Cloudflare's Melissa Kargiannakis: What It Takes To Become One of Canada's Top 100 Most Powerful Women

Melissa receiving an award from The Queen of England. PHOTO: COURTESY MELISSA KARGIANNAKIS

Melissa Kargiannakis is an executive coach with a track record of bringing 300+ founders to success raising their first $1M - $10M.

As a former founder, she led an AI/NLP startup called skritswap, before moving on to GTM Customer Retention at Cloudflare. As Vice-Chair of the Technical Committee on Plain Language at Accessibility Standards Canada, Melissa has also made significant contributions as a Board Director for various non-profits related to plain language, accessibility, and education. 

Melissa has also been honored as one of Canada's Top 100 Most Powerful Women, recognized among the Top 20 Most Innovative Companies, and won an award from The Queen of England at 25. At Fetti, we had an exclusive interview with Melissa, delving into what it takes to to build a career on your own terms, whether as a founder or in a big company. Here are the highlights of our conversation:

Could you tell us a bit about your background and career journey?

I have two science degrees. I studied a typical BSc, and I have a Master's of Health Information Science where I did research on people with an in-home medical monitoring device for a long-term lung condition. I did that in Canada. And then, after graduating with my master's, I started an AI company long before it was cool and did that for four years and now I'm working at Cloudflare. All my prior work [because I worked throughout school] was in public health or health innovation. I also worked at the largest innovation center in Canada. I thought I was gonna go work for a health tech company like Cerner or Medtronic or something. So, to end up with an AI startup and then now in cybersecurity is totally different than I expected.

Melissa Kargiannakis, founder of skritswap. PHOTO: COURTESY MELISSA KARGIANNAKIS

What does a typical day in the office look like for you?

For me, a typical day is not in the office; it's right here. This [my house] is my office. Most of the time, I'm at home. On a typical day, I try to exercise first thing. I also block most of my mornings [to do work] because if you don't block it in your calendar, it's not gonna happen. You actually need to put the blocks in and say no, and actually have boundaries. Then if I have meetings, I try not to have them until 11:00 or later. Usually, it could be anywhere from 11:00 to 4:00 and then I try to go for a walk again and get fresh air, get outside. Finally, I sing opera so I'll practice it in the evening and that's a typical day for me.

What qualities or traits do you believe are essential for young professionals and students to develop as they embark on their careers or entrepreneurial endeavors?

If you're early in your career, and you're thinking what do I focus on—first is communication. It literally doesn't matter what you do or what you achieve if you can't effectively tell people about that. For example, I did X, I improved the metric you asked me to improve by Y And I did it by doing A, B, and C. So that clarity in communication and allowing people to lean in when they want to ask you more is necessary. Even now, I have to always remind myself to take a step back, lead with the punchline first, say less, tell them only what they need to know and then they'll ask you more questions. So communication is absolutely far and above number one whether you want to go into a company or as a founder. 

The second is confidence, but without the BS. You have to be supremely confident in yourself. And don't lie ever. Don't make things up, but be sure. Confidence allows you to push back in a respectful manner. If you believe it really is the right thing and have the data to back it up, you can say it to anyone.


The third is what Barack Obama said when people asked what his advice would be for early career people and he summed it up in three words: Get Stuff Done. I wholeheartedly agree with this and it’s something I've gotten better at, certainly, across my career. The more you can produce, the more you can point to. These days the way we write our resumes is all very specific, so the more things you get done, the more proof points you have. 

The fourth and final thing would be technical skills. And I don't mean the ability to code per se, but being able to go deep and know how to do something really, really well. If you are learning Python or want to go into data analysis, do it really well. 

So those are the four things you should do or have: 1. communication, 2. confidence (but without BS), 3. get stuff done—just keep achieving and getting things done–and then 4. is specific technical skills.

Can you highlight a few success stories or lessons you've learned from coaching that might be valuable for aspiring entrepreneurs? 

Lessons I've learned from coaching over 300 founders, predominantly on traction, closing their first customers, and then fundraising anywhere from their first $1 million to $10 million is that everyone is struggling. 

Everyone has things that they are dealing with, personally or professionally. Nobody has it figured out, and everybody is just trying to do the very best that they can with the circumstances that they have. Understanding this allows you to operate with grace and really extend grace to other people. You don't know what's going on, and it's a platitude of how someone treats you is more a reflection of them than you. It's not about them not liking you or them even necessarily having an issue with you. Sometimes it is, but a lot of the time it is just that things are going on for them. So to have the grace to respond with grace, poise, and kindness rather than being combative will really serve you greatly. 

Could you share any personal strategies or habits that have contributed to your success, and how young professionals and students can implement similar practices in their own lives to achieve their goals?

Habits that contribute to my success include exercising because getting that physical energy out of your body gives you mental clarity. There's a lot of science around that. I hate running, but I still run all the time. It's not fun, but it really helps you mentally. So, expelling that energy physically which will help you mentally to have hobbies. 

I am a coloratura opera singer, and I have been in paid productions outside of work. It was incredibly demanding to do a paid show in San Francisco while working a full-time job because every night, you're on stage rehearsing, and then you're performing. But it gives you so much joy and just expands your brain. 

[It’s crucial to] have hobbies, but in order to have hobbies, you need boundaries at work. So have boundaries with work, know when you're going to work and when you're not going to work. That's okay as long as you're getting done what you said you would do. That's the most important thing.

What key piece of advice would you offer students and young professionals seeking to enhance their communication and persuasion skills?

So, for communication, the single most important thing you can do is always start with the conclusion. Anytime you're communicating with investors or executives, the message or the ask should be upfront for investors. For example, begin with, I am raising $2 million to execute one to three things for the company. So always start with the bottom line first. That's communication. 

And then persuasion. To be persuasive, first and foremost, you have to actually genuinely believe in what you are trying to persuade people to do. Because genuineness is just that “je ne sais quoi,” that gut feeling that people will feel, especially more experienced people. I would say only try to persuade someone of something if you wholly believe it is the right thing to do with your whole heart so then it is authentic.


How has seeking feedback from your network, including colleagues, mentors, and contacts, contributed to your professional journey? 

One of the single best things I started doing early in my career in my 20s was surveying my contacts and mentors, formal or informal professors, and even lateral colleagues or people who reported to me. You need to ask your network and create space for them to show you who they perceive you to be because perception is reality. For them to hold up that mirror to you to see what they see can be empowering and also help point out your blind spots. 

Here are some questions that you should be asking on a consistent basis, maybe every two years to various people who've experienced you in a few different capacities. 

  1. How do you experience me? How do I make you feel? How have our interactions been over the years? What do you say when you're introducing me at a party or telling someone about me? 
  2. What are three of my strengths and superpowers? 
  3. What are three areas for improvement, things that I can focus on that will have an outsized impact on my career if I improve them? 
  4. Where am I holding myself back? What could I do to become unstoppable? And how do I improve myself to ensure I reach my full potential?

I’ve been surveying key people in my network on these Qs for a decade now–since I was still in school myself–and it is extremely illuminating. 


What are three books you would recommend, and why?

The three books I would recommend reading are:

  1. “It Doesn't Have To Be Crazy At Work” by the Basecamp founders.
  2. “Radical Focus” which is how you can use an OKRs framework, which is objectives and key results, to become clear on what work you need to do, how to do it, and when you're going to do it. 
  3.  “The Night Circus,” which is a fiction book and just phenomenal. You need to read it. It's a fantastical fiction story. 

Connect with Melissa Kargiannakis on LinkedIn for more insights into startup success. If you want to learn how to become a founder and raise your first $1M to $10 million, click here to access Melissa's "So You Wanna be a Founder?" course.

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