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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.

Luke Vnenchak, VP of Engineering at BuzzFeed

Luke Vnenchak shared this recommendation for Rajiv on August 26, 2016 via LinkedIn:

One thing that stood out in working with Rajiv was his ability to mentor and coach people at all levels. He does not overlook the people side of things and took great care in developing the careers of those working for him. He was very accessible to the entire technology org and genuinely interested in what was working well on my team and others so that he could look to apply those things elsewhere rather than blindly dictating a path forward.

As Executive Director of Technology, Content Management at The New York Times, Luke reported to Rajiv.

Fastly’s Altitude Summit

Rajiv spoke at Fastly’s Altitude Summit in San Francisco. #Altitude2016 was a full day conference featuring technical content and idea sharing about the edge, web performance and content delivery from industry experts. Rajiv spoke from his personal knowledge of a CTO’s role in getting, maintaining, and developing buy-in for infrastructure engineering projects from business stakeholders.

 

Denise Warren, Executive Vice President, The New York Times

Denise Warren shared this recommendation for Rajiv on Aug 5, 2016 via LinkedIn:

It is with strong conviction that I recommend Rajiv Pant. During our work together over four years at the New York Times, his exemplary leadership skills directly contributed to the success of dozens of major initiatives. Rajiv and the teams he built played critical roles in the acclaimed NYTimes mobile apps, the industry leading digital subscriptions implementation and numerous innovative data-driven journalism projects. His expertise in product development, software engineering and technology operations brought our organization to the next level. He consistently displayed strong leadership and deep technical expertise. Rajiv created a culture of collaboration, high performance and productivity. When I joined Tribune Publishing as President of Digital and CEO of East Coast Publishing, I immediately knew I wanted to bring Rajiv on to lead product management, user experience design, and engineering. Not only is he an accomplished product development leader, he is a pleasure to work with on a personal level. He is consistently proven himself to be reliable, collaborative and open minded. His approachable attitude and kindness towards coworkers made him loved by the teams reporting to him as well as his stakeholders. I know many colleagues who have followed him from job to job as he brings out the best in those working with him – creating successes for all. These traits have made Rajiv well respected and a highly sought after CTO in the tech and media industries.

As Executive Vice President at The New York Times and then as President of Digital & CEO of East Coast Businesses at Tribune Publishing, Denise managed Rajiv.

How to be an effective CTO

A CTO’s job combines Culture, Technology, and Operations. Each of the three is necessary; a field of knowledge, experimentation, and learning in itself; and interdependent with the other two. To be successful as a CTO, you need to work on and continually master all three areas. If you’d like to see the responsibilities of a CTO as a picture, here is a mind map illustrating things CTOs are responsible for.

Culture

Culture, as the first part of a CTO’s job is the answer to who you are you as a team. A CTO’s role starts with the culture they develop, evolve, and lead by example.

Culture can be described as people, knowledge, and behaviors in a community connected by relationships, norms, and purpose.

The people in a CTO’s job include internal stakeholders and colleagues, engineering and product teams, partners, and external customers. As CTO, it is your job to foster constructive collaboration among them.

Regular sharing of knowledge among members and teams is essential for a culture to be developed, sustained, and evolved. As CTO, you are accountable and responsible for compiling, updating, and sharing knowledge among your teams, stakeholders, and customers.

Observed behaviors describe your culture as it really is. Talk is hollow if you and your teams don’t walk the walk. If you are in a leadership role, people observe what you do, and learn from and emulate what you do, far more than from what you say.

An article in the New York Times about Google’s findings on what makes teams effective reports: “Norms are the traditions, behavioral standards and unwritten rules that govern how we function when we gather: One team may come to a consensus that avoiding disagreement is more valuable than debate; another team might develop a culture that encourages vigorous arguments and spurns groupthink. Norms can be unspoken or openly acknowledged, but their influence is often profound. Team members may behave in certain ways as individuals — they may chafe against authority or prefer working independently — but when they gather, the group’s norms typically override individual proclivities and encourage deference to the team.”

I recently participated in a week-long Design Thinking workshop hosted by Matter.vc that used various activities to reinforce the critical importance of having norms in a team. The Matter boot camp is valuable because it brings many best practices in product development from successful startups to traditional media companies wanting to embrace lean and agile product engineering. The path to mastery is to practice, test, and learn.

The path to mastery is to practice, test, and learn.

As CTO, you need to appreciate, learn, and apply cognitive science, behavioral psychology, and social science with integrity and in ethical ways to develop a culture of excellence. You must not let a mentality of us-versus-them take root between technology staffers and other parts of the company. Remind yourself and your team members that your allegiance to your whole organization is not less than that to your department or team.

For example, if as CTO, you are resentful of the marketing department and you mock the Chief Marketing Officer and her team, then your team will absorb this poisonous behavior from you. If you disparage your boss behind her back while pretending to be loyal in front of her, your team will learn to do the same to you. If you put the needs and desires of the technology organization ahead of those of the overall organization, then the teams that report in to you are going to act similarly towards your overall technology team. To be a good corporate citizen and team player with your peers is not only the right thing to do, but is also in your self-interest.

A mistake that CTOs sometimes make is that they organize their team and prioritize their work based too much on what they think is best for the company mainly from the perspective of technology.

A mistake that CTOs sometimes make is that they organize their team and prioritize their work based too much on what they think is best for the company mainly from the perspective of technology. This results in their stakeholders not seeing eye to eye with the tech team, and stakeholders complain that “things here take forever to get done.” Whenever you hear something like “work takes ages to complete,” there is a deeper problem underneath: The real problem is that engineering and stakeholders are not on the same page about priorities and are not communicating sufficiently with each other about value, progress, problems, and risks.

You can implement the most suitable rapid development practices (e.g. continuous delivery, agile, and lean startup methodologies) and use the best modern techniques, tools, and technologies (e.g. microservices, machine learning, and magic :-)  ), that deliver projects with great speed, scalability, and success, but if you and your stakeholders are not in sync, things will be perceived as too slow, stubborn, and substandard.

Without a good culture, technologies and products decay and operations fail because people do not do the right things towards the shared mission.

Technology

Technology, as the core part of a CTO’s job, is the answer to what you do as a team.

Technology includes engineering, architecture, data, infrastructure, scalability, reliability, trust, security, privacy, and other ingredients. The specific areas of technology in a CTO’s purview vary based on the organization, its scale, and condition. Here is an example of an organizational structure that worked well for a smaller media company and another that helped a larger media company be successful.

Even though most CTO’s job duties do not include writing code yourself, to be a credible CTO, you need to not only know how to write good software code, but you should also enjoy doing it as a hobby. You must have a passion for many areas of technology combined with a perpetual desire to keep learning as technologies progress.

As CTO, you are the head coach, mentor, and guide to the technology staff. You preside and govern, not dictate or micromanage. You are not a middleman requiring every communication, decision, or solution to go through you. You are sincerely interested, engaged and involved in the work your teams do but you are not an obstacle. You are a connector who links the technology staff with other members of the organization.  You remember that you have two ears and two eyes but only one mouth, so you listen and observe more than you talk. You respect the makers and the managers who report in to you because you are both their teacher and their student.

Without good technology, operations are inefficient and have trouble overcoming roadblocks, resulting in undesirably slow progress and heavy costs. With good technology, there is a strong sense of pride and that helps develop a culture of excellence where recruiting, retention, and productivity flourish.

Operations

Operations, as the integrating part of a CTO’s job, is the answer to how you do your job as a team.

Operations can be described as how and how well things get done and are delivered. Operations span how resources (including costs) are allocated and managed, how processes and systems work, and how trade-offs should be made. They involve managing the portfolio of projects, products, and services; prioritization; and decommissioning and letting go of products and projects.

Any team that does product development, infrastructure engineering, or provision of services needs to be operationally effective. For this, you and your team need to track progress, record data, measure results, report results, compile lessons learned, and implement improvements. Continuously.

Operations are critical to every organization’s success. This is where the rubber hits the road. You can have a wonderful culture and innovative technologies, but if you don’t get projects done successfully, you won’t have the other two for long.

To put the above in context, I am sharing some tips from my recent talk at the Fastly 2016 Summit.

5 Lessons I learned as a CTO in major media companies

To succeed as a CTO or head of engineering, you need to work with the APIs of your fellow human beings

1. Instead of trying to be salesperson, be a friend

  • It is better to win people over, than to sell them your idea
    • Don’t push your solution. Draw others to your solution
    • Don’t pander either. Win over
  • Don’t make B.S. claims about future benefits of the project. Instead, emphasize the purpose and passion
  • Don’t try to falsely attach your infrastructure project to a product development the business has asked for. Present it on its own merit
  • Don’t spend your time as a technologist writing a business justification. Partner with a finance or business analyst to do that
  • Empathize with your business colleagues and help them empathize with you

2. Speak to the heart, not just to the brain

  • Go beyond making a rational business case. Generate excitement about the engineering work
    • Getting true buy-in requires evoking emotion and passion
    • Identify an external enemy
  • Share your genuine fears about potential losses resulting from getting hacked or systems crashing.
    • We are all averse to losses
  • Make it “our” project instead of “my” project. Request business stakeholders to talk about the project to their colleagues’ stakeholders, and bosses. Encourage them to include it in their presentations.
    • By doing this, they make a public commitment to it

3. Leverage reciprocity

  • Deliver successes to the business to build credibility first
    • Before you pitch a major infrastructure project
    • As a new employee, don’t use up your honeymoon credits on a project whose benefits to your stakeholders aren’t as clear
  • When your colleagues ask for something that you don’t value as much, be open minded to them
    • Your colleagues will reciprocate by embracing your ideas if you embrace theirs

4. Don’t be a “middleman.” Be a connector

  • If you are a CTO or senior manager, it is in your interest that your business colleagues know, appreciate, and have direct connections with your teammates
    • Their expertise supports and complements yours
    • They bring additional credibility
    • You make a stronger case as a team

Invite business colleagues to select gatherings of the product engineering teams

5. Regularly discuss your projects and their value with your colleagues

  • Never assume that your business colleagues won’t understand or appreciate technical stuff. Be a translator
  • A critical part of your job as a technologist is to regularly describe what you do and its value to your colleagues
  • …and vice versa. Take an interest in what they do

Where to go from here

So you are about to or have just started as a CTO or other technology leadership position. What’s a practical way to proceed? Here is a template for a 90 Day Plan for a CTO in a New Job.


This article is mirrored at LinkedIn.

Rajiv Pant is managing partner at Solutions at Scale, a technology leadership and management consulting firm that advises established companies and startups. Prior to this, as CTO at The New York Times, he led the development of numerous acclaimed products during his four year tenure. His leadership experience includes Conde Nast, Reddit, and Cox Media Group. Rajiv was honored as a Young Global Leader by the World Economic Forum.

Malu Menezes, Executive Director of Technology, The New York Times

Malu Menezes shared this recommendation for Rajiv on June 24, 2016 via LinkedIn:

I worked with Rajiv at the New York Times while he was VP of Engineering and then CTO.
I was really impressed with his accomplishments during this period – brought with him key executives and placed them in the right positions to modernize the NYTimes Technology organization faster than I ever thought possible. I am incredibly proud of the company the New York Times has become and honored to have witnessed first hand this transformation. I cannot recommend Rajiv enough as a Technology Executive.

As Executive Director of Technology at The New York Times, Malu reported to Rajiv.

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.

Joe Simon, Chief Operating Officer at Encompass Digital Media, Inc.

Joe Simon shared this recommendation for Rajiv on Apr 23, 2016 via LinkedIn:

Rajiv has deep technical expertise and has continued to build his skills and remains hands on even as he’s progressed in his career. Has a good understanding of software engineering and has the ability to both architect as well as operate the solutions he’s created.

He’s good at building and managing teams – from small to pretty large ones, while both retaining and upgrading the skills of the team. He can clearly articulate a vision, motive the team and deliver quality output. Can remain calm under challenging circumstances and create a collaborative and fun culture.

He’s also a pretty good photographer with a great eye and has captured some amazing images. He does pretend to love the theatre – the reader needs to find out why for themselves.

As CTO at Conde Nast, Joe managed Rajiv.
[Rajiv’s note: The “pretend to love the theatre” part is an inside joke.]

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.