Q&A: Sanish Mondkar, Founder & CEO @ Legion

What problem does your company solve?

Legion is  a workforce management platform that helps companies manage their hourly employees’ schedules, timesheets and payroll. Legion’s key differentiator is that it is very inclusive of employees allowing them to play an active role in their own schedules. Using machine learning, Legion does all these things while helping employers maintain time and cost efficiency.

What was the hardest part of launching your company?

Like so many new startups, reaching conviction that the solution we’re building is something a customer needs is one of the hardest things to do when you’re getting started. You can call it product-market fit. Labor problems are not new problems. Trying to maximize productivity and minimize employee churn are not new problems. We wanted to figure out how our solution could actually move the needle in a meaningful way. We had to figure out the right boundaries of the problem, how much of it to actually solve, and how to maintain focus. We had to think about how we perfectly align the solution that companies need most with what we’re able to build. And our earliest execution had to reflect that clearly.

Tell us about your partnership with XYZ. How did the relationship begin?

When I first left SAP, I was contemplating my next adventure. I didn’t think to start a company per se. I was introduced to Ross early on, many months before I founded Legion, who since day one has been a great sounding board.  We discussed at length how labor management had been broken and hadn’t been disrupted by the cloud.  Why weren’t there any big logos attempting to solve this?  During my time at SAP, I had heard from customers that labor is one of their biggest problems. And as the workforce becomes much younger, companies struggle to satisfy their employees’ changing needs.  

I set out on a two-month road trip and it was great to get a chance to see so many small businesses outside the bay area and talk to their owners and employees. I realized that there’s this whole other side, the employees’ side. They are dissatisfied and it wasn’t because of their pay but because of lack of flexibility and perceived favoritism exhibited by their managers.  It was very eye opening. Employers are worrying about labor budgets, and compliance. But there was a huge missing piece. I realized that this system has to be inclusive of solving employees’ problems to ultimately solve labor problems.

I remember coming back from that trip and had a very long conversation with Ross which provided so much clarity around the mission of this company and how I should get started.

What’s a concrete problem that you solved with XYZ? 

There are so many over the years to list. And the range of problems we worked on together are across the whole business. We worked on fundraising, on go-to-market, on product focus, on sales, and so much more. 

As a first-time entrepreneur, and while fundraising, I spoke with Ross daily. He helped me figure out when to raise, who to raise from, and how much to raise. He had helped me through both the A and B rounds. He introduced me to other investors like First Round Capital, helped me shape the pitch and advised me to have an amazing reveal of the product that blew everyone away. With Norwest, the pitch highlighted the enterprise-level opportunity and how this company will be able to grow in really great ways. Ross helped in defining the right KPIs and metrics for the different rounds. He helped steer us through the process and back channeled to make sure the process goes smoothly. And when the term sheets came,  Ross was instrumental in helping with that as well. 

As I was developing the product, we had a closed beta with one customer for 18 months with Philz Coffee. I had a desk next to the CEO. And Ross was so supportive and aligned on the mission and goals of this phase. There was no pressure to start selling and getting more users. 

 As we grew the team, Ross helped with introductions to candidates and recruiters. He even helped screen important hires and helped with due diligence to ensure we’re hiring the right people.

Ross is an incredible partner and investor and is an asset to any entrepreneur he works with.



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