CEO Cassidy Ventures, Brendon Cassidy: LinkedIn, Echosign + Talkdesk: Building Successful Startup Sales Teams

Integrity and humility barely begin to describe Brian McCarthy, CRO at Rubrik. Brian’s story is one of hard-won progress that is bound to inspire anyone who listens. Coming from a blue-collar household, Brian has always viewed work as a gift and now takes advantage of what it has afforded him and turns it back to building strong communities.Brian’s humble beginnings set the stage for his inspiring life story. What his family did not have in money, they made up for in an abundance of love. For that, Brian never felt like he was without and carries that with him in his life and work. In this episode, Brian talks about his upbringing and explores his professional journey. He also provides insight into why he strives to drive those around him to be the best version of themselves each day. Brian’s criteria for a good sales leader are also invaluable and worth deep consideration!In this episode, we cover:Brian’s journey towards his first job as an adult - and why selling life insurance felt natural to him. (03:59)All in the family: Brian’s early years growing up in a blue-collar household, the legacy his father left behind, and how his family came together after his passing. (07:16)How Brian and his wife navigated their lives and careers as a young married couple - and the moment he realized he could build wealth to make a positive impact on the lives of others. (16:36)How Brian’s unique and humble mindset as a young VP contributed to his success at Qlik. (25:11)A discussion about the fear of losing and impostor syndrome - and why Brian's short time at AppDynamics had a positive influence on his professional trajectory. (31:33)Feeding the beast: Brian talks about finding creative outlets in and outside of work - and delves into the two buckets that first-line sales leaders fall into. (39:55)How the words “I love you” translate into “I desire what’s best for you” and how Brian embodies those words at his core and incorporates that into Rubrik’s company culture. (51:08)Why Brian loves his role as CRO - and his perspective on why grit and gratitude go hand in hand. (59:16)Links:Connect with BrianLinkedInRubrikConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

15 Nov 20211h 7min

"Crypto" is a term that has recently re-shaped the way the world thinks about money. For Emilie Choi, President and COO at Coinbase, it has been at the forefront of her work and mind for quite some time. Emilie is a true workplace warrior and that is reflected in her leadership at Coinbase as she has cultivated an ethos that endears her entire organization and those she works alongside.In this episode, Emilie doesn’t pull the punches as she divulges her own strengths and weaknesses and how she strives to make them both equal assets. She also expounds on fostering connections in the workplace, her mission-oriented mindset, and how it is a mindset she likes to see in entrepreneurs. Emilie also offers essential insight into the current shape of cryptocurrency and the exciting direction that it is headed.      In this episode, we cover:Emilie’s competitive advantage and how she transformed her weakness into an asset. (3:35)Sensitivity in the workplace: Emilie opens up about a time when she showed her vulnerability in her “top of mind” email to the organization and how that cultivated a connection across the teams. (7:34)Building out LinkedIn’s Corp Dev team in its early stages and how entrepreneurs successfully ran LinkedIn’s three business lines. (9:21)Missionary vs mercenary: Emilie shares why it’s refreshing to work with crypto entrepreneurs who are mission-oriented - and Joubin taps into his recent experience with hiring a candidate. (13:00)Why Emilie admires Amazon’s core business strategy - and her opinion on companies she would hypothetically buy. (17:36)How Emilie’s desire to continue learning led her to make a lateral move from LinkedIn to Coinbase - and how she navigated the recruitment process of her team. (22:10)An overview of Coinbase: assets, revenue, long-term trajectory, and their three main focuses - and Emilie breaks down Coinbase’s innovation by comparing it to the evolution of mobile phones. (31:10)‘Volatility is a feature, not a bug’: What volatility means for Coinbase - and why Amazon and Adobe serve as an influence for Coinbase as they invest in their future acts. (38:38)Weathering the crypto winter: How Emilie frames investing in crypto to potential buyers - and how she integrates grit and resilience into her role and across the organization. (43:47)Emilie shares her thoughts on Coinbase’s %5 employee departure after their pledge to be apolitical - and what she admires about the Coinbase CEO, Brian Armstrong. (49:09)Emilie reflects on what she has learned as she grew into COO and President - and how Coinbase grew to be the number one regulated crypto custodian in the world. (56:22)Links:Connect with EmilieLinkedInCoinbaseConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

8 Nov 20211h 4min

Carving her own path is certainly one way to describe how Christina Augustine, COO at Bloomreach, has chosen to do her work. With a distinct set of experiences, beginning with a unique college thesis, to owning her own patent, and eventually leading Bloomreach through successful product launches, Christina has held her own over the course of her career. And her fortitude is now paying off. Christina’s natural competitiveness has not only helped her shape her own leadership abilities, but she continues to carry these skills forward. While her decision to leave Bain & Company was a difficult one, that decision has returned its value tenfold. From her role as an individual contributor to the now COO at Bloomreach, Christina has brought a tenacity that deserves attention. Check out this episode to learn how she has honed her abilities to evaluate and consciously decide where she wants to be, and how she applies her own grit to the workplace.In this episode, we cover:Christina’s college thesis on the Julia set, her experience at HBS, and a look at her patent. (2:20)More on Christina’s background and the “gnarly” aspect of her role at Bain & Company - and why she loves volunteering at Girl Scouts. (06:18)Why competitiveness is a great leadership trait and how Christina puts it into practice - and why she chose to make the difficult decision to leave Bain and join Bloomreach as an individual contributor. (15:13)‘It’s an every year decision’: Christina explains why she rewrites her resume and reflects on her contributions on an annual basis. (21:51)Powered by Bloomreach: Christina provides an overview of Bloomreach and shares her perspective on their high valuation and what it indicates as they focus on building long-term products. (26:17)The evolution of Christina’s roles at Bloomreach, from individual contributor to COO - and how the ‘“north star product vision” impacted the team’s decision to build a second product. (35:15)Christina reflects on her early days at Bloomreach and explores their product development journey - and she talks about the impact of Google’s SEO algorithm change. (45:09)What Christina’s mentors helped her prepare for as she transitioned into her COO position - and why it is important to know when to “do nothing.” (54:18)Links:Connect with ChristinaLinkedInBloomreachConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

1 Nov 202159min

Mark Anderson, CEO at Alteryx, joins Joubin to talk about how he crafted his leadership ethos, which he often compares to a great game of golf. While Mark is currently at Alteryx, it is his foundation at Palo Alto Networks that serves as the bedrock for how he approaches his work. In this episode, Mark reflects on his time at Palo Alto and offers insight that anyone would be wise to pay close attention to; close attention being an essential part of Mark’s ethos, as he says the “absence of a plan” is not part of his DNA. With this mindset, Mark breaks down the deep value of his meticulous planning and how it allows time for each important focus in his life, ranging from work, family, golf, or crucially as salient, when to leave some things by the wayside. Mark and Joubin also discuss their experiences during Palo Alto’s acquisition of Evident.io, how it has impacted Mark’s approach to the gritty specifics of acquisitions as a whole, and more.In this episode, we cover: How Mark used his grit to put himself through college - and the parallel between sales and the game of golf. (3:22)Why “the absence of plan” is not part of Mark’s DNA - and why he is intentional about the time he puts into work, family, and friends. (7:15)Palo Alto Networks: factors Mark considered as he evaluated the company, a look at his recruitment experience, and his 3 non-negotiables for hiring. (12:55)Mark reflects on some of Palo Alto’s wins, including their major stock increase in 2014 and the acquisition of Evident.io. (20:46)More on Palo Alto: Mark talks about Palo Alto’s change management approach and some of the challenges of the acquisition process. (26:08)Mark provides an overview of Alteryx and talks about the joys of being on the Alteryx team -  and shares why 2021 became “the year of transformation.” (31:55)Why good leaders should help their teams learn from failures. (42:28)Mark’s advice to the aspiring CEO and his takeaways from his journey thus far. (47:26)Links:Connect with MarkLinkedInAlteryxConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

25 Okt 202153min

Mike Gamson, CEO of Relativity, has joined the show this week to provide his take on leadership, sales, and the evolution of his career leading up to Relativity. Mike’s path into becoming a CEO is a varied one and his diverse range of experiences has helped him hone in on essential insights, which he very humbly shares. With a background in liberal arts, Mike has an interesting story about how he became a leader in the world of sales and technology. It all began when he made the decision to move to Costa Rica after an epic surfing trip along the coasts of South America. At one point, he faced a crossroads and had to decide between staying in Costa Rica or going back home. He chose the former and opened his own burrito shop. Afterward, Mike served as Advent’s head of product development, which set the stage for the rest of his career.In this episode, Mike walks through the transitions in his career and shares why he was initially hesitant to join LinkedIn. He also talks about the crucial leadership skills and values he gained at LinkedIn under Jeff Weiner’s tutelage and dives into Relativity, Chicago’s “best-kept secret,” and the exciting innovations that Relativity is bringing on board. In this episode, we cover: Mike’s fascinating professional journey leading up to LinkedIn; from turning down Goldman Sachs to opening his own burrito shop in Costa Rica - and he and Joubin discover some of the striking similarities they share. (02:03)The evolution of Mike's role at LinkedIn - and what factored into his decision to come on as an individual contributor. (9:47)The challenges LinkedIn faced in its early stages, as leadership navigated the company’s identity - and how the question, “what kind of leader do you aspire to be?” helped Mike tap into his core leadership principles. (15:37)Mike recounts moments when he was challenged to make decisions to preserve LinkedIn’s values as he grew into his sales leadership role - and how Jeff Weiner’s coaching gave him a more compassionate understanding of how to do business more broadly. (21:17)Why Relativity was the “best-kept secret in Chicago” - and why Mike feels passionate about leveraging tech companies to build ecosystems within their communities. (28:04)Mike’s views on investing in companies full-time and how his love for learning plays a role in his decision - and more on his transition to CEO of Relativity and how he gained his footing. (33:37)A look at Mike’s life as CEO: what he factors into his daily decisions, lessons learned, and his advice to those who are thinking of the next layer up job. (40:34)Mike elaborates on philosophies that he lives by, including his stance on hiring talent, why “yet” is the most powerful word in the English language, the power of being here by choice, and more. (45:21)Joubin and Mike discuss three important leadership traits - and the importance of asserting agency over your time to create a personal life harmony. (50:33)Links:Connect with MikeLinkedInRelativityConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

18 Okt 202156min

Mike Clayville, CRO at Stripe, joins this week’s conversation to discuss what it's like to turn companies into forces of nature, using Mike’s chosen metaphor, the tornado. While Mike might be the first guest to compare company growth to a natural phenomenon, his insight is invaluable. Mike comes from a small town outside of Declo, Idaho, and grew up working on the family farm and ranch. It was there that Mike gained the hard work ethic that has catapulted him into the worlds of engineering and then finance. All along the way, he made himself known as “the guy in the cowboy hat” - be it in board meetings, or on business trips to Paris or Japan.In this episode, Mike and Joubin discuss the cultural significance of Mike’s hat and the importance of not forgetting where you came from. They also discuss Mike’s tenure at IBM when it was in decline, and how Mike shifted things there into an upward trajectory. Mike also explains his idea of first principles as a means to leading tornado companies, the innovation of Amazon, The Clayville Foundation and their fight against cancer, and more.In this episode, we cover:Mike’s early life in Declo, Idaho, where he worked on his family farm - and the symbolism behind his cowboy hat. (3:11)The reason behind Mike’s switch from engineering to finance - and a look at his tenure at IBM, the tremendous challenge he faced during its decline, and how he turned it around. (7:06)Mike’s philosophy on uncovering the first principle mindset and the qualities of a tornado. (13:44)The early days of Amazon and public cloud - and how Mike used first principles to lead some of the largest enterprises into a new world of technology. (18:33)An overview of Stripe: How Stripe helps companies understand their customers and how it compares to AWS in today’s internet economy. (26:42)Why you should fail as an innovator and be willing to be misunderstood- and how Amazon’s innovation model contains the secret sauce of success. (32:56)Selling as a muscle memory sport: Why Mike refers to prospecting as the calisthenics of sales - and a dive into the stages of prospecting. (39:42)More on the importance of prospecting and why cold-calling is the best way to start a sales career. (43:15)Mike talks about his detailed briefing process and how it helps maintain efficiency when getting to the heart of their customer’s needs. (48:50)How Mike’s daily runs inspire some of his best ideas - and an in-depth look at his effective decision-making process. (53:51)The Clayville Foundation: How The Clayville Foundation honors his late wife and seeks to find cures for cancer through technology and science. (01:03:00) Links:Connect with MikeLinkedInStripeConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

11 Okt 20211h 12min

Rob Lehman, Chief Business Officer at Compass, has an entrepreneurial spirit that has already set him forward in a burgeoning and exciting career at a young age. Rob’s path has come by no accident. His determination to be at the innovative edge and his unconventional approach to finding his bearing at Compass speak to Rob’s unique take. Rob’s business-focused mindset developed early on in his childhood. In the fourth grade, Rob started a basketball camp with an all too original name. As Rob advances his career, he continues to cultivate that mentality and brings a unique offering to the world of real estate.In this episode, learn more about Rob’s highly unconventional job search and why he makes the case for the value of the real estate agent as a deeply underappreciated asset to any business. Rob and Joubin also talk about what it is like to be the young guns at their respective companies and how they push to make the more senior members around them see their value, strengths, and much more.In this episode, we cover:An overview of Rob’s background - and his earliest memory as an entrepreneur beginning in the fourth grade. (1:22)Searching for Compass: Rob details his methodical research and what he turned down as he sought opportunities to work for an early-stage company. (3:43)Rob’s pivot from finance to strategy and operations - and why the real estate agent is a profoundly misunderstood professional. (10:15)Rob reflects on his first signs of product market fit - and the power of momentum when building a company. (16:09)A deep dive on finding the best talent - and why real estate agents are a powerful business entity. (21:39) Rob explains why it is crucial to think in the future and be comfortable with rapidly adapting your business. (31:40)Understanding the diversity of the real estate industry - and Rob’s mindset as a younger person surrounded by veterans in the field. (37:01)Creating Space: Joubin and Rob discuss the impact of effective time management and how your calendar can be your strategy. (42:09)Looking back on Rob’s earlier days at Compass and some key takeaways. (46:22)Links:Connect with RobEmail: rob@compass.comConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

4 Okt 202152min

To say that Brian Frank, Chief Operating Officer of Cameo, comes from a non-traditional background into the career field of sales might be an understatement. Brain’s career began in law and he spent nearly a full career there before transitioning to sales in 2008, where he has been exceedingly active. Brian’s multifaceted background has given him a wide range of skillsets and a deep wisdom that has become invaluable to the organizations where Brian has worked. His focus on constantly learning through experience, as well as an emphasis on transparency has led him to the hard won successes that allow him to gain these perspectives. In this episode, Brain and Joubin talk about Brian’s shift from law, his tenure at LinkedIn, and how experiential learning led to the inspiring story behind Brian’s decision to take up the guitar. Brian also goes into the details on Cameo and their meteoric rise, his influence there, and more.In this episode, we cover:Brian talks about his shift from law, to finance, and finally to sales. (1:09)Brian’s colorful employment history (which began at age 13) prior to graduating from UC San Diego. (6:41)How Brian approaches outbound opportunities - and how a quick LinkedIn message led to a business partnership. (10:37)What Brian’s LinkedIn colleagues have to say about him - and his inspiring anecdote about how he met his guitar instructor, Marty Schwartz. (13:34)The story behind Brian’s ban from LinkedIn - and why his experiential learning style works for him. (17:15)All things sales ops: From defining the role to hiring and developing talent. (21:53)‘What do you value most?’: Joubin and Brian rank and discuss career, money, company and manager. (32:17)The lowest points of Brian’s LinkedIn ride - and what led him to be more transparent and open with his team. (36:37)What is Cameo? Breaking down Cameo and its fascinating growth. (45:34)How Brian assessed Cameo to determine if he was a fit - and his mindset when joining the company. (51:06)Why most businesses are demand constrained - and more on Cameo’s B2B expansion. (54:16)Links:Connect with BrianLinkedInCameoConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

27 Sep 20211h 4min