Category Archives: Entrepreneurship


There is a an old myth that 80% of the jobs are not advertised. Depending on who you talk to, you will get a variation of this number – from 40% to 80% of jobs are apparently filled without more than 2 people being interviewed. While that is not true in my experience for all jobs (it is closer to 20% or less), it is very high for senior roles. In this post I will give you a few actionable tips on how to make your name on the shortlist when founders, CIOs, CEOs and board members are looking to fill that crucial role of CTO for their organization.

Once you have decided that your goal is to become a CTO, you should direct your career to become a Chief Technology officer. The best way is to break down the goal into a working backwards plan to achieve your goal.

CTO open positions are rarely advertised

The first thing to realize is that there are far fewer positions than there are # of qualified candidates and for roles in the C suite, the right fit is absolutely crucial. So, while you may be interviewed, it is also likely that in 70% of the cases an internal candidate is chosen. The reason I mention this is so you realize that in most cases, you should be looking internally within your organization to see if there is a need for a CTO position.

The best way is to create your own role.

In this post my goal is to give you more “at bats” – or more chances of being interviewed for external positions.

The hiring executive for a CTO tends to be the CEO or founder in 34% of the cases (more for technology companies), the CIO (Chief Information Officer) in about 30% of the cases (especially larger companies) and CDO (Chief Digital Officer), CPO (Chief Product Officer) or board member in the remainder.

The CTO is hired by the CEO / Founder or CIO in over 65% of the cases. Data from CTO searches of executive search firm databases

If you were to leverage this data, then the strategy to get shortlisted for CTO positions becomes both easier and harder.

Easier because you know who are likely the key people to hire CTOs.

Harder because those people are very difficult to network with.

There are 5 primary strategies you can use to make sure you are “Top of mind” for these positions.

  1. Make a short list of potential CEOs and CIOs in the companies you would like to work for (market segment, size) and find a way to add value to their work. I would recommend curating articles and content for them which helps them get a summary of key trends weekly.
  2. Build and maintain relationships with colleagues at your current company who are thinking of starting their own venture
  3. Build relationships with recruiters – there are specialty CTO hiring firms such as CIO Partners, YScouts and CTO Recruiter.
  4. Build a comprehensive social profile so you get inbound requests for CTO positions – GitHub, LinkedIn, Twitter, Blog and speaking engagements
  5. Contribute and work with a open source project which gives you an opportunity to work with the founder who could use help from you as a CTO

Now that you know ways to network your way into a job, what are the ways to find out about CTO jobs that are open?

There are 7 sources that have some listing of CTO positions. In no particular order, I would keep tabs on them every other week. The links below will only list the CTO open positions.

  1. LinkedIn
  2. Glassdoor
  3. Indeed
  4. Ladders
  5. Google jobs
  6. Zip Recruiter
  7. Experteer

From goal to plan – Putting a PLan to become a CTO #CAreeradvice #CTO

If you have decided your goal is to become a CTO, the next question is how do you make progress towards that goal? To direct your career to become a CTO, you need to commit to the goal, and put a plan in place to achieve that goal.

In this post I will provide you a data driven plan, using the Amazon Working Backwards approach.

To recap, there are 5 primary requirements you need to satisfy to become a CTO, a) a large body of work, b) great written and spoken communication skills, c) ability to attract high quality talent, d) build trust with others and e) spot technical trends quickly.

Plan to become a CTO

The plan itself comprises of elements you have to do each week, month and year. I have outlined several steps you might have to complete in each of the 5 areas.

You can take as long as you wish (2-3 years or 12-15 years), but being consistent and disciplined helps.

Body of work

Most items on this list will be “must have”. Either you have to show where you did these, or the products and solutions you built have to have the level and sophistication of success.

Area of workExperience
Understand and outline customer problemsHave you been able to talk to and solve specific customer problems and show that you can articulate the problems in good detail
Define use casesOutline what use cases are defined by the customer problems
Architect the solutionDisplay the ability to architect the solution using components
Choose the right stackAsses the technical details of the problem to pick the right stack to build the solution
Develop MVP / early versionEither build it yourself, use no code / low code tools, get it developed or outsource it
Iterate and scale the solutionShow that you can go beyond the initial MVP
Deliver multiple versionsShow that you can build multiple versions and ship products through the stages of the product
Body of work


Most of the items in communication need not be external (For e.g. you dont need to have a YouTube video or Twitter profile) but they help if you can get inbound inquires for CTO positions that are not published.

Area of workExperience
Requirements outlineProof of documents that outline detailed requirements Tip: Most CTOs I know use a blog or SlideShare to showcase this
ArchitectureShowcase complex architecture tradeoffs that were made. Tip: If you can showcase a few on SlideShare it would be great
BlogMaintain and drive content for an engineering blog with examples of your work, etc.
SpeakingShowcase ability to connect with developers and other technical teams by speaking at conferences, etc.
VisualShow your ability to communicate at scale Tip: Record a few YouTube videos (one or two a month will suffice)
EngagementEngage with thought leaders on platforms such as Twitter (don’t need to tweet daily, but some engagement is preferred)


Most of these items will be asked in interviews and also checked on during references.

Area of workExperience
Hire talentAbility to hire first set of developers, who are willing to work on problems without clear definition
Develop talentShow that you can groom and develop talent over time. Tip: Most CTOs I know have 3-4 public recommendations on LinkedIn of people who have worked for them
Discern potentialShowcase the ability to hire early interns / young members who can be groomed over time
Performance ManageDisplay the experience to manage individual performances by either coaching or dismissal
Coach and MentorShow how you can help team members grow in their roles and careers
MotivationHelp team members achieve potential by helping them see the bigger picture, convince them to achieve greatness


Most of the items in trust are in display during interview questions.

Area of workExperience
Goal outlineShow how you can collaborate with other senior leaders to set goals that the team can align on
Metrics definitionProof that you can align to metrics, drive metric definition, and outcomes using scalable processes
Goal alignmentExplain how you worked with other leaders to help achieve corporate goals
Active listeningExamples of how you changed your mind, based on data or otherwise.
Intellectual honestyDisplay examples of architecture decisions that were made from your “gut” – how do you make decisions?
RespectHow you treat others especially those who are junior and not yet tenured


Most of these items will be based on opinions of other people’s view of you – analysts you interact with, customers you talked to, others you interviewed. The best way to showcase these is to have an opinion and outline it – in any way you are comfortable doing so.

Area of workExperience
ProcessShow how you have streamlined development, testing, release and operational processes and are adopting new trends (Agile, Scrum, etc.)
TechnologyPerspectives on open source tools, latest technology trends (Containers, Service Hub, Serverless for e.g. in 2020)
ToolsWhat tooling and infrastructure trends can you outline to help you develop faster and with fewer resources

How do I direct my career to become a CTO? #Careeradvice #CTO


If you have decided that your career goal is to become a CTO, one of the things we spoke about in the previous post is that only 1 in 30 engineers have the opportunity to do so.

If you look at the pipeline above, (these are rough numbers I got (via LinkedIn) by searching for Developers (Satista), Software Managers, Directors and CTO. While not accurate, they are directionally right.

There are some caveats to this data.

I agree that a) it is not a perfect pipeline – i.e. not every one who is a developer wants to become a CTO, b) most people dont go through a straight line in terms of career growth and c) 29 million developers in 2020, is much larger than 10 million in 2010 or 5 million in 2000, when most of the 1 Million CTO’s started their careers.

One of the things that I enjoyed about working at Amazon was a mechanism called “Working backwards”, or what Steven Covey called “Begin with an end in mind”. Applying that mechanism to one’s career is a very interesting use case and an effective one that I recommend.

If you want to work backwards from “becoming a CTO” to currently “am an engineer”, then we start with the definition of what all is needed to be in that role.

The working backwards mechanism has 3 components:

a) Define the requirements with metrics to measure,

b) put a plan that shows how to achieve those requirements over time and

c) measure and track towards the plan monthly, quarterly and annually.

The top 5 requirements & metrics that qualify a person for that role are:

  1. A body of work that shows the ability to solve complex business and technical problems with technology solutions, as measured by the impact of those products in terms of revenue and customers.
  2. A proven ability to communicate (written, spoken) technical challenges with customers, employees, and media in a simple, concise way as measured by the number of documents (articles, papers) and speaking engagements.
  3. A history of being able to attract high quality talent and build and develop high performance teams as measured by the size of the teams and the current roles of the individuals they hired before.
  4. A willingness to build trust with other executives (sales, marketing, etc.) and help align on objectives to generate outcomes for the company as measured by the business impact (revenue, profit) of the companies they were a part of.
  5. An ability to “see around the corners” and spot technical trends that will impact customers as measured by the new products introduced to market by the individual and the market impact of those products.

There are other subjective criteria as well, but what I have observed is that when two candidates are close on these requirements and there is little to choose between them, other factors – personal relationship / chemistry with the CEO, industry specific knowledge or expertise and brand of the individual become more important.

Now that we have the 5 requirements and a high-level overview of how to measure them, the next step is to put a plan in place and then track to the plan each quarter and every year.

I will try to outline a version of a plan in the next few posts.

How do I become a CTO?


A frequent question I get that I want to help answer in the next few blog posts is “How do I become a CTO? or Chief Technology Officer.

I used to give a few simple answers before: a) Focus on building a great technology profile -e.g. GitHub profile, speaking engagements, etc., b) Network as much as you can with potential founders and c) Learn as much as you can about the business elements of your industry, especially customer trends.

I realized these were good enough for a 30 minute career counseling call, but not very valuable for people who want to plan their career for the long term.

Now that I have more time, I thought I would take a data driven approach to answering this question.

There are great articles on what a CTO does, so I am not going to answer that question.

Instead lets focus only on what it takes to become a CTO.

There are about 780K people with the title “CTO” on LinkedIn and roughly 159K with the title “Chief Technology Officer”.

Filtering them by size of company, indicates 11% are in large organizations (> 10K employees), and over 75% are in small (<100 employees). Many of the large organizations have multiple CTOs (e.g. Microsoft has 38 people in my network alone with a CTO title). Many of them are CTO of a specific business unit, or industry vertical function.

Segmenting by location, 38% of CTOs are in the USA, 27% in Europe and the rest in other locations.

There are 29 Million software developers in the world.

So roughly 1 in 30 software developers could become a CTO.

In my LinkedIn network, I have 1st degree connections with 541 colleagues with the title of either CTO or Chief Technology Officer.

I spend a few hours learning to deploy a LinkedIn scraper. It took me a lot longer than I thought it would, but that’s another story.

I scraped my network for 7 parameters:

  1. Name: E.g. Mukund Mohan
  2. Title: E.g. Chief Technology Officer
  3. Location: E.g. Greater Seattle Area
  4. Company / Organization: BuildDirect
  5. All organizations they worked at before, title and tenure in each organization. E.g. Director of Engineering, Microsoft, 5 years
  6. Education: E.g. Bachelor of Engineering and years at school (If available)
  7. Skills: e.g. product management, startups, etc.

I put this data into an CSV file just to view it in an easy way for me to visually review it.

Three patterns (or archetypes) emerge:

The career technologist (52% of my network)

This individual has over 16.5 years of average experience after graduating, working at 4.6 organizations with an average tenure of 6 years in each.

This indicates that the most frequent way to become a CTO is to have tenure as a developer and grow in organization(s) over time. There were CTOs with over 27 years of experience in my network, and the lowest in this segment had 14 years of experience as a technical leader.

Some examples: Kamal Hathi, Joseph Sirosh and Marianna Tessel.

The startup technologist (35% of my network)

This individual has about 10.2 years of experience after graduating, working at 3.1 organizations with an average tenure of 3 years in each.

This indicates the 2nd most likely way you can become a CTO is to start your own company (likely with a co founder). I tend to have more startup CTOs in my network than others do, so this may be due to my background and experience.

Some examples: Tom Harel, Aravind Bala and Farah Ali.

The fast break upstart (6% of my network)

This individual has 8.7 years of experience after graduating, working at 2.3 organizations with an average tenure of 4.6 years.

This archetype is unique and hard to find because they were at the right place at the right time. They joined a fast growing company (Google, Facebook, etc.) at the early stage and grew with the organization quickly enough to then get a role elsewhere as a CTO.

Some examples: Gaurav Oberoi, Palak Dalal

The rest (7% of my network)

The rest are a motley crew of technologists with long tenure, but I am not able to put them into a specific bucket. They have done several roles, including software development, product management, etc.

In the next few posts I will address questions such as

How do I direct my career to become one of the 30 people who can become a CTO?

How can I put a plan together to achieve my goal to become a CTO?

What skills / work experience should I have to be considered for a CTO position?

How do I get a job interview for a CTO?

Where do I look for CTO positions?

How to bring the X-Factor in your role

I am going to start writing again. This is for myself. I don’t expect anyone to read this. I am trying to rebuild my confidence after having lost and still not regained it, the best way for me to do that is to journal.

I met a banker a few months ago. He was the CEO of a small bank and very engaging.

I expected him to be a banker and meet my perception of bankers – conservative, risk-averse, do-it-by-the-book type of people.

He was all that. What surprised me was he had one other thing.

He was willing to be creative.

His follow up was excellent and he was engaging (asking a lot of questions about my ideas and business, as opposed to only questions related to finance and accounting).

He was an unexpected swan in a river of ducks.

Which is why I enjoyed working with him and respect him a lot.

Which brings me to the point about the X-Factor.

Most people expect you to play a role and fit their “stereotype” when they interact with you.

For e.g. Sales people are “expected” to be outgoing and gregarious. Engineers are “expected” to be introverted and detail-oriented.

What if your X-Factor is that besides having the expectations of the role or title that’s expected, you also have another trait or characteristic that is unexpected?

Like in the banker’s case the ability to think creatively.

Those are the folks who are highly valued, I think.

Screwing up

I did screw up. Cant’ say no. I hurt people who trusted me, believed in me, and now are besides themselves. Unfortunately I cannot talk about the details given the legal circumstances, but I truly apologize.

I am sure most people cannot forgive me. Unfortunately throughout my career, I hurt many people either because I was blunt or because I was mean spirited.

I own my mistake, and now I have to course correct. Seeking help is what I am doing. I think the road ahead, though, will be very long.

If you have been trying to reach me, I apologize for not returning your email or WhatsApp note, text or LinkedIn message. I just don’t know yet how I can face or talk to anyone. Most days are filled with tears, reflection and a series of questions about “Why” or “What prompted this”?

Until I can answer those questions, I will have to keep to myself.

I am truly sorry. I don’t ever expect things will be back to “normal” again for most / all of you. I don’t blame you for it at all. I am not taking the high road. I know it is very hard to recover from breaking trust.

I have to now over correct to the other side and fix myself for the sake of others who I have to help.

What matters? SKILL OR LUCK – a thesis paper summarized

In 2013, I read a paper by Credit Suisse – Alpha and the paradox of Skill. In the podcast “How I built this” – the host Guy Raz interviews successful entrepreneurs and ends with the question “Do you believe your success was luck or skill and hard work”? If you look at summary of answers to that question, successful people attribute 60% to luck and 40% to skill – on average.

Back to the paper on paradox of Skill. The summary of the paper in one quote:

In investing, as in many other activities, the skill of investors is improving on an absolute basis but shrinking on a relative basis. As a consequence, the variance of excess returns has declined over time and luck has become more important than ever.

Credit Suisse, 2013

To be clear there are opportunities for skill to shine. Those are opportunities where “game” is played by people with lesser skill.

The main lessons are that sometimes it’s more important to worry about the game you’re in than the skill you bring.

Summary of the REMITTANCES market Worldwide and key players

The WSJ has a piece today about the worldwide remittances market. It is roughly $554 Billion worldwide with the top recipient countries (no particular order)

  1. India $46B (from US, Dubai and Saudi Arabia), 3% of GDP
  2. Mexico $38B (from US primarily), making up 3% of GDP
  3. China $24B (<1% of GDP)
  4. Pakistan $11B (8% of GDP)
  5. Philippines $20B (10% of GDP)
  6. Guatemala $10B
  7. Vietnam $12B
  8. Bangladesh $15B
  9. Ukraine $11B
  10. Egypt $9B
  11. Nigeria $8B

The market was largely owned by Western Union, but now a host of startups are in the space including:

  1. Transfer Wise
  2. Xoom
  3. Remitly
  4. Money Gram
  5. Ria

What is force Majeure and why is it trending on google search?

The impact of Covid19 on several businesses is catastrophic. Many businesses entered into contracts with vendors, suppliers and partners for their business.

In legal terms, “Force Majeure” means a clause that has an “out”, caused by an event or effect that can be neither anticipated nor controlled. You may no longer meet the obligations of the contract since the events (e.g. Covid were beyond any parties control.

A force majeure clause in a contract would typically include an exhaustive list of events such as acts of God. War, terrorism, earthquakes, hurricanes, acts of government, explosions, fire, plagues or epidemics or a non- exhaustive list of events wherein the parties narrate what constitutes these events and thereafter add “and such other acts or events that are beyond the control of parties”.

Can Covid19 be a reason for Force Majeure?

You most certainly should consult your lawyer, but there are multiple startups I know that are reducing their ongoing costs of systems and technologies, by invoking this clause.

So how do we get back to the “new Normal”? #AFterCovid

1 in 10 Americans believe economy will never return to normal from ...

The biggest bottleneck with Covid19 right now is rapid testing and centralized reporting. If we can fix that then we can start to reopen “parts of the quarantine”.

Most data points to the fact that people who are suffering or dying from Covid19 are those who have preexisting medical conditions or poor immunity (old, infirm, etc.).

That is likely between 5% to about 15% of the population. (source)

The rest of the people would likely suffer mild to no symptoms from CoVid.

Instead of allowing them to go about their lives, everyone’s life is being disrupted to ensure the 5-10% dont die.

In no way am I implying that the 5-10% be dammed. In fact we should take more precautions to ensure they are safe. Quarantine them, provide extra medical attention, support and safety.

If we had a quick (say < 15 minutes) way to test Covid and an easy way to aggregate the data and report it to local, regional or central authorities, then those who dont test positive could be allowed to go on with their lives.

So how does this play out?

Imagine 5-10 startups that are all innovating on “rapid test” with reagents from your home. They send you a kit (pack of 12 test kits), you take the test and test results are uploaded to a service via your phone. If the test is positive, you have to quarantine. If the test is negative, you can go to “work” or elsewhere. Assume the tests will be valid for some short period – maybe a day if you are in a high exposure role (e.g. nurse) or once a week if less so (e.g. software developer). This sounds simpler than it is, but bear with me for the sake of argument.

Each kit comes with its own app to upload results, and they are all reporting their aggregate and specific data to local government.

Now public health and other officials know who is and who is not infected and can provide “discerning guidance”, instead of a diktat for the entire population.

Now to the next question: How do we ensure that those that don’t test positive infect those who are old / infirm / or with poor immunity?

More than ever we need the strong and able bodied to help those who are unable.

So the precautions that are recommended by physicians and medical professionals apply more to those that are infirm that those for who this is “like a flu”.

Wash your hands, use masks are all good recommendations regardless of whether you test positive or not. Everyone should take those recommendations.

Having everyone have their lives upended is hard for 85% – 90% of the population.

Only rapid testing can solve that for now.

Thanks to Bal for helping me think through this.