They all speak of obstacles, some in the natural course of creating a business or a self-styled niche, but too often in terms of something more subtle: an attitude, an amorphous resistance, almost a resentment.
You might call it lowered expectations or a tacit doubt, but the women in business have all felt it at one time or another, to one degree or another.
The quiet sexism – oddly among both men and women – is an old story, making it both bane and boost. Because it is not new, no one is a stranger to it, and has learned to manage it with a minimum of fuss, a deft deflection.
Simultaneously, however, it is one more challenge, both wearisome and predictable, that most men never face.
Caroline Barton is a partner at Appleby, and says the resistance she has faced has been modest at worst, and looks forward to increasing “diversity” at the firm as women all around her move into positions of authority.
“I have been fortunate to be part of an organization in which I have felt valued in its continued growth,” she says, although not ignoring the “gendered” challenges.
“It is undeniable that partnership can be difficult for women for various reasons. Notably, the point at which attorneys are most often prepared and identified for potential partnership frequently coincides with the time when many women would ideally like to start a family and take some time away from the office.”
Barton’s timing was fortuitous, however, coming after she had already started her family – while support from her colleagues proved crucial.
“In my situation, it was the point at which I returned from maternity leave after my first child, where my practice flourished because I had the encouragement and support of the senior partners in my team. I decided – as do many women – that I could make both family and partnership work,” and Appleby, she said, “believed it and facilitated it.”
At Fountainhead, a “marketing communications agency,” nearly six years old and a relative newcomer, founder and owner Denise Gower says she had “always had an entrepreneurial spirit,” and part of her wanted “to do things a bit differently or to be more engaged in all elements of the companies that I had worked for, and not just my little section of it.”
More personally, however, Fountainhead was the product of “a purpose – the really important stuff,” she says.
“Purpose is where we ask ourselves what it is that draws us close; where do our hearts lie? How can we help to make the world or even our own community, a better place?”
That sense of direction carried her through, knowing she had to keep going and get on with it.
Too often, the gentle hum of sexist stereotyping rang in her ears: “I have come across this more times in my career than I really care to remember,” Gower says, “the ‘don’t-you-worry-your-pretty-little-head about this strategy stuff – just organize the company Christmas party’ kind of response.
“It is ugly and depressing and very difficult to deal with. This is, in part, what inspired me to start my own business, because it is frustrating work, swimming up that stream all the time.”
Headlines about sexual harassment at Fox News and in Harvey Weinstein’s Hollywood, and September’s Everett, Washington, challenge to a city ordinance prohibiting female baristas from working in their bikinis, do not appear to have made much difference.
“Even recently, I had someone demand to liaise with a male employee about an issue,” Gower says. “It is a difficult thing to maneuver.
“Ultimately, I would love to be able to change these people’s minds and show them the light, but, of course, that is not possible – we cannot change people’s minds for them. We have control only over how we react to things like this. So I have a choice to let it upset me or to find some other way of finding a win-win resolution to issues. Forcing or demanding is not the answer.”
Lesser recognized is a similarly skewed response from other women: “I have experienced that too,” the Fountainhead founder says. “Sentiments inspired by jealousy perhaps? Or thoughts of ‘I could do this much better than you?’ Again, difficult and ugly. Maybe it isn’t a gender issue, but a human issue?”
And that is where Gower’s and Barton’s personal ambitions and intelligence rise to the surface.
“I have met and know more people – men and women – who are supportive, uplifting, encouraging and overall wonderful than I do the ones who are the opposite,” Gower says. “I guess it is up to me to choose the ones I listen and give credence to. The choice seems obvious, right?”
Barton, who became an Appleby partner in January 2016, sees an erosion of stereotypes, a rising tide that will boost business for everyone.
“Diversity,” she proclaims. “Appleby has approximately 60 partners globally and about 25 percent of those are women. The Cayman office partnership includes seven Caymanians. Again, approximately 25 percent of the Cayman office partners are women.”
This still means women fall 25 percent short of parity, both globally and locally, but the process, Barton says, is well under way: “Looking at my own team, there are a large number of women across various service lines in the firm including lawyers. In a short space of time, I think we will see a powerful female force in the legal market which could ultimately tip the balance.”
Last year, she says, almost 70 percent of U.K. admissions to law school and slightly more than 60 percent of admissions to the bar were female.
In late 2016, the New York Times reported women had for the first time outpaced men in U.S. law school admissions, saying 55,766 females were studying for a “juris doctor” degree, compared with 55,059 males, and that more than 51 percent of first-year law students, 19,032, were women, while 48.6 percent, 18,058, were men.
Still, at least in the U.S., according to a 2017 survey by the Chicago-based National Association of Women Lawyers, women have some distance to go before achieving parity in the profession. Only 19 percent are equity partners and 30 percent non-equity partners; women earn between 90 percent and 94 percent of men; the top earner at 97 percent of U.S. firms is male while 70 percent of those firms have one or zero women among their top 10 “rainmakers.” And women make up only 25 percent of any firm’s governing bodies, such as the top “governance committee,” the compensation committee or as a managing or practice group partner/leader, although, National Association of Women Lawyers says, this appears to have doubled in the last decade.
More generally, an Oct. 26 Washington Post “Outlook” piece asked, “Can we talk about the gender pay gap,” leading with “the median salary for women working full-time is about 80 percent of men’s.” That gap, put in other terms, means women are working for free 10 weeks a year.
Barton acknowledges growth in the number of women in the practice has been slow, but “I believe we will see women continue to move up the ranks in increasing numbers and hopefully the playing field will even out.
“We are the examples of working in an environment where women can, and are, encouraged to succeed. Appleby has embraced diversity, and has set this example in its leadership, and we can now see the talent pool expanding. “
She indicates the key to that diversity is “this new workforce,” referencing millennials as they come of age.
“With our commitment and contribution, all of the assumptions and unconscious bias[es] about women in the workplace can then erode and, in the words of Sheryl Sandberg, ‘there will be no female leaders. There will just be leaders.’”
Sandberg is chief operating officer at Facebook and the first woman to serve on the company’s board of directors. She previously served as Google’s vice president of global online sales and operations, and between 1996 and 2001, was chief of staff for U.S. Treasury Secretary Lawrence Summers. In 2012, she was named to Time magazine’s annual list of the 100 most influential people in the world.
While Sandberg is exceptional, she is emblematic of a slow, if steady, increase of women in the “C-suite.” Cayman insurance leader Island Heritage boasts two women with suite seats: Chief Financial Officer Alissa Matthews and the company’s first female Chief Underwriting Officer and Senior Vice President Annette Jim. Island Heritage’s Bermuda headquarters boasts another top-tier female, Chief Administrative Officer Abigail Clifford.
Jim, of Trinidad and Tobago, joined the company in 2006 as underwriting manager, gaining her chief underwriting officer role in 2010. Before Island Heritage, she was the first female insurance broker in Port of Spain, ultimately gaining appointment as supervisor, then general manager before arriving in Cayman.
Jim boasts more than 20 years in the industry, and serves as chair of the General Insurance Standing Committee of the Cayman Islands Insurance Association. Yet even with one of the highest-level senior-management titles in the business, she still, at least initially, smacked her head against the glass ceiling.
“The saying ‘men are promoted on potential, women are promoted on performance’ comes to mind here,” she says, recalling earlier days. “So does the remark of one of my first clients as a broker in Trinidad. During our first meeting, he told me outright that he’d never had a female manage his affairs and didn’t think I would be up to it.
“Well, by the end of the year, he gushed that I was the best account executive he’d ever had,” she says, but had digested the lesson about “performance.”
“From that initial interaction, I knew I’d have to work harder than any man to win clients. So I made sure that I knew everything. I stayed on top of industry knowledge, was proactive in making recommendations to my clients where I’d learned about something that might benefit them and I met all deadlines.”
Described, rather ironically, by Island Heritage Marketing Manager Monique Bush as a “ballsy force in the industry,” Jim, as head of the insurance association’s standing committee, oversees technical issues, education, training and regulatory challenges.
“To break through the glass ceiling,” Bush says, “Annette had to put in longer hours than most men and she made sure her opinion mattered and was heard.”
While insurance remains largely “a man’s world,” Bush says, Jim observes a degree of progress through the years, but is not naïve: “Though nowadays the industry comprises a number of women, many still don’t hold very senior positions and are often overlooked for promotion.”
The underwriting team, she says, comprises 25 people under three managers, reporting to Jim, who records the lowest attrition rate in the industry. Apart from her tenacious determination, the chief underwriting officer attributes her success to a collaborative management style – and this is where women appear to diverge most often from their male counterparts.
New York’s Fast Company business magazine this summer published “6 Leadership Styles, And When You Should Use Them,” subtitled “great leaders choose their leadership style like a golfer chooses his or her club, with a calculated analysis of the matter at hand, the end goal, and the best tool for the job.”
All of which is to propose that a mix of styles, judiciously applied in a timely fashion is likely to produce superior results.
Writer Robyn Benincasa quotes author and management consultant Peter Drucker, offering pithy advice in banal chiasmus that “management is doing things right; leadership is doing the right things.”
“Manager and leader are two completely different roles,” Benincasa writes, “although we often use the terms interchangeably. Managers are facilitators of their team members’ success. They ensure that their people have everything they need to be productive and successful; that they’re well trained, happy and have minimal roadblocks in their path.”
The author proposes six types of leadership: The pacesetting leader, who “expects and models excellence and self-direction” when quick results are needed; the authoritative leader, who “mobilizes the team toward a common vision and focuses on end goals,” leaving individuals to tap their “entrepreneurial spirit and vibrant enthusiasm”; the affiliative leader, who creates “emotional bonds,” fuelling a sense of organizational unity; the coaching leader, seeking “to build lasting personal strengths,” making teammates more successful; the coercive leader, who “demands immediate compliance” – effective in times of crisis, but dangerous “because it can alienate people and stifle flexibility and inventiveness”; and the democratic leader, who “builds consensus,” asking, for example, “what do you think?” in pursuit of “fresh ideas from qualified teammates.”
“If you take two cups of authoritative leadership, one cup of democratic, coaching and affiliative leadership, and a dash of pacesetting and coercive leadership,” Benincasa writes, “and you lead based on need in a way that elevates and inspires your team, you’ve got an excellent recipe …. ”
Barton, Gower and Jim appear to employ a kind of collaborative technique, a collegial approach that seeks cooperation from their teams.
At Appleby, Barton says, “our clients are situated across the globe and all have differing experiences and demands,” which requires a calibrated range of responses.
“The more diverse our firm’s leadership is, the better we can understand our clients’ needs and provide exemplary service,” she says.
A corporate culture of “collegiality, integrity and excellence” affects both the firm and its clients, themselves “becoming more diverse and inclusive,” she says.
As per Benincasa’s “recipe,” Barton thinks “any successful organization benefits from a few leadership styles working in tandem.”
Her own leadership, she says, blends “affiliative and coaching.”
“My personal belief – and part of Appleby’s ethos – is that people come first, and it is key to our success that our people are motivated and developed for the future.
“Building relationships, creating a clear path for communication and developing others are ultimate motivators for any team and will improve performance,” ultimately boosting the “long-term strengths” of both employees and the organization.
Fountainhead’s Gower has an intensely personal approach to her five-member shop, among the reasons she has “experienced some incredible growth over the past six years.”
“Sometimes people will come in and say ‘we need a print ad.’ Well, maybe they do, but maybe they don’t. Maybe they need something else that will have more impact, will provide a more measurable result, will be more cost effective, will reach a wider audience, both increasing target audiences or furthering geographic reach, etc.”
The initial process is “exploratory,” both prolonged and deliberative; “we don’t want to just put together pretty pictures for our clients and then tick the box and say we are done.”
Gower describes her leadership as “definitely a collaborator and consultative in approach.”
“I listen to, and value, everyone’s opinions when we address an issue. I involve everyone in our own strategic-planning process and am open about where we stand financially as a company. I am not a micro-manager, and I do believe that people need to be trusted to do their jobs to the best of their abilities.”
She acknowledges her approach at times can be a little bumpy, and “sometimes … lead to learning experiences,” but, she says, “it is always useful.
“We work in an open-concept office where we discuss and collaborate and solve problems together. I try to create an environment where people feel that their contributions are valued and where they can speak their minds. I also believe that this is one of the ingredients of our ‘secret sauce’ that allows us to create good work that works.”
Fountainhead’s focuses on the “integrated” in “integrated communications agency.”
“Some agencies in Cayman specialize in particular areas such as digital marketing, whereas we like to get more involved in understanding a client’s business objectives and finding the best way to meet those objectives. We are careful to walk clients through a process that helps us all find the best solutions and then execute them.”
Island Heritage’s Bush speaks with an economy of expression about the company’s chief underwriting officer’s leadership.
“Annette makes decisions quickly, but likes to empower her team by including them in the decision-making process.
“She is supportive of others’ initiative, especially when she recognizes a passion for insurance – which is unfortunately, commonly overlooked by young people as a career,” Bush says.
The three prognosticate where “women in business” might go in the next five years.
Barton thinks change will come, measured and steady.
“In the next five years, I hope to help move the firm towards our own established vision,” she says. “Change starts from the top and we are aware of that. We are also aware of the changing needs of the workforce.”
Millennials, she says, will comprise almost half the workforce in the next half-decade.
Personally, she falls “just on the cusp of the millennial movement and [I] understand the changing values and demands of millennials – they want mentors, more emphasis on work/life balance. Their value in the office is not solely monetary – they want to believe they are part of something bigger and making a real contribution.”
Understanding this emerging force, “and coupling it with the traditional ‘hard work gets results,’ work-centric attitude,” she says, Appleby hopes to build an “empowered workforce,” producing top-notch work and fresh ideas.
“Because, at the end of the day,” Barton says, “it still is about business.”
Gower’s “vision” for Fountainhead is a “boutique agency that provides integrated marketing communications services for companies that are entrepreneurial, companies that hope to make the world a better place or contribute to it in a meaningful way.
“What actions could I take to help grow someone else’s business, helping them to employ more people and to enjoy their own success?” she asks. “We blend traditional and digital, working together to provide a consistent experience for the end customer. There is too much gobbledygook in the marketing world. We want to cut through all of that, make things simple, directed toward the business objectives.”
Finally, Jim, with that economy of expression, says she hopes to lead Island Heritage to do better what it largely does already: “From an underwriting perspective, Island Heritage’s current focus in on innovation towards greater customer convenience while maintaining high security standards.”