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

Episoder(276)

CRO Obsidian Security, Bob Kruse: Building a Winning Sales Culture

CRO Obsidian Security, Bob Kruse: Building a Winning Sales Culture

In this episode of Go to Market Grit, Obsidian Security CRO and sales veteran Bob Kruse shares his thoughts on culture, and how it impacts sales teams. Bob and Joubin discuss why having a strong culture is critical in sales, as well as the benefits of deploying a multifaceted channel program.In this episode of Go to Market Grit, we cover: Why having a strong culture on your sales team can serve as a competitive advantage — and why it needs to be treated as a top-down initiative.Why it’s important to prioritize transparency, integrity, trust, and authenticity in sales.Viewing sales as a team sport — and why reps need to work together as a single unit. How inclusivity, and bringing different types of employees into the sales process like engineers can be beneficial to the company and help to achieve common goals.Tips for improving your odds of success when hiring, such as being completely comfortable with prospects and prioritizing referrals and recommendations.Tips for keeping sales teams motivated, yet working hard and in touch with reality — and why complacency is death. Bob’s thoughts on the channel — including how it’s changed due to SaaS, and how a multi-faceted channel program can help sales teams expand and grow, and open new doors.LinksConnect with Bob on LinkedIn: LinkedInObsidian SecurityConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

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VP of Sales at Palo Alto Networks, Jeff StClair : Discovering, Recruiting, and Coaching Sales Talent

VP of Sales at Palo Alto Networks, Jeff StClair : Discovering, Recruiting, and Coaching Sales Talent

In this episode, Jeff StClair, currently VP of Sales at Palo Alto Networks and most recently VP Sales at Evident.io shares his thoughts on how startups can more effectively discover, attract, and retain top talent, and in doing so take their organizations to new heights. We also dive deep into what makes a great sales rep.In this episode of Go to Market Grit, we cover: Key qualities that Jeff looks for when recruiting sales associates.Why hiring should be a group effort for startups, with team members agreeing on new reps before bringing them on board. Considerations for hiring in a startup environment, versus an organization that’s growing at scale.The importance of nurturing and developing talented sales associates, by giving them opportunities to continuously challenge themselves to work beyond their capacity. Why top tier sales associates typically make poor managers and leaders -— and what it takes to thrive in a leadership role. The difficulty — and importance — of building a competitive team that  integrity and a strong culture. Links Connect with JeffLinkedInPrisma CloudPalo Alto NetworksConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

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Chief Sales and Success Officer at Slack, Bob Frati: Exploring Slack’s Key Growth Levers and Competition

Chief Sales and Success Officer at Slack, Bob Frati: Exploring Slack’s Key Growth Levers and Competition

In Episode #1 of Go to Market Grit, Slack’s SVP of Sales and Customer Success, Bob Frati, gives the inside scoop about the company’s sales and go-to-market strategy, and why they have been able to scale their go to market so quickly and effectively over the last few years. Bob and Joubin discuss two key topics in detail, outlining the next four years for Slack and key growth levers they can pull, along with growing competition in Slack’s market and what that means for their future. In this episode of Go to Market Grit, we cover: Key growth levers for Slack, and why the company is positioned for continued market dominance.Slack’s response to growing market competition, and why it’s ultimately better for the consumer and for the company.How Slack identified a business need and strong product market fit, and then worked to expand the solution to a broader audience. The importance of having a strong and developed customer-facing team to navigate complexities in large enterprises, and push business forward to completion.How Slack grew its sales team from 300 to 2,000 people — quickly, and effectively. Some of the factors that Slack looks for when hiring customer-facing sales staff, and why they value these characteristics.Why hiring should be a mutual fit for both the candidate and the employer.Identifying motivated individuals, and finding ways to tap into their motivation that will drive them to be successful. Bob’s career journey from sales rep to manager — including why and how he executed the leap. Why much of Slack’s success can be attributed to tight collaboration between its engineering, product, sales, and success teams. Slack’s ability to not only deploy a solution in an organization, but to help manage through the change and ensure success — and why this is a game-changer.Slack’s role in ushering a new way of working, and why it transcends the tired and overused digital transformation narrative in business.Links Host company: https://www.kleinerperkins.com/Loom: https://www.loom.com/ Guest LinkedIn: https://www.linkedin.com/in/rfrati/Host Twitter: https://twitter.com/JoubinmirHost Email: gtmg@kleinerperkins.com

16 Jun 202050min

Grit Trailer

Grit Trailer

About the Joubin MirzadeganJoubin has been with Kleiner Perkins since 2019 where he advises the KP portfolio companies on how to build and scale a robust go-to-market strategy. Additionally, he enables the firm’s portfolio through high impact relationships with F500 executives and key ecosystem partners. Joubin was previously at Palo Alto Networks as a global district sales manager for the Central US based in Chicago where he scaled the Central Cloud business from 1 enterprise rep and $2M ARR to 12 reps and $50M+ ARR in 4 quarters. He has also worked for Evident.io as an enterprise account executive and at Bracket Computing (acquired by VMWare) where he built the inside sales team from the ground up.

20 Apr 202045s

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