Playing to Win! Lessons in Building Pendo Well Past $100M ARR

Build a winning business strategy by being aggressive, prioritizing features with data, and pivoting when necessary, as demonstrated by Pendo's journey from 50M to 100M ARR.

Key takeaways

Playing to win means being aggressive in business decisions, like acquisitions, and not being afraid to make bold choices.
Prioritize features by intersecting platform areas, using data to inform decisions.
Lead by example, being on sales calls and being willing to get hands dirty to close deals.
Don’t get married to your roadmap; be willing to pivot and change directions.
Surround yourself with good people, like COO Hannah Chaplin, who has a similar vision and approach to business.
The CEO plays an always-on role, with no “off” switch, requiring constant energy and commitment.
Pendo’s focus is on building a product-led motion, with a future in digital-led companies.
Data is crucial in decision-making, and having a data scientist on board can provide valuable insights.
The company has grown from 50 million to 100 million ARR, with challenges in messaging and educating users along the way.
Winning mentality is key to success, and being willing to take risks is important.
Todd Olson believes in the importance of being a technologist as CEO, and hiring for specific skills.
Lessons learned from building Pendo include believing in bold choices, playing to win, and being willing to pivot.
The company has made a number of acquisitions, including Receptiv.
The CEO is not directly involved in sales now, but is willing to get involved to close deals if necessary.
The future of most companies is digital-led, with a focus on product-led motion.

Playing to Win! Lessons in Building Pendo Well Past $100M ARR

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