Grit

Dan O’Connell’s career is an impressive display of how hard work can catapult a person from the bottom of the sales hierarchy to the very top of business leadership.

Having started as an account coordinator at Google AdWords in 2003, Dan has climbed the corporate ladder — eventually becoming the CEO and President of TalkIQ in 2017. Now, Dan serves as the Chief Strategy Officer, Chief Revenue Officer and as a board member at Dialpad, a company creating an AI-powered cloud communication suite.

On this episode of Go to Market Grit, Joubin and Dan discuss Dan’s experience selling online advertisements for Google in the early to mid 2000s, Dan’s experience of becoming a CEO, and the importance for senior leaders to make an effort to connect with employees.

In this episode, we cover:

• 'Shooting fish in a barrel': Dan's experience working for Google and selling online advertisements in the early 2000s. (5:00)
• 'I wanted to do more': Taking risks and avoiding career complacency. (7:36)
• Identifying skilled salespeople when demand is insanely high — and the moment when Dan realized Google was a big deal. (12:45)
• The key character traits of people hired on Google's go-to-market team — and how to identify ‘coachability’ in a job candidate. (22:31)
• Why Dan decided to become CEO and president of TalkIQ in 2017 after working in sales — and how his father’s example motivated him.
• Humility, ambition and optimism: The qualities Dan would want his children to have — and the role of parents in encouraging new opportunities and growth. (34:10)
• 'An awesome experience': The complexities and fun of being a tech CEO. (37:02)
• Dan's current company, Dialpad, and its AI-powered cloud communication suite — and how he deals with the transition from CEO to a lower senior position. (43:47)
• The skills and qualities of a successful business manager. (47:48)
• What the word grit means to Dan. (51:35)

Links:

• Connect with Dan
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins

When it comes to building a profitable business, Amanda Kleha has learned by doing. 

Amanda’s seven-year tenure in multiple senior marketing and sales positions at Zendesk saw the company make an IPO, grow from 12 employees to 2,000, and go from $1 million to $300 million in revenue. Now, as Chief Customer Officer at Figma — a company recently valued at $10 billion that is creating collaborative design user interface platforms — Amanda is cementing her status as a top-tier business leader.

On this episode of Go to Market Grit, Joubin and Amanda talk about Amanda’s very successful run at Zendesk, her current work as CCO at Figma, and the importance of keeping the voice of the customer in focus during decision-making.

In this episode, we cover:

• Structured, yet open: Amanda’s strategy for interviewing job candidates. (6:14)
• Zendesk's massive growth and how it correlated with Amanda's feeling that she was having less fun working at the company. (11:22)
• Building experience, gaining traction, showing impact: The benefits of sticking with a company for the long term. (14:51)
• 'This is the next Adobe': Figma's collaborative design user interface platform. (21:05)
• How Amanda started working for Figma — and how she simplified the company's go-to-market through a combination of self-service and sales-assisted motions. (24:50)
• Keeping the voice of the customer front-and-center during decision-making. (29:43)
• Reflecting on negative and positive career milestones. (37:50)
• How Amanda felt when others were hired to more senior positions before her at Zendesk — and how that experience helped her become more empathetic. (41:34)
• Ways that sales reps at Figma stand out since quota attainment is so high. (45:33)
• Leaders, fillers, and killers: Amanda's framework for product bundles. (52:11)
• What the word grit means to Amanda. (1:03:07)

Links:

• Connect with Amanda
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins

When Steve Rowland studied at Texas A&M University to get his degree in engineering, he likely wouldn’t have expected that his career would shift into one of an extremely successful sales leader.

Over his 20+ year business career, Steve’s built successful teams at technology companies such as BMC Software, Appigee, and DataStax. Now, Steve serves as Chief Revenue Officer of Okta, a company selling identity security software.

On this episode of Go to Market Grit, Joubin and Steve talk about what Steve looks for in a company before deciding to join, the ins and outs of an acquisition integration, and the importance of leadership development.

In this episode, we cover:

• How Steve's upbringing informed his work ethic. (1:46)
• 'The beginning of many career pivots': Steve's first job at BMC as an inside sales rep. (5:43)
• Size, product, and leadership: What Steve evaluates in a company before deciding whether to join. (7:51)
• Curiosity, relevance and new experiences: Why (and how) Steve continues to reinvent himself and his career — and his process for analyzing risk. (12:11)
• Steve's current company, Okta, and its successful identity security software. (21:46)
• How company culture can make or break an acquisition integration — and how change can lead to positive growth. (25:26)
• Examples of the 'core DNA' Steve looks for in future leaders — and how he uncovers these unteachable qualities during job interviews. (32:26)
• Working with potential leaders on their professional development. (40:36)
• What the word grit means to Steve. (46:01)

Guest: Steve Rowland, Chief Revenue Officer at Okta

Links:

• Connect with Steve
  • Website: https://www.okta.com
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins

Take one look at Renu Gupta’s resume and it’s immediately clear that she is a talented — and successful — sales leader. 

With experience at companies such as Google, Dropbox and Slack, Renu has led large sales teams and produced results. Now, Renu serves as Vice President of Sales at Thrive Global, a company founded by CEO Arianna Huffington, that seeks to end workplace burnout with behavior change technology. 

On this episode of Go to Market Grit, Joubin and Renu discuss personal and professional habits, the importance for sales reps to practice “proactive communication,” and Thrive Global’s lead generation strategy.

In this episode, we cover:

• What Renu's one-year tenure as an account executive at Google taught her about different styles of management. (4:04)
• Why Renu was apprehensive about transitioning from an individual contributor to a manager at Dropbox — and why she hasn't looked back since. (7:06)
• Thrive Global: How Renu's current company is helping businesses empower employees to build positive life habits and reduce burnout through technology. (9:16)
• Personal and professional habits: The habits Renu never misses — and the lessons about hard work and gratitude she teaches her children. (16:03)
• 'We're all human': The aspirational habit Renu has that she often breaks — and how she works to make up for it. (20:32)
• Why 'proactive communication' is a common habit among successful sales reps. (23:35)
• 'Multi-year enterprise-wide deals': Thrive Global's B2B sales strategy. (26:53)
• ‘Brand recognition’: How Thrive Global generates sales leads through referrals. (32:35)
• The recruiting benefits of having a powerful mission. (35:30)
• What the word grit means to Renu. (38:45)

Guest: Renu Gupta, VP of Sales at Thrive Global

Links:

• Connect with Renu
  • Email: [email protected]
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins

When Jan Zeman was hired as a sales development representative in the early 2000s, he had a unique background in management consulting and venture capital. 

Jan has since risen through the sales ranks, having helped his previous company, Responsys, grow from $25 million in ARR to $200 million, among other successes. Now, he serves as SVP Sales, America at Iterable, a company creating a cross-channel marketing platform.

On this episode of Go to Market Grit, Joubin and Jan talk about Jan’s career working at Responsys, how Jan determines his personal and professional priorities, and tips for identifying successful sales talent.

In this episode, we cover:

• From venture capital to cold-calling: How Jan started his sales career. (2:17)
• Jan's nine-year run working in sales and sales leadership at Responsys — and why he never chose to leave. (5:37)
• The personal and organizational challenges Jan faced while working at Responsys — and why Jan wanted to become a sales leader. (10:23)
• 'I was very open-minded': How Oracle's purchase of Responsys helped Jan learn how to lead larger teams. (14:05)
• How Jan's current company, Iterable, uses data to personalize communications between a company and a customer. (16:35)
• 'Lean into the change': The importance of learning new business and life skills. (18:50)
• The importance of finding balance between work and life — and how Jan uses weekly journaling to help determine his personal and professional priorities. (24:22)
• How Jan evaluates curiosity in job candidates. (31:32)
• The value of listening, collaboration, and recruiting known and undiscovered talent as a sales leader. (36:43)
• The three segments of Iterable's business and how the company goes to market. (40:30)
• The benefits of having a product with a unique and changing differentiation — as well as how Jan teaches enablement to his team. (42:27)
• What the word grit means to Jan. (46:16)

Guest: Jan Zeman, SVP Sales, America at Iterable

Links:

• Connect with Jan
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins

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 Xero

Links:

• Connect with Rachael
  • Xero
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins

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 Ryan
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins

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 Erica
  • GitHub
  • Email: mailto: [email protected]
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins

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 Harry
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins

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 Laura
  • LinkedIn
  • Email: [email protected]
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Learn more about Kleiner Perkins