AI expert Willson Cross on how to hack the AI hiring machine

For this week’s MVP, we’re chatting with Willson Cross.

Any frustrated job-seeker will tell you it’s a tough job market out there. Things are different now—thanks largely to AI, of course, which has infiltrated the recruiting and hiring process, as it has everything else. Though many job-seekers lament AI-based hiring, and just as many hiring managers frown at (and then promptly toss) an obviously AI-generated resume, both employers and employees are using AI just the same. Statistics show almost 90% of companies use some form of AI screening during their hiring process while more than half of would-be employees turn to AI help them write their resume. 

To make sure your resume isn’t flagged for the “no” pile, we went right to AI expert Willson Cross. He is the 33-year-old CEO and co-founder of the Toronto-based Borderless AI, which helps hundreds of companies onboard talent via artificial intelligence. In this week’s MVP column, Cross tells us all about the business he’s built and how to hack the algorithm to get hired in the age of AI.

Tell me about Borderless and how you use AI.

We’re a global payroll platform, and we use AI to automate a lot of how companies onboard, manage and pay their international workforce. Basically, a company like Ritz-Carlton or Vidyard would use us to pay their international team members, offer them benefits, employment agreements or the international equivalent of a T4 tax slip. 

I started the company just over three years ago. Before that I did another company in the pet space—it was like Airbnb for dog sitting. I’ve only ever worked at companies that I’ve started.

So, you’ve never even needed a resume to apply for a job? 

It’s true! But I know lots about the job market and specifically how younger folks can break through. I see tons of resumes and can tell you exactly what I, as a founder looking for new hires, am looking—or not looking—for. It’s probably not what you think.

Oh, this is exciting. I assume you get 500 resumes and the AI overlords veto all but a handful. 

No, actually. Hiring is a committed process that starts long before that. We work with various recruiters and recruiting firms for various roles. 

They use AI to sift through LinkedIn profiles for candidates that meet basic criteria—let’s say seven years of experience, and someone looking for an in-office role. If your LinkedIn says you only want remote work, you’ll be automatically filtered out. 

People tend to think vague is best, but it’s not. If you’re looking for a specific role, you’ll have to put some detail on your LinkedIn profile. Don’t just say “director of marketing” and the company. Tell me what you actually did while you were there, like “managed a budget like this” or “grew revenue like that.” If you used Google Ads or some creative brand thing, that’s cool. If you onboarded Coca-Cola as a customer or hired 25 people in a week, tell me. 

But you haven’t even looked at a resume yet.

Everything starts on and comes back to LinkedIn these days. After the recruiter finds you there, that’s when they’ll want a resume. It should be one page, not front and back—one page in PDF form. Don’t send a Word doc because of formatting issues. That’s the quickest way for a recruiter to toss a resume. 

Since they’re only going to bring us, say, 15 resumes, they’ve all got to look great. You’ve got to make it easy for them with your resume. I like to see lists and bullet points that interest me, with specific examples. Tell me what you did but also how you did it. 

Do you care if I went to Yale or whether or not I have an MBA? 

Not really. That stuff can help, of course, but by this stage, I know if your education and experience fits. At this point, the biggest thing for me and I think a lot of other technology founders is, what have you actually built? 

Today in AI, anybody can build anything. Even if you just bought your domain name and created a website for yourself, it’s your chance to show me what you’ve built. Your resume should make me want to check it out and know more about you. I want to be curious and excited about your story and how the world tomorrow is going to be different because you exist today. 

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How do I nail an in-person interview? 

The interview stage is almost a negotiation stage. When we’ve come this far and I ask if you have any questions for me, you should have lots. 

I’d ask: 

• What is the role in detail? 
• What is a day like? 
• What tools do you use? 
• How’s the team constructed? 
• Do I report to you? 
• Do I report to someone else? 
• What’s the culture like? 
• What’s strong at the company? 
• Are there any areas where you need help? 

All these questions show me you’re not just up for any job, but that you truly care about the company and what to know what you’re getting into. That’s important for me to see before I bring you aboard.

OK let’s say you’re down to two fabulous candidates. How do you choose? 

I might hire both, actually. If I meet two people and I really want them both, I might figure out a way to fit them both into the organization. It gives me more insurance. And if maybe one doesn’t work out or isn’t here for that long, I’ve got some bandwidth. 

I always check references too, and I’m always shocked to hear of other founders who hire without them. 

This might be a risky comment, but I also contact blind references. Of course, the two references on your resume say you’re the best thing since sliced bread. But I’m probably going to check your LinkedIn and find someone you worked with but that you didn’t list as a reference. AI is really helpful with this too; it’ll tell me lots of people you potentially worked with and how to get in touch. And you’d be surprised how often these people love to chat.

Read more from this issue of The Get:

1. What’s your financial personality?
2. True or false: Cheap clothes never last
3. What is the Canada Strong Pass?
4. How can I reduce costs on a limited pension?