Robyn Shutak is a Partner at Infinite Equity and one of the sharpest minds in equity compensation. She joins me to talk about what happens when equity stops working the way it was designed to - and whether it was ever designed well in the first place.

We get into underwater equity and the real cost of doing nothing about it. Vesting schedules built for a tenure reality that no longer exists. The gap between telling employees they are owners and what the cap table actually says. Why equity in VC-backed companies functions more like a lottery ticket than an ownership stake. And whether giving employees structured choice within their equity grants can close the gap between perceived value and actual value.

We also explore a harder question: if equity compensation depends on stock price cooperation to feel real, what does that tell us about the instrument itself?

Takeaways

• Underwater equity is not a passive problem - inaction sends its own signal and concentrates retention risk among the people you can least afford to lose
• Vesting was designed to protect the cap table, not retain employees - and there is little evidence it does
• Most employees in VC-backed companies hold less than 20% of shares collectively - calling that ownership is a stretch
• Structured choice within equity programs can increase perceived value without increasing spend
• Equity works best when companies treat it as trust, not control

Chapters

• 00:00 Understanding Underwater Equity
• 42:23 Equity Compensation and Volatility
• 51:21 Employee Ownership in VC-Backed Companies
• 01:20:52 The Skeptical Side of Equity Ownership

ICYMI Kim Minnick, Kim Rohrer, and I lost a debate on pay for performance recently. We were debating against Mark Frein, Jessica Zwaan, and their team captain, Matt McFarlane. The whole thing was moderated by the amazing Jessie Schofer.

So we regrouped to chat about what we might have done better, discuss some of the reactions, and we meandered into other areas too.

We got into the history of how pay for performance became the default - how individualism got baked into compensation design, why corporate culture reinforces it, and what it would actually take to change it. We talked about legal personhood and how the way we define corporate success shapes everything downstream, including how we pay people. We got into bias, social media's role in calcifying bad management orthodoxy, and whether systemic change is even possible given the structures most of us are working inside.

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Stefan Gaertner has been thinking about pay equity longer than most people have known it was a problem. He's a long-time friend, colleague, and one of the sharpest minds in the field - so when I get him on the show, we have a lot to talk about.

In this episode, we get into the uneven global landscape of pay equity legislation and what that patchwork means for multinational employers trying to build coherent compensation programs. We talk pay transparency - what it's actually changing inside organizations versus what companies say it's changing. From there, we dig into the mechanics: point-factor job evaluation, salary band design, and why the methodology underneath your pay decisions matters more than most HR leaders want to admit.

We also spend real time on flat organizational structures and what happens to pay equity when you strip out the career ladder - and whether that's a feature or a bug. Then we close on AI: what it can genuinely do to support pay equity analysis, where human judgment is still non-negotiable, and why handing compensation decisions to an algorithm is a different kind of equity problem.

Chapters

• 00:00 The State of Pay Equity
• 08:06 Pay Transparency's Real Impact on Business
• 23:06 Point-Based Job Evaluation Systems
• 34:47 Salary Bands and Pay Fairness
• 43:03 Flat Structures, Career Decisions, and Pay Equity
• 1:10:33 AI's Role in Pay Equity

Luke O'Mahoney is the founder of SapienX, a platform of content, courses, and community for what he calls the "post-HR generation." His central argument is that People teams should operate like Product teams - designing, measuring, and iterating on the employee experience rather than administering it through siloed functions.

We dig into the limitations of the Ulrich model - the framework that split HR into Business Partners, Centers of Excellence, and Shared Services decades ago and has dominated ever since. Luke makes the case that those silos have produced systems that serve the function rather than the people, and that product thinking offers a way out.

We explore the Jobs to Be Done framework applied to HR, the difference between enabling performance and trying to drive it, and why reverse engineering problems matters more than jumping to solutions. I push back on some of the measurement assumptions embedded in product thinking and whether it risks falling into the same traps that broke performance management.

Whether you're a People leader feeling like the current model isn't working, or a compensation professional wondering why your systems aren't producing the outcomes you expected, there's a lot to chew on here.

Contact Luke O'Mahoney:

LinkedIn: Luke O'Mahoney

Website: sapienx.co.uk

Chapters

• 00:00 Introduction and Post-HR Generation
• 15:42 Adopting a Product Operating Model
• 26:27 Shifting to a Product-Centric Approach
• 33:49 Implementing Product-Centric Thinking
• 45:06 Challenges of Traditional HR Models
• 55:29 Cut the Cape Request
• 01:03:05 Measuring Success
• 01:18:24 Pushing Back and Asking Questions

This episode with Tom Hill goes into the changing landscape of Salesforce effectiveness, highlighting the shift from a transactional role to a more consultative role. It explores the impact of AI and stakeholder management on sales, as well as the shift to team-based decision-making in the sales process. The conversation delves into the challenges of aligning sales with organizational goals, the complexities of quota setting, and the impact of long sales cycles on sales crediting. It explores the need for collaboration, understanding the organization, and the evolution of sales effectiveness in response to changing market dynamics.

Takeaways

• Salesforce effectiveness is shifting from a transactional role to a more consultative role
• The changing nature of sales and Salesforce effectiveness is driven by AI, stakeholder management, and the shift to a team-based decision-making process Sales Quota Setting
• Sales Effectiveness
• Sales Cycle Complexity

Chapters

• 00:00 The Shift to Team-Based Decision-Making in Sales
• 38:52 Aligning Sales with Organizational Goals
• 45:11 Challenges of Quota Setting
• 55:15 Long Sales Cycles and Crediting Challenges

The conversation delves into the complexities of sales compensation, debunking myths about seller motivation, and exploring the challenges of modern sales models. It emphasizes the importance of understanding customer segmentation, sales process, and product-market fit before designing sales incentives. The role of technology in trapping uncertainty and the significance of data-driven quota setting are also highlighted. The conversation covers the negotiation of sales targets, the role of leadership and authority in sales, dealing with big deals, sales plan design and philosophy, and financial modeling and governance. It emphasizes the importance of understanding the struggles of the sales team, treating salespeople as assets, and involving finance from the beginning of the process. The conversation covers the importance of governance in decision-making, the role of Compensation Cost of Sale (CCOS) in sales compensation, the impact of pay mix and plan complexity, and finally, the motivation behind the book 'What Pay Costs' focusing on pay for performance and innovation.

Takeaways

• Understanding the complexities of sales compensation is crucial for effective incentive design.
• The role of technology in modern sales and the challenges of quota setting require a balanced approach to navigate tensions and achieve sales targets. Understanding the struggles of the sales team is crucial for effective leadership
• Salespeople should be treated as assets, not costs
• Involving finance from the beginning of the sales plan design process is essential for successful financial modeling and governance Effective governance is essential for decision-making
• CCOS plays a crucial role in sales compensation
• Simplicity, alignment, and motivation are key in incentive plans
• The book 'What Pay Costs' explores the impact of pay for performance and the importance of innovation

Chapters

• 00:00 Understanding Sales Compensation
• 19:39 Sales Compensation in Modern Sales
• 32:36 Navigating Tensions in Quota Setting
• 38:13 Negotiating Sales Targets
• 44:00 Sales Plan Design and Philosophy
• 51:16 Financial Modeling and Governance
• 01:01:11 The Importance of Governance
• 01:09:34 Pay Mix and Plan Complexity
• 01:20:34 The Book 'What Pay Costs'

In this episode, I wanted to share with you a sample from the upcoming audiobook recording of my book, What Pay Costs. I also wanted to take the opportunity to introduce myself and share a bit about why I started this podcast, and what you can expect to hear.

What Pay Costs and my guide to sales compensation, Nothing Left to Take Away, are both available on Amazon in physical and Kindle editions, as well as on Kindle Unlimited.

In this conversation I pepper Dan Walter with questions about the evolution of equity compensation, highlighting the early days of equity distribution and the impact of IPOs on equity compensation. We also explore the challenges in valuing equity, the impact of high valuations on equity compensation, and the use of equity as a wealth creation tool. We discuss the use of equity as a differentiating component of rewards in the tech industry, the concept of employee stock purchase plans, and the evolution of equity compensation in the tech industry. We delve into the challenges and misconceptions surrounding equity as a retention mechanism and the need for improved communication and education around equity. Finally we explore the historical context of equity, its intended purpose, and the evolving landscape of equity compensation in modern organizations.