2021 CXO Summit – A Recap

Our 16th Annual CXO Summit convened virtually again this year to highlight the latest insights and innovations on important topics like Data, Cloud, Security, Healthcare, and E-Commerce. Our lineup of speakers included the CEOs of Snowflake, VMware, and eBay, and leading executives from hyper growth companies including Atlassian, ChargePoint, and PayPal. 60+ CXOs from F500 companies attended including AmerisourceBergen, Delta Airlines, GE, Intel, Mastercard, Prudential, Sephora, TIAA, and more. 

3 main themes anchored the event: 

  • The CIO Role is at a Crossroads
  • The Software Supply Chain is Evolving
  • This is the Age of the Consumer 

The CIO Role is at a Crossroads 

“[The modern enterprise] really needs to be enabled and empowered. There is a rebalancing in the relationship between Global IT and the business, and we’re seeing it everywhere.” – Frank Slootman – CEO, Snowflake

The overwhelming sentiment was that the CIO role will go through a rapid transformation over the next 5+ years and the “relevancy” of the CIO role will be scrutinized within many organizations. Speakers suggested the following to adapt for the changes to come:

  • Speak the CEO’s language. Frank Slootman, CEO of Snowflake,
  • Operate knowing that every company will eventually be like a SaaS company. Raghu Raghuram, CEO of VMware
  • Strategy = Processes + Platforms + People. Sri Shivananda, CTO of PayPal
  • Speak the CEO’s language. Frank Slootman, CEO of Snowflake, advised CIOs to present CEOs with solutions and programs that address priority problems or opportunities for the business, or their budgets may be imperiled.
  • Operate knowing that every company will eventually be like a SaaS company. Raghu Raghuram, CEO of VMware, said that CIOs must recognize that there is a software operations shift happening and every company, regardless of industry, will look like a SaaS company at some point.
  • Strategy = Processes + Platforms + People. Sri Shivananda, CTO of PayPal, advised CIOs to think about their strategy in 3 elements:
    • 1) Processes - workflows that are critical to the organization’s success and create a control panel for the team
    • 2) Platforms - technologies that will help enterprises achieve their digital transformation goals
    • 3) People - hiring a best in class team to address today’s modern technology demands (the most important of the three)

The Software Supply Chain is Evolving 

“Cost of goods in the Digital Era reflects how businesses spend on their Software supply chain. This has a number of implications. These days, by the time you react to technology costs, it is too late. You have to design the right architecture upfront. Just like we talk about shift left for development, you have to shift left your thinking around spend, cost, governance, and security. Otherwise, you’ll be overwhelmed with operational problems.” – Raghu Raghuram, CEO, VMware

It is becoming increasingly difficult to account for all the assets within a business and the number of 3rd party partners and technology providers continues to increase. This requires a new software supply chain strategy. Important considerations include: 

  • Move to modern distributed architectures. 
  • De-risk your software supply chain.
  • Embrace rapid and collaborative software development. 
  • Move to modern distributed architectures. There is no longer a one size fits all strategy when it comes to an enterprise’s infrastructure. CXOs must look at both business and technical factors as they evaluate each potential new enterprise application.
  • De-risk your software supply chain. Our panel of CISOs and Heads of Engineering all agreed that attackers have grown smarter and new software supply chains can be easier to attack at scale, with remote work only increasing the attack surface area. They suggested:
    • Being focused on mitigating the risk within easy access targets like customer data, internal libraries, and employees.
    • Knowing the specific risks within your own business environment and working to mitigate them with proactive tools, processes, and training rather than taking a reactive approach.
    • Taking more of a product approach when it comes to Infrastructure Security, App Security, and Compliance rather than treating them as separate pillars.
  • Embrace rapid and collaborative software development. There is a new level of complexity involved in today’s software supply chain ecosystem and now more than ever, communication between security and development teams is a must. Security teams should provide crucial security guidance along a developer-friendly life cycle while serving as a context shop, not a control shop.

This is the Age of the Consumer 

“For us, it’s all about how we use technology to dramatically simplify and take a lot of friction out of the customer experience“ – Jamie Iannone, CEO of eBay 

Consumers are driving the technology transformation agenda across every industry and events like the pandemic have escalated this trend. Digitally-native companies that were born in the cloud will have to adapt to release products even faster, while avoiding loss of quality or security while more traditional industries will need to invest in processes and tools that enable product development and keep the loyalty of their customers. If they are not able to adapt they will be left behind. 

We heard from experts in two industries that have been specifically impacted and required to adopt a “consumer-centric” mindset to stay competitive.

  • E-Commerce – Jamie Iannone, CEO of eBay
  • Healthcare – Aneesh Chopra, President of CareJourney and the first CTO of the US Government and Jazz Tobaccowalla, Partner at Boston Consulting Group’s healthcare advisory arm


Jamie Iannone, CEO of eBay, leads the charge for an ecosystem that includes 159M online buyers, 19M sellers and spans 190 countries. eBay has adapted to the consumer by developing a number of technologies to respond to consumer needs and Jamie acknowledged that many of their technology solutions today come from direct feedback within their customer base. 

  • Computer Vision to reduce listing times and improve authentication processes for items
  • AI and Data Science to support real-time pricing for things like collectibles
  • Next-Gen Payment Solutions to create better experiences for buyers and sellers and reduce unpaid items
  • QR codes for items that require more complicated logistics processes

These new technologies have generated more trust from users which has led to newer categories like validating and purchasing rare collectibles (sneakers, watches, trading cards). 


The patient's voice is becoming louder in Healthcare and all stakeholders - healthcare providers, payers, and pharmas - are finally starting to see patients as their true customers. With this shift in mindset, they are becoming more willing to adopt new technology platforms to meet customer needs directly. 

Aneesh Chopra, President of CareJourney and the first CTO of the US Government, talked about the new age we are in as the “Era of Consumer-Designated Networks”. In this era, the patient will have more control over who they choose to obtain treatment from, more control over their patient data, and access to new platforms to drive engagement and flexibility within their healthcare experience. 

Jazz Tobaccowalla, Partner at Boston Consulting Group’s healthcare advisory arm, interviewed two Sierra companies building the next generation of technology solutions for healthcare that will ultimately empower consumers to take control of their own healthcare journey:

Reify Health and Outcomes4Me are among the wave of many new healthcare startups striving to improve the patient experience, saving more lives, and even saving healthcare organizations millions of dollars in the process.

We would like to thank all of our speakers for sharing their insights at the Summit. We will continue to explore these and other topics with our CXO Advisory Board Members. 

If you are a CXO and are interested in joining our CXO Advisory Board, please get in touch at brendon@sierraventures.com. Also, please reach out if you’d like to discuss any of these trends or new ones you are seeing.

Learn more about our Annual CXO Summit.

Brendon joined Sierra Ventures in 2017 and leads business development operations for the firm, including the CXO Advisory Board and Annual CXO Summit. In addition, he partners with management teams in the Sierra Ventures portfolio to accelerate their growth by identifying mutually beneficial CXO engagements, key strategic partnerships, and providing support with analyst relations strategies. Brendon also works with the Investment Team on sourcing and due diligence. Brendon has a background supporting CIOs in the healthcare industry and investors in the Venture Capital & Private Equity sectors through his work at Gartner. Brendon holds a MS in Entrepreneurship and BA in Environmental Science from the University of Florida. Outside of work he’s an avid golfer, traveler, and big Florida Gators fan.

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