Episode notes
In Part 2 of Selling Intelligence, Todd Cassler, Chief Revenue Officer at Wilshire, rejoins Mark Petruzzi and KK Anderson to explore how revenue leaders build organizations that can execute across different buyers, channels, and levels of complexity.
Todd shares his “future back” approach to revenue strategy, starting with the outcome the organization needs to achieve and working backward to align talent, priorities, reporting, and pipeline discipline. He also explains how leaders should approach third-party distribution as a true partnership, giving external sales teams the same support, resources, and accountability they would provide on their own.
The conversation then turns to AI and its role in modern selling. Todd explains why experience, context, and the ability to ask great questions can dramatically increase the value sellers get from AI. He shares how AI can help identify signals and “money in motion” events, allowing salespeople to focus their limited time on relationships and opportunities where change may actually be happening.
Todd also shares his approach to coaching the next generation of talent, why people need to take ownership of their careers, and how investing early in personal development can compound over time.
What You’ll Learn:
- Building Revenue Strategy Backward: How a future back approach connects long-term goals with talent, priorities, KPIs, and pipeline execution.
- Selling Across Different Buyer Tiers: How team structure and specialization should evolve based on organizational size and buyer sophistication.
- Making Distribution a True Partnership: Why third-party sales teams need the same support, resources, communication, and accountability as internal teams.
- Using Leading Indicators to Measure Progress: How activity, pipeline movement, relationships, and business trends can reveal performance before revenue appears.
- Where AI Creates Sales Leverage: How experienced sellers can use AI, context, and better questions to identify signals and prioritize opportunities.
- Taking Ownership of Your Career: Why personal development is the career lever individuals can control and how early investments in learning can compound over time.
Key Topics:
- Future back revenue strategy
- Building teams for multi-tiered buyers
- Generalists versus technical specialists
- Channel sales and third-party distribution
- Pipeline hygiene and KPI measurement
- Leading indicators of sales performance
- AI as a multiplier for experienced sellers
- Identifying money in motion signals
- AI and sales territory prioritization
- Coaching and mentoring emerging talent
- Personal, corporate, and compensation development
- Hiring for attitude and drive
- Curiosity as a leadership skill
Guest Spotlight: Todd Cassler
Todd Cassler is Chief Revenue Officer at Wilshire, where he leads global growth and distribution across wealth management, retirement, alternatives, and data and analytics. With more than 20 years of experience across wealth management, asset management, and institutional advisory, Todd brings a practical perspective on building revenue organizations, developing talent, strengthening distribution partnerships, and using technology to improve sales execution.
Resources & Mentions:
- Book: Never Eat Alone
- Wilshire
- AI for sales and opportunity identification
- Career development and mentorship
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Disclosures:
Recording Date: August 10, 2026
This does not constitute advice or a recommendation or offer to sell or a solicitation to deal in any security or financial product. Except where otherwise indicated, the information contained in this presentation is based on matters as they exist as of the date of preparation of such material and not as of the date of distribution or any future date.
The views and opinions expressed are those of the speaker and do not represent Wilshire as a whole.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Selling Intelligence (formerly Selling the Cloud) is hosted by Mark Petruzzi and Alan Rudolph.