A Woman and LegalTech CEO’s Take on Bay Street’s Astounding Gender Pay Equity Issue

Over a week ago, I came across a Globe and Mail article on the pay equity gap for female lawyers on Bay Street.
This struck a sensitive chord in me. 
What prompted me to write this post was this comment specifically:

It’s not enough to work 60 to 80 hours a week and hit sky-high targets for billable hours. To succeed at a private law firm, lawyers must build a strong book of business.”

And thisreferring to additional challenges faced by BIPOC women:  

“Unless you can culturally relate to clients in positions of power – golfing, whiskey tasting or whatever activity it may be – that’s another layer that’s going to impact your ability to build that book of business and garner that higher compensation.”  

As a “woman of color”, engineer, serial entrepreneur, and now CEO of a tech company selling to law firms, I have sympathy for and deep insight on every aspect of this problem.   

1. As an engineer, I did not learn to “sell/build business relationships” at school; 

2. As a woman, I took the maternity leave that this article refers to as impacting women’s career trajectory; and  

3. As a woman of color, I certainly still suffer the impacts of being “different” from my clients. This, even though by this stage of my career, I have succeeded sufficiently to be a member of the same communities as the executives I am selling to. 

I feel strongly that leaders of firms who are realizing such an equity gap should take responsibility for enabling their female associates and partners to become as, if not more, successful in building their practice. This requires reconsidering outdated norms and client development practices that serve as barriers for women in “private practice law”.  

I share my story on how I overcame these biases for the consideration of every Bay Street partner – female and male.

Client development is no easy feat. Mindset and mentorship matters. 

Engineering programs in India and Canada did not teach me any part of the business of the profession. They left me unprepared for my big lessons during my first job as Software Engineer at IBM. I realized very quickly that to move up the career leader and become an executive, I had to master the sales and marketing side of the business, so I took a break from my comfortable paycheque to go to business school.   

Looking back now, even at business school, courses on traditional marketing and business strategy concepts like the 4P’s and 3C’s were taught, but none in sales and client management – those were still considered to be “lowly door knocker” tasks.  A few years after business school, I interviewed at IBM again and stated proudly that I had prior business development experience and the executive interviewing me said “We use the term business development for activities related to strategy and M&A – can you sell?”.   

That was a wakeup call. “Sales” was a not a bad word . In fact, it’s a hugely underappreciated skill and I needed to build that muscle. 

Fortunately, I made the cut and even more fortunately, there were many successful female Account Executives at IBM that set a high bar and were great mentors to meI still remember watching admiringly from the sidelines in my first year in sales as they closed some of the biggest deals at the time. To name a few, Maureen Waterson who closed a $5M deal at AT&T, Lynn Pilmoora $1B deal, and Rosemary Walker who was a great sales manager and mentor. I was also lucky to have some great male mentors like Graeme McKay 

The big takeawaySales is not a bad word or a lowly task 

The way to get better is by first, changing our mindset, and embracing mentorship (formal or informal). A mentor is valuable for every stage of your career, not just in the early days but as you continue to grow and break new ground in your field.

Overcome the biases (where possible) to own your career trajectory 

My real lessons in client development however only came when I stepped away from the corporate world to start my own business. Returning to work after my first maternity leave, I applied for an Account Executive role, managing a large telecom account and was turned down by the Client Executive with a disappointing message:  

“This job isn’t for you – you’re a mother now. 

Disheartened, I reached out to my mentors and was then told by a well-meaning mentor that every two months I took on maternity leave put me behind 5 years in my career trajectory 

I had just returned from a full one year maternity leave. You can imagine how devastating this information felt. Had I received this advice earlier, would I have truncated my maternity leave? 

Difficult to say. Twenty years later, I certainly have no regrets – having enjoyed every moment of each of my two year long maternity leaves.    

It did however make me decide not to return to the corporate world. I made this decision 15 years ago.  Readers will recognize that this is the exact journey that many female lawyers make. For me, the decision to leave the corporate world was a great one. Working in my basement office, where I could still listen in to my two kids under the age of 4 playing upstairs, I grew my business, a Canadian franchise of a global professional services company, to a $5M revenue run rate.  wasn’t completely freed of the motherhood bias because a few years later, the CEO of the franchisor company decided I was earning too much considering I was a mother and should really only care about homemaking. I did not take this lying down and fortunately for me in the litigation that ensued, these were the words that got put on record: 

I thought she was a mother and she wouldn’t be interested in earning more than $250,000/year”.  

Since there may be some who will look up my LinkedIn profile at this point, I want to mention that the CEO is not at the company anymore and I maintain the greatest respect and camaraderie for my team members who remain at the company. 

In the Globe article, Shaneka Shaw Taylor, a partner at Boghosian + Allen, a litigation law firm says that factors such as a lawyer’s track record and book of business become more important. 

That is all determined, to some degree, based on your exposure to those clients, to those files, to the decision makers. Taking a parental leave can limit that exposure. It can also be hard for women to get good files back when they return to work says Ms. Shaw Taylor.  

Equally hard on women is the “facetime” requirements. A female lawyer friend of mine shared with me a few years ago that the holiday season was her worst nightmare. She felt compelled to show up for 3-4 events each evening while also attending her kids holiday events. If she didn’t show up, clients would not send her the files. 

It’s astounding to know this even happens in 2021. But perhaps 2020 and the new virtual world will serve as a trigger to change this. 

My messages:  

To Managing Partners, it’s time to overcome the maternity leave and facetime bias. 

Ladies, lean in.  I turned the bias to my advantage and exited my business with a seven-figure sale—an outcome I am extremely proud of. To GC’s and clients of law firms everywhere – the next time you’re considering who to send your matter to, make a conscious attempt for it not to be the last lawyer you met at a cocktail or sporting event.  

My current journey and commitment to relieving business development stresses for lawyers 

I founded my current company #Kaitongo based on my journey and barriers to becoming a rainmaker. What were my learnings and how can women lawyers use Kaitongo’s solution to SLAM their way to BD success and achieve pay equity? 

Focus and Strategic Selling (S): It took me 3 years to get to $1M and I felt tapped out managing a $1M book of business across 25+ accounts. Four years later, my $4M business was being generated across 4 key accounts.  I had hired an Account Executive along the way and taken the risk to tell him to simply be laser focused on the big banking accounts, even if that meant almost a year of no revenue from these accounts. This focus and strategy isn’t something I see even today at law firms 

Client Centricity and Learn (L) – Being laser focused on the client’s business issues mean dedicating time and effort to learning about them. Every client that I landed was because I took the time to know their business and understand the issues. In my time at Evalueserve, it meant learning about a lot of different sectors and more specifically about the actual functions within the companies who would be my buyers.

Relationships matter, so Act (A)– Absolutely, in the professional services business, revenue generation is a direct result of the depth of client relationships. When I started a previous business in the legal services industry, I knew a total of 5 lawyers that included my husband and his former partners.  In the five years since then, I have built a network of industry contacts – by understanding business issues and staying top of mind – that’s the “A = Act” in SLAM.

Finally M = Measure: Know your pipeline, monitor the movement of your accounts through the funnel and just as importantly know when it is time to walk away. In 2009, five years after starting my business, I had to tell an early client that I couldn’t serve them anymore. The fees they were paying me did not meet key account criteria anymore.  The client took it very well, even congratulating me on taking the next step.


So to my female peers and lawyers, I say, lean in. Start with this assessment here to know where you are in your journey to becoming a rainmaker and let’s get started.