Hannah Willson is the SVP of Sales and Partnerships at Modern Health. Prior to joining Modern Health Hannah led high-growth sales teams at Zenefits, Rainforest QA, and HelloWallet (acquired by Morningstar). She spent more than eight years at CEB (acquired by Gartner) where she was a top revenue generator for seven consecutive years and consistently exceeded targets for renewals and upsells. In this episode we talk about what it was like joining Modern Health as one of the first ten employees, th...
Feb 09, 2022•34 min
Toby Espinosa is the VP of Ads at DoorDash. Toby joined DoorDash as the 70th employee to launch new markets and has grown the business development team from 3 to 75 people. Prior to joining DoorDash, Toby was an investor at Lux and Henry Crown & Co. He is also a lecturer in the engineering department at Stanford University. In this episode we talk about where Toby’s urge to build companies comes from, why he decided to leave the VC world and join DoorDash, and what the company was like when he f...
Dec 07, 2021•49 min
Anand Chandrasekaran is an EVP at Five9. Prior to joining Five9, Anand worked at Facebook, Snapdeal, Yahoo and Aeroprise. He has a Master of Science in Electrical Engineering from Stanford and is currently on the board of Future Group India. In this episode we talk about Anand’s childhood goal of attending Stanford, the early days of enterprise software, and his views on publicly stating goals. We also discuss cultural differences between Yahoo in the US and Snapdeal in India, what Anand learned...
Nov 15, 2021•46 min
Jaimie Buss is the SVP of Commercial Sales, North America at Zendesk. Jaimie is a veteran sales leader with experience selling everything from SaaS to virtualization, storage, and networking. During her first 4-years at Zendesk, she was VP of North America and led SDR/BDR, SMB, Commercial, and Enterprise sales. During her 20+ year sales career, she has held sales and leadership positions at Andreessen Horowitz, VMware, Coverity, Meraki, Coraid and Inktomi. In this episode we talk about Jaimie’s ...
Nov 01, 2021•55 min
Alyson Welch is the VP of Enterprise Sales at Twilio. Prior to Twilio, Alyson was the Head of Sales at Zignal Labs, an early stage startup specializing in real time media intelligence, and also spent 15 year at Akamai Technologies. She has been an advisor at First Round Capital and Bessemer Venture Partners. She currently sits on the Board of Directors for Girls in Tech, and also founded Poppy, a financial wellness organization for women. In this episode we discuss Alyson’s timing of joining Aka...
Oct 18, 2021•40 min
Ben Braverman is the Chief Customer Officer at Flexport. Prior to becoming the Chief Customer Officer, Ben was the Chief Revenue Officer at Flexport. He also worked at URX as the Head of Growth and at HeyZap as their Director of Sales. In this episode we cover a wide range of topics including Ben’s decision to drop out of college and pursue Buddhism in India, meeting Flexport CEO Ryan Petersen at the dog park, and the ramping-up process Ben went through to learn the freight forwarding industry. ...
Sep 20, 2021•47 min
Denise Persson is the Chief Marketing Officer at Snowflake, where she’s been for the last five years. Prior to joining Snowflake, Denise served as CMO for Apigee, an API platform company that went public in 2015 and was acquired by Google in 2016. She also built and led a global marketing organization at Genesys through their expansion and successful IPO. In this episode I talk to Denise about the impact of marketing automation, the craft of sales, and her various expertise across marketing disc...
Aug 23, 2021•45 min
Dod Fraser is Vice President at Opendoor, which he joined right after the company closed their Series C. Prior to joining Opendoor, Dod was an Associate at TPG and Perry Capital. In this episode I talk to Dod about his initial ambitions in medicine and how that changed, his time at TPG and why he left for Opendoor, and the importance of underwriting standards. He also shares about why in the lending industry he’s always looking at the downside, his observations on the IPO process, and some surpr...
Jul 12, 2021•49 min
Jeanne DeWitt Grosser is the Head of Americas Revenue & Growth at Stripe. Prior to joining Stripe, Jeanne was the CRO at Dialpad and also spent over seven years at Google. In this episode I talk to Jeanne about her aspirations early on to be a global leader, how she thinks holistically about business, and what Google was like before it had a contacts list and still needed an invite to open an email account. We also discuss what it was like joining Stripe at 400 people, growing her team from 10-3...
Jun 22, 2021•46 min
Nilam Ganenthiran is the President of Instacart. Prior to joining Instacart in 2013, Nilam was a Management Consultant with AT Kearney’s Consumer Retail practice, and also worked in shopper marketing and brand management at Proctor and Gamble. Nilam is a graduate of York University’s Schulich School of Business and also holds an MBA from the Harvard Business School. In this episode I talk to Nilam about how he found the sales and marketing career path, why he thought he’d never be working at a t...
Jun 08, 2021•50 min
Jennifer Burke is the Head of Sales and Account Management at Faire. Prior to joining Faire, Jen worked in sales at ClassPass for 4.5 years, and at Bain & Co, McCann Erickson and Disney before that. In this episode I talk to Jen about how her general manager role at ClassPass turned into a sales role on day one, what she first thought of sales, and why she was immediately drawn back when she tried to move into other areas. We also talk about her transition from working at large companies to earl...
May 24, 2021•46 min
Erik Bernhardsson is the ex-CTO and now Senior Adviser at Better. He joined as one of the first 10 employees when the company was less than a year old. Prior to joining Better, he worked as the engineering manager at Spotify. In this episode I talk to Erik about why he took an early-stage Spotify job over an offer from Google, how he found the commercial side of Spotify just as interesting as the engineering side, as well as why he left and then rejoined Spotify. We also dive into what got him e...
May 11, 2021•47 min
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...
Apr 20, 2021•36 min
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 appro...
Apr 05, 2021•46 min
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 ...
Mar 24, 2021•46 min
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 la...
Mar 01, 2021•47 min
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...
Feb 15, 2021•49 min
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 wit...
Feb 01, 2021
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 p...
Jan 19, 2021•59 min
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 ...
Jan 05, 2021•48 min
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 ...
Dec 10, 2020•49 min
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 ...
Nov 24, 2020•38 min
Keith Rabois is currently a general partner at Founders Fund. Prior to joining Founders Fund, Keith was an early executive at several successful companies including PayPayl, LinkedIn, and the COO of Square. He also spent six years at Khosla Ventures prior to joining Founders Fund. In this episode we talk about Keith’s start as a lawyer and why he decided to leave law, the moment he knew PayPal was going to be a success, and his philosophy on goal alignment. He also shares his thoughts on the joy...
Nov 09, 2020•1 hr 12 min
Shani Taylor is a Mid-Market Customer Success Manager at Airtable. Shani joined Airtable as the first customer success hire and the fourth go-to-market hire four years ago. Prior to joining Airtable she worked at Matthews Media Group and Cross Culture Ventures. In this episode we talk about how Shani went about building her first Customer Service Team, her advice on adaptability, and the advantage of unscalable behaviors early on. She also talks about how her background in psychology has helped ...
Oct 26, 2020•42 min
Thomas Dimson was the former Director of Engineering at Instagram. Thomas joined as one of the first 50 employees and the 16th engineer there. During his time at Instagram he developed prominent features such as the polling sticker in stories, hyperlapse, emojineering, and authored the feed algorithm. He left Instagram in February of this year and is currently working on a new project. In this episode we talk about the origin and rationale of the algorithmic feed, why he advocated for the Instag...
Oct 14, 2020•49 min
Andrew Munday was the former Director of Operations and on the founding team of DoorDash. He has also started and run operations at several companies including Open, Future Fit, Pilaris, and currently Local Food Group which he co-founded. In this episode we talk about Andrew’s first job delivering pizzas, why he thinks hard work is the key to success, how a good COO aligns with the CEO, and several of his thoughts on hiring. He also shares what it was like in the early days at DoorDash, why he s...
Sep 28, 2020•50 min
Joseph Abebe was the first FP&A hire at Slack when it had around 70 employees. Prior to Slack Joseph worked at Glassdoor, YuMe and in investment banking. He is currently an advisor at Techstars and an angel investor. In this episode we discuss how Joseph thinks about monitoring resource allocation, assessing talent, and the importance of listening, trusting and being able to delegate. He also shares his views on why companies should hire finance managers earlier than they think and a Bezos tip h...
Sep 14, 2020•37 min
Lindsey Fielding is the VP of Growth and Marketing at YieldStreet. Lindsey worked previously at IBM and HealthiNation and joined YieldStreet as a founding member within its first year. In this episode we discuss how Lindsey's background in Psychology has been applicable in the world of investing, why she loves building at young companies, and the popularity YieldStreet's investment opportunities has received. I hope you enjoy the show. Transcript available Get full access to Operators at delian....
Aug 31, 2020•41 min
Willem van Bergen is the Principal Production Engineer at Shopify. He joined as the 25th hire, before Shopify had even raised a Series A. He's been there for over 10 years and currently leads the product and engineering team. In this episode we talk about the massive growth he's learned to navigate, advice he'd give to early-stage engineering teams, how he thinks about hiring, and what has kept him at Shopify for over a decade. I hope you enjoy the show. Get full access to Operators at delian.su...
Aug 17, 2020•54 min
Bob Meese is the Chief Revenue Officer at Duolingo. He joined the company at In this episode we talked about how Duolingo runs experiments, both to optimize their funnels, but also new revenue lines, including their newly introduced successful revenue line, a digital version of the toefl test. We also talked about how enabling monetization has allowed the company Get full access to Operators at delian.substack.com/subscribe...
Aug 03, 2020•41 min
