Mentor Spotlight: Shubham Chhabra

Mentor Spotlight

To summarize Shubham's career journey in one line: BComm. in Finance and BA in Economics → Strategy and Operations Consulting (worked as a generalist with an industry focus) → Customer Operations @ → Business Operations @ → Sales Operations at a Stealth Startup

Where are you currently located?

📍 Toronto, Canada

Describe yourself with 3 emojis 👇

🛫 - I have had the chance to grow up in a few different counties and travel. It’s has played a huge role in who I am as a person.

✍️ - I love to write out my thoughts and structure problems I am evaluating on a whiteboard. I am definitely an old school pen to paper > typed up thoughts person. 

🤪 - I am a mix of goofy and serious. I try my best to embrace who I am and bring my goofy personality to most social (and professional) situations.

Career Pivots

What prompted you to want to pivot industries?

Consulting → Tech: My move from Consulting to Customer Ops was focused on moving from an advisor role to actually operationalizing changes and facing the challenges that come with actually building new products and processes.

Customer Ops → BizOps: After a few months in Customer Ops, I realized that I wanted to go back to being a generalist and tackle the interesting (and ever changing) challenges that are faced by a scaling startup. got a chance to work with a number of functions at the company. At some point started to take a lot of interest in the go-to-market function, and wanted to get more intimate with it.

BizOps → SalesOps: A few months into my BizOps role, I started to really enjoy working with the company’s go-to-market teams. As such, I made the decision to move into my current Sales Ops role to build subject matter expertise in sustainably scaling go-to-market teams.

How did you find your various roles in tech? was stealthy when I initially came across the company, so I reached out to a 2nd-degree connection to learn more about the company. I liked the company and the timing clicked since the company was on the verge of signing a pretty big client. A few months later, I moved to and went through a remote onboarding in the middle of covid.

My current company reached out to me on LinkedIn, and after an initial call with the recruiter, I knew this was an opportunity I wanted and a company I saw a lot of potential in.

How has your thinking around your career path changed over time?

I have always been in a constant internal battle between staying a generalist or finding an area (or areas) of operations I love and want to specialize in. I am sure it is a battle faced by a lot of other generalists in the Chief of Staff and Business Operations role. After a few years of pushing to be a generalist, I have finally started to listen to the advice of one of my early mentors to build a broad skill set, with a few areas of specialization.

The Commons

What is your favorite part about being a mentor?

  1. Getting to meet new Mentees who are willing to put in the effort to build the foundation to successfully pivot into a new field is always very inspiring. 
  2. Seeing how people approach the same problems in different ways and then get together to negotiate a solution is a constant reminder of the power of combining different perspectives. 
  3. The community - I think that is one of the greatest parts about The Commons - how people are excited to share their knowledge, help others grow, and support each other in this community.

What should people who are thinking about joining The Commons know about it?

The Commons is a great place to learn from people who work in the industry to pivot into a new career, but more importantly, the support of this community is its biggest value add. You constantly get to see people who may not be looking to switch careers, but use the community as a sounding board and pool of subject matter experts to perform better at their current jobs and learn.

Tell us about working at a Stealth Startup!

What exactly is a "Stealth Startup"?

A stealth startup is any startup that wants to limit public information about its activities and products. A startup may choose to be in stealth mode for a variety of reasons - including wanting to protect its IP from other market operators, limit competition, and to focus the company’s effort on building rather than advertising / narrative management.

How does one join a stealth startup? Is everyone contacted by a recruiter? How do you learn more about the company to decide to work there?

Occasionally, stealth startups would post on job advertising platforms with limited information about its operations. Stealth startups also focus on outreach to build its candidate pipeline, with recruiters reaching out to individuals who might be a good fit for a position. Typically, the recruiter would share more information about the company as one progresses through interview stages.

What's your role?

I work as a Sales Ops Lead for our US and Canadian market. My team falls under the growth team and our team's goal is to help the company grow in a sustainable way, making sure we have the right processes, incentives, and structure in place to grow our top-line revenue.

What are some of the big pros and cons about working at a Stealth Startup?

Pro - Everyone at a stealth startup is hyper focused on building the product, scaling, and focusing the attention on the end customer. Instead of focusing on the PR and controlling the narrative, we are focused on constantly growing our offering and improving our processes to ensure our customer’s success. 

Cons - Not being able to talk about where you work is definitely a difficult conversation at times. It’s also hard to run ideas and problems by people outside the company since you cannot disclose details about the company’s operations.

Just how stealthy is a Stealth Startup? Can you tell your family and friends where you work!?

We have been strongly advised not to discuss the company’s operations - as such, I plead the fifth.

Any words of wisdom for someone looking to make a similar career move to the one you made? 

To talk to people and learn about what they do, even if it does not relate to what you think you want to pursue right now. There are so many cool roles in tech, and most people go after the more well-known roles, but there are tons of other roles that are upcoming and get scarce attention.

Some fun stuff!

Your favorites:

📰 Where you get your daily news: My Google Home wakeup sequence gives me a daily blast of political, business, and tech news from different sources. 

🎨 What you're doing outside of work: Biking, Tennis, Travelling, and watching F1

Interested in operations roles in tech? Hone the skills you need to succeed in the Strategy & Operations Sprint, and receive 1:1 mentorship mentors like Shubham!

Interested in more?
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Mentor Spotlight: Aritra Ghosh
Meet Aritra, Product Manager at Azure (Microsoft) and Product Mentor at The Commons!
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