Harry Stebbings’ Kill Shot @ Sales

The 10/23 episode of the wildly popular 20VC Podcast was extra juicy and I’m writing about it again, but with a different mission.

Harry Stebbings went Mohammad Ali on Tech Sales: “ if you’re a sharp and insightful person, you’re not going to be an AE.”  Ouch!

But his interviewee, AJ Tennant, VP Sales at Glean and Harvard grad who previously scaled Slack from $6M to >$1B ARR responded “tech enterprise sales has the potential to capture the smartest minds because when you peel back the layers…it’s taking what happens in consulting and IB and actually putting in the work to drive company transformations.  There’s two ways to make impact in a tech company - product and sales.” 

Two main takeaways…

Point 1: Drive Massive Transformations through Sales (not IB/Consulting)

Chris and I work at Metronome and have a front row seat to the greatest technological revolution of our generation - AI.  OpenAI is one of our company’s large customers and they are truly one of the most innovative and fastest growing companies in history. We are a core piece of their mission-critical infrastructure and one of their most valuable vendors because we allow them to test new pricing models to stay ahead of competition in a fiercely competitive market (among many other things).  

How did this partnership start and grow?  Through Sales and a deep understanding of their rapidly evolving needs. 

Seems a bit more impactful than working at JPMorgan’s FIG IB group making pitch slides til 3AM about which one of 1000 RIAs has the best risk-adjusted returns? (yes, my roommate out of college actually did this).  

Point 2: People who Think Outside the Box Get Ahead in Sales

When I started my first stint in sales, I had to build pipeline (duh). 

My company’s founder had hosted a podcast called “How I Grew This” which she used to help generate leads.  Most AEs would slack our founder, “Hey, can you send this note to CXO of ABC company and interview them?”   The ex-banker in me thought, “nah, that isn’t good enough for me.”

Instead, I pitched my founder on why I should lead the interview on the podcast episode.  

My motivations?  First, I was going to put in 10x more work prepping because this was my deal.  Second, this was about much more than a deal - I was personally motivated to do well because I wanted to build relationships with highly successful executives to grow my network and meet smart people.

It paid off - the deep research on the company and my guest enabled me to build a strong relationship with him and he eventually became my Champion.  This was critical because he helped me navigate a complex deal cycle with 15+ stakeholders who were butting heads, and eventually got me access to his CEO, which enabled us to get the deal signed.  

This was a huge win on two fronts: (A) This deal helped me make President’s Club and the top of the leaderboard with basically no previous “traditional” sales background, (B) I went on to do this with several other companies and got to build 1:1 relationships with some very smart C-Suite executives who I still text and ask for advice.  

Bisous, 

Julian

P.S. Here’s a link to my favorite episode with the former CMO of Sweetgreen.  

Please note: nothing in this article is endorsed by Metronome.  These are solely my opinions.