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Why I left being CTO of The New York Times, joined a startup, and am pledging 20% of my equity to charity

As The New York Times’ chief technology officer, I had a crucial role in guiding the company’s successful transition to digital, and an opportunity to work with and learn from some of the most talented journalists and software engineers in the world. It’s undeniably one of the world’s most influential institutions doing work in the public’s interest, and has been since 1851.

I love The Times and its vision, and cherished my four years there. But, there was something missing in my career. I had been in CTO roles at four major media companies, with accomplishments I was proud of. However, I didn’t want my 3 year old son Fitz Raj to know me for only being a successful corporate executive, but for accomplishing something significant for the greater good.

So I took a leap: A couple of weeks ago, I left The Times to join Vinit Bharara and fellow Times alum Paul Smurl at Some Spider–a startup creating a network of brands dedicated to community, content and commerce. In many ways my move is not surprising. Throughout my career friends and colleagues asked me why I hadn’t “done the startup thing yet.” People saw me as an entrepreneur inside and wondered why I hadn’t already become one.

However, until I met Vinit and Paul, I hadn’t come across a company with all the right ingredients. The most important thing about a startup, even more important than the idea, is the team that supports it. An idea evolves over time, the product and business pivot as the environment changes, and the technology improves and gets disrupted. But throughout, the people make all the difference between success and failure. Both Vinit and Paul share a dedication to building an outstanding team, which is a large part of why I chose to become invested in the company’s vision.

The people also make all the difference when it comes to giving back, and working for the greater good.

Dr. Krishna Chandra Pant (Rajiv Pant)
Dr. Krishna Chandra Pant (Rajiv Pant)

My grandfather, Dr. Krishna Chandra Pant, was a doctor under British rule in India. As the chief medical officer (i.e. the only doctor) at an institute in Mukteshwar, his job was to only treat the (mostly British) employees of the institute. But he knew no borders when it came to helping the sick and injured. There was no other doctor for more than 50 miles, so he welcomed all patients who came to him and he gave them the same treatment. His British employers didn’t appreciate that, and a drawn out lawsuit ensued. The courts finally ruled in his favor and he prevailed in not only keeping his job, but also in gaining the formal authority to treat all patients equally.

He continued his medical practice out of the family home long after his formal retirement. I remember he used to treat poor patients without charging them fees. He would even give them the medicines free of charge.

In 2014, the World Economic Forum selected me to join its Young Global Leaders community. I didn’t realize at the time the impact it was going to have in my life. I thought it was simply another award. But I met exemplary leaders like Ayesha Vera-YuAnalisa BalaresPardis SabetiLorna Solis, and others who have dedicated themselves and already accomplished more for the greater good of humanity than I could imagine accomplishing in a lifetime. I realized that YGL wasn’t really an award for past accomplishments, but an invitation to start a new journey committed to help make the world a better place.

We should challenge ourselves to make the world a better place
in the ways that we can.

Making the world a better place is no small feat. Last year, when the Ebola epidemic was at its peak, I felt a strong desire to help, but I didn’t know how. I have always admired the organization Doctors Without Borders for the work they do around the world. While many people and organizations claim to work for a greater good at personal cost, people who work at Doctors Without Borders live (and die) by that. In the past, I helped out by giving them small donations here and there, but I wanted to do something more impactful.

My move to Some Spider gives me a chance to use my specific abilities to make a substantial contribution to a cause that I believe in. As a part of my hire, I decided to pledge 20% of my equity to charity, most of it to Doctors Without Borders. This may come as a surprise, especially to those who know me only as a CTO. But just because we have talents in one field doesn’t mean that we can’t be of service in another.

The author and his son, Fitz Raj Pant (Rajiv Pant)
The author and his son, Fitz Raj Pant (Rajiv Pant)

We should challenge ourselves to make the world a better place in the ways that we can. For the doctors serving overseas, their commitment may be their life. For me, it’s dedicating myself to a company that shares my vision, and dedicating part of the reward from being at that company to the people on the ground who can make a difference where I can’t.

My grandfather passed away before I could make him proud. I pray that I am able to do something for this world that fills his great-grandson with pride.


Follow Rajiv on Twitter. This essay was originally published in Quartz.

Joe Adamo, VP, Digital Technology at Tribune Publishing Company

Joe Adamo shared this recommendation for Rajiv on June 23, 2016 via LinkedIn:

I was fortunate enough to work with Rajiv for the past year.

He’s a highly intelligent individual, an inspiring leader, and a brilliant technologist. He’s able to understand and provide recommendations on correcting complex technical & organizational issues quickly.

He was a great addition to the team, and it was a pleasure working with him.

As VP, Digital Technology at Tribune Publishing Company, Joe reported to Rajiv.

Megan Garvey, Deputy Managing Editor at Los Angeles Times

Megan Garvey shared this recommendation for Rajiv on Jun 15, 2016 via LinkedIn:

Rajiv is a sharp manager who does his homework before making decisions. He was able to assess a complicated technological infrastructure and get things changed for the better quickly. He listened, acted and brought in top-notch engineers to help us, cutting through years of delayed requests. He understood newsroom culture, recognizing and supporting good ideas that came out of the newsroom. He was a great partner and it was a pleasure to work with him.

As Deputy Managing Editor at Los Angeles Times, Megan worked with Rajiv.

Paul Smurl, COO & President at Some Spider LLC

Paul Smurl shared this recommendation for Rajiv on May 31, 2016
via LinkedIn:

I worked with Rajiv at The New York Times for five years and then recruited him away to join a start-up as CTO and Chief Product Officer. He is a student of the latest technologies, a master of group dynamics and motivation, and beloved by his teams. Among many examples at NYT, he arrived during the paywall implementation and dove in immediately. He deftly juggled team conflicts, technical quagmires and epic expectations. We could not have launched on time or on budget without him. At Some Spider, he was instrumental in putting the original plan together, overseeing a major CMS migration, and making introductions to potential investors. And he continues to act as an advisor to us today.

As COO & President at Some Spider, LLC, Paul worked with Rajiv. Previously, Paul was Head of Product at The New York Times.

90 Day Plan for a CTO in a New Job

This is a checklist for a new CTO, head of Product, or leader in a similar role starting in a new job. It is meant to kickstart continuous improvement in your product engineering organization. I encourage you to take a scientific test and learn approach to everything you do. You should customize this template based on your own experiences over time. If you find it helpful, please feel welcome to send me additions and improvements to this list.

Repeat the following seven steps iteratively to make incremental and continuous improvements.

1. Understand your job. Learn the organization and industry you are in.

  1. Make a list of the areas you are responsible for. These are likely to include:
    1. Technology: Software Engineering, Infrastructure Engineering, DevOps, Cyber Security, Systems Operations, Application Support
    2. Product: Product Management, Project Management, User Experience, User Interface Design
    3. Data: Data Science, Data Engineering, Data Visualization
  2. Review what it takes to be an effective Chief Technology & Product Officer.
  3. Create a mind map of culture, technology, and operations parts of your CTO job.
  4. Meet customers, executives, stakeholders, colleagues, and team members.
  5. Connect with a network of your peers outside your organization.
  6. Get feedback.
  7. Collect, compile, and synthesize information into knowledge.
  8. Check: How are we doing in relation to our existing metrics for success?
  9. Identify common themes, patterns, and problems.
  10. Consider retaining the services of an executive coach.

2. Define and revise measurements for success.

  1. List metrics for the success of the company as viewed by shareholders.
  2. Prioritize metrics for the success of the teams you manage and how they relate to the metrics for the success of the whole organization.
  3. Determine: What metrics are no longer a priority?
  4. Determine: What new metrics do we need to add?

3. Articulate your vision and strategy.

  1. Clearly communicate it to customers, executives, stakeholders, colleagues, and team members. On a regular basis.
  2. Meet regularly with your team members, peers, executives, stakeholders, customers, partners, and vendors. Human relationships and face to face communications (when feasible) are essential.
  3. Host regular 1:1 meetings with your direct reports, at least once a week. team members
  4. Host regular all-hands meetings and communications. Monthly all-hands for staff less than ~100 people depending on space. Quarterly all-hands for staff more than ~100 people, depending on space. Encourage your departments to hold regular all-hands meetings of their own.
  5. Host regular social, relationship building events and activities. For example, a monthly celebration event to mention professional and personal milestones that people want to share.
  6. Implement processes to have productive business meetings.

4. Organize people for success.

  1. Reorganize teams and redeploy people.
    1. Ensure that your organizational structure factors in products, stakeholders, and career growth needs of your team members.
    2. Here is an example of a technology team organization for media companies.
  2. Reinvigorate people.
    1. Implement managerial and technical career tracks.
    2. Standardize titles while still retaining flexibility, and fun.
    3. Consider that career pathways are not linear.
  3. Recruit talent.
    1. When feasible, interview people by putting them to work.

5. Build culture.

  1. Align team members towards common good, shared goals.
  2. Ask team members how they are doing. Are they happy in their jobs? Are their jobs exciting, challenging, and rewarding?
  3. Solicit advice, including leadership advice from your colleagues, regardless of their level or experience. You can learn important leadership lessons from people who report to you. This also encourages your colleagues to become leaders.
  4. Remember to thank people when they deserve it.
  5. Implement a performance evaluation and career development system.
  6. Build and maintain a cohesive leadership team. Make it well known that internal rivalries are strongly discouraged and not tolerated.
  7. Encourage good life/work balance, including a sensible vacation policy.
  8. Experiment with ideas to keep the workplace interesting.

6. Revise processes for success & delivery, and suitable for the environment and the times.

  1. Create checklists to help you do your job better (like this one itself). These checklists will also help your colleagues. Encourage others to collaborate on checklists and share them.
    1. Here is a sample one I made about reviewing managed services contracts
    2. and another one for dealing with outages.
  2. Encourage a culture of sharing best practices, like simple personal productivity tips.
  3. Design evaluation scorecards and criteria to justify, prioritize, and classify projects.
  4. Ensure that your project portfolio management system and your people role definitions factor in the need to regularly evaluate and decommission projects and products that don’t make sense to continue.

7. Upgrade technologies.

  1. Pay off technical debt [external link]and continue performance enhancements.
    1. App, site, and service reliability
    2. Automation (QA, deployments, support, etc.)
    3. Performance
    4. Security (e.g. start down the path to HTTPS)
  2. Make each team increasingly autonomous and self-sufficient while enabling collaboration and economies of scale.
    1. For example, by moving to a microservices model, using tools such as Docker, hosted on a cloud service provider (AWS).

Thank you for reading this and for sending me suggestions to make this list even more helpful to others.

This article is mirrored on LinkedIn. It is a part of the ctobook series of articles related to #culture, #technology, and #operations: three critical part of a Chief Technology & Product Officer’s job.

Rajit Gulati, Vice President, Enterprise Products Engineering at BlackBerry

Rajit Gulati shared this recommendation for Rajiv on Apr 15, 2016 via LinkedIn:

I was reporting to Rajiv at COXnet and developed deep admiration for him ever since. He is the type of executive who ensures that the team gets all the credit for successes under his leadership and takes it upon himself to advance careers of each individual in his team. He has this calming influence when everyone is under pressure and is extremely innovative in suggesting product solutions thinking out of the box. I always look forward to opportunities to interact and learn from Rajiv.

As Senior Manager, Software Engineering at COXnet (now Cox Media Group), Rajit Gulati reported to Rajiv.

Robert A. Sauerberg Jr., President & Chief Executive Officer, Conde Nast

Bob Sauerberg shared this recommendation for Rajiv on Apr 14, 2016 via LinkedIn:

Rajiv is a visionary and a great tech leader. He has all the skills necessary to envision , direct, and execute great products. Most importantly, he is a team player and a great communicator. The full package!

As President at Conde Nast, Bob Sauerberg indirectly managed Rajiv.

Mark Thompson, President & Chief Executive Officer, The New York Times Company

Mark Thompson wrote this recommendation for Rajiv on April 13, 2016:

Rajiv is a very strong digital executive with rock solid credentials in both engineering and product, but with great creative flair. At The New York Times, he was a real magnet for talent and built a very strong team. He also showed an exceptional ability to work closely and empathetically with our own journalistic and design creative elite.

Mark Thompson

As President & Chief Executive Officer at The New York Times Company, Mark Thompson indirectly managed Rajiv.

Matthew Bischoff, Mobile Product and Engineering Lead

Matthew Bischoff shared this recommendation for Rajiv on Apr 10, 2016 via LinkedIn:

Rajiv is an incredible leader of technical organizations. His ability at The Times to zoom in and solve small problems one on one with a single engineer without losing focus of the entire team’s goals was unparalleled and the teams he helped build have remained strong long after he stepped away. I can count on one hand the number of people I’d want running my engineering organization and Rajiv is definitely among them.

As Senior iOS Software Engineer at The New York Times, Matthew reported to Rajiv. Matthew subsequently became Product Manager and iOS Engineering Manager at Tumblr before becoming Partner at Lickability, a boutique mobile mobile product development firm.

Leon Shklar, Managing Director at BNY Mellon

Leon Shklar shared this recommendation for Rajiv on Apr 10, 2016 via LinkedIn:

Rajiv played an important role in transforming the technology organization at The New York Times, He succeeded in attracting new talent and made a major contribution to creating a balance between product, editorial, and technology organizations. Rajiv promoted transparency, never set hidden agendas, and was a recognized “force for good” in the organization.

As Vice President of Technology for Ecommerce, Digital Subscriptions, and Marketing at The New York Times, Leon reported to Rajiv.

Hackathon: Impact Journalism in New York

On April 8-9 2016, the Global Editors Network (GEN), The Huffington Post and Change.org will gather the best media innovators in New York for a two-day Editors Lab focused on developing innovative news prototypes.

Theme

Impact Journalism: How can news organizations develop innovative and interactive ways to create impact by connecting audiences with issues they care about?

Jury

Further information at the source: http://www.globaleditorsnetwork.org/programmes/editors-lab/the-huffington-post-and-changeorg-editors-lab/