Monetizing SaaS: Episode 19 with Tim Olshansky, CPTO & Founder

Tim Oshansky, a serial founder and technology leader, shares his career journey and experiences in various industries, including derivatives trading, construction technology, and restaurant technology.
He discusses the importance of reducing friction in product, buying, and commercial aspects of a business. He also explores the complexity of pricing and packaging in B2B software and the challenges faced in implementing a flexible and scalable framework.
The conversation explores the importance of data flow and integration in pricing and packaging management, as well as the use of feature flags and entitlements. It highlights the challenges of implementing standardized monetization infrastructure and the trade-offs between speed and correctness.
The discussion also touches on the need for clear boundaries and decision-making processes in product offerings, as well as the separation of emotional reactions from rational decision-making. The conversation concludes with advice for product and engineering leaders at growth-stage SaaS companies.
Takeaways
- Tim has had a diverse career journey, working in derivatives trading, construction technology, and restaurant technology.
- Reducing friction is crucial in product, buying, and commercial aspects of a business.
- Pricing and packaging in B2B software can be complex due to the lack of structure and the need for short-term decisions.
- Implementing a flexible and scalable framework for pricing and packaging is essential for long-term success.
- Tight integration in data flow between Salesforce, product, and user analytics tools is essential for effective pricing and packaging management.
- The use of feature flags and deployment flags allows for decoupling deployments from releases and enables more effective launch strategies.
- Entitlements, both in terms of security and pricing, are important for managing user access and monetization.
- Building a consolidated platform that combines billing, usage, product data, and CRM is crucial for leveraging data in all aspects of the business.
- Early decision-making on product boundaries and a clear catalog of offerings can simplify implementation and avoid future challenges.
- Separating emotional reactions from rational decision-making is critical in high-pressure situations, and having predefined processes and rules can help mitigate risks.
- Product and engineering leaders should prioritize building a strong data infrastructure and incorporating relevant tools and products to support monetization efforts.
Sound Bites
"Software is eating the world."
"The natural friction between product and engineering"
"Opportunity in well-established markets"
"Tight integration in data flow between Salesforce, product, and user analytics tools."
"Using feature flags to decouple deployments from releases and partner with marketing and customer success."
"Entitlements refer to what users can do or what customers have access to within a product."
Chapters
00:00
Introduction and Career Journey
17:19
The Changing World of Business and Economy
22:39
Reducing Friction in Business
25:47
The Complexity of Pricing and Packaging
28:51
Data Flow and Integration
32:45
Entitlements and User Access
35:08
Building a Consolidated Platform
38:29
Speed vs Correctness in Implementation
43:37
Early Decision-making and Clear Boundaries
51:43
Separating Emotional Reactions
54:38
Advice for Product and Engineering Leaders