Last Day Celebration! Photo courtesy @KahneRaja.

Epic 3 of my Pivotal odyssey starts today

TL;DR. Today begins Epic 3, in which I will apply lessons from my Pivotal decade to build solutions for social good. Epic 2 ended on March 17, 2017, my last day as a Pivotal employee. I wrote about Epic 1 here.

I’m so grateful to Rob, Edward, Siobhan, Bill and Andrew for embracing my exploration inside Pivotal, then for gently closing the door at the right time.

Sometimes you don’t get perspective until you can see it from the inside.

It is as if we are in the early Renaissance, when a tidal wave of new technologies and methods enabled new social organizations and governance models to emerge in stark contrast to feudalism, ultimately bringing about the end of the Medieval era. Today, ‘next generation’ tools — the Internet, open source software, agile and cloud — have empowered a new mercantile class to prosper and grow, forcing ‘legacy’ enterprises to defend territory and mind share. As in the early Renaissance, savvy leaders seek to adapt to survive but often confront the resistance of their people, especially in the middle management. Now, the front lines have moved inside the fortress walls of the largest companies in the world — and government — pitting next generation against legacy in what too often feels like hand-to-hand combat in a war of attrition.

My 14 months and 14 days inside Pivotal made me an advance scout, a tactician and strategist on the front lines. I touched nearly every part of Pivotal: PCF (Pivotal Cloud Foundry, Pivotal’s flagship product) sales and engineering; data sales, engineering and services; transformation services; Pivotal Labs; HR and legal. From my vantage point in transformation services and later in sales, I participated in the titanic efforts of the world’s largest companies to transform organizations, business processes and technology.

12 observations:

  1. Continuous improvement for the benefit of end users is the ultimate goal ; winning and retaining end users creates competitive advantage. Innovating for the benefit of internal end users may be as important as for customers.
  2. User experience innovation is reaching its natural limits without investments in innovation at the mid-tier and back-end.
  3. Refactoring or re-platforming legacy systems can provide value to next generation; this approach also suggests strategies for decommissioning legacy software monoliths and mainframe systems.
  4. No system other than Pivotal Cloud Foundry can better enable the largest global enterprises to innovate with the speed, scale and sustainability of Silicon Valley startups. It’s like asking if it’s faster and more reliable to travel by building a railroad or riding a railroad. PCF is the railroad. Ride it.
  5. But PCF alone will not bring about innovation; cultural transformation is an absolute requirement.
  6. Attaining the owner-operator mindset is at the heart of transformation; ownership by the individual is the most difficult mindset change.
  7. Transformation is never done.
  8. Technology transformation requires three roles that may not exist in an enterprise— product manager (PM), product owner (PO) and technical program manager (TPM) — and reinvention of the software developer and operator roles.
  9. Co-existence of next generation with legacy systems, organizations and waterfall processes is necessary but will only succeed with fully-enabled TPMs performing at the highest level.
  10. Unlocking the full potential of next generation requires the business to assume their rightful place as active stakeholders in technology.
  11. Successful transformations will work backwards from a vision of that success, then will march forward informed by data.
  12. Liberal arts skills have never been more important in technology, including story-telling, contextual awareness, communications, empathy, analysis and systems thinking.

Sometimes you don’t get perspective until you can see it from the outside.

This is my 20th year since my first software startup. Over these two decades, I have been part of 13 tech startups, 2 incubators, 3 startup non-profit programs, 4 non-profit/government Boards, 2 startup broker-dealers. I’ve sold 3 companies, failed 4 times, built dozens of software products, advised countless entrepreneurs, hired over 100 people, helped raise tens of millions in funding, and mentored dozens of people.

10 years ago, I met Rob, who showed me the Pivotal way. I bought it hook, line and sinker, and then some. I embraced Pivotal’s model for software development using the tenets of extreme programming: pair programming, CICD (continuous integration, continuous delivery), TDD (test-driven development) and DevOps and instilled it in my startups. Pivotal helped me build the product manager capability; I built the product owner and technical program manager roles. Together, we built 3 projects: Cookstr, Casebook and NYC Votes. Each successfully integrated with legacy/waterfall systems. Today, Casebook and NYC Votes continue to support mission critical government functions that re-imagined delivery of government services. These have been the most satisfying achievements of my professional life. I can say without exaggeration that these successes would have been impossible had I not met Pivotal. I will be forever grateful.

When I joined Pivotal as an employee, my friends thought that was such an obvious move. But in hindsight, it differed significantly from anything I’ve done in over 20 years.

Sometimes perspective requires you to leave.

I am grateful for my time inside Pivotal, since it brought what I do into stark relief: I build products that solve meaningful problems. I build mission-driven organizations that unify people to solve those problems. I try to elevate everyone around me by being a connector, an advisor, a mentor and an advocate.

My advice often starts here:

  1. Find a meaningful problem to solve.
  2. Surround yourself with great people.
  3. Make sure you have sufficient resources.

Time to take this advice.

Former 2021 Democratic Candidate for NYC Mayor. Reform activist. Technology innovator. Writer, thinker, strategist, photographer. Opinions are my own.