How should I choose between 3 PM opportunities?

A post dated story on how I went about evaluating three career options to making a decision in 7 days in the summer of 2016. The decision I made in the end didn’t end up panning out due to visa issues however I decided to still share this post to shed some light on my decision making process.

Early 2016, I decided to start making mission driven career and life choices. I deeply care about improving access to economic opportunities for people globally. To that end, I got connected with several amazing companies that are working towards access to education like Khan Academy and Udacity. While KA’s approach has been to focus on providing free educational content in the K12 segment, Udacity’s approach has been to focus on the higher education market. KA offers it’s lessons free to students while Udacity is a for profit startup that charges students about for 6 month courses. KA is a non profit organization while Udacity recently raised a big funding round to expand internationally. In terms of size of the teams, KA has about 100 people while Udacity is about 250.

This brings me to the reason I am sharing this post with you. Faced with the toughest decision I’ve had to make this year, I needed to evaluate three exciting career opportunities with these two organizations; each offering incredibly unique career & life experiences.

  • PM contractor at Udacity Germany
  • International product lead at Udacity Headquarters
  • Head of Growth at Khan Academy India

The three job opportunities I mention above had not turned into final offers at the time; however I was in late stages of conversations. I had verbal offers on two and a strong indication of an offer on the third. As a result, I did not have perfect information about several pieces. However, I was also far along that I needed some clarity on what would be best for me especially because they were in different locations & required move planning.

My goal was to develop clarity about how to prioritize the opportunities over a one versus three year time horizon. I also needed to make this decision quickly so I could spend my time chasing the right opportunity.

I needed to prioritize these options on the basis of my current life and career stage. To tell you a little bit about me, I have been working in the technology space for about 10 years including PayPal and other startups in India and Silicon Valley. I enjoy helping mission driven teams develop early stage offerings, find product market fit and get to sustainable growth in new markets. Most recently, I was Director of Product Management at Hapara (Google apps partner and K12 education technology startup) where I was in charge of launching new products to enable personalized, 21st century learning in schools globally. Here’s my linkedin profile.

When I visualized my next gig, here’s what I hoped for:

  • Join a company that is aligned with my mission in education (must have)
  • Have a high level of influence on product decisions so the team/ company must be early stage (must have)
  • Work in a full time role that can sustain my career and life over the next 3–5 years (good to have)
  • Join an organization that offers financial upside and where I can grow into senior management given my career trajectory (good to have)
  • Cultural fit with organization: non hierarchical, leadership that believes in empowering people and supportive of work life balance (good to have)

I am also lucky to be married to a loving and supportive spouse for 7 years. We’ve been living in the bay area for many years and are in a unique situation where he is taking on a new role in Germany for 15 months to run eBay’s Motors B2B business. This is an amazing career opportunity for him and we are both excited about what this could mean for both of us.

  • We’ve been thinking about having a baby in the next year, biology permitting so the lifestyle must support a baby if we’re successful (must have)
  • We want to enjoy the new life experience of being together in Berlin and travel in Europe (good to have)

Here’s what I knew about these opportunities:

(1) PM contractor at Udacity, Berlin

This is a contracting gig at their newly opened regional offices in Germany. One of their key investors in Europe is committed to Education as a key pillar and believes in their ability to grow as an online learning provider in Germany and Europe. The contractor role would work within the International team to grow their business in German speaking countries (Austria and Switzerland along with Germany).


  • Opportunity to address online learning needs for students & professionals in Europe. Angela Merkel’s government has been committed to promoting digitalization of education.
  • Key role on landing team in Germany. Focus on localizing their product & growing their user base in German speaking markets through local offerings and partnerships.
  • Work with a fantastic product & leadership team in HQ and talented country manager in Germany.
  • Work with a solid engineering team to grow product usage & adoption (1 Engineer dedicated to Germany, potential for hiring contractors?).
  • On a personal note, the opportunity to be co-located with my husband & travel in Europe; experience a completely new lifestyle from what we’ve been used to for the last 6 years in the Silicon Valley.
  • Flexi work arrangement as a contractor.


  • Lack of local language skills and local networks.
  • Being a contractor in a regional office might mean lack of visibility, resources and fewer growth opportunities with regards to the HQ team.
  • After 12–15 months when we leave Berlin, I would need to find a new full time role.
  • Dearth of dedicated engineering resources compared to HQ.
  • Fast paced startup could mean unpredictable hours (based on my initial interactions with people during their recruitment process).

(2) International PM Lead at Udacity headquarters

The second option was a full time gig based at their headquarters in the bay area. International expansion is an area of strategic focus for them next year, one that their investors and markets will keenly follow. The international PM lead is their first product hire towards expanding into China, India, Brazil and Europe. The role reports into the exec leadership and includes company equity as well future growth potential.


  • Help young students & professionals at countries like India, China and Brazil at a time when developed economies are going through GDP stagflation. Emerging economies are going to be key to global economic growth in the next 20 years and that can’t happen without education and up-skilling talent.
  • Being at the headquarters of a high growth startup would offer opportunities for visibility with execs, growth & resources.
  • Focus on internationalization of their product end to end in key markets. Work with a team 9 engineers globally. Work with a fantastic product team in HQ.
  • Be based in bay area and spend 20% of my time in key international markets (offer opportunities to travel to Berlin to be with my husband once/ twice a quarter).
  • Leverage existing set up in bay area like our house, support system and professional networks (important if we are starting a family).
  • Ability to plug & play in the role for the next 3–5 years (important if we are starting a family).


  • Lack of continuous co-location with my husband for 12- 15 months.
  • Distributed engineering team: 3 in bay area, 3 in India, 1 in Brazil and 1 in Germany. Engineering lead in Shanghai.
  • Reporting line exec located in Shanghai.
  • Fast paced startup could mean long, unpredictable hours (based on my initial interactions with people during their recruitment process).

(3) Head of Growth at Khan Academy, India

The third option was a full time gig based in New Delhi, India. This is the city I grew up in and it’s the city I still call home in India. KA has been a pioneer in the online learning field. India is the first market outside of US they focus on. They are hiring a team based out of New Delhi which will focus on growing their user base and addressing the needs of Indian students.


  • Opportunity to improve the educational outcomes for 250M Indian students with a product offering that is free and top quality.
  • As a member of the landing team, shape the strategy and growth of their products in India.
  • Work with a fantastic product & leadership team in HQ and talented country manager in India.
  • On a personal note, living in the same city as my parents after 16 years of being away from New Delhi and reconnecting with my roots.
  • Flexi work culture, promotes work life balance (based on my initial interactions with people during their recruitment process).


  • Company unable to sponsor Green card process.
  • Lack of continuous co-location with my husband for 12–15 months with little opportunities to travel on business.
  • Working in a regional office might mean lack of visibility, resources and fewer growth opportunities with regards to the HQ team.
  • Since KA is a non profit organization, zero equity and below market compensation (in rupees) resulting in substantial financial differential.
  • After 12–15 months, if we have a baby we’d need to move out of New Delhi and find a new role back in the bay area.
  • Mature product and slow moving culture (based on my initial interactions with people during their recruitment process).

My decision in the end came down to minimizing my personal risk and maximizing the professional reward for the next 1 to 3 year period. I decided to pick (1) i.e. the contracting opportunity in Berlin as my top choice. It met ALL of my must have criteria and most of my good to have criteria. From a risk perspective, it presented the lowest personal risk. If the contracting opportunity didn’t work out for some reason, I would still have been with my husband and gained tons on a personal level. If it did work out, I could carve out a role to join Udacity long term in the 3 year horizon. However in both options (2) and (3), my personal downside was much higher living away from my family.

If you enjoyed my post, I’d appreciate some 💚 below!