CRO Stripe, Mike Clayville: Building Tornado Companies

Not many people can say they’ve held leadership positions in marketing, sales, and HR during their business career. Well, maybe except for Rachael Powell, who has done all three and says it’s just her “natural curiosity” that brought her on such a path. Having worked for over 25 years at digital and technology companies, Rachael now serves as Chief Customer Officer at Xero, a company creating cloud-based accounting software for small businesses. On this episode of Go to Market Grit, Joubin and Rachael discuss ways to apply positive psychology within an organization in order to improve customer experience, as well as how Rachael recruits for talent.In this episode, we cover:How Rachael's current company, Xero, is focused on improving lives across the globe through its cloud-based accounting software for small businesses. (4:59)How Rachael's 'natural curiosity' helped her build a broad skill set. (7:55)‘I'm definitely a builder': The apprehension Rachael felt before taking the Chief People Officer role at Xero — and why she took the job. (10:44)This is absolutely a vocation for me': Why Rachael loves her job and is invested in Xero's purpose. (16:32)'Don’t ask, show': Why Rachael believes that results come from ‘showing what you’re capable of’ and not by asking for them. (20:26)‘The human ripple effect’: How enthusiasm for a company can transfer from employees to customers — and the benefit of putting all elements of the customer journey under one executive. (23:33)Recruiting talent: Why Xero focuses on having a conversation with job candidates to gauge their values, passions, and strengths. (27:17)How to develop new talent and build a strong foundation of wellbeing within an organization with ‘positive psychology.’ (30:40)Why Rachael hired communication, recruiting and diversity roles when she became Chief People Officer at Xero — and how the company tries to foster an authentic workplace environment. (34:07)Why putting 'play' into an organization is crucial for innovation. (38:58)'It is an enormous opportunity': Xero's strategy for bringing their product to market in the Northern Hemisphere. (44:10)How Rachael defines the word grit. (51:21)Guest: Rachael Powell, Chief Customer Officer at XeroLinks:Connect with RachaelXeroConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

5 Juli 202151min

Ryan Barretto knows all about what it takes to successfully scale a business.After an impressive 10-year career in sales leadership roles at Salesforce, Ryan took a role as SVP of Global Sales at Sprout Social — a business creating social media management tools — where he helped grow the company from $30 million in revenue to $170 million. Now, one IPO later, Ryan is President of Sprout Social — and, also, today’s guest on Go To Market Grit! On this episode, Joubin and Ryan discuss Sprout Social’s content-led inbound lead generation engine, as well as the importance of delivering a compelling company vision as a leader.In this episode, we cover:How Ryan's company, Sprout Social, is streamlining and improving social media management for businesses. (5:31)Early stages and IPO: The most stressful aspects of growing and scaling Sprout Social sales operation from $30 million to $170 million of revenue. (8:27)Leveraging content-driven marketing to support an inbound lead model. (13:55)How Sprout Social's product-led trial model makes account executives focus more on 'customer success' — and the evolution of the 'enterprise rep.' (16:19)The importance of asking for and taking feedback from colleagues as a leader. (19:59)Self-critical learners: Characteristics of successful new hires at Sprout Social — and how Ryan identifies learners during job interviews. (22:49)Why Ryan cares so deeply about learning and self-improvement — and how his upbringing as a first-generation Canadian informed his work ethic. (26:23)Instilling and supporting a culture of learning within an organization. (33:31)Fostering trust and rapport: Using collaboration with various business departments to communicate and build an inspiring company vision. (37:10)Learning and building credibility as a leader through being hands-on in all areas of a business. (41:08)'Nailing the why': The importance of clear internal communication during periods of change. (43:01)What does the word grit mean to you? (46:27)Links:Connect with RyanLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

28 Juni 202148min

Erica Anderson had never carried a bag before she was promoted to Vice President of Worldwide Sales at GitHub in 2019. With a successful career as a sales operations leader under her belt, Erica has since been promoted twice at GitHub — most recently to Senior Vice President of Revenue. On this week’s episode of Go to Market Grit, Joubin and Erica talk about the lessons Erica has learned about leadership throughout her career and the combined bottom-up and top-down selling approach of GitHub.In this episode, we cover:'The Home of Open-Source Software': How GitHub is used for software development and when Erica joined the company. (3:12)How Erica was promoted to VP of Worldwide Sales at GitHub despite never having been a quota-carrying salesperson herself. (5:35)The Value of Partnerships: What a successful relationship between sales operations and a sales leader looks like. (8:51)'Listening and learning': The methods Erica used to develop a new skill set for the sales leadership job she had never done before. (10:47)Hiring too soon: The 'very painful lesson' Erica learned at GitHub about hiring and expanding before fully understanding product-market fit. (15:43)Finding what fuels 'internal drive' — and the differences between external and internal competitiveness in sales. (19:18)How Erica's overall focus changed when promoted to a sales leadership role from a sales operations position — and the importance of individual forecasting for sales reps. (23:36)Sales motions: The 'internal selling' Erica did to convince GitHub to embrace top-down selling in addition to its existing bottom-up sales structure. (27:41)'Aggregating customer feedback': How GitHub decides which product feature requests to prioritize. (34:01)The counterarguments made when Erica and her team advocated for a top-down selling motion to enterprise clients at GitHub. (38:03)How Erica defines grit. (41:37)Links:Connect with EricaGitHubEmail: mailto: eanderson@github.comConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

21 Juni 202143min

Growing up in a farm town in Pennsylvania with a population of just 183 people, Harry Ault had big career aspirations.After working for CitiGroup in management positions, Harry built a successful career as a sales leader in the tech industry. As a go-to-market guru, Harry now serves as the Chief Revenue Officer of DataStax, a data management company.On this episode of Go to Market Grit, Joubin and Harry talk about Harry’s three steps to a technology company turnaround, transitioning from legacy revenue to SaaS subscription revenue, and the importance for salespeople to demonstrate their product.In this episode, we cover:Harry's experience moving to Australia for a job in his early 20s — and the importance of seeking out new learning opportunities. (3:49)Adapting to change: The relationship between curiosity, taking ownership, and grit. (8:18)Learning from failure and the galvanizing impact of company cultures. (12:10)Changing company strategy, go-to-market, and external perception: Harry's three steps for a tech company turnaround. (17:46)'Make change in hours': The benefits of fostering a non-hierarchical, mission-oriented company culture — and the importance of listening to customer feedback. (21:31)Transitioning from legacy to SaaS: Why DataStax separated its SaaS sales team from the organization that works with its legacy customers. (26:38)'Elevating our sales capability': Growing a successful SaaS go-to-market strategy by focusing on product demonstration and partnering with customers. (31:07)Communicating a product's value to a customer by personalizing a hands-on demonstration as a salesperson. (38:22)How Harry defines the word grit. (42:41)Links:Connect with HarryLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

14 Juni 202144min

Laura Palmer will never forget the first big technology sales deal she ever closed.Having only worked professionally as an inside sales rep, Laura took a leap of faith early in her business career and negotiated a half-a-million deal with a customer while “kind of knowing what I was doing and kind of not knowing what I was doing,” she says. So when Laura stood up for herself by telling the CEO of her company that she believed she should be promoted to a field rep, it’s no surprise she was given the job on the spot.Since then, Laura — who now serves as Vice President of Sales, Americas & EMEA at Unity Technologies — has built an extremely successful career in sales and sales leadership. On this episode of Go to Market Grit, Joubin and Laura talk about returning to the office in a post-COVID world, as well as the importance of building relationships with customers by physically showing up.In this episode, we cover:From inside sales to top field rep: How Laura 'demanded the ball', closed a large sales deal, and earned a promotion. (0:52)Career changes: Laura's story of leaving Google — and what her decision making process looked like. (8:02)Unity Technologies: Unity's successful video game engine — and the applications this technology has outside of gaming. (16:19)Create and operate: The 'two sides' to Unity Technologies' business operation — and the company's 'complicated' go-to-market model. (18:55)Finding a balance: The framework through which Laura is making decisions on how to run her sales team post-COVID — and the importance of community building within an organization. (23:42)People buy from people': Why Laura believes that field sales is not 'dead' — and redefining 'inside sales' to 'strategic sales.' (29:51)Joubin and Laura share stories about the value of building relationships with business customers by physically showing up. (32:59)Gaining satisfaction as a leader by helping people grow and learn — and how women can help other women succeed in business. (38:24)How Laura defines grit. (43:19)Links:Connect with LauraLinkedInEmail: laurap@unity3d.comConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.comLearn more about Kleiner Perkins

7 Juni 202145min

Throughout his over 18 years working for the Golden State Warriors, Brandon Schneider has held several positions and seen it all.From the depths of rarely making the playoffs, to the heights of making it to the NBA championship five times in a row with three wins, Brandon has held 10 titles at the Warriors — most recently, the role of President and Chief Operating Officer.On this episode of Go to Market Grit, Joubin and Brandon geek out over their shared love of the Golden State Warriors, talk about building resilience in business, and the traits Brandon looks for in new sales hires.In this episode, we cover:Record-setting: The Golden State Warriors’ recent successes and its $4.7 billion valuation. (2:01)Making an impact: Why Brandon stuck with working at the Warriors during the team's downturn — and the importance of finding a job you love. (6:20)How the Golden State Warriors evolved after Joe Lacob and Peter Guber took charge — and the importance of hiring and recruiting great talent. (12:44)Fan experiences, arenas, and digital presence: Creating an economically sustainable business despite 'the inevitable ups and downs of a basketball team.' (22:03)Why the Warriors look at talent and character when recruiting athletes — and the relationship between fan experience and revenue. (26:49)Building resilience in business: Withstanding adversity and making the most out of challenges. (31:17)Work ethic, passion and confidence: The traits Brandon looks for in sales hires — and the parallels between sales and athletics. (34:51)How the digital age has changed the importance of geographical markets in professional sports. (38:43)How Brandon defines grit. (41:53)Links:Connect with BrandonLinkedInConnect with JoubinTwitterLinkedInEmail: gtmg@kleinerperkins.com Learn more about Kleiner Perkins

31 Maj 202144min

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 Maj 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 Maj 202143min