I’m kick-starting Her Take on Tech’s first feature interviewing a female tech leader who I am very excited about. Caitlin MacGregor is the Founder and CEO of Plum.io, a vastly growing tech start-up that combines AI and Industrial/Organizational Psychology to help companies hire, grow and retain top talent.

Caitlin is most definitely a tech entrepreneur who I have admired from afar and is someone I was thrilled to connect with. The successes she’s made in pushing the boundaries in the start-up space are exceptional – and definitely haven’t gone without challenges, barriers and extreme hard work.

Let’s get this interview started!

As a CEO of a growing tech company what would you say is the most exciting part of your work?

Growth. When you’re an entrepreneur there’s no greater accomplishment than building something from scratch. To build something that’s never been done before and tie it to something you believe in is a truly a great feeling. With Plum.io we have the opportunity to make an impact on hiring across the world and change how the economy is run by identifying talent differently – it’s incredible.   

What has been a career defining moment for you so far?

This past fall we closed $5M in funding lead by Real Ventures. This was huge moment for me and the business. As a female, the odds are constantly against you – this was a big achievement for us because the chance of failing was so much greater.

When I set up to fundraise, Business Development Bank of Canada, had never had a portfolio company raise $5M in one go. I was eager to change this. A couple of women beat me to this, but it’s amazing that now there are a half a dozen of us that have achieved this milestone. It’s a sign that times are changing and the opportunity for female entrepreneurs to flourish is possible.

What are some of the biggest challenges that women who want to venture into the world of technology face today?

Most companies look to pattern match. Every employer, especially VC’s, want to de-risk decisions and make bets on things and talent that look safe. We are bad as a society at recognizing potential overall.

Unless a woman is currently doing that job – in that similar scaling tech start-up – its often hard for companies to see the potential and transferability. Unless you are starting from a very junior role, it can be difficult for women get their foot in the door. There are less women in tech, because the more they progress in their jobs outside the tech space, the less chance they have in transitioning to the industry.

So much is starting to change, but the tech industry is often biased still, and tends to continue to look for their own.  If you’re already “in it” you’re fine, but it can be tough to get in if you’re not.

Technology is a male-dominated field. What steps should be taken to attract more women to tech?

Companies need to be more open to innate talent and look at transferable soft skills. If a candidate has only worked in enterprise, it doesn’t necessarily mean they can’t handle a start-up. If the industry wants to include more women, we need to look at more transferable talent – and put a welcome mat out.

We don’t recycle marketing campaigns if we want to target a new audience. If we want to recruit women, we need to make an effort to reevaluate how we bring in women to the tech space. We need to do things differently. We need to attract for potential, instead of proof of existing experience.

What’s your advice for other women growing in the tech space?

Research and look at all the different roles available within a tech company. A lot of people think that you have to be technical to work in this space – but that’s not the case. There are so many roles that make up a tech company that don’t require a technical background – such as a Copywriter, Customer Success Manager, Business Development/Sales reps or Project Manager.

Once you’ve done some research, define what areas might match some of your core strengths. Then get involved in any way you can – and start as early as you can!  Even if you’re still in school, apply for internships, part-time work, or volunteer opportunities.

Lastly, develop a portfolio of your work and your ability to build things. This can be through school projects, internships, or simply make-work projects – anything you can do to show case your ability to be a Rockstar.

What would be your message to women trying to get into technology?

Enter in early and build a portfolio of your experience. Get your hands dirty and show how you’ve been able to build something from nothing. The sooner you get involved the easier it will be to find your foot in the door!

Who has been your biggest advocate/mentor in your career and why?

There has been many, at different times and in different ways. I would have to say my Mom is one of my biggest role models. She was a lifelong learner that spent her entire life growing as in individual. She truly proved that you can get better with age and that with determination and resilience, you can achieve whatever you want. My mom was who helped champion me and encourage me to continue striving to build something that didn’t exist. Learning and growth isn’t easy – it is the harder path that is usually the most fulfilling path.

As a headhunter in Toronto’s tech space, I’ve had the opportunity to meet and get to know countless experts who have played a key part in building and growing some of the most innovative products in today’s market. From founders, product management experts, designers, growth marketers and more – no interview/conversation is the same, and I’ve loved hearing about all of the challenges and achievements these individuals have gone through to get to where they are in their careers.

Although I’ve had the chance to hear these incredible career stories  – I’ve realized that many others haven’t, especially from women who are doing some kick-ass work in Toronto’s tech space. So, that’s where Her Take on Tech comes in – a blog focused on shining light on women who are doing extraordinary work and bringing their stories to the forefront.

Each month, I will be profiling a female tech expert and sharing their stories through a tell-all interview. My hope is that these stories will help inspire and motivate others who are trying to build their own career in the tech space. In between interviews, I will also be sharing career tips and resources on topics such as networking, resume building, team management, and much more.

So far, I’ve had the opportunity to interview some truly inspirational women, I can’t wait to share their stories with you. Stay tuned for the first Her Take on Tech interview next week!