and tools. It feels good to be helpful. And if I’m going to have extra time on my hands, I might as well use it for something meaningful.
I’ve also been dedicating time to pet services. I loved working with animals when I was younger, and it turns out: walking dogs and feeding cats is a pretty solid way to earn some walking-around money. NYC has no shortage of pets in need, and for that, I’m thankful.
Commissioner Gross was right when she said “if you’ve got a dream and drive, this city will meet you halfway.”
But here’s the thing I wrestle with: How do I convince small businesses that I genuinely want to help? That they can compete with the big guys by making thoughtful, sustainable tech choices? That I’m the right person to help them?
The other day, I sent out a bunch of cold emails (yes, by hand). But most of the businesses I researched had little-to-no contact info. No email address. No form. A few had phone numbers, but I’m not cold calling. I believe in consent-based sales. Only one business replied (shout out to Stone Road ). The rest? Not even sure if they got my messages… this is exactly what I want to help with.
So… do I go in person?
Am I a modern-day door-to-door consultant now?
Oh no.
But let’s bring it back to the real emotional reality of starting over. I’m not the expert in the room anymore. And my discovery calls have shown me I still have a lot to learn, but I also have a lot to offer.
I’m afraid of failure, rejection, and irrelevance. (and so are you, be serious.) If I go all in on SunshineCX and it flops, I’ll have to crawl back to corporate. If I don’t go all in, I’ll probably end up there anyway, but with the added regret of never having tried. I’ve never been afraid of hard work, but this fear is deeper. It’s about being seen as someone without a title, without a logo behind them. In the CX and tech world, I wonder if people think I’ve lost my edge. In the small biz world, I worry I come across as too corporate, too polished, like I’m trying too hard to sell something they don’t need. But I’m not chasing sales, I’m chasing purpose. And I know those two things can look the same from the outside.
I’m working on a new introduction, who am I now that I’m not the XYZ of Big Tech, with a giant team and a shiny title? Now that I don’t have an org chart to point to or execs to vouch for me?
There’s still a lot I can’t predict, like whether this community will respond or if I’ll find enough clients to sustain myself. So I’m learning to live with the fog. I focus on what I can control and try to let go of the rest. My tools are pretty unremarkable: Lexapro, therapy, my community, and a job-to-be-done that actually means something to me. I’m working toward the version of me who goes out and does the thing even though she’s scared. That’s what gets me out of bed right now, late in the day but out of bed all the same and that’s what counts.
I think most importantly, I’m going to keep being myself, because being myself is what got me to the top in the first place. I’m still at the top. I just have a different view now, and a new way to give back.
If you’re a small business owner who needs help, I’m here. And if you’re a career-changer like me, I see ya.
This is weird. But let’s f*cking go.
PS: go to Puerto Rico. Like, now.