Podcast Episode 5 - Kaitlen Kelly

Posted by Bec Turton

From Fashionista to Sales Dynamo: Kaitlen Kelly's Rollercoaster Ride to Success

In this episode, Kaitlen Kelly shares her gritty, behind-the-scenes journey from fashion racks to sales, transforming her initial struggles into monumental triumphs. Packed with raw honesty, this conversation is a treasure trove of practical advice and inspiring anecdotes, making it a must-listen for anyone looking to excel in sales.

Kaitlen’s journey is anything but ordinary. Picture this: she started her career at Nordstrom, interned her way up, and then took a bold leap into the high-stakes world of sales development at Outreach. Despite admitting to being a "crap" salesperson early on, rating herself a mere 3 out of 10, she didn't let that stop her.

Her first sales event was a whirlwind of “robotic” over-enthusiasm, requiring her supporting Account Executive to have to literally pull her away. Fast forward to today, and she's dominating the sales industry as a Sales Leader at Klaviyo, proving that initial awkwardness can evolve into unparalleled expertise - if you know the key steps and attitude you need to overcome it and improve.


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Highlights from the episode:

00:00 - Introduction and background on Kaitlen Kelly's career

10:11 - Kaitlen rating her early sales skills and an awkward sales moment

16:16 - Kaitlen's bold career switch from fashion to sales

31:34 - Kaitlen turns into a robot at her first sales event

39:29 - Developing the mindset to overcome fear and rejection in sales

46:11 - Kaitlen's blueprint to success for new SDRs in their first six months

53:10 - How Kaitlen gets organised, plans and time blocks

1:00:00 - What Kaitlen would do differently if she could start her career again


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