Take A Chance On Yourself - Sooner Than Later

#HerStory is a series of conversations with some of the best women in tech in all areas of business and at all levels. They share their stories on their career path, lessons learned and points of success and failure. I hope they inspire, resonate and help you on your own journey. 

Today we’re speaking with May Tsang-MacIsaac. She is the Director, Sales Operations and Effectiveness at Adlib Software a growing tech company located in Burlington, Ontario. May considers herself late to the startup tech world but fortunate to have found her way there now. Here, she shares a bit about that journey and offers advice to women considering a career in tech - take the chance sooner rather than later. 

May, you describe yourself as a late bloomer in tech. Can you tell me how you made your way to where you are now in tech?

My story is that I’m late but not too late. I joined the tech scene in my early thirties, after starting my career in automotive marketing and finance. I find a lot of women enter the software industry right out of school. I would encourage women who have even a vague interest in technology to try it early; you won’t regret it. But don’t feel it’s too late if you start somewhere else – it just means you bring other valuable perspectives, skills and knowledge to the table. Don’t be intimidated.

Women often describe a breakthrough moment in their career; a point where they knew they had to make a change. What was the catalyst that propelled you in a new direction?

The last five years of my career have been extremely rewarding, and it all came together when I was fired from a previous job! The ‘AHA’ moment came when I called my Dad – a company man, who built a career by working hard – thinking he would be upset that I “couldn’t make it work.” And you know what he did? He laughed and said, “Thank God they let you go. That job was going to kill you – it made you miserable. Go. Be happy. Be valued. Do good work. You’ll be fine.”   I’m pretty sure he hung up on me too!

Looking back, it was the worst two years of my professional life - I was sitting in a stale industry, with no growth or support. I just couldn’t see it because I was too stubborn to admit it. It was my “quicksand job” – the more I moved and tried to figure things out, the more I sank and suffocated.

So, I decided to roll the dice. I went to work for a startup that was huge globally but didn’t have much of a North American footprint. They needed someone who understood the broad vision from HQ, but could also be grassroots and tactical in the field. After that I worked for a fast growing tech firm for two years. It was there that I worked with some great people who fostered a supportive environment that allowed autonomy and mistakes. In my experience I find the tech industry extremely collaborative and supportive, across departments and companies. In tech I’ve been fortunate to work with people who offer insight, help or support when you’re trying to solve a problem. There’s an inherent ‘bootstrap’ mentality – at an aggregate level - of “we’ll figure it out together, we’ll get through it together.” No one approaches success like a zero-sum game. It’s refreshing.

What have you learned? How as your approach changed? If you could go back, what would you tell yourself?

My favourite takeaway lesson from the last few years is “imperfect action is better than perfect inaction.” I can’t recall who said it… J/K, thanks Dan Marcus and Mark Jaine. It took me a while to embrace this mindset, but sometimes you must just act quickly and take some calculated risks. 

I wish that I had found tech sales and the Toronto tech scene ten years ago, but am thankful I found this field after an unhappy chapter in my life. It forced me to answer questions we all face at some point, “What matters to me as an individual? What do I bring to the table?” The experience taught me to embrace my weaknesses just as much as my strengths. 

As a woman, it took a while to find a happy middle ground between professional success and being true to myself. I grew my career in traditionally male-dominated industries and when I was younger, I felt I had to be “one of the guys” or the “token woman/visible minority” in the room. It was exhausting. In the end I realized, that if I was in the right place, I didn’t have to be either. I wouldn’t have to join the ‘boys club’ to find success, I could just be myself...or better yet, build a girls club! 

How has Adlib Software supported your career growth?

I love that we are a tech shop in the Halton area as that’s where our family has decided to build our lives. It reinforces what a great fit this move has been for me; I don’t have to sacrifice meaningful, challenging work to be close to home. I also feel there’s some great stuff brewing west of the city (and this comes from a born and bred Torontonian!), especially with so much talent migrating to the Burlington and Hamilton region. 

Adlib is an exciting place to be: We are growing. We are changing. We are solving big problems for our clients. We have visionary leadership that walk the talk in hiring and retaining female talent. This is the first time I’ve worked with a sales team that is predominantly women - which is amazing and unfortunately rare. But hopefully, with more programs, leadership, mentoring and education we can change the ratios in tech, both on sales teams and on leadership teams.

If you’re looking for a diverse and inclusive culture and shorter commute Adlib Software is hiring!