When Jessye Kass Karlin asked for a raise, she didn’t just need one person to say “yes.” She needed eight. 

A director of programs at a women’s shelter in Cambridge, Massachusetts, Karlin was in her mid-twenties, making around $60,000 per year. She sought a $20,000 salary increase and a new title: executive director. “I sort of had that role already but didn’t have the title or pay to honor the work that I was doing,” she tells me. 

Karlin felt she was doing everything right, and then some. Before, the shelter had no formalized volunteer prep, so she created trainings focused on de-escalation tactics and dealing with trauma, as well as an official eight-hour onboarding process. During her tenure, Karlin also increased volunteer retention by almost 80 percent and boosted the shelter’s revenue. 

When it came time to ask the board for a raise, she came prepared with documents and a presentation that detailed everything she had accomplished. To get the promotion, she needed unanimous approval from all eight board members – only six gave the green light. They said she could change her job title, but they didn’t offer her more money.

“It was frustrating,” Karlin says. “My impact felt so clear…. I did all the things I was supposed to do and exceeded expectations.” 

Asking for a raise can be uncomfortable for anyone, but it’s a pain acutely felt by working women. Only 36 percent of women say they feel comfortable asking for a raise, according to a recent survey from Glassdoor. That number is higher among men, at 44 percent. 

That doesn’t mean they aren’t asking. A study from the Academy of Management found that over the past two decades, women are negotiating their salaries more often, not less, than men.  Still, women are earning less: Bankrate’s analysis of the latest U.S. Census data found that women earned 81 cents for every dollar men did. Plus, women are more likely to have been unsuccessful in negotiating a raise compared to men, Bankrate’s Financial Habits Survey found. 

Most working women won’t see equal pay before they retire, Bankrate analysis finds

Here’s exactly why it’s taking so long. Read more.

Three months later, Karlin went in front of the board again, this time with more evidence in her arsenal: “I didn’t threaten to leave, but I did say ‘I want this to be reconsidered.’” Her second ask persuaded the two holdout board members. 

For Karlin, what stood out was how much she felt she needed to plead her case, despite having already been working the job without the higher pay and different title for some time. Now in her thirties, Karlin runs her own talent consultancy agency, and she uses her experience to help younger women push through discomfort and craft their pitch. “We still often don’t get the permission to be proud of ourselves and advocate for the impacts that we’ve had,” she tells me. 

I spoke to two other women who asked for a raise to hear how they prepared, how it went — and what they learned.

One woman tried to negotiate her salary. She lost the offer

For Thalia Shehan, asking for more money resulted in a rescinded job offer. 

The former IT professional and Detroit resident had been looking to break into the field of robotics. With more than two decades of IT experience on her resume, robotics seemed like a natural fit for Shehan, as she’d always been inclined to learn how things work. 

“My motto is I break things to figure out how to fix them; I take them apart, figure out how they work and then I put them back together,” she tells Bankrate. 

By many measures, Shehan excelled in her new field. She was top of the class in her robotics and programmable logic controller course, where she would step in to help her fellow students with their projects when their instructor wasn’t available.

During her coursework, Shehan was encouraged to get Smart Automation Certification Alliance (SACA) certifications to make her a more competitive job candidate. The recommended number was 13, but she graduated with 28. 

Afterward, Shehan was offered a travel position as an automation engineer. She ran the offer by her job coach, who thought the compensation looked low compared to the industry standard. Shehan expressed gratitude for the offer and asked if there was room to discuss the salary. Shehan said she felt qualified for the entry-level position, but wanted the pay to reflect the added expectation that she’d be on the road much of the time. 

“It was going to require around 60 percent travel and disrupt my life a lot,” Shehan says. “If I’m going to do that, I need to make enough money to make it worthwhile.” 

Shehan responded to the offer email with a pitch for more compensation. 

“I gave them a bunch of different options,” Shehan says. “I said I’d be interested in maybe doing a review after 90 days or continuing education.” The company emailed back, rescinding her offer letter. 

Shehan followed up asking to be reconsidered at the original offer terms, but the company never responded. “It felt like a betrayal,” Shehan says. “I felt like the rug had been pulled out from under me.” 

Since, Shehan has redoubled her job search efforts and is focusing on expanding her professional network. Although it didn’t work out in her favor, she says the experience hasn’t dissuaded her from negotiating her salary in the future. “I feel like you’re just leaving money on the table if you don’t ask,” she says.

And she’s right. Over the course of a 40-year career, women stand to lose an average of $585,000 in compensation due to the gender pay gap, according to Bankrate’s calculations.

One woman simply wanted her fair share of the pie

In Sabrina Fabbri’s case, she didn’t just ask for a raise, she had to fight for one. A 28-year-old medical device sales representative for spinal surgical screws, Fabbri spends her days in scrubs alongside neurosurgeons in the operating room. “It’s definitely a boys club,” she says. 

Fabbri and her male co-worker are compensated on a split commission basis: 30 percent of the territory’s commission went to her and 70 percent went to him. The split was mostly based on seniority; Fabbri’s co-worker had worked there longer, and helped establish much of the San Francisco Bay Area sales territory. When their contracts were up for renegotiation, Fabbri wanted a 50 percent slice of the pie.

She went to her manager, prepared with a list of her accomplishments and ideas of how to grow the business. Fabbri’s work also spoke for itself: Ahead of the contract renegotiations, some of her surgeons and upper management advocated on her behalf for a raise. “[It] was not me telling them to do that,” Fabbri shared with me. “They did that independently.” 

She insists she wasn’t putting anyone down to lift herself up. Rather, she knew she could pursue other options and wasn’t afraid to relay that to her boss. “I basically threw a bottom line and told them, if it wasn’t 50 percent I would not be staying with the company.” 

Fabbri got the raise, but it came at a cost. Since the pay restructuring, she and her male co-worker split their territory’s commission equally, but she’s noticed a steep decline in his communications with her. Communication, according to Fabbri, is essential to their jobs; they need to be on the same page in terms of who can cover which surgeries and who will be on call over the weekends. “I don’t know if it’s directly related to this pay structure, but the timing does seem a little suspicious.” 

Where do women go from here? 

For now, the pay gap persists and will likely stick around. Bankrate’s analysis of U.S. Census Bureau data found that women and men won’t reach pay parity until 2059 — 33 years from now. It’s not just a statistic; for women in the workforce, the gender wage gap is a reality they face every time they clock in. Although asking for more didn’t work out for all three women I spoke to, when I asked if they regretted it, not a single one said they did. 

But your paycheck doesn’t need to be your only source of income. My colleague, Hanna Horvath, certified financial planner, shares her top five strategies on how women can out-invest the pay gap to level the playing field. Men might continue to make more in the office, but investing could very well be a woman’s game.

We don’t want this to be our last word on the gender wage gap. If you have a story to share, I’d love to hear from you. Connect with me via email at [email protected].

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