Jen Ayers, COO of a private firm and experienced leader in information security and ops, shares her career journey and insights on building software companies, establishing trust between product and engineering teams, and the complexity of B2B SaaS monetization.

She emphasizes the importance of delivering on commitments, understanding market behavior, and being flexible in pricing and packaging. Jen also discusses the challenges of achieving flexibility in engineering, the need for data-driven decision-making in pricing and packaging, and the formative experiences that shaped her professional career.

Takeaways

- Career journeys are rarely linear, and it's important to embrace the winding path and seize opportunities in different industries and roles.

- Building trust between product and engineering teams is crucial for success, and it can be achieved by delivering on commitments and open communication.

- B2B SaaS companies face complexity in monetization due to different go-to-market motions, billing models, product evolution, and customer customization.

- Flexibility is key in pricing and packaging, and companies should consider the impact on engineering, sales, and customers when making decisions.

- Data-driven decision-making is essential in pricing and packaging, and companies should analyze customer usage and preferences to optimize their offerings.

- Formative experiences, such as discovering new possibilities outside of a structured environment and building trust with visionary leaders, can shape professional growth. Sound Bites

"Deliver on what you say you're going to do. Period. Hands down. That simple."

Chapters

00:00 Jen Ayers' Interesting and Textured Career

03:19 Big Market Inflections in Building Software Companies

07:00 Building Trust Between Product and Engineering Teams

08:47 The Complexity of B2B SaaS Monetization

14:54 Data-Driven Decision-Making in Pricing and Packaging

18:51 Formative Experiences and Professional Growth

Keywords

Jen Ayers, career journey, software companies, trust, product and engineering, B2B SaaS monetization, pricing and packaging, flexibility, data-driven decision-making