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Operators & Delian’s Ramblings

I interview non-founder/VC/CEO operators that make the startup world go round delian.substack.com

Weekly hand curated podcast episodes for learning

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Operators Ep 24: Jen Ong Vaughan (Assembled)

Jen Ong Vaughan is the Head of Sales and Customer Success at Assembled where she joined as the first business hire in 2019, when the company was less than one year old. Prior to Assembled, Jen worked at Stripe for four years in Business Operations, and was a Senior Associate Consultant at Bain & Co before that.  In this episode I talk to Jen about starting her career in Singapore, her time leading the Operations Platform team at Stripe, and how that led to wanting to join an earlier stage company. She also shared strategies that Assembled has used to improve sales and the customer experience, how to figure out pricing, and what gave her confidence in building Assembled from the very early days.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

35mins

20 Apr 2021

Rank #1

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Operators Ep 23: Nik Koblov (Ramp)

Nik Koblov is the Head of Risk and Financial Engineering at Ramp.  Prior to joining Ramp, Nik spent three years at Affirm working as the Head of Bank and New Markets Engineering, and 18 years at Goldman Sachs.In this episode I talk to Nik about the engineering culture at Goldman and how it set him up well for the startup world, why Affirm’s innovative model was such a breath of fresh air, and what got him so excited about Ramp. He shares about the uniqueness and ambition of Ramp’s holistic approach, how the company works to empower its employees, and some benefits over the past year of being remote.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

45mins

5 Apr 2021

Rank #2

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Operators Ep 22: Dan Wright (DataRobot)

At the time we recorded this episode Dan Wright was the President and COO at DataRobot, and was just last week named CEO of the company. Prior to joining DataRobot Dan was the COO (and before that the General Counsel) at AppDynamics.  He also spent two and a half years at Goodwin Law Firm as a technology and venture capitalist lawyer.  In this episode I talk to Dan about how lawyers can get involved in the startup world, some of the mentors he leaned on when deciding next steps in his career, and the value of listening when you’re new to a company. He also shares about the importance of building great teams, the partnership dynamics between CEO and COO, and why he believes DataRobot and AI is changing the world.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

45mins

24 Mar 2021

Rank #3

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Operators Ep 21: Morgan Brown (Shopify)

Morgan Brown is the VP of Growth at Shopify. Prior to joining Shopify, Morgan was the Director of Product Management at Facebook, COO at Inman News, and Interim Head of Growth at Qualaroo and TrueVault.  He also authored the book, Hacking Growth: How Today’s Fastest-Growing Companies Drive Breakout Success. In this episode we talk about his experience at FaceBook and why he chose to leave, what his current role at Shopify entails, and why in retrospect he would have started his career off at a large company. He also shares about his college studies in zoology, his success at blogging, and how his approach has always been to outwork everyone else.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

46mins

1 Mar 2021

Rank #4

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Operators Ep 20: Travis Boyce (Allbirds)

Travis Boyce is the Head of Global Retail Operations at Allbirds. He joined as one of the first 10 employees when the company was less than a year old. Prior to joining Allbirds, he worked in operations and finance at Chobani and in investment banking at Morgan Stanley. In this episode we talk about the strategy behind Allbirds retail locations, how Covid has affected the shipping process for consumer business, and the importance Allbirds puts on offsetting their carbon emissions. He also shares about how his finance background helped him learn to solve problems, the benefits of generalists in the early days of startups, and why he’s happy he waited for the right opportunity. I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

49mins

15 Feb 2021

Rank #5

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Operators Ep 19: Michal Cieplinski (Pipe)

Michal Cieplinski is the Chief Operating Officer and Chief Legal Officer at Pipe, a financing platform.  Michal joined Pipe nine months ago when the company was less than a year old. Prior to joining Pipe, he was the General Counsel at LendingClub and Fundbox.In this episode we talk about Michal’s time being a GC at a public company, how he got involved at Pipe, and launching a company one week before lockdown hit and fundraising completely over zoom. He also shares about his early learnings with venture capital, who he seeks for outside counsel, and why he loves massive amounts of uncertainty.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

1 Feb 2021

Rank #6

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Operators Ep 18: Chris Degnan (Snowflake)

Chris Degnan is the Chief Revenue Officer at Snowflake.  Chris was the first sales hire at Snowflake and has grown his team to over 300 people. Prior to joining Snowflake, Chris worked at Aveksa and Dell EMC for over nine years.  He is also on the board at Clumio.  In this episode we talk about the most difficult product he’s had to sell in his career, his secret interview question and what sold him on Snowflake. He also shares about his fear of failure, how realizing he didn’t want his boss’ job prompted him to make a big job change, and the importance of grit.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

58mins

19 Jan 2021

Rank #7

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Operators Ep 17: Ian Fliflet (OfferUp)

Ian Fliflet is the Chief Growth Officer at OfferUp.  Prior to joining OfferUp, Ian was the General Manager at GameHouse, a computer games company.  He also spent 10 years at Real Networks, a digital media company where he worked in Corporate Development.  In this episode we talk about Ian’s motivation for moving to a higher risk company, why he finds that focusing too much on the minutiae can result in missing big opportunities, and his largest M&A deal to fall through. He also shares his thoughts on the tech space in Seattle back in 2000, how the metrics were able to show him that OfferUp was something pretty special, and why creating value for customers is still the biggest motivator for him.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

47mins

5 Jan 2021

Rank #8

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Operators Ep 16: Emil Michael (ex-Uber)

Emil Michael was the former Chief Business Officer at Uber.  Prior to joining Uber, Emil worked at two other successful tech companies: Tellme Networks (acquired by Microsoft) and Klout (acquired by Lithium).  He also worked for the Secretary of Defense for a term, and started his career with a brief stint at Goldman Sachs.In this episode we talk about why Emil disagrees with the famous adage “great companies are bought not sold”, why he feels that the art of business development is getting lost in Silicon Valley, how he closed an $8B deal in 30 days, and why UberX was the turning point for him. He also shares his thoughts on forming partnerships with huge companies like American Express and Toyota, why we don’t need to get jealous when other people get lucky, and his rationale that Silicon Valley still has the most concentrated ecosystem of tech in the world.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

48mins

10 Dec 2020

Rank #9

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Operators Ep 15: Olivia Chen (Faire)

Olivia Chen is the Product Lead at Faire, an online wholesale marketplace, where she joined as the second full-time hire. Prior to joining Faire, Olivia spent time interning at Barclays and Bain & Co. after graduating from Duke University. In this episode we talk about the myriad of projects that Olivia’s worked on at Faire, the advantages she’s seen come out of remote work, and why more supply is almost always better in a marketplace. She also shares her thoughts on the synergy of working with logical people, why she finds the fast paced world of Faire less stressful than consulting, and how she’s had to scale her communication methods as the company’s grown.I hope you enjoy the show.Full transcript available. Get full access to Operators & Delian’s Ramblings at delian.substack.com/subscribe

37mins

24 Nov 2020

Rank #10