#142 President of DocuSign, Robert Chatwani: Get Uncomfortable
Grit12 Kesä 2023

#142 President of DocuSign, Robert Chatwani: Get Uncomfortable

Guest: Robert Chatwani, President and General Manager of Growth at DocuSign

Robert Chatwani’s first reinvention was in his early 20s, when he left McKinsey & Company to start a people-powered commerce startup called MonkeyBin. And in the ensuing decades, his entrepreneurial energy hasn’t slowed down, with hops to eBay, Spring, Atlassian, and now DocuSign, where he is the President and General Manager of Growth. He cites a “healthy anxiety” that comes from getting too comfortable in any role, where he finds himself solving the same problems over and over again; but when you’re in a little bit over your head, Robert explains, “that’s a good place to be, because that’s where the best learning comes from.”

In this episode, Robert and Joubin discuss trusting your intuition, reinventing yourself, personal boards of advisors, people-powered commerce, betting on people, career coaching, taking time for family, being the same person in every room, bone marrow donors, energy takers vs. creators, and leading with empathy.

In this episode, we cover:

  • Networking through venture capitalists (02:18)
  • Leaving high-profile jobs (04:29)
  • How to know when it’s time to leave (07:55)
  • 12 years at eBay (11:05)
  • The seeds of doubt (15:10)
  • Finding purpose in company-building (17:51)
  • Robert’s personal mission statement (21:01)
  • Growing up in Chicago and his parents (24:40)
  • Losing a parent (27:16)
  • True North by Bill George (29:35)
  • Finding ways to be human (32:45)
  • What accomplishment Robert is most proud of (34:35)
  • MonkeyBin and meeting eBay (36:08)
  • Sameer Bhatia’s battle with leukemia (38:30)
  • Building a global bone marrow campaign (42:38)
  • “You can’t control every outcome” (48:07)
  • Unexpected side effects (52:56)
  • Business is a force for good (56:26)
  • Working at Spring, and then Atlassian (01:00:01)
  • Self-doubt and leaving Atlassian (01:06:29)
  • Making tough calls with IQ & EQ (01:10:24)
  • Who DocuSign is hiring, and what “grit” means to Robert (01:13:48)

Links:

Jaksot(276)

The Grittiest Conversations of 2025: AI, Business & Beyond

The Grittiest Conversations of 2025: AI, Business & Beyond

In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year.Featuring:David Rubenstein (co-founder of Carlyle) Yamini Rangan (CEO of HubSpot) Ben Chestnut (co-founder of Mailchimp) Winston Weinberg (co-founder and CEO of Harvey)Garrett Lord (co-founder of Handshake) Aidan Gomez (co-founder and CEO of Cohere) Michelle Zatlyn (co-founder of Cloudflare) Evan Spiegel (co-founder and CEO of Snap) Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: grit@kleinerperkins.comFollow on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

29 Joulu 41min

How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader

How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader

What happens when AI becomes your most influential referrer?As consumers turn to ChatGPT for answers, James Cadwallader and his team at Profound help brands like Eight Sleep and MongoDB gain visibility and leverage inside AI models.On this episode of Grit, he explains why brand narrative has shifted away from content, and why Profound is scaling globally ahead of traditional SaaS timelines.Guest: James Cadwallader, co-founder and CEO of Profound and Ilya Fushman, partner at Kleiner PerkinsConnect with James CadwalladerX: https://x.com/thejamescad?lang=enLinkedIn: https://www.linkedin.com/in/jsca/​Connect with Ilya FushmanX: https://x.com/ilyafLinkedIn: https://www.linkedin.com/in/ilyafushman/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: grit@kleinerperkins.comFollow on LinkedIn:https://www.linkedin.com/company/kpgritFollow on X:https://x.com/KPGrit​Learn more about Kleiner Perkins: https://www.kleinerperkins.com/

22 Joulu 50min

How Snap Plans to Win the AR Race | Evan Spiegel on Spectacles

How Snap Plans to Win the AR Race | Evan Spiegel on Spectacles

Turning down a $3B offer from Facebook is a bold move for any young CEO.Evan Spiegel shares how Snap’s early dream was to stay independent and give its community an authentic voice, a bet that proved right.He also explains why they are now doubling down on AR glasses and why the anxiety around AI deserves far more attention from tech leaders.Guest: Evan Spiegel, co-founder and CEO of Snap Inc. and Bing Gordon, Advisor at Kleiner Perkins​Connect with Evan SpiegelX:https://x.com/evanspiegel?lang=enLinkedIn:https://www.linkedin.com/in/evan-spiegel/​Connect with Bing GordonX: https://x.com/bingfish LinkedIn: https://www.linkedin.com/in/binggordon/Connect with JoubinX: https://x.com/JoubinmirLinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/Email: grit@kleinerperkins.com​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

15 Joulu 1h 11min

The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner

The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner

What does it take to go from advising founders to becoming one?On this week’s special Reverse Grit episode, we flip the script and put our Grit podcast host Joubin Mirzadegan in the guest seat.Joubin recently founded Roadrunner, where he is now co-founder & CEO. Roadrunner is building an AI‑native CPQ to modernize the quote‑to‑cash stack, drawing on years of conversations he’s had with enterprise revenue leaders.Stepping into the host role, Mamoon Hamid joins Joubin to talk about his transition from sales leader to founder, how Roadrunner came together, and why it became our first incubation since Glean.Roadrunner is hiring! Check them out: https://www.roadrunner.ai/Guest: Joubin Mirzadegan, Partner, Kleiner Perkins​Connect with MamoonXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.com​Learn more about Kleiner Perkins

8 Joulu 1h 14min

Building Cloudflare for the Next 50 Years | Co-founder Cloudfare Michelle Zatlyn

Building Cloudflare for the Next 50 Years | Co-founder Cloudfare Michelle Zatlyn

Fifteen years in, it can still feel like “we’re just getting started.”Michelle Zatlyn, co-founder of Cloudflare, returns to Grit with Joubin Mirzadegan to share how Cloudflare secures the internet for millions, with a vision built to last generations.She also shares why staying close to reality and to customers becomes harder as success compounds, and how Cloudflare is helping content creators regain control in an AI driven internet.Guest: Michelle Zatlyn, co-founder and President of CloudflareConnect with Michelle ZatlynXLinkedIn​Connect with JoubinXLinkedInEmail: grit@kleinerperkins.com​Learn more about Kleiner Perkins

1 Joulu 58min

She Sold Her Startup for $500 Million, Here’s Her Next Idea

She Sold Her Startup for $500 Million, Here’s Her Next Idea

Screens have pulled families apart. Brynn Putnam set out to bring them back together with Board, the world’s ‘first face-to-face game console.’On Grit, she tells Joubin Mirzadegan how every venture she’s built, including Mirror, started as a personal need, and how her true edge is the ability to strip an idea down to what actually matters.Guest: Brynn Putnam, founder and CEO of BoardConnect with Brynn PutnamXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.com​Learn more about Kleiner Perkins

24 Marras 1h 12min

Synthetic Data and the Future of AI | Cohere CEO Aidan Gomez

Synthetic Data and the Future of AI | Cohere CEO Aidan Gomez

How do companies like Salesforce and Dell scale intelligence across every cloud?Aidan Gomez, co-founder and CEO of Cohere, explains how they’re building AI that works across all enterprise systems and deploys anywhere, giving companies true flexibility and security.He joins Joubin Mirzadegan for a wide-ranging conversation on why synthetic data went from dismissed to indispensable, and how the race among AI labs is really unfolding.Guest: Aidan Gomez, co-founder and CEO of CohereConnect with Aidan: XLinkedInConnect with Joubin: XLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

17 Marras 1h 11min

From Yext to Roam: Howard Lerman’s Second Act

From Yext to Roam: Howard Lerman’s Second Act

The hardest company to build is the one you start after you’ve already succeeded.After scaling Yext into a platform powering millions of businesses, Howard Lerman chose to start over with Roam, the “Office of the Future,” where humans and AI work side by side from anywhere.On Grit, he joins Joubin Mirzadegan to talk about the solitude of leadership and what happens when you stop building for Wall Street.Guest: Howard Lerman, co-founder and former CEO of Yext, and founder and CEO of Roam​Connect with Howard LermanXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.com​Learn more about Kleiner Perkins

10 Marras 1h 25min

Suosittua kategoriassa Liike-elämä ja talous

sijotuskasti
psykopodiaa-podcast
rss-rahapodi
mimmit-sijoittaa
ostan-asuntoja-podcast
pomojen-suusta
rss-seuraava-potilas
taloudellinen-mielenrauha
rss-neuvottelija-sami-miettinen
rss-porssipuhetta
rss-lahtijat
rss-bisnesta-bebeja
rss-sisalto-kuntoon
rss-paasipodi
leadcast
sijoitusovi-podcast
rss-rahamania
jahtaa-unelmiasi
rss-ammattipodcast
rss-turvacast