Operators
Delian Asparouhov
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I interview non-founder/VC/CEO operators that make the startup world go round
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Feb 9, 2022
Operators Ep 36: Hannah Willson (Modern Health)
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, the importance of building trust with buyers, and how the tiny things add up in career trajectory. Hannah also discusses how much variety there is in sales, what she looks for when hiring, and advice for getting started and staying in the industry.
I hope you enjoy the show.
Full transcript available.
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Dec 7, 2021
Operators Ep 35: Toby Espinosa (DoorDash)
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 first joined. He also shares thoughts on the focus of moving very quickly early on, how he thinks about hiring, and the dynamics with some of DoorDash’s biggest partnerships.
I hope you enjoy the show.
Full transcript available here.
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Nov 15, 2021
Operators Ep 34: Anand Chandrasekaran (Five9, SaaS Decacorn and formerly Facebook)
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 while scaling Facebook Messenger, and why he wishes he’d known earlier about how to have a growth mindset.
I hope you enjoy the show.
Full transcript available here.
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Nov 1, 2021
Operators Ep 33: Jaimie Buss (Zendesk)
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 competitive nature, how she created a brand for herself, and the misperception that one needs to be an extreme extrovert to be good in sales. She also shares about the strategies she uses for surveying her team on engagement, her views on various leadership styles, and the importance of product led growth.
I hope you enjoy the show.
Full transcript available here.
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Oct 18, 2021
Operators Ep 32: Alyson Welch (Twilio)
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 Akamai a month before the dotcom bubble burst, starting and building a sales team from day one, and the evolution of onboarding at high growth startups. She also shares about why she prefers slightly more mature companies, how crucial it is to be passionate when in sales, and her decision to be an advisor to VC’s.
I hope you enjoy the show.
Full transcript available here.
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Sep 20, 2021
Operators Ep 31: Ben Braverman (Flexport)
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. We also discuss how the pandemic has affected business, the Suez Canal blockage, and at the end, Ben gets a chance to ask me his burning questions about manufacturing in space.
I hope you enjoy the show.
Full transcript available here.
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Aug 23, 2021
Operators Ep 30: Denise Persson (Snowflake)
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 disciplines. She also shares job advice on saying yes to the opportunities that arise, and how not to over-engineer one’s career.
I hope you enjoy the show.
Full transcript available here.
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Jul 12, 2021
Operators Ep 29: Dod Fraser (Opendoor)
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 surprises that came from the Covid pandemic.
I hope you enjoy the show.
Full transcript available here.
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Jun 22, 2021
Operators Ep 28: Jeanne DeWitt Grosser (Stripe)
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 10-300 people, and why it’s important to not let your job description define your role.
I hope you enjoy the show.
Full transcript available here.
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Jun 8, 2021
Operators Ep 27: Nilam Ganenthiran (Instacart)
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 tech startup, and his first job as (appropriately) a grocery store clerk. We also discuss how Instacart responded at the start of the pandemic, Instacart ads, and other opportunities he sees for the company.
I hope you enjoy the show.
Full transcript available here.
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May 24, 2021
Operators Ep 26: Jennifer Burke (Faire)
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 early-stage startups, what she’s learned along the way, and specifically how she’s refined what to look for when hiring.
I hope you enjoy the show.
Full transcript available here.
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May 11, 2021
Operators Ep 25: Erik Bernhardsson (Better)
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 excited about Better, the advantages and disadvantages of machine learning, and why hiring is such a priority for him.
I hope you enjoy the show.
Full transcript available here.
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Apr 20, 2021
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.
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Apr 5, 2021
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.
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Mar 24, 2021
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.
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Mar 1, 2021
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.
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Feb 15, 2021
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.
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Feb 1, 2021
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.
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Jan 19, 2021
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.
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Jan 5, 2021
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.
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Dec 10, 2020
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.
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Nov 24, 2020
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.
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Nov 9, 2020
Operators Ep 14: Keith Rabois (Founders Fund)
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 he has for team building and mentoring, why regulatory risk doesn’t scare him, and the days when he used to scan every LinkedIn profile.
I hope you enjoy the show.
Transcript available here.
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Oct 26, 2020
Operators Ep 13: Shani Taylor (Airtable)
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 navigate customer needs, the close relationship customer service has with product and engineering, and her genuine love of Airtable.
I hope you enjoy the show.
Transcript available here.
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Oct 13, 2020
Operators Ep 12: Thomas Dimson (ex-Instagram)
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 Instagram engineering team to not share Facebook’s office but rather have their own space, and the story behind polling stickers. He also shares his claim to fame feature on Kindle, why he considers himself a generalist, and his passion for building things, which ultimately led to his decision to move on from Instagram.
I hope you enjoy the show.
Full Transcript Available
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Sep 28, 2020
Operators Ep 11: Andrew Munday (ex-DoorDash)
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 still thinks of it as the best deal of his life, and what a tough decision it was for him to leave.
I hope you enjoy the show.
Transcript available
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Sep 14, 2020
Operators Ep 10: Joseph Abebe (ex-Slack)
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 he recommends.
I hope you enjoy the show.
Transcript available
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Aug 31, 2020
Operators Ep 9: Lindsey Fielding (YieldStreet)
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
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Aug 17, 2020
Operators Ep 8: Willem van Bergen (Shopify)
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.
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Aug 3, 2020
Operators Ep 7: Bob Meese (Duolingo)
Bob Meese is the Chief Revenue Officer at Duolingo. He joined the company at <$1m in revenue and has helped them scale up to $100m+ through app subscriptions. Previously he was at Google for a number of years focused on Google Play.
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
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Jul 20, 2020
Operators Ep 6: Babak Siavoshy (Anduril)
Babak Siavoshy has had a remarkable legal career focused on privacy and civil liberties, having worked on the landmark Supreme Court Case, States v Jones. He then got into tech, working first at Palantir as their Global Data Protection Officer, and now at Anduril
In this episode we talked about States v Jones, the ethics of working in defense, the role of a general counsel at a startup, and much more.
I hope you enjoy the show.
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Jul 6, 2020
Operators Ep 5: Zach Kitschke (Canva)
Today’s guest, Zach Kitschke, is one of the earliest employees at Canva. During his time there he has had a few roles, including head of people, head of brand and marketing, and head of comms. With such a wide range of roles we talked about how early employees can scale up with a company, how Canva maintains such a strong and distinct culture, and how to effectively switch between operating disciplines.
I hope you enjoy the show.
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Jun 29, 2020
Operators Ep 4: Sanne Manders (Flexport)
Today’s guest, Sanne Manders, is COO of Flexport. We chat about everything from scaling international logistics, how to make your startup more full-stack over time, and their covid PPE-delivery project.
I hope you enjoy the show.
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Mar 10, 2020
Operators Ep 3: Brett Browman (Square/Opendoor)
Today’s guest, Brett Browman, has been head of performance marketing at two killer startups in a row. He first worked at Square, now publicly trading at $37b, then Opendoor which just raised at $4b, I hope you enjoy the show.
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Jan 31, 2020
Operators Ep 2: Richard Ni (Cruise + Scale AI)
My guest is Richard Ni, formerly the first recruiter and then head of recruiting at Cruise which got bought for $1b, and now the head of people at ScaleAI, which was recently valued a $1b in a round led by Founder’s Fund.
Richard has a very unique background for the world of HR/people given he studied computer science at MIT the same year as me. I think it gives him an incredibly unique perspective on how to manage recruiting and talent, I think you’ll enjoy our conversation.
If you’re enjoying these and want me to make more episodes and invest in a studio etc. feel free to sign up for a paid subscription and I’ll re-invest that all into the show.
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Dec 6, 2019
Operators Ep 1: Kelly Wright (Tableau)
Kelly Wright is today’s guest who led Tableau from $0 -> $1b in ARR. In this episode we discuss sales culture, how to interview reps, what companies fail at in go-to-market and how Kelly got into sales and scaled Tableau.
Hope you enjoy! Let me know what you think. I’ll have this cross-published to Apple Podcasts etc later today
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