#110 Former CRO / Advisor at Notion, Olivia Nottebohm: Grow Fast or Die Slow

By her own admission, Kayti Sullivan was having a “quarter-life crisis” when she realized the jobs she could get with her Masters degree in Early European Art were not careers she had envisioned.What followed for Kayti was the start of an incredibly successful twelve-year run in sales leadership at Yelp — where she traveled the globe and rose through the ranks. Now, Kayti is Chief Revenue Officer at The RealReal, an online marketplace for authentic luxury consignment.On this episode of Go to Market Grit, Joubin and Kayti discuss the importance of falling in love with learning, what it takes to go from being an individual contributor to a manager, and strategies for balancing work and personal life.In this episode, we cover:Falling in love with learning: The connection between intellectual curiosity and success — and why Kayti believes that 'leaders are readers.' (2:47)From art history to Yelp: Kayti's story of finding her career in sales. (10:20)'Competitor to advocate': How Kayti went from salesperson to sales manager at Yelp — and how to succeed during transitional periods. (20:20)Careers and relationships: Why Kayti 'never really questioned' moving across the globe for jobs. (28:03)'Play the tape all the way to the end:' How Kayti prioritizes tasks when leading high-growth, high-opportunity companies. (31:24)‘Time is only one measurement:’ Strategies for balancing work and personal life. (35:06)Why Kayti left Yelp in 2019 — and what she saw in The RealReal. (47:02)How Kayti defines grit. (51:41)Links:Connect with KaytiEmail: kayti.sullivan@therealreal.comConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

24 Touko 202154min

For Thomas Hansen, chasing a passion was key to unlocking the path toward an impressive career. An avid windsurfer, Thomas started his professional life managing a small windsurfing company in Denmark — an experience where he learned what it takes to succeed.Now, Thomas serves as Chief Revenue Officer of UiPath, a growing business that develops software for robotic process automation — freeing up time for companies to focus on innovation. On this episode of Go To Market Grit, Thomas and Joubin discuss essential communication tips for sales leaders, as well as how to balance the science and art of sales.In this episode, we cover:Accountability, consistency, and predictability: The sales lessons Thomas learned during his early career working for Dell in Denmark. (0:59)'It’s the passion in my life': Thomas talks about his love of windsurfing. (6:15)How UiPath helps companies free up time through automation software — and the methods Thomas used to assess the company’s technology. (9:33)Breadth vs. Depth: Why Thomas believes in the importance of getting exposure to different disciplines, functions, and geographies. (17:15)'Crisp, and clear, and to the point:' How Thomas connects with his global sales team during the COVID-19 pandemic. (20:40)The importance of sharing difficult feedback with people as early as possible 'in an authentic, humble and kind way.' (24:50)Using reference calls to determine the qualities of a job candidate. (28:56)Coupling science-enabled sales techniques with the art of connecting with a customer. (32:16)How Thomas defines grit. (41:04)Links:Connect with Thomas HansenUiPath's websiteConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

17 Touko 202143min

Marcy Campbell knows a thing or two about taking risks. Over her almost 40 years in business, Marcy’s worked at 11 different startups — building several sales organizations from the ground up.Now, as Vice President of Global Professional Services at PayPal, Marcy employs grit on a daily basis as she leads sales teams on the newest company products. On this episode of Go to Market Grit, Joubin and Marcy discuss the challenges women face in business, creating sales motions and the qualities of a successful sales rep.In this episode, we cover:Marcy's career working at 11 startups — and the challenges women face in reaching senior sales positions. (1:05)'I’ve never done anything in a straight line': Taking risks and finding success. (7:50)'Fail up': Using the lessons learned from failure to take more risks. (12:48)How Marcy deals with always having been ‘the underdog’ — and why she mentors other women. (16:11)Being 'immersed in the actual event of learning' — and how failure builds maturity. (19:26)Why understanding a company's products, customers, and market dynamics is key to establishing successful sales motions. (23:19)Collaboration and chemistry: The characteristics that Marcy looks for in companies she's looking to join. (28:20)Belief, commitment and support: What it takes to work at a company where 'there's a puzzle to fix.' (30:27)Why Marcy goes on 'a big listening tour' to understand all aspects of a company when she first joins. (34:30)The value of curiosity and intelligence in a sales rep — and the qualities Marcy evaluates in sales candidates for during job interviews. (37:15)How Marcy defines grit. (43:59)Connect with MarcyLinkedInEmail: marcycampbell@paypal.comConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

10 Touko 202146min

In 2008, when Ryan Longfield took a contracted account executive position at LinkedIn without any prior sales experience, he knew he had to be “all-in.” “‘I’ll sleep under my desk if I have to,’” Ryan remembers telling a recruiter who asked if he was worried he won’t be able to hit $50,000 in sales in only three months. Now, after an almost 10-year run at LinkedIn where he worked in five different sales positions, Ryan serves as Chief Revenue Officer of Gong, a revenue intelligence platform for B2B sales teams. On this episode of Go to Market Grit, Joubin and Ryan have a wide-ranging discussion about the importance of pushing boundaries as well as failure.In this episode, we cover:'I was all-in': Ryan's experience as a contracted account executive at LinkedIn in 2008 having never previously done sales — and what motivates him. (2:52)The importance of setting boundaries and creating a healthy work-life balance. (9:46)Why Ryan believes that 'constantly remaining uncomfortable’ is key to career acceleration. (17:10)Learning from the process that led to failure versus focusing solely on the failure itself. (20:43)Imposter syndrome, insecurity, and the benefits of having diversity of perspective. (27:16)Why Ryan believes that quotas should "represent a minimum bar for effectiveness" in sales roles. (37:03)How Ryan's current company, Gong, gives leaders insight into the sales conversations reps have with buyers. (39:17)Coachability; previous history of success; intelligence and business acumen; grit; and curiosity: Attributes of a great sales rep. (48:01)How Ryan defines grit. (51:35)Guest: Ryan Longfield, Chief Revenue Officer of GongLinks:Connect with Ryan LongfieldLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

3 Touko 202153min

When it comes to building startups from the ground-up, Brendon Cassidy knows it all: Having held some of the first sales leadership roles at LinkedIn, Echosign, and Talkdesk, Brendon helped position each company for success. Now, Brendon consults startups on go-to-market operations as founder of his own consulting firm, Cassidy Ventures. On this episode of Go to Market Grit, Joubin and Brendon talk about what Brendon learned throughout his impressive career working at successful startups, as well as what Brendon looks for in new sales hires when building a team.In this episode, we cover:How Brendon became one of the first 20 employees at LinkedIn during the company's early days — and how he helped LinkedIn monetize its recruiting services. (3:17)The sales leadership lessons Brendon learned at LinkedIn and his departure from the company in 2008. (10:29)'I'm betting on me': How Brendon became VP of Sales at Echosign as one of the company's first employees after working at LinkedIn. (15:34)Startup number three: How Brendon helped build Talkdesk's sales operation as the company's first United States employee after working at Echosign. (20:26)Why Brendon looked for drive and commitment in new sales hires when building a team at Talkdesk. (23:58)'Don’t quit; don’t give up; be solution-oriented': Dealing with failure and hardship in business. (26:31)Hiring a VP of Sales: Brendon's take on stretch VPs and why "a diverse search" is key to the right hire. (38:58)How Brendon defines grit. (49:00)Links:Connect with Brendon CassidyLinkedInEmail: brendon@cosell.ioConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

26 Huhti 202150min

As Chief Revenue Officer of cloud content management and file sharing company Box, Mark Wayland and his team have taken on a “land, adopt, and expand” business model to attract new buyers across various industries and locations.This strategy seems to be paying off — according to Box, 68% of the Fortune 500 currently use the SaaS company’s products.On today’s episode of Go To Market Grit, Joubin and Mark talk more about Box’s go-to-market strategy, as well as the importance of learning from failure.In this episode, we cover:The importance for a sales leader to hone sales operation and strategy skills. (3:01)How sales has changed as technology evolves. (9:37)How Box is changing how people work through cloud content management — and why sales leaders should focus on forging a positive workplace culture. (18:25)Selling across segments: Box's go-to-market strategy. (24:29)Why Box aspires to be a ‘trusted advisor’ to enterprise businesses. (27:16)How remote work during the COVID-19 pandemic has made it more difficult for Mark to make personal connections with his sales team. (31:27)'You have to fail a lot in order to succeed': How Mark defines grit. (33:58)'Land, adopt, and expand': Box's future plans for growth. (43:03)Links:Connect with Mark WaylandLinkedInBox’s websiteConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

19 Huhti 202149min

Impossible Foods has a mission to eliminate the use of animals in the food system by 2035. With the growing success of the company’s plant-based meat products, such as the Impossible Burger, this vision is becoming reality.Feeling as though the company was “aligned with my own personal mission,” Dana Worth, former VP of Sales at Impossible Foods, joined the company in 2015 before it brought any of its plant-based meat products to market. Now, Dana has moved on from Impossible Foods, taking a position as SVP, Commercial at Plenty.On this episode of Go to Market Grit, Joubin and Dana talk about how Impossible Foods’ go-to-market strategy changed as the company grew, as well as the company’s history.In this episode, we cover:'What makes meat, meat?': Why Impossible Foods is working towards eliminating the use of animals in the food system by 2035. (3:28)The factors behind Dana's decision to join Impossible Foods in 2015. (9:22)Partnerships with high-credibility and meat-forward chefs: Impossible Foods' early go-to-market strategy. (13:11)‘True believers’: The benefits of having a unifying mission as a company. (23:13)How Impossible Foods analyzed its organizational structure as its products became more commercially successful. (28:32)The supply and demand challenges Impossible Foods faced when the Impossible Burger 2.0 became a massive success in 2019. (31:28)Impossible Foods’ current strategy for selling its product direct-to-consumer — and why its main competition isn’t other plant-based meat companies. (39:18)How Dana defines grit. (45:33)Links:Connect with Dana WorthLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

12 Huhti 202147min

Just take it from website security industry executive Chris Merritt — the internet was not designed with security and performance in mind. As President of Field Operations and CRO of Cloudlflare, Chris and his company are dedicated to fixing this problem by protecting websites for a more secure and reliable internet. On this episode of Go to Market Grit, Joubin and Chris discuss how Cloudflare’s go-to-market strategy has evolved, as well as how Cloudflare helps prevent bad actors from conducting internet attacks.In this episode, we cover:How Chris' current company, Cloudflare, is creating a more secure and reliable internet network. (3:44)Chris' experience working at Cloudflare during the company's early stages. (8:23)The evolution of Cloudflare’s go to market strategy. (13:18)Content-driven strategy: How Cloudflare uses an engineering blog to help enable its freemium model. (17:54)Stopping DDoS attacks: How an increase in security awareness among the general public benefited Cloudflare. (25:03)‘A community watch’: Why Cloudflare’s large and diverse user base enables a better and more competitive product. (31:17)Change management: The incremental and careful process of bringing Cloudflare up-market. (36:37)The qualities Chris looks for in new hires. (44:23)How Chris defines grit. (50:10)Links:Connect with Chris MerrittLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

5 Huhti 202152min