Operators Delian Asparouhov

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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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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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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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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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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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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