Forging a Career in Tech requires both patience and risk

After graduating from college, Alex de Leon started his career as a management consultant at Deloitte, but 6 months in, left to take a role at Google. It was a bit of risk, but it opened the door to a career in tech with a stint in Business School and now leads product marketing for Instagram Asia. Along the way, Alex worked in sales, account management, and now product marketing, and has learned great career lessons working alongside smart and hard-working people. He shared with us some of his thoughts on taking career risks, being patient, and what he’s learned along the way developing his career.

CareerSchooled: You started your career as a consultant, but quickly jumped to a role at Google. What led you to decide to make a move so quickly, and with the benefit of hindsight, what did you learn from taking that leap?


This stands out as one of the toughest decisions I’ve made in my career. I had just joined the firm and loved the people I was working with. Out of the blue, I received a call from Google and somehow made it through the hiring process to join a new team they were forming. Given that I was only six months into my Deloitte tenure, a lot of people said that it would make me look ‘flighty’ and that that perception would follow me around for some time. I was fresh out of college and wasn’t quite prepared for the burden of making a decision like this.


Looking back, joining Google changed my life trajectory entirely. Although I consider myself hyper-rational, especially when it comes to my career path, I learned that every so often you just need to take the plunge. There’s a quote from Sheryl Sandberg that I love where she said, “If you’re offered a seat on a rocketship, don’t ask what seat. Just get on”

CareerSchooled: What were some of the most important lessons and experiences you took away from your time at Google?

Five years at Google gave me the strongest foundation I could have imagined. When you’re working with the smartest people in the world, you need to be the best version of yourself as often as possible. Convincing high achievers to support an idea means that you have to be able to stand up to immense scrutiny. Did you do extensive due diligence? What does the data tell us? What’s been done before and why will this work differently? What tangible metric will we be driving?


One other important life hack I learned was ‘the meeting before the meeting’.  Let’s say you’re proposing a new strategy or project to a senior audience. Instead of showing up the day of the presentation and hoping for buy-in, you schedule individual discussions beforehand with each stakeholder.

At best, by the time that you present it’ll be smooth sailing because everyone will have already pre-committed, and at worst, you’ll be better prepared for objection handling.


CareerSchooled: After spending a few years at Google, you also decided to go get your MBA. What led you to this, and what was your experience like in business school?


I think a lot of the decision to go to business school stemmed from my personal insecurity. I was a liberal arts major working in tech and often felt that I was overlooked for more senior job opportunities due to a lack of credentials.


Studying at INSEAD was an absolutely amazing experience. Given the international focus of my career, INSEAD was really the perfect environment for me. Nearly every student is ‘international’, and everyone I met had incredibly diverse backgrounds like ethnically Chinese but born and raised in Kenya, studied in Europe and worked in oil and gas in Latin America. I think this global focus manifests in other ways – all students need to be conversational in at least three languages in order to graduate, case studies are written about companies outside the US, and every weekend there are immersion trips (both school-planned and those hosted by students inviting us to their home countries).


CareerSchooled: After business school, you transitioned into Product Marketing. What led you to make the move into Product Marketing?


It was actually by accident, if I’m being honest. Whenever I meet with students, I always say that it’s important to segment your career into industry and function. In my case, I knew that I loved tech and was definitely in the right industry. However in terms of job function, I had sort of bounced around between partnerships, sales, and account management without really settling anywhere. After business school, I felt strongly that I wanted to work at Facebook but didn’t want to do sales again, fearing that it would be too repetitive from my time at Google. Out of the non-sales roles available, I saw an opening for a Regional Product Marketing Manager for Southeast Asia. On the product side, I definitely didn’t have sufficient relevant experience but I applied hoping that my background in Southeast Asia would make up for it.


After going through the full interview process, my application was put on hold for a couple of months. I’ve heard rumors that I wasn’t the first choice candidate for the role, but everything worked out 🙂


CareerSchooled: You’ve spent a few years working overseas and working for large technology companies serving APAC markets. What do you enjoy about working in Asia, and what are some of the similarities/differences between working in region versus working at Company Headquarters?


In a lot of ways, Asia is a completely different world. Several years ago, Google coined the term ‘The Next Billion’ as a way of describing the next billion people that would be coming online for the very first time, particularly through a mobile device. From a product perspective, that also begs the question – how do you build for these unique consumers? How do you run an e-commerce business when credit card penetration is as low as 5% in some developing countries? How do you improve watch time on video services when mobile data is expensive and users need to pay per kilobyte? There are no easy answers and that’s what I love most about Asia.


Internally, it can sometimes be difficult being physically so far away from the people that actually build the products. Living and working in Asia means that it’s incredibly easy to underestimate how well the local nuances and insights are understood by the the product teams.

Given how essential both consumer insights and feedback are to understanding product-market fit, trying to figure this out at a global scale is a challenge I think about almost every single day.                                                                             

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CareerSchooled: You’ve made a number of big career decisions in your career thus far. What advice do you have for others who are pondering large career decisions?

My biggest piece of advice is to plan your career and then work the plan. It sounds fairly straightforward, but I’ve met so many people that haven’t created long term visions for their professional life. When you’re imagining an ideal job, think about what your priorities are – normally, it’s some combination of location, industry, and role. From there, start thinking through how you’ll drive each one, beginning with the highest priority.


In 2013, I was really eager to pivot to Asia. However, when I began the search, I couldn’t find a role that would be even a lateral move in terms of scope. Eventually the only opportunity was doing direct sales in a really tiny office Google was launching in the Philippines. The role definitely wasn’t what I wanted in the long term, but it was also the clearest way for me to get to Asia.

After satisfying my location priority, I then focused on developing the other aspects of my career. Six years later, I’m still in Asia, working on products for a large tech company. It took a little longer than I hoped, but I’d like to think this was all (mostly) part of the plan.


CareerSchooled: What’s the most important lessons you’ve learned in your career?


Patience. In the early part of my career, I often fell victim to being overly ambitious, always eager for the next best thing. In any role, I would say it’s at least six months before you have any idea what’s happening and typically a year before you’re making any meaningful contributions.

At Google, I prematurely transferred to another internal team on two different occasions. In both cases, I still had a lot more than I could have learned if I stuck around a bit longer and was more patient.


CareerSchooled: As you think about growing and building your career, what are some goals or aspirations you have that you want to achieve?


I’m at an incredibly fortunate place right now because this is mostly where I wanted to end up when I was creating my five year plan in 2013. I just joined Instagram, leading our product marketing efforts for Asia and am still trying to figure out what my big bets will be.

I identify deeply with Instagram’s mission of connecting you to the things and people that you love. Consequently, I think my next set of career goals will be thinking through the small part I can play in enabling that mission.

5 Career Mistakes I Made That You’re Smart Enough To Avoid

Shyna Zhang is the Founder of Rigging Academy, and a former Product Marketing Leader at Marketo and Microsoft. She shares with us five career mistakes she made and how you can avoid them

Domain expertise, a lot of hard work, critical thinking, problem solving, raw horsepower, strong leadership skills, and the ability to drive consensus across teams. Nothing controversial there, right? But none of this actually matters. For those that are myopically focused on this, I’ll let you out in a secret — you will plateau at some point.

As someone who has been in the room when decisions are made on who to promote or bring in for a People management role, I’ll add one more critical category that young professionals may overlook which hold them back: soft skills.

I recently put together gave a talk called ‘5 Career Mistakes that I Made that You’re Smart Enough to Avoid’ in an attempt to reflect on this topic. Frankly, I didn’t invest in the ‘soft skills’ enough because I greatly underestimated their place in the workplace. The longer that I worked, the more I realized that being smart and hardworking would only get one so far, and the ones that were at the leadership level, weren’t always the smartest and hardworking. Growing up as a first-generation immigrant, these skills weren’t as valued and emphasized in my household, but they are crucial in the individualistic society of corporate America, especially Silicon Valley.

Lesson 1: I didn’t realize hard work and long hours only leads to more hard work and long hours, unless you short circuit

School teaches us that achievement (grades, test scores, winning competitions, etc..) leads to rankings, which Universities deem important. In this system, working harder and being smart leads to direct outcomes.

Work is a very different place. Things like perceived impact on business, relationships with colleagues and management are paramount to getting visibility, promoted and recognized. Therefore, working harder and long hours only leads to burnout.

Instead, be cognizant to both physical and emotional burnout and truly pace yourself and ensure you’re setting up for success in the long run with things like visibility, working on high impact projects, aligning yourself with strong leaders, and getting shit done – the key is doing it over and over again. It’s truly a marathon, not a sprint.


Lesson 2: I let others define my value and didn’t advocate for myself

Everyone is in the business of marketing themselves as much as they are in the business of marketing their solution/product. Ensure you’re setting up a Coach, Advocate, and Sponsor within or outside of your organization that are helping to champion your cause. What’s the difference?

  • Coach: Day-to-day person that can be real as shit with you, providing regular constructive criticism
  • Advocate: Have similar experiences to you which allow her to empathize, understand your issues and offer you useful advice.
  • Sponsor: Person with a high status in an organization who can advocate for an individual’s future successes, when they are not in the room


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Lesson 3: I didn’t show up, because it wasn’t ‘mandatory’

I often found myself the only female or the only person under the age of 35 in a room and frankly, I had better things to do with my time than to go to social events – things like happy hours and get togethers outside of the office or outside of work hours. Because I didn’t feel like I had much in common with my colleagues, I often just didn’t show up. Big mistake.

In hindsight, those relationships and being open and curious about them would have been a great investment for my own growth and learning, not to mention, to develop a connection outside of work.

Lesson 4: I cared too much what other people thought – catastrophically

Whenever my boss or my skip level manager would do a drive by my desk with a, ‘Hey, do you have a few min to catch up?’ or a text popped up that said, ‘Can you chat?’ My heart fluttered with a bit of anxiety.

In My Head

•“Shit, that presentation didn’t go well”

•“They are going to let me go or cut my hours”

•“Someone had negative feedback about me or someone on my team”


•Update on a project

•Ask me a quick question

•Compliment me on a presentation

Too much catastrophic thinking and anxiety, unwarranted :). Manage Your Manager, Otherwise they will Manage You. I use the 5-15 template and methodology, although I’m sure there are others that work just as well.

Lesson 5: I tried to ‘make it work’ vs knowing when it’s time to leave.

Posters line hallways and Instagram is full of motivational statements about ‘never getting in’ and ‘leaning in’ and ‘hustling for your goals.’ Although I’m completely supportive of hard work and working your ass off, there’s something to be said about knowing about a sunk cost. A simple exercise I try to do yearly to ensure I’m working at a place that’s aligned tomy values:

1)Stack rank your values yearly as it relates to your stage in life

2)Stack rank your organization’s values

3)Is there overlap? Is there a glaring disparity?

4)Realistically, will this change in the near future?


Last thing I’ll say on this is that I’ve made many more than 5 career mistakes :). It’s been a journey of trial and error, with lots of learning and luck. Interested in more content like this? Sign up for Rigging’s newsletter. While you’re there, Rigging’s 9-week online program for highly motivated young professionals that looking for the knowledge, access, and community to achieve their professional and personal goals through learning the soft skills that school doesn’t teach.

What got you here, often doesn’t get you there.

How taking risks and thinking ahead can help you chart your path to career success

Nathan Tanner knows a thing or two about building a career. Taking the lessons he learned from pivoting careers from Finance to HR, and getting laid off after 6 months from graduating college, Nathan published Not Your Parents’ Workplace to share the lessons he learned so others could learn how to chart career success. As the Head of People Ops at Doordash, Nathan is constantly thinking about how his people can build successful careers, and he took the time to share his approach to transitioning careers, how professionals can take risks to fuel growth, and to share his own view on achieving career success.


CareerSchooled: After writing a book about your career journey, creating a monthly newsletter, and being a featured career strategy columnist at The Muse, I think it’s safe to say you’ve learned a thing or two about careers! Since you began your career, has your view and outlook on careers evolved or changed? How so?

Nathan: I learned a lot of valuable lessons early in career, mostly through trial and error. I published Not Your Parents’ Workplace with the goal of sharing those lessons with young people so they could find their dream job and be successful in their careers.

For the most part my outlook on careers is similar with the exception of risk evaluation. A year or so ago I heard a podcast interview with Chase Jarvis where he said, “This is the first time in the history of the world where the risky thing is to do the traditional thing.” I think there’s a ton of truth to that. When I got laid off from my job 6 months after graduating college, I spent all my time looking for jobs, mostly corporate jobs. If I could do it over again I would have looked harder at startups or maybe even tried to start something myself. At the time I viewed those options as being too risky.  

I think that always doing what we’re told and playing it safe in our modern, dynamic economy may lead to situations where our skills become obsolete. Many of the career moves I’ve made over the last few years were viewed as being risky. But I think the riskier move would have been to stay put and do nothing. Often times the “safe” option is actually the risky option.   

CareerSchooled: You’ve pivoted roles, functions and industries a number of times in your career. What has enabled you to transition into new opportunities?

Nathan: Most of the career pivots have been relatively minor, but leaving the finance world to move into HR was a big one. When recruiting for jobs I was really concerned that I wouldn’t be competitive because I didn’t have enough HR experience. I eventually learned to abandon that way of thinking. I started telling companies that not having HR experience was a positive and that’s actually the reason why they should hire me. I’d share how my finance experience taught me many invaluable skills which would allow me to bring fresh perspective to a field that is fairly traditional. Career changers tend to be overly concerned about areas of deficiency, but it’s critical to focus on how our unique experiences will set us apart.

CareerSchooled: How do you know when it’s time for a change, whether that’s to a new job, or a new career?

Nathan: I think the answer depends on whether you’re looking at changing jobs or careers. When evaluating whether to change jobs, the most critical thing to consider, in my opinion, is skill acquisition. Are you still growing? Are you learning things that may be valuable in the future? What skills are you developing? If you’re not constantly learning, I’d be a little concerned, especially if you’re early in career. Stagnation is the enemy of career satisfaction.

Evaluating a complete career change is more nuanced. One question I encourage you to ask yourself is whether you can, or even want, to become world class in your current field. I was a decent finance professional, but it always felt like work. I rarely got excited to analyze financial statements or build a new financial model, but many of my peers lived for that stuff. Eventually I reached the point where I knew I had to change careers and I spent a lot of time identifying a field where I could be world class. Here’s an article I wrote that goes deeper into this topic.

CareerSchooled: As an applicant, it can be a challenge to stand out when you are going against other candidates who have more direct relevant career experience. How can you stand out if you are changing careers?

Nathan: If you’re a career changer, it’s really hard to get a job coming through the front door (AKA, applying online). I recommend focusing your efforts on getting in through the back door. What I mean is that those tasked with reviewing your application, whether they be a recruiter or machine, likely won’t know what to do with you. Career changers don’t fit the mold so they often get rejected.

Coming through the back door requires you to be more proactive. You’ll need to build relationships You’ll need to network. I’ve found informational interviews to be extremely effective (I wrote a 10 page guide on this topic here). These methods require more work, but they put you in the driver’s seat which allows you to tell your story rather than waiting to be picked.

CareerSchooled: What advice do you have for professionals who are thinking of making a career transition?

Nathan: Don’t just look at your current job. Look at the job you’d have five and ten years down the road should you stay on your current path. I’d get on the phone or grab lunch with these people. I think many jobs early in career aren’t that interesting so it’s important to get a sense of what’s to come in the future. If you don’t like your current job function and you’re convinced it’s not going to get better as you advance, I’d start learning about opportunities that may be a better fit..

CareerSchooled: What do you define as success for you in your career?

Nathan: A few years back I was eagerly anticipating a promotion. I thought that when the promotion came I would be happy and I would finally view myself as a success. But a funny thing happened. Within a week or two of getting promoted, I started focusing on the next career milestone. I then caught myself thinking that I’d be successful once I reached that new goal.  

I recently heard an interview with legendary coach John Wooden. In it, Wooden shared his personal definition of success. He said, “Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.”

Wooden’s words taught me that individual success comes less from extrinsic rewards, which we don’t fully control, and more from personal growth and development, which we completely control. If you can look back at the end of the month or year and say that you’ve done your best and that you’ve grown as a professional, then I say you’re a success.