How To Ask For A Raise, According To NYC’s Official Career Guru

Before Faye Penn became a government employee two months ago, she was a New York City tabloid reporter, newsroom leader, magazine editor, television vice president, and founder of Brokelyn, the iconic local site for broke Brooklynites trying to live large on a budget. Now, as the first-ever Executive Director of Women.NYC, Penn has parlayed her 25 years in the notoriously hard-edged world of New York media to become the city's official career guru.
Women.NYC launched in 2018 as a website and search tool to connect women to dozens of city services designed to help them succeed at work, from pro-bono legal services for small businesses, to (free!) classes in javascript. Penn’s job is to serve as a kind of guidance counselor and connector, making sure women are a force in the future economy of the country’s largest city. During our interview this week — her first in her new role — Penn was chomping at the bit to share her best career advice for young women, including how to ask for a raise, how to balance kids and career, and why we need more women leaders.
Ahead, we talk about all of that plus how New York City is changing the game for women, including putting money in their pockets.
Women.NYC is a city initiative to make sure women can get the bag. Why is it important for city governments to be advocating for women in this way?
Because the gender pay gap is real. New York City is already better place by comparison for women to have their careers and businesses, but there’s still a gap here. There is very clear research showing that women get less funding for their businesses. They are less likely to get loans. A lot of women do not have the network in the same way men do, and it’s important. There are a lot of ways that we need to help women catch up.
But what is the benefit of having this as a government program, specifically?
Our goal with Women.NYC is to be a model for cities and countries around the world on how to empower women. We’ve created actual tools and resources in New York City that put money in women’s pockets. For example, the Department of Small Business Services came up with a program called WEnyc, which is a suite of tools for women business owners. There are funding options. There’s a mentorship program. There is a pro-bono legal program, so women entrepreneurs can get pro-bono legal from some of the best law firms anywhere. There are programs in tech, in food businesses, in film. There are dozens of programs with real resources that people need to know about.

The city is investing in a very real way in women’s economic advancement. When we’re investing $10 million, you can’t tell me that’s window dressing.

Faye Penn, executive director, Women.NYC
There are a ton of “women’s empowerment” initiatives out there. What would you say to critics who might think that the Mayor’s office is just trying score political points?
There’s a lot of chatter about women’s empowerment out there. A lot of people see this as a lucrative field. There are conferences where you can pay $500 for a weekend and you leave with just inspiration. But here, you could leave with a $100,000 loan. Our community of women entrepreneurs is free. Our services are free. And you often leave with actual money in your pocket.
For example, Mothercoders is one of my favorite programs. One of the hardest challenges of being a woman with kids is balancing child care and your job. A lot of women decide to take some time out of the workforce to care for their children, and it’s incredibly difficult to get back. So Mothercoders is a program that offers women tech training (javascript and front end web development) — with child care — to get them back in the workforce and into a lucrative growing career.
There’s a New York City Housing Authority (NYCHA) food business pathways program, where people can take an 8-week class if they’re a NYCHA resident and get trained in how to have a food business. The FDNY has active efforts to recruit women. We have finishing grants at the Mayor’s Office of Media and Entertainment, aimed at women filmmakers where you get $50,000 to finish a project. That’s huge in the film business. We can give you the funding to help you finish your film and help you tell your story.
I’m also very excited about the WeVenture fund. It’s $10 million that we’re investing— so we’re expecting a return on it. We’re partnering with 5 VC firms led by women of all backgrounds, and we’re identifying start-ups, led by women of all backgrounds, to invest that money in.
The city is investing in a very real way in women’s economic advancement. When we’re investing $10 million, you can’t tell me that’s window dressing. I didn’t come here for political points.
Amazon’s HQ2 is coming to Long Island City. Mothercoders for example is a partnership with Google. Are we going to be funneling women to those jobs at Amazon, or otherwise working with Amazon to provide new trainings or other programs?
It’s very early. I have not been involved with Amazon at all up until now but I know those efforts are underway. Everybody is trying to do right by the city and that’s genuinely what motivates people here. People just want to know how can they diversify their projects. So based on that alone, I know the answer is yes.
What do you think is the biggest barrier for women at work today?
I would say it varies by industry. And I think it varies for your level also. The most widespread one is the pay gap: It’s not making as much money as men. And that is true whether you’re a small business, if you have a start up, or if you have a job.
What’s your advice for asking for a raise?
You need to demonstrate your value. Your ask can’t be because you should have more money. It’s got to be because you’ve earned more and you contribute more and you help the bottom line. It’s great to ask for a raise in conjunction with a promotion, so you can say you will add value in these ways.
One of the things I think is especially important for women is to make sure you’re seen as someone who had leadership abilities. Very often, we are the workhorses, right? I think you need to be buttoned up, but you also need to be seen as someone who can lead. I think that requires taking initiative. I think it’s speaking up in meetings. It’s also the way you comport yourself, the way you dress, and being somebody who sees the big picture of the company.
I’m also thinking about paid family leave and making that transition from not being a mom to being one. That’s so scary. You always feel fear that it will hold you back in some way. I’m curious how you navigated that?
Ugh, Terribly.
Do you have advice?
Yeah, have your damn kids and be proud of it.
What makes you say you did it terribly?
I was at the New York Post when I had my first kid, and I had those same fears. I ran a department at the Post, and I thought I’d lose my edge and I wouldn’t be seen as a newsroom leader. Looking back, I was at a really good place in my career. The boss liked me. I had a great team. I was thriving. I was in a great position to have a baby and leave at 5 o’clock. But I didn’t want to. I would leave at 7:30 or 8. I remember Col Allan, the editor-in-chief, would step out into the newsroom and say, “Go home Faye.” In my perverse way, I saw that as a badge of honor. I’m still fighting, I’m still here.
I’m going to be honest, I came home to a sleeping baby a lot of the time that first year. I missed a lot. I’m not sure my priorities were in the right place.
With my first baby, I acted like nothing changed, when really everything did. But at the time I didn’t have any models to show how it could be done. What would it be like if their were 50 percent women in leadership across all industries and we didn’t feel like we had to sweep our families under the rug?
What are some lessons learned over your career that you would do differently with hindsight now?
I think that millennials are really good at self-promotion, and I mean that in a good way. Building a platform for yourself and using social media is important. I should have paid more attention to my own profile.
I also wonder if I needed to sell Brokelyn. I didn’t have pro-bono lawyers. I never got a loan. I didn’t have mentors. When I was thinking about selling Brokelyn, I called a guy that someone told me sold businesses. This was a guy who sold $200 million coal mines. He didn’t really have anything helpful to tell me about my small business in Brooklyn but this was the only guy I knew. I feel like if I had other people to talk I might have made some other decisions.
What’s a piece of advice you wish someone gave you in your 20s?
I wish I had gotten a job as an assistant. I was an intern but never an assistant, and I think getting a job as an assistant helps you become very buttoned up and systematic. You pick up all this sort of professional communication. Things like decks! Even if you come from a really top notch school, make sure you have office skills. People always need decks. They always need spreadsheets and word docs to look good.
Same question, but for your 30s?
I would say, no matter what you do, stay in touch with your creativity. Write on the side, play music, be in a band, have a cool blog, do comedy. Number one: It’s good for you. And two: That’s what distinguishes you. And you never know where those things go.
This interview has been edited and condensed for clarity.

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