My 10 year journey from Associate to VP in silicon valley

July 31, 2022

Over the last decade, I’ve been asked for startup career advice 100s of times. This year, I’ve decided to write out my top 10 tips. Check them out and get in touch if you’re looking for personal advice.

I landed in Silicon Valley in 2011 as an Associate on PayPal's strategy team. In the past decade, I've been fortunate to experience startup success in various forms - $10B IPO (Dropbox), multi-hundred million and billion-dollar exits (Magento →Adobe, Invoice2go →, growing to unicorn status (Pilot), and going through YC + raising a seed round (Padlet).

This post recounts ten lessons from my startup career. If you're in the early/mid stages of your startup career, this will be a helpful reference as you navigate what success and happiness mean to you.

Two things to keep in perspective before we get into it. First, there are multiple paths to achieving success. You can learn from many happy and successful people. My story is one of so many in tech. Second, it wasn't a straight path or a grand plan that led to the success I've experienced. I was at the right place at the right time for those opportunities. Luck had a significant role to play.

Ok, so let's get into the top 10 tips I have for you.

#1 Seek out startup/business experience early in your career

I was conflicted about writing this. It might seem counter-intuitive. Earlier in my career, I would advise many folks to get experience at a larger company (e.g., FAANG) to learn how the best companies do things and set a good foundation for their career. The brand doesn't hurt either.

I've now changed my advice. 

I saw my mom start and grow a business from home (her story is pretty cool, so I'll do a post someday on how she cracked go-to-market back in the 90s in India). I started a bootstrapped student jobs marketplace in college. I went through YC in 2013 for Padlet (it didn't work out exactly as I'd hoped, but it was a damn good experience).

All of these experiences honed my ability to understand business. While the lessons from these experiences were unstructured and subconscious, they were critical reference points as I grew in my career.

Larger companies are suitable for structured learning but have some significant cons. More risk-averse. More defined roles. Both of these things are natural inhibitors for entrepreneurship and trying new things. If you're working at a large company or in school, I recommend starting something on the side. You'll learn a ton from that experience that you can apply directly to your career.

Is there a best of both worlds? Yes. Work at a high-growth startup on a rocketship trajectory—more on that in #6.

#2 Don't let school get in the way of your education

I was never great at school. I did well enough in the exams that mattered, but I was average throughout. This was because I didn't know my "why." Don't get me wrong - if I had focused on my why earlier in life, I believe college would have been a game-changer. It was a missed opportunity for me. 

Later in life, as I figured out my "why" (startups, entrepreneurship, helping other businesses), I developed various learning methods - studying people, books, and communities that excelled at the things I wanted to. Formal schooling is an aid in this process and shouldn't be viewed as the end all be all by itself.

This is the same principle I hold near and dear to my heart as we raise two young kids.

Once you find your "why," with the available resources on the internet, I find it hard to believe that you won't be able to learn what you need to succeed at your goals, regardless of your formal/structured education.

#3 Business communication is the most important skill of them all

Regardless of your role and your level, you will often have to influence brilliant people about the why, what, or how of critical business decisions you want to be made. That's when good writing and presentation skills are going to come in handy. Without those, your ability to influence others is severely limited. The idea's merit doesn't matter if you can't communicate it effectively.

I was fortunate to spend time in a consulting startup with some former McKinsey, Bain, and BCG consultants straight out of college. In the three years there, I learned both the theory of how to communicate well and the execution of presenting complex ideas to senior leaders at large & successful companies.

You don't need to be a consultant to do this well. Learn the basics through this book (and this course by a former consultant) and then go to town every day/week practicing those skills. Also, check out the books I've recommended on psychology, writing, sales, and pitching. While they are focused heavily on sales & marketing, business communication can also benefit from the tips in those books.

#4 Understand basic business metrics and finance

This tip can be a true superpower. Most startup employees often don't pay it the attention it deserves. They don't understand how their P&L works. Interestingly, most of them also don't know how various business metrics impact the P&L directly.

Being so far removed from your day-to-day metrics and OKRs, the P&L is easy to ignore. You end up focusing on the metrics and OKRs you can move. Having a narrow focus is excellent. But, if you don't understand the impact of those metrics on the P&L, you're operating with some dangerous blinders. Not saying you need to become a finance savant but get to know the basics. You owe yourself and the business that much.

I was excited to learn this stuff when I took on a GM role at Magento focused on growing a new business/revenue line. I'm pretty sure that if I had paid more attention to this earlier, I could have had a more profound impact on the businesses I was at before then. Since then, I've incorporated this tip more closely into my work - regardless of the company and the role I've had.

This tip applies to everyone. Not just to Product and Go-to-market team members but also Engineering, Design, and Operations teams. Understanding the P&L makes it significantly easier for you to know how the work you're doing will make the business successful (or not). 

So, how do you learn this? Well, first, start by understanding the key metrics critical for your business (here's an excellent article for SaaS metrics, thanks to the legendary David Sacks). Layer on a foundational understanding of the income statement and balance sheet. Spend time with your analytics and finance leads, discussing how the two are related and what drives your business's revenue, profitability, growth, and valuation.

Review these regularly, especially as your work moves the numbers in these statements.

Here's another way to think about #3 and #4 together. Own a number, ideally hit or exceed that number, and communicate what you learned along the way. Do this consistently, and career progression is pretty much guaranteed.

#5 Build your personal brand

Your brand is your reputation. What differentiates you from everyone else who's competing for the same startup job, the next promotion, the next leadership role, the next round of funding, the next deal. 

Your brand is not a set of fuzzy adjectives and buzz words.

Whether you know it or not, you're always selling and marketing your brand. By taking control of it and doing it consciously, you might accelerate your path towards your goals. 

Building and maintaining your brand isn't rocket science. It's knowing your niche and then developing proof points that demonstrate how you excel within that niche. Whether that's through your Github repo, LinkedIn profile, blog, Twitter feed, or portfolio. In other words, know your niche, do great work in that niche, tell people about your work.

Ideally, you're in a role that helps you build your brand. I believe there are two starting points for this. First, turn things you do and learn daily into your brand online. Alternatively, if your primary line of work isn't offering this opportunity, start a side hustle - it'll make you better, AND it'll help you build your brand.

#6 When you get offered a seat on the rocketship, don't ask what seat!

When evaluating where to work, I force myself to think like a VC. I don't invest capital, but I think of my time as my investment, and I want to ensure the ROI will be high. I look at three things:

  • Market - is the market large and growing?
  • Team - is the team uniquely equipped to build and sell into this market?
  • Traction - is the team able to show progress towards its vision?

There are other things to evaluate for sure - who will your manager be, what's your compensation, does the role align with your skills/career growth ambitions. Few companies will check all the boxes.

The most crucial factor is traction (aka growth). Traction trumps everything else. If you're offered a seat on a legit rocketship, don't ask which seat. Just take it and go! :)

It'll be messy. There'll be lots of growing pains. Lots of systems and processes will often stop working as the growth of the business outstrips its ability to uplift its infrastructure. BUT, the traction/growth is the clearest signal of strong product-market-fit / pull from the market. You might even have six managers in three years (true story :P), but it'll be worth it for the experience!

Having that experience under your belt will teach you things that are not possible at places where traction is slower. Eventually, growth solves all problems.

Ideally, besides being on a rocketship, you'll find a manager who is your advocate and supports your career. The combination is potent.

A final note on this. When you're on a rocketship, look around, build relationships, learn from the best. Your colleagues will go on to be founders and leaders at the best places in their next play. Don't miss the chance to learn from them. It's a rare opportunity.

#7 Identify whether you want to build or sell

If you simplify any business, there are only two core activities - building or selling. Most other functions support these two activities and increase the efficiency of each exercise. A tight feedback loop between building and selling unlocks faster growth.

When I started my career, I thought I would be a builder. It took me a while to figure out I was more passionate about selling. I pivoted my career to go-to-market and haven't looked back when that occurred.

Earlier in your career, identifying how you want to contribute - building or selling - helps you focus more on how to impact the business and build your career. Even better if you do stints in both areas to see for yourself how symbiotic the two are and then pick the activity that is best suited for you.

When I first got into tech, there was a prevailing belief that eng/pm roles belong at the top of the corporate food chain. Maybe I was just not in the right circle, but that belief has so clearly been dispelled. Go-to-market roles have reclaimed their well-deserved position in the ecosystem.

#8 Do things that don't scale

Y Combinator made this famous. 

My first experience with this was working on our first startup in college in 2005. We went door-to-door with physical signup sheets to sign students up for our student job portal. We'd then create accounts for them and email them with the details. It was grueling work, and it took us a year or so, but I think we got most college students in Singapore to sign up for the service. To see the demand side of the marketplace, we advertised that we had a database of students up for different types of student jobs in the classifieds section of the newspaper. We took phone calls and listed those jobs on the portal. Voila, we had traction.

Another excellent example of this principle appeared a few years ago. To get a better sense of why people buy or churn from a productivity software we were working on, a colleague evaluated hundreds of churn surveys manually, painstakingly. This exercise laid bare the knowledge gaps preventing us from building and selling the best possible version of our product. That colleague went from being a product specialist to a PM to a founder backed by top VCs in a few years.

One of the startups I worked at began by offering its service manually in the first few months. Almost zero software at the beginning. They built the tech in parallel and validated it with the manual service they were providing. This is the perfect embodiment of this principle.

There are hundreds of examples of this in the journey towards rocketship-like growth. More people can accelerate their careers by doing things that don't scale.

#9 Make things people want

Another thing that Y Combinator made famous! :)

Making something people want is the ultimate goal. No matter what you're building or selling, if enough people don't want it, you're just going in circles. 

So, regardless of your role, pay close attention to what people want. Make sure you direct your energy and influence in the organization to solve the most pressing needs of the most number of people in your target market. If you can do that, nothing can stop you.

If you're a builder, make sure you find out for yourself if people genuinely want what you're building. Work with your colleagues to get confidence in it before you build it. Do things that don't scale to get higher confidence before you invest all your time and energy in building a solution.

If you're a seller, try to close the sale before even having the product. Then work with your builder colleagues to build it. :)

Always be asking the tough questions on whether people want what you're offering. Get real + tangible data points to support your hypothesis.

#10 Aim high

While this is the last one, it's probably the most important. 

Aim high. Don't settle. 

Look for 10x and not just 10% improvements in whatever you're doing. Whether that's your personal finance planning, the signup funnel you're working on, the win rates for your sales team, your ad impressions, and click-through rates.

Aiming high doesn't mean that you don't make tactical improvements consistently. Aiming high means you're setting your sight on the global maxima (true innovation) in whatever you're building and selling instead of optimizing for the local maxima.

Aiming high also means you're constantly questioning the status quo. "It's always been done like this" shouldn't be in the vocabulary. 

I recognize that companies do not always support this. There's lots of perceived risk inherent in big ideas, and it's hard for companies to trust everyone to aim high. 

Having said that, if you're consistently practicing the other principles (do things that don't scale, make something people want, build your personal brand, communicate effectively, understand business finance), you make it easier for your colleagues and your company to trust you with big ideas.

Finally, aiming high can mean different things. I remember chatting with my mentor one day, and I said something like, "I'd love to run marketing one day." We discussed the why behind that statement in grave detail. 2 years later, he remembered and offered me a marketing leadership role when the opportunity presented itself. Ask the universe for what you want, and it may just happen.

If you liked what you read here and are interested in building your go-to-market skills, follow GTM Digest on Twitter, where I post tips on leading go-to-market teams.