Managing Men (and Other Lessons Learned as a Woman Sales Leader)

To all women facing challenges, know that you are not alone — and there is a very bright light at the end of the tunnel if you fiercely go after what you want.

Published on Apr. 06, 2022
Managing Men (and Other Lessons Learned as a Woman Sales Leader)
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This month, I had a very meaningful sit-down with Priya Sachdev, Vengroso’s chief customer officer. In the spirit of International Women’s Day, we had an honest conversation about what it means to be a woman sales leader in 2022, how my experience with bias has shaped my career and leadership style and the takeaways I can offer my fellow women. 

As Hootsuite’s chief revenue officer, my support for the organization comes in the form of empowering and enabling all of our salespeople to be their best selves. I achieve this by creating an environment where everyone is encouraged to invest in themselves, inspire their customers and be part of the growth of Hootsuite. Leading in this way doesn’t come without its challenges; to deny the everyday biases I work to break would be to deny the lived experiences of all women, at all levels of any organization. 

3 Lessons I’ve Learned as a Woman in Sales

  1. Conscious and unconscious biases are international.
  2. Women in tech are working against a socially structured clock.
  3. Lead with compassion, and emphasize that diversity means representation — not a takeover.


Bias Has No Geography

Conscious and unconscious biases are international. In 2010, when I moved my whole life to Singapore with the expectation of leading a sales team and being my company’s face in the region, I was introduced to a new (but familiar) type of bias. 

I arrived ready and excited to take on this new role, but I was suddenly no longer considered qualified. Because I was a young American woman, the image I portrayed did not fit the business narrative, and it was perceived as not being the best look forward for the company. I watched as my position was handed to an older man, and I began to understand the complexities of bias: It comes in all shapes and forms. In this case, not only was my gender a disadvantage, so was my age. I am sure far too many women can relate to this experience, regardless of where they find themselves in the world.  

When the company realized that being a young woman did not preclude my ability to bring value to the role, they handed me back what I had rightfully earned. For the remainder of my time in Singapore, I did my absolute best to learn from this experience and let it be reflected in the talent-driven hiring choices I made for my team, which led to 50 percent of my sales team being local, Singaporean women. 

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Society’s Pressure on Women’s Business

During our chat, Priya made a great point that women in tech are working against a socially structured clock: You need to be old enough to be taken seriously — but not too old that you’re deemed uncool. 

Throughout our careers, Priya and I have both witnessed decisions being made for women in their careers that were based on what society thinks a woman should be doing at different stages in her personal life. For example, I have personally watched as otherwise kind, male leaders provided unwarranted opinions about an applicant's qualifications based on the fact that they had just had a child. 

How to Know If You’re Presenting Bias

We need to let women make their own career decisions. Leaders need to become more critical of themselves and their biases while hiring for a role. If you’re unsure of whether or not you are presenting bias, ask yourself the following question: “Would I be second-guessing this person’s qualifications for the role if they were a man with similar life circumstances?” 

This is where unconscious bias training can be very eye opening, and it’s why I am so proud that Hootsuite has made it mandatory. Without awareness, we will continue behaving in a way that we think is compassionate, not realizing that we are actually getting in the way of another person’s growth. 

This is not to say that picking a woman for a role means we are checking the diversity box. Picking the qualified person for the role, bias aside, is what diversity in the workplace should mean. 


Advice to Melissa, Age 20 

There is no way to plan for what’s coming your way. 

I could have never imagined where my career has taken me. I spent so much of my 20s concerned with a clear path, goals and specific steps. It felt like my career depended on every single move I made, which made any risk feel a lot riskier than it should have. 

When you lead with fear, you miss out on potentially life-changing opportunities. In fact, some of the best opportunities are sometimes the riskiest and least obvious. Moving to Australia earlier in my career felt like a very risky move, but it ended up changing my trajectory in the most positive way. Priya said it best: “In an Excel file, you can insert and delete rows. So give yourself the space to do that in your life as well.” 

If I had one message for my younger self — and for all women across industries — it’s to actively go after what you want. 

Never expect anyone to simply know what you want. The best way to achieve the things you want in your career is to voice them, loudly, to as many people as you can. Many of the roles I have landed thus far have been due, in part, to the visibility I created for myself by connecting with colleagues and sharing openly what it was that I wanted. 

A popular stat in the working world is this: “Men apply for a job when they meet only 60 percent of the qualifications, but women apply only if they meet 100 percent of them.”  Don’t be a statistic. Don’t wait until you feel like you are fully qualified for a role. No single person fits a role like a puzzle piece; the right fit goes beyond shape. So put yourself out there and allow yourself to be surprised by what you get in return. 

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Managing Men as a Woman in Sales 

Earlier in my career, I have had my fair share of experiences working with men that simply could not wrap their heads around reporting to a woman. I have experienced being undermined and challenged. It’s extremely difficult and frustrating. 

From these experiences, I’ve learned to lead with compassion. I am always very conscious of the innate fears that men can have as it relates to diversifying a team. What I try to emphasize is that diversity means representation — not a takeover. 

I am very lucky to be working alongside the best in the game, a team of very talented and empathetic people. The sales leadership team at Hootsuite has shown consistent effort in doing the work of challenging biases, setting an unprecedented standard of what it means to build a diverse and inclusive sales organization

We are all human at the end of the day, and if we are not constantly challenging ourselves and each other’s biases, we will not move forward. The more conversations we have about our lived experiences, the more space we are making for equal opportunities. Women absolutely need to lift up other women if we ever want to not be a minority in the sales industry. But men: You play a significant role in achieving that, too. 

To all the women facing or expecting challenges, know that you are not alone on your journey, and that there is a very bright light at the end of the tunnel if you fiercely go after what you want.  

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