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entrepreneurial spirit

In December of 2012, I was the CEO of Wagepoint, a payroll tech startup in Halifax targeting small businesses that I had founded earlier that year with Bill Murphy and Ryan Dineen.

Our beta test had been a resounding success, and we were now facing the scary and overwhelming challenge of growing our business. We needed a strategic-thinking marketer who could launch the company on a shoestring, and who wasn't afraid to get into the trenches and do all the hands-on work needed to execute. I also wanted someone who would share in our goals, values and care about our success.

Yup. That was the extent of my delusion.

Unsurprisingly, by mid-March, after meeting way too many people who didn't quite fit, I was starting to worry that my requirements were the stuff of fantasy. Most of the candidates I met with were perfect for a steady 9-to-5 marketing job with specific job descriptions offered by a big company. They didn't seem prepared to take on all the unknowns that come with life in 24/7 Startup-land.

I decided to talk to my girlfriend, Leena Thampan, about the problem.

Leena and I met at her doorstep in Dubai when we were just teenagers. I was moving to Canada to start university and a mutual friend of the family had made an introduction to the parents of another girl planning to do the same.

As fate would have it, Leena opened the door to find a seemingly bored, would-rather-be-doing-anything-else 19-year-old staring back at her. Despite that (or perhaps because of it), she says she fell instantly in love with me – a claim that has yet to be verified via time travel and a blood test to check for a spike in endorphins.

We didn't start dating until Leena moved to Canada. By the time I launched Wagepoint, we had already been dating for seven years and were committed for the long-term.

Leena had been my sounding board from the day my founders and I started the business, but we had never really talked about her taking on any kind of formal role. We didn't need the stress of having both our eggs in the same basket. Leena's job was holding down a steady salaried position while I played entrepreneur – until it either bested me or I was successful at it.

And yet, as I began to explain to her what I needed in a marketer, I noticed that she was giving me precisely the feedback I was longing to hear during all those coffee dates with potential hires. Could the answer to all my problems be sitting right across the dinner table munching on kale chips and excitedly telling me all about the potential of the role?

Once again, I was convinced that she was "the one." Now came the hard part – I had to actually convince her.

At the time, Leena worked as a media planner at WPP's MediaEdge, a global media agency. She was managing multimillion-dollar media campaigns for global brands such as Chanel and CARA. When she asked me what our marketing budget was and I said "What can you do for $5?" she laughed hysterically.

Leena was worried about her lack of startup marketing experience. She was also legitimately concerned working for Wagepoint would impact her professional resume and personal life. Most couples can go home at the end of day and celebrate their successes or vent about their failures. When your partner is also your employer, the boundaries are far more fuzzy.

On the other hand, she was intrigued by how much control she could have over the entire process of business building. Setting up a marketing team from scratch meant that she could break down traditional departmental silos and incorporate marketing approaches into every aspect of the business, particularly customer service and product development.

In reality, it would be many years before she could impact that kind of decision-making if she continued working at media agency, or even in the corporate world, where the tiers to becoming a C-level executive are much harder to scale.

All that considered, Leena made the leap to join Wagepoint as our CMO in April 2013. We have never looked back. Our fears about finances were abated once we landed angel and VC investment and we could pay ourselves a decent living wage.

The other interesting aspect is that we rarely have disagreements about work because we both understand the implicit hierarchy in our roles and who has veto power over a particular decision.

As for how the company has fared since we hired her? Well, with 1,700 customers using Wagepoint, responsible for paying more than 10,000 employees, it is pretty evident that we made the right choice and are on the right track.

Given her exposure to almost every aspect of business building, Leena is now considering her own entrepreneurship path. She believes she would never have been inspired to take on that challenge without her time at Wagepoint.

I always knew I'd picked the right life partner. The opportunity to work with her as a business partner was just the icing on the cake.

Shrad Rao is the CEO of the online payroll software company Wagepoint. He's getting married to Leena in 2017.

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