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Lessons in Leadership

Scale Your Business: Sid Upadhyay on the Step It Up Entrepreneur Podcast

Wizehire CEO, Sid Upadhyay, joined Tomas Keenan on his Step It Up Entrepreneur podcast to discuss Wizehire and how he approaches running a growing startup with continuously evolving needs.  Sid and Tomas highlight the importance of taking advantage of opportunities presented to them, and also how leading without controlling are keys to scaling your business effectively.

About the podcast

Podcast Name: Step It Up Entrepreneur

Podcast Host: Tomas Keenan

What the podcast is about: Step it Up Entrepreneur features Tomas Keenan, an entrepreneur with over 20 years of experience  running and coaching businesses.  Keenan is passionate about helping entrepreneurs and their businesses thrive. The podcast features a variety of guest entrepreneurs and each episode contains wisdom and advice for small business owners to take and apply to their own companies.

How to listen: Apple or Spotify

Top takeaway from the podcast

“Life is all about showing up and saying yes, and incredible things happen” – Sid Upadhyay

Sid emphasizes “showing up and saying yes” as motivation for everything he does, and the way he approaches business. What does it mean? Making the most of the opportunities that present themselves. Sid’s long term vision for Wizehire reflects this. He wants Wizehire to be more than just a hiring platform, but something that can improve entire employee onboarding processes. “You only get to onboard somebody once,” Sid says, “it’s important to get that right.” When new opportunities to solve problems for small businesses arise, we want to create solutions for them.

And when it comes to hiring, it’s just the same. Capitalize on opportunities that present themselves. Sid and Tomas both rely on feedback from their team to recognize when those needs arise. If you’ve planned for a team to grow over the course of a year, but needs escalate, it’s important to foster an environment of feedback, and then take action.

“What we want to do is lead with, not control, but with context” – Sid Upadhyay

When you are open to feedback, and you’ve applied proper context for your team, letting go of control becomes much easier for leaders. Early in a company’s journey, the leadership scrutinizes every hire and employee, but as companies scale making that context clear is increasingly important – this way the feedback received both for employment growth, or even difficult employee changes, becomes more valuable and actionable.

A great way to provide context, Sid and Tomas believe, is through OKRs (Objectives and Key Results). These can act as barometers for your team to ask if they are working on the right things every day to achieve those OKRs, and if they’re properly equipped to do so.

How do you scale effectively? Tomas argues, “Do it, document it, delegate it… it’s literally the formula to scaling – but it’s not easy.” 


This conversation underscores the value of flexibility and adaptability. As businesses grow and evolve, their needs change and “hiring becomes the #1 job as companies begin to scale” as Sid says, but hiring processes aren’t cookie cutter.

Wizehire is an adaptable and flexible solution for hiring. Rather than forcing companies to abide by the Wizehire way, we exist for companies to perfect their hiring process.

Learn how you can build your dream team today.

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