Uncappd Insider

Beyond the spreadsheet, a comp plan is a story reps either trust or don't.

Winnie Maignan, VP of Sales Compensation at McKesson, sits with Siva on Uncappd Insider for the comp plan conversation most teams aren't having: AI's real role in comp, the SPIF ceiling rule, the 30-day audit, and why low rep attrition can be a red flag.

Presented by: Everstage • Uncappd Insider Podcast
Guest: Winnie Maignan, VP Sales Compensation at McKesson
Host: Siva Rajamani, CEO & Co-founder, Everstage

If you design comp plans, run RevOps or Sales Ops, manage SPM or ICM, or sit closer to the CRO than the spreadsheet, this is your masterclass on what separates a comp plan that ships from one that survives the year. Winnie shares the five data points she pulls in her first 30 days at any new comp role, where AI earns its keep in comp planning and where it absolutely does not, the comp plan red flags hiding inside healthy-looking metrics, why sales comp is a year-long cycle, not a Q3 sprint, and more.

Join Uncappd - an exclusive sales comp community with over 700 professionals from Notion, Anthropic, Klaviyo, PepsiCo and more.

Chapters
00:00 - Intro: why this conversation matters
2:12 - Winnie and Sales Compensation
4:55 - Factors defining the success of your sales comp program
6:10 - Minimizing gaps 
6:53 - Keeping your plan relevant through the year 
7:45 - Customer experience in sales compensation
9:37- Cross-functional collaboration - organized chaos?
12:41- When & where AI works in sales compensation
16:22- Thriving in a sales compensation role
18:35- Bring value to the table
20:34- Communications as a sales comp strategy
24:20- Stepping into a new company? Look for these signs
27:00- Top data points to watch out for
28:36- Low attrition- a red flag 
30:03- Territories as a metric
30:48- Cost of compensation
32:32- Sales comp as a year-long cycle
33:39 - Mid-year plan changes
35:44- Designing your SPIFs 
36:40- Final thoughts
42:42- Inside Uncappd

What does it take to design and run one of the world’s largest sales compensation organizations, paying out nearly half a billion dollars in commissions?

In this episode of Uncappd Insider, we sit down with John Lee, Senior Director of Sales Compensation at LinkedIn, who leads a team that manages compensation for 5,000+ sales reps.

Presented by: Everstage • Uncappd Insider Podcast
Guest: John Lee, Senior.Director of Sales Compensation, LinkedIn (   / johnlee49ers    )
Host: Shiva, CEO & Co-founder, Everstage  (  / sivasrajamani    )

If you’re in RevOps, Sales Ops, or SaaS leadership, this is your masterclass on how sales comp becomes a growth engine. John Lee shares 25 years of lessons from spreadsheets to AI agents on scaling compensation systems, driving growth, and turning governance from red tape into trust.

Join Uncappd - an exclusive sales comp community with over 700 professionals from Notion, Anthropic, Klaviyo, PepsiCo and more.

YouTube Chapters
00:00 – Intro: The hardest part of building a modern revenue engine 
02:20 – From analyst to architect: John’s journey into sales comp 
05:10 – From spreadsheets to systems: the rise of cloud-based comp 
08:55 – Designing plans that drive the right behavior 
10:30 – How LinkedIn scaled comp for 5,000+ reps   
14:45 – The art of agility: how priorities shift during the year   
22:00 – Building one of the largest global comp teams 
27:20 – Inside LinkedIn’s comp org structure 
32:00 – Building resilient systems and processes   
37:40 – AI in sales comp: the first inning 
38:30 – How John’s team uses AI agents to flag and automate 
40:20 – Why AI won’t replace judgment—it’ll scale it 
44:30 – What future leaders in sales comp need to master 
48:10 – Storytelling and stakeholder influence as core skills 
50:30 – The biggest lesson learned in 25 years 
52:00 – Why execution beats perfect strategy 
56:40 – Lightning round: metrics that matter 
1:00:20 – The most underrated enablement artifact   
1:04:00 – Closing analogy: run comp like a Michelin-star restaurant

John Waldron is currently the Total Rewards Director, Global Compensation at PepsiCo. He is a time-tested veteran in sales compensation with over 27 years of experience across multiple roles in sales management, sales operations, and sales compensation.
This episode of the Uncappd Insider features John, where he shares about:

• His unique journey from a sales rep to a global sales leader
• Advice for novice sales compensation professionals
• New-age trends in sales compensation to keep an eye out on

Connect with John Waldron
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David Miller is currently the Sr. Manager of Global Incentive Compensation at Integrated DNA Technologies. With over 15 years of experience spread across 3 decades, he is a seasoned veteran in sales compensation.
This episode of the Uncappd Insider features David, where he discusses:

• The role of technology in shaping sales compensation
• Tips for upcoming sales comp professionals for career growth
• The changing landscape of sales compensation and the opportunities in it

Connect with David Miller
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Ryan Wheeler is currently the Manager of Sales Compensation at Altus Group. Previously, Ryan was a Senior Sales Compensation Analyst at Rapid7, a software technology company based out of Boston.

In the latest episode of the Uncappd Insider, Ryan talks about:

• Transitioning from business development to sales compensation
• Tips for novice sales compensation professionals for career growth
• The challenges and new age approaches in sales compensation

Connect with Ryan Wheeler
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Tatiana Silverman is the Director, Compensation and HRIS at Transportation Insight. Previously, Tatiana was an Assistant VP, Risk Analysis & Specialist II at Bank of America and also held positions at Bank of America Merchant Services, Siemens, InComm Payments, DeVry University, and E*TRADE. She is also a co-founder of DRG Group, a sales compensation and performance management administration.

In the latest episode of the Uncappd Insider, Tatiana discusses:

• How sales compensation acts as a liaison between leadership and field teams
• The ideal skillset required for potential career growth
• The current challenges and future trends in sales compensation

Connect with Tatiana Silverman
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Leo Rocha is the Head of Incentive Design & Governance at Moody's Analytics. With over 16 years of corporate experience in sales compensation, incentives, rewards, consulting, and project management across various industries and markets, Leo is passionate about understanding how incentives influence behavior and drive performance. Leveraging his analytical, problem-solving, and communication skills, he delivers effective and innovative solutions for his clients and stakeholders. Prior to Moody's Analytics, he held key positions at Equifax and IBM, spearheading the global incentives/sales compensation team.

In the latest episode of the Uncappd Insider, Leo discusses:

• The best practices in Sales Compensation, drawing from his vast experience.
• The nuances of Sales Compensation and outlining potential career trajectories.
• The contemporary challenges and essential considerations to address pressing issues in Sales Compensation.

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Dan Johnson is an experienced Sales Compensation professional with a demonstrated history of working across various business functions to design, deliver, and execute motivational sales compensation plans. Currently, he holds the position of Senior Sales Compensation Manager at FullStory, where he leads the sales commission team, focuses on process excellence, and builds rewarding commission plans for the GTM teams. Dan has accumulated over 20 years of experience in sales compensation and has previously worked at BD and Microsoft.

The latest episode of the Uncappd Insider features Dan Johnson, during which we discuss:

• How collaboration is the key to Sales Compensation effectiveness: How do you actually get all those different individuals to collaborate?
• The various intricacies of Sales Compensation and what the career trajectory looks like.
• Modern-day challenges in Sales Compensation and the key pressing issues everyone needs to consider.

Connect with Dan Johnson
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