Sam Yagan and Lindsay Verstegan worked together as the CEO and CHRO of ShopRunner from 2016 until it sold to Fedex in early 2021. These two leaders worked closely from day one, setting a purposeful people strategy that led to 300% growth during their four years together.

This conversation was recorded as part of Chicago SHRM‘s “HR Strategy Series”. Chicago SHRM is a regional chapter of the Society for Human Resource Management, a global organization dedicated to furthering the HR function and building better businesses.

Time Codes:

(2:28) – What is Shoprunner?
(4:33) – How much did you help scale the business in your 5 years as CEO?
(5:16) – What is it like to take over as the CEO? How do you set the vision and what is your mindset toward evaluating the needs of the business?
(7:40) – How did you come into the picture?
(11:13) – What were the conversations with Sam like when being honest about what you needed and did not want from your position within ShopRunner?
(15:28) – What was going through Sam’s mind as Lindsay set these boundaries?
(17:09) – Defining “People Strategy”.
(23:42) – What was the process like of making DEI a key part of decision making?
(33:04) – How Lindsay was able to add value helping Sam deliver messages to the company that struck a chord.
(34:50) -Hard conversations Lindsay and Sam had as they were building Shoprunner
(39:56) – What was the transparency like with the employees in terms of communication during the pandemic?
(43:09) – Communicating with Values.
(46:38) – Lindsay’s balance of tactical elements while also creating strategy within the HR functions.
(50:34) – How are you pushing peers to help evolve the people strategy in other areas of the business?
(55:42) – What Sam is looking for in an HR partner and what HR listeners can take away to add more value to the leadership team.
(58:29) – Are there any decisions you made that you look back on that were maybe the wrong ones but helped you make better ones going forward?
(1:00:22) – Team dysfunction.
(1:03:48) – Rules for conflict within a team.
(1:08:06) – Questions Sam starts every executive meeting with.
(1:09:44) – How do you help people make the change when they’re committed to DEI in theory but not in practice?
(1:13:13) –  What happens if trust on the executive team is compromised?
(1:16:08) – Wrap Up