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Decoding Sales

Episode 47: Hiring first GTM hires that last

Decoding Sales

Peter & Alex

Enterprise Sales, Business, Virtual Selling, Sales, Entrepreneurship, Software Sales

520 Ratings

🗓️ 20 August 2025

⏱️ 44 minutes

🧾️ Download transcript

Summary

Send us a text I sat down with Harry and Uddhav from The Inflection Group - the recruiting firm behind successful hires at Coinbase, Pinterest, Snowflake, and more. We dive deep into the biggest startup hiring questions: When should you actually hire your first salesperson? How do you avoid the "halo company" trap?Why do first sales hires fail so often?They share stories from 300+ executive searches and explain why being brutally honest about your startup's challenges actually attr...

Transcript

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0:00.0

Welcome to Decoding Sales, a podcast for an engineer that's Alex Elaine and a sales

0:13.0

that's me, Peter, talk about the art and science of sales. Today, I'm repurposing another one of my

0:19.3

virtual webinars where I hosted Harry and Udof from

0:23.4

the Infliction Group, a search firm specializing and placing go-to-market executives at fast-growing

0:29.5

startups. So let's dive into this one. I'll give an intro for Harry first and then Udof,

0:34.7

and then I'll get into some questions I have pre-built and then we'd love to

0:38.8

also take questions from the audience. Some of you have pre-submitted questions, so we'll try to get

0:44.1

to those as well because I have them up on my screen. So I'll introduce Harry first. Harry is a CEO of

0:49.6

the inflection group. He has nearly a decade of experience in go-to-market search across both B2B and BDC

0:55.5

Ventureback startups. He was previously a top national producer for Michael Page, where he actually

1:02.2

earned five promotions and five years across two locations. He's led over 300 executive searches.

1:08.7

Wow, that's a lot for companies ranging from one million to over

1:11.7

one billion in ARR. So I mentioned they specialize in placing execs for startups, but it's not

1:16.6

just startups because he's worked with clients like gong.io, coinbase, Pinterest, ironclad,

1:22.5

gecko robotics, snowflake, and the list goes on and on. So thank you, Harry, for being on.

1:28.8

He's joined by Udov, who's the first non-co-founder hire at the convention group. He also specializes in

1:35.0

go-to-market leadership, specifically for VC and piggyback tech startups. He jokes that Harry's made the

1:41.7

mistake of hiring him now at three different places,

1:45.9

including one large publicly traded in one boutique company where he's been the top performer.

1:51.8

Earlier, he was actually in growth at Snapchat and Dark Trace,

1:56.3

both of whom have gone to do great things.

1:59.2

And he currently runs a music production company

...

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