By Deb Boucher Stetson

Lynn Mason-Small, chief marketing officer at Rogers & Gray Insurance, is not alone in wishing gender wasn’t an issue in the workplace. “I can’t wait for the day when we don’t have to call attention to the fact that it’s a woman in business—that women in business is just a given,” she says.

It actually is something of a given at Rogers & Gray, where many of the top managers are women — despite the fact that insurance is still viewed as a traditionally male-dominated industry. Mason-Small notes that at Rogers & Gray, 70 percent of the management positions are held by women and 40 percent of senior positions held by women.

Her colleague, Rogers & Gray Chief People Officer Allison McEachern, says women have come a long way since the 1980s movie “Working Girl” depicted a toxic work environment in which women felt compelled to sabotage one another in order to get ahead. “I can chuckle at that image now because it’s so different today,” she says. “It is so much more supportive and women are reaching out with both hands to pull in peers, to collaborate and support each other.”

McEachern, who taught school before launching her career in human resources, says Rogers & Gray has a culture that is “inherently supportive of the development of all employees with progressive approaches to learning systems, techniques, and tools.” Women in the company, she says, “have naturally seen success and have contributed to the success of the women around them.”

The company, with offices across Cape Cod, the South Shore and Boston, consistently promotes women, she says, and that practice is very visible to women joining the firm.

A recent report in the Harvard Business Review noted that nationally, women have filled the majority of new management positions created between 1980 and 2010. While men still make up the majority of managers overall in the U.S., they account for about 60 percent of management jobs as opposed to the 75 percent they held back in 1980.

There have also been some reconfigurations, the report said, noting that while back in 1980 “not a single management occupation was majority women,” by 2010 it began to look like some occupations were female-dominated while others were male-dominated. “Female managers are concentrated in fields that emphasize people-centered caring skills, while men are concentrated in fields dealing with production-centered skills,” the report observes. Unfortunately, “The occupations where female managers were concentrated by 2010 were also those with the largest gender wage gaps.”

The wage gap between men and women has been documented. According to the federal Bureau of Labor Statistics, in 2017, women in Massachusetts who worked full-time had weekly earnings of 80.6 percent of the median weekly earnings of their male counterparts. The median weekly earnings for women in the Commonwealth that year came to $971, compared with $1,204 for men.

According to the Bureau of Labor Statistics, in 2016 nearly 40 percent of all managers were women — but in some industries, the percentage was higher. The Bureau listed human resources, medical and heath services, public relations and fundraising, social and community service and education administration as areas with higher percentages of women managers.

Mason-Small says Rogers & Gray is more progressive than many of its counterparts, promoting and hiring women in key leadership positions. Still, she concedes, the industry as a whole is “patriarchal,” with “the majority of senior leadership positions and high-earning positions held by males.” But “the industry acknowledges the fact that it must become more diverse and inclusive,” she points out, and that awareness, “creates tremendous opportunity — large employers are actively focused on recruiting and training a more diverse workforce.”

Another one of the high-powered women at Rogers & Gray, Chief Operating Officer Erin Schaaf, says women have much to contribute in any industry. “Women are adding to the ideas, rounding out the thought process, and bringing valuable perspective to the table,” she says. She is pleased with the progress Rogers & Gray has made in helping women succeed. “I would say it’s a case of actions speaking louder than words: about half of the management team is made up of women.”

Schaaf, who has been in the insurance industry for three decades and joined Rogers & Gray last year, said she feels “fortunate to work in organizations that have had significant female populations at the staff and middle management levels.” One change she has observed over the last 25 years, she said, “is the frequency of women in senior roles.” That, she points out, “provides younger women coming into the business with the opportunity to have a female mentor or role model.”

Hollywood and Her Stars

Darlene Hollywood, founder and CEO of the Hollywood Agency (formerly Hollywood Public Relations), based in Hingham, has made mentoring part of her career. “As women leaders, I think we have a responsibility to mentor younger women, because the men aren’t going to do it,” she says.

Her growing firm has a dozen employees, most of whom are female. “We just hired our second gentleman. For five, six years now there has been only one guy,” she says, noting the public relations industry as a whole is tends to be dominated by women. Reflecting on that trend, she says, “I think it’s because we’re communicators, and women in general communicate well.”

Hollywood, who last year won the Boston chapter of the Public Relations Society of America’s Diane Davis Beacon Award for professional achievement, service and mentoring, said she has not encountered much gender discrimination since launching her firm six years ago. “Over the course of my career there have been clients who did not take me seriously because I was a woman, but that’s not the kind of person I want to work with,” she says, so she simply left such clients behind.

One challenge she said she has faced is the need to stand up for herself in certain business dealings. “Over the past few years I’ve had to get a lot tougher, on things like, for example, clients who didn’t pay,” she says. “I’ve gotten a lot stronger and tougher. I don’t back down as much as I used to on things like that.”

That toughness, especially when it comes to finances, doesn’t always come easily to women, she notes. “That’s where the pay disparity comes into play now because women don’t want to demand more… There’s always that tendency to want to play nice,” she says. These days, “I don’t let clients talk me down as much as I used to.”

With a client roster that includes Honeywell, Samsonite, Boston Interiors, Necco, High Sierra, Lipault Paris, Welch’s and South Shore Bank, it’s clear she’s doing something right. The firm now has a West Coast location in San Francisco in addition to its South Shore office.

“We’re definitely growing — we took more than 5,000 square feet in the Hingham Shipyard,” she says of the firm’s most recent move. “We have pretty aggressive growth goals.”

In her approach to business, “I definitely follow my intuition,” she says, musing, “I think this is where being a woman is helpful … There’s the danger of analysis paralysis — if you don’t move as fast as the business you lose out on opportunities.”

Hollywood, who has two teenage daughters, says women have always faced a challenge in balancing work and home. “I think women really struggle to find their place as busy moms and business leaders; they struggle with the idea that they can’t be both. When my girls were young, I had a support system, but I always felt that guilt,” she says. “I hope for my daughters it will be different but I don’t see that happening anytime soon. I think women are going to continue to carry that baggage.”

Hot Diggity: Woman-Launched, Woman-Owned

Ashley Lancaster is taking over ownership of Cape Cod’s Hot Diggity dog boutique after a nearly 11 years with the firm, the last two as co-owner with founder Nicole Merriman. She has no qualms at all about stepping into sole ownership, having grown along with the company, which began in Mashpee Commons.

“I’ve always loved it and I’ve always treated it as my own,” she says of the business. “It’s always been really important to me that everything was run smoothly, and that the employees are happy.”

She and Merriman will continue to partner on the business they launched together in 2017, a live-action adventure games “escape room” called Riddle in Mashpee Commons. It was that venture, Lancaster says, that most challenged her as a female entrepreneur, because in developing the business she and Merriman did experience some interactions with contractors when they felt they had to be tough — something that can be hard for women. “It’s that standing up for yourself, saying no, this is your mistake,” she says. During the physical development of Riddle, she recalls, she and Merriman would often “play good cop, bad cop” with contractors, taking turns being tough. “That’s been a huge learning curve for us because we hadn’t had to deal with that.”

Occasionally, she says, she encounters people who do not treat her like the entrepreneur she is. “I’ve been to events where people will as me a question and then look at my husband to answer it,” she says. But that, thankfully, is rare, largely because of the nature of the business. “The pet industry as a whole is very women-oriented,” she says during a tour of the Dennisport location. “Our entire team here is women, and our team in Mashpee is women.”

Lancaster (née Carr) found her passion for dogs early in life, but only quite by accident did it turn into a career. A dog-lover from early childhood — “My first word was dog,” she says — she stumbled on a job at Hot Diggity not long after returning home to Falmouth after graduating from Simmons College in Boston.

“It was five minutes from my house, and I didn’t like commuting, so I said I’ll do it temporarily,” she recalls. Soon Merriman offered her the position of store manager. In addition to a salary and benefits, “The clincher was I could get a dog and bring it to work,” she says.

That was in 2008. In 2012 Hot Diggity opened its second location in Dennisport, where the dog boutique expanded to offer services. It started with self-service dog bath stations, then took the plunge into full-service grooming. “That has really taken off — it’s gone beyond anything we ever dreamed of,” Lancaster says. “We have three full-time groomers, and I’m always looking for more.”

In 2013 the business bought an existing collar and leash company and developed Hot Diggity Designs to begin producing its own products to sell in both stores. In 2014 it began wholesaling, and in 2016 Lancaster became co-owner.

Married a year ago, Lancaster and her husband now have four dogs, so whether she’s at home or at work, she’s surrounded by the four-legged friends she loves.

Peabody Properties: Like Father, Like Daughters

Sisters Karen Fish-Will and Melissa Fish-Crane took over Peabody Properties from their father, company founder Ed Fish, and have worked to carry on his legacy of creating affordable housing. They are also guided by the values he and their mom instilled regarding the importance of community service and helping those less fortunate.

That’s why veterans’ housing remains a top priority, along with a commitment to resident services “as a unique area of expertise within the field of property managements,” Melissa notes. The firm also supports a faith-based orphanage in Guatemala, and its “Helping Hands” mission supports the Elizabeth Stone House in Roxbury.

Karen credits their father with the success of the business. “If it wasn’t for our dad, we know that we would not be where we are today. Family — whether our work family or our home family — is the foundation of our success.”

In terms of gender, the two women acknowledge that the property management industry is still dominated by men. But Karen notes, “Our professional development efforts are helping to continually support more women in our industry, in positions with increasing responsibilities.”

“Honestly, it’s hard to speak to the challenges we might have faced in another industry, since housing and property management is what we’ve always known,” Melissa says. “But we are very proud of what we have achieved – from adding more than 2,400 apartment and condominium homes in the last two years alone, to our property management portfolio, most located in the greater Boston area, and many of which are affordable, bringing the firm’s overall total to more than 13,000-plus today.”

The sisters are especially proud to have been named in Glassdoor’s 2018 SMB Top CEO list (ranked 31 out of 50) this past July. Other awards include Outstanding Women in Family Business by The Warren Group in April 2018, Women of FIRE by Banker & Tradesman in July 2017, and the 2017 Professional Women of the Year by the Boston IREM® Chapter #4 in December 2017.

Melissa says she attends professional events across the country, “and I see more and more women in leadership positions at various organizations all the time. We have a lot more work to do,” she says, “but it’s encouraging to see the progress we’ve made.”