HubSpot CEO on the Future of SaaS, AI, & Leading Through Change

The episode begins with the host Jubin, a partner at Kleiner Perkins, introducing the show and today's guest, Yamini Rangan, CEO of HubSpot.

The host provides context about HubSpot as "one of the few public tech companies pulling off over $2 and a half billion dollars of revenue and growing over 20%." He also explains Yamini's journey to becoming CEO, having joined HubSpot as the chief customer officer in 2020.

Timestamp: [01:03-01:41]

The conversation begins casually with Jubin reflecting on his recent interviews with former salespeople who have reached executive positions, connecting Yamini to this trend.

Yamini confirms her sales background, and the host mentions other successful executives like Carl, whom Yamini knows from her time at Dropbox when Carl was at Seoa serving as an advisor.

The conversation turns personal as they discuss Yamini's name and origins.

Yamini notes the uniqueness of her name, mentioning that despite India's billion-plus population, she has never met another Yamini face-to-face, though she has heard of others with the same name.

Timestamp: [01:41-03:14]

Yamini discusses how she maintains connections to her Indian heritage, particularly through trips with her teenage sons.

She explains the challenge of helping her American-raised children understand her different upbringing and background.

Yamini mentions that her husband is also from India, and they go back together to visit their origins. She shares that she has two sons, ages 18 and 16, with the older one heading to college.

Timestamp: [03:14-03:59]

When asked about her financial background growing up in India, Yamini reveals her modest upbringing.

With a touch of humor, she recalls how the small space felt sufficient at the time.

Yamini describes her family as "squarely middle class," with her father running a small business "month to month, year to year" while her mother was a stay-at-home mom. She emphasizes how her parents "did everything possible" for her and her sister, and they "had no desires beyond what we got."

She shares a vivid memory of how she and her sister, who is two years older, would compete for limited resources in their small home.

Timestamp: [03:59-05:07]

The conversation shifts to Yamini's current role, with Jubin asking about the scale of HubSpot today.

Yamini provides key metrics about the company, stating it has "9,000 people" and "three billion-ish" in revenue. When Jubin asks about the market cap, Yamini hesitates to check the current day's figure.

Jubin mentions the figure from his notes: "30 billion," which Yamini confirms.

The host then raises an interesting question about the public nature of executive compensation and how Yamini's children might be aware of her high income, asking if this creates any discomfort given her humble origins.

Yamini acknowledges this reality with a simple, "And they do."

Timestamp: [05:07-06:02]

Yamini reflects deeply on her concerns about raising children in affluence when her own drive came from humble beginnings.

She describes how her mother instilled strong values and high expectations in her and her sister.

Yamini recalls how dinner conversations would center around trailblazers and achievers.

Her mother's focus was particularly on female achievement, creating an inspired childhood.

This upbringing created challenges when Yamini reached college, as her engineering aspirations clashed with societal expectations for women in the 1970s and 80s.

Timestamp: [06:02-08:01]

Yamini emphasizes that despite her achievement-oriented upbringing, money was never the primary focus.

She shares how she tries to instill similar values in her own children by taking them to an orphanage in India that she sponsors.

Yamini explains the purpose behind these visits.

When Jubin asks if her sons are aware of her wealth, she acknowledges they are but maintains firm boundaries about expectations.

Yamini shares an example of how her sons might approach her about her income.

She emphasizes her philosophy on raising children with drive and purpose.

Yamini concludes by stating her and her husband's parenting goal.

Timestamp: [08:01-10:00]

• Yamini Rangan transitioned from Chief Customer Officer to CEO of HubSpot following Brian Hallagan's accident in 2021
• HubSpot has grown to 9,000 employees, approximately $3 billion in revenue, and a market cap of around $30 billion
• Yamini grew up in a modest 350-square-foot home in south India, which she credits as the source of her drive and ambition
• Her mother instilled achievement-oriented values, particularly emphasizing female accomplishment and economic independence
• Despite her current success and wealth, Yamini maintains that money was never her primary motivation
• She actively works to instill similar values in her teenage sons by taking them to India and having them spend time at an orphanage she sponsors
• Yamini is deliberate about not passing wealth directly to her children, believing they should earn their own success
• She prioritizes raising children who desire to make an impact rather than simply enjoying privilege

Timestamp: [01:03-10:00]

Companies:

• HubSpot - Yamini's current company, a public tech company with $2.5B+ revenue growing at 20%+
• Dropbox - Where Yamini previously worked
• Seoa - Company where Carl worked as an advisor to Yamini
• Kleiner Perkins - Venture capital firm where the host Jubin is a partner

People:

• Yamini Rangan - Current CEO of HubSpot, former Chief Customer Officer
• Brian Hallagan - Former HubSpot CEO who had a snowmobiling accident in 2021
• Carl - Mentioned as an advisor who influenced Yamini during her time at Dropbox
• Jubin - Host of the podcast, partner at Kleiner Perkins

Concepts:

• Fire in the belly - Yamini's phrase for the inner drive that comes from humble beginnings
• Achievement-oriented upbringing - The value system Yamini's mother instilled, focusing on accomplishment rather than wealth

Timestamp: [01:03-10:00]

The conversation begins with a discussion about the challenge of creating meaningful constraints for children who grow up in privilege, contrasting with Yamini's own naturally constrained upbringing.

Jubin points out the fundamental difference in their situations:

He questions whether artificially created constraints can truly instill the same drive that comes from genuine need:

Yamini acknowledges the uncertainty, given that her children are still teenagers.

She shares that this concern has been on her mind since they were young:

Timestamp: [10:06-11:08]

Yamini reveals that rather than just talking about values, she and her husband have found that modeling strong work ethics has naturally influenced their children.

She proudly shares evidence that this approach may be working with her older son:

Yamini emphasizes the difference between teaching values explicitly versus embodying them:

She believes in the power of consistent demonstration rather than lectures:

Timestamp: [11:08-12:23]

Jubin asks Yamini to define what "working a lot" actually means in her life, seeking to understand her specific routine.

Yamini reveals the consistency of her work ethic:

She then describes her typical schedule during the workweek:

However, Yamini explains that she's developed a critical boundary to maintain balance:

When Jubin asks if she still receives work-related communications on Saturdays, she reveals her firm boundaries:

Even with board members reaching out, Yamini maintains her boundary:

Timestamp: [12:23-14:25]

Yamini reveals that while she preserves Saturdays for rest, Sundays are dedicated workdays that follow a specific purpose and rhythm.

She explains her approach to communication on Sundays:

Jubin shares that he follows a similar Sunday routine and explains an unexpected benefit:

Yamini enthusiastically agrees:

She expresses genuine excitement about the tech industry and how her Sundays allow her to explore and learn:

Yamini shares a recent example of how she spent a Sunday:

She concludes by describing her Sunday as a form of play:

Timestamp: [14:25-16:40]

Jubin shifts the conversation to explore Yamini's early days at HubSpot, which coincided with the beginning of the COVID-19 pandemic.

Yamini confirms she joined HubSpot in January 2020 as Chief Customer Officer, overseeing "marketing, sales, customer success, and operations" – essentially all go-to-market functions. This was just before COVID-19 became widely known.

She recalls how her onboarding plan was completely upended by the pandemic:

However, the situation changed dramatically in March 2020:

Facing this crisis, the original onboarding plan was scrapped:

Yamini describes the bold plan they developed:

She recalls the board's skeptical reaction:

Yamini explained their reasoning, focused on their small business customers:

When pressed about when they'd recover the $20 million relief fund investment, Yamini remembers her candid response:

Timestamp: [16:40-20:42]

Yamini describes how HubSpot's bold customer-first strategy during the early pandemic ultimately led to explosive business growth.

Jubin expresses amazement at this growth rate:

Yamini confirms:

She reflects on the unexpected nature of this growth:

However, Yamini also acknowledges the operational challenges that came with such rapid expansion:

She concludes by noting the dramatic shift in their strategy, from initially preparing for contraction to suddenly managing hypergrowth:

Timestamp: [20:42-21:40]

• Creating artificial constraints for privileged children may not easily replicate the natural "fire in the belly" that comes from genuine need
• Modeling strong work ethics and values can be more effective than explicitly teaching them to children
• Yamini maintains a rigorous work schedule (12-15 hours on weekdays) but strictly protects Saturdays as a non-work day
• Sundays serve as dedicated deep thinking and preparation days, providing a sense of control over the upcoming week
• When COVID hit, HubSpot made a counter-intuitive decision to cut prices by 75% and create a $20M customer relief fund
• Despite initial board skepticism, the customer-first approach during crisis led to unprecedented growth – 85% growth on a $1B revenue base
• Rapid growth created significant operational challenges as the company wasn't prepared for such sudden expansion
• HubSpot experienced a dramatic strategic "whiplash" – initially preparing for contraction before pivoting to manage hypergrowth

Timestamp: [10:06-21:40]

Companies:

• HubSpot - Where Yamini serves as CEO, experienced 85% growth during pandemic
• Loveble - App development platform Yamini used to create an app on her weekend

People:

• Brian Halligan - HubSpot co-founder and CEO when Yamini joined in January 2020

Concepts:

• Customer Relief Fund - $20 million fund HubSpot created to help customers during pandemic
• Peak performance requires peak rest - Yamini's philosophy on balancing intense work with necessary recovery
• Net new AR - Annual recurring revenue metric mentioned in context of HubSpot's 85% growth
• Sunday strategy - Approach of using Sundays for deep thinking and preparation for the week
• Living values vs. teaching values - Yamini's parenting philosophy of modeling behavior rather than lecturing

Timestamp: [10:06-21:40]

The conversation begins with reflections on the pandemic-era business mindset that pervaded the tech industry during HubSpot's explosive growth period.

Jubin characterizes the progression they experienced:

He describes how companies responded to this unprecedented demand:

Yamini acknowledges this characterization while admitting there were signs this wasn't sustainable:

She confirms the prevailing business imperative of that moment:

Timestamp: [21:46-22:52]

Jubin questions the now-common narrative that pandemic-era growth was "irresponsible," pointing out the practical challenges companies faced.

He highlights the inevitable trade-offs:

Yamini pushes back against the revisionist perspective:

She acknowledges specific challenges they faced:

Yamini also reflects on the competitive hiring environment:

She maintains that their growth wasn't irresponsible but contextual:

Timestamp: [22:52-24:07]

Yamini explains the challenges that emerged as the pandemic-era boom subsided and how the company had to adjust.

She highlights a specific skills mismatch in their pandemic hiring:

This realization forced difficult personnel decisions:

Yamini summarizes the challenging transition period:

Timestamp: [24:07-24:47]

Jubin draws a thought-provoking parallel between the pandemic growth ethos and the current AI frenzy.

He wonders if this is simply history repeating itself:

Yamini acknowledges the similarity while asserting this technological shift is more fundamentally transformative:

She argues for AI's distinctive impact:

Timestamp: [24:47-25:58]

Yamini provides a vivid historical perspective on how CRM systems have evolved, using it to illustrate why the current AI shift is genuinely transformative.

She begins by recalling the original CRM experience:

Yamini describes the labor-intensive process that defined early CRM usage:

She emphasizes the fundamental purpose of these systems:

Yamini then contrasts this with the AI-powered CRM experience emerging today:

She outlines the automated workflow this enables:

Timestamp: [25:58-27:16]

Yamini articulates why AI represents a fundamental paradigm shift in how technology supports human work, distinguishing it from previous tech trends.

She acknowledges certain similarities to past tech cycles while emphasizing the deeper impact:

Yamini highlights the transformative potential:

Jubin strongly agrees, sharing his own experience:

He mentions a company in his portfolio addressing this inefficiency:

Jubin reflects on the wasted effort:

Timestamp: [27:16-28:35]

Yamini expands on Jubin's point, articulating how AI can free salespeople to focus on their true value-add rather than administrative tasks.

She describes the extensive preparatory work that traditionally consumed salespeople's time:

Yamini shares a striking statistic from her years in the industry:

She highlights the minimal improvement despite massive investments in sales technology:

Yamini recalls her own experience managing sales teams:

She concludes with optimism about the current transformation:

Timestamp: [28:35-30:13]

• The pandemic created a "pulled-forward" growth environment where companies experienced years of digital adoption compressed into months
• While many now characterize pandemic-era growth as "irresponsible," Yamini believes they were appropriately responding to customer needs during digital transformation
• Companies faced significant infrastructure and hiring challenges during hypergrowth, including hiring people with "order-taking" rather than "fishing" skills
• Today's AI boom has parallels to the pandemic tech boom in terms of investment patterns and competitive dynamics
• Unlike previous tech cycles, AI represents a fundamental shift from "software helping you do tasks" to "software doing tasks to help you"
• CRM systems have evolved from being record-keeping tools where users input data to intelligent systems that can capture, process and act on information automatically
• Despite decades of sales technology development, the percentage of time salespeople spend with customers has remained stubbornly at 25-27%
• AI promises to dramatically increase this customer-facing time by automating the administrative burden of sales roles

Timestamp: [21:46-30:13]

Companies:

• HubSpot - Yamini's company, experiencing hypergrowth during pandemic and now embracing AI transformation
• Zoom - Mentioned for its extraordinary 350% growth rate during pandemic, compared to HubSpot's 80-85%
• Meta - Referenced as setting competitive compensation packages during pandemic hiring spree
• Google - Referenced alongside Meta for aggressive pandemic-era hiring and compensation
• Anthropic - AI company mentioned as source of frontier models businesses are building upon
• OpenAI - AI company mentioned as source of frontier models businesses are building upon
• Siebel - Described as "the original CRM company" where Yamini worked early in her career
• Nooks - Company in Jubin's investment portfolio automating sales outreach tasks

Concepts:

• Pandemic ethos - The belief during COVID that digital/remote trends represented a permanent, accelerated shift
• Order taking vs. fishing - Metaphor for different sales skills: passively processing incoming demand versus actively creating opportunities
• Target account selling methodology - Traditional sales approach mentioned from early CRM days
• Software helping you do tasks vs. software doing tasks to help you - Yamini's distinction between traditional software and AI
• The 25% statistic - The persistent finding that salespeople spend only about a quarter of their time in front of customers
• SaaS to AI transition - The industry shift from Software-as-a-Service to AI-powered platforms

Timestamp: [21:46-30:13]

The conversation begins with a discussion about the difficult strategic decisions companies face when determining how aggressively to invest in emerging technology trends.

Jubin highlights the high-stakes dilemma executives faced during the pandemic:

He elaborates with a concrete example:

Yamini emphatically agrees:

Jubin then draws a parallel to current AI investments by major tech companies:

He points out the potential downside of not investing:

Yamini reiterates:

Timestamp: [30:21-31:31]

Yamini articulates her philosophy for navigating technology hype cycles by anchoring decisions in customer value rather than technological trends.

She emphasizes the fundamental business principle that guides her approach:

Yamini shares HubSpot's guiding principle:

She explains how this principle filters technology decisions:

Yamini contrasts this with technology that lacks staying power:

She acknowledges the uncertainty inherent in early technology adoption:

Timestamp: [31:31-33:01]

Yamini draws parallels to previous technology transitions, particularly the shift from on-premise software to cloud computing, highlighting how established companies often struggle with disruption.

She contrasts this historical skepticism with today's AI adoption:

Jubin suggests that SAP's fate could have been different:

Yamini agrees:

Jubin concludes:

He then predicts a similar fate for current SaaS companies that don't adapt:

Timestamp: [33:01-34:15]

Yamini challenges the traditional disruption narrative, suggesting that AI represents a market expansion rather than just a replacement of existing technologies.

She first acknowledges the lessons of past disruptions:

Yamini then reframes the conversation about AI disruption:

She contrasts this with what she sees happening with AI:

Yamini elaborates on this expansion:

She explains why this shifts the strategic focus:

Jubin agrees:

Yamini concludes with optimism about incumbent companies:

Timestamp: [34:15-36:05]

• Companies face a high-stakes dilemma when deciding how aggressively to invest in emerging technology trends - under-investment risks missing massive opportunities
• Major tech companies like Meta, Google, and Microsoft are making unprecedented infrastructure investments for AI, recognizing the existential risk of being left behind
• Amid technology hype cycles, customer value should remain the North Star - successful innovations must transform from "neat features" to "necessary features"
• HubSpot uses "Solve for the Customer" (SFTC) as their guiding principle for navigating technology decisions
• Historical parallels exist between AI adoption today and cloud computing adoption in the past, when established companies like SAP questioned whether cloud would replace on-premise software
• Companies that failed to embrace previous technological shifts (like Siebel with SaaS) were ultimately cannibalized by more adaptive competitors
• Current SaaS companies that don't effectively leverage AI technology face similar existential threats
• Unlike traditional disruption where startups eat into existing markets, AI represents a 10x expansion of the addressable market by combining software with labor
• This expansion shifts the strategic focus from defending against disruption to capturing a portion of a much larger market
• Established companies that understand this dynamic are moving quickly to redefine their offerings within this expanded market

Timestamp: [30:21-36:05]

Companies:

• Meta - Mentioned for making massive AI infrastructure investments
• Google - Referenced alongside Meta for unprecedented AI spending
• Microsoft - Cited as making massive AI infrastructure investments
• Amazon - Mentioned in the context of AI investment strategy
• SAP - Where Yamini previously worked, used as example of company that questioned cloud adoption
• Siebel - Referenced as example of company that failed to adapt to SaaS, enabling Salesforce's rise
• Salesforce - Mentioned as the company that disrupted Siebel by embracing SaaS
• HubSpot - Yamini's company, which uses "Solve for the Customer" as its North Star
• Blockbuster - Cited as classic example of disruption that current tech executives have studied
• BlackBerry - Mentioned alongside Blockbuster as cautionary tale of disruption

Concepts:

• SFTC (Solve for the Customer) - HubSpot's guiding principle for evaluating technology
• Innovator's Dilemma - Book by Clayton Christensen about disruptive innovation, mentioned as required reading for tech executives
• TAM (Total Addressable Market) - Referenced in discussion of how AI expands rather than cannibalizes existing markets
• Neat vs. necessary features - Yamini's distinction between flashy AI capabilities versus those that deliver lasting customer value
• Software plus labor market - Yamini's concept of how AI expands the addressable market by 10x by taking over work previously done by humans
• Hot takes - Referenced multiple times as the excessive hype that surrounds technology cycles (crypto, web3, AI)
• Cloud computing transition - Used as historical parallel to current AI transition

Timestamp: [30:21-36:05]

The conversation begins with a frank discussion about AI's impact on labor, particularly in customer support roles.

Jubin states directly:

He emphasizes the financial implications:

Yamini confirms:

Jubin notes how this fundamentally changes business models:

Yamini agrees:

Timestamp: [36:10-36:47]

Jubin explores how data advantages create defensibility for incumbents in different markets, using specific examples.

He illustrates with a concrete example:

Jubin explains Axon's evolution:

He describes their AI initiative:

This represents a significant efficiency gain:

Jubin reflects on the competitive implications:

He contrasts this with other markets:

Timestamp: [36:47-38:35]

The conversation shifts to the complex question of data ownership in AI systems and how that impacts competitive advantages.

Jubin raises a provocative point:

He uses a specific example to illustrate:

Jubin contrasts this with Axon's situation:

He acknowledges Yamini's position:

Yamini responds by articulating HubSpot's approach to data aggregation as a value proposition:

She elaborates with a concrete example:

Yamini explains how AI expands this capability:

She emphasizes their strategic positioning:

Yamini provides a specific use case:

She summarizes the key advantage:

Timestamp: [38:35-41:52]

Jubin raises the critical challenge of attracting top AI talent when competing against exciting new startups.

He points out the competitive disadvantage established companies might face:

Jubin frames the strategic challenge:

Yamini acknowledges the challenge while explaining HubSpot's approach:

She highlights HubSpot's structural advantage:

Jubin interjects with recognition:

Yamini confirms their acceleration:

She describes their pitch to potential talent:

Yamini acknowledges different risk preferences:

She emphasizes the learning opportunity in the current moment:

Yamini shares how she frames this with her team:

Timestamp: [41:52-44:28]

Jubin asks Yamini about the emotional impact of leading through this period of intense competition and transformation.

He notes the intense competitive landscape:

Yamini responds with remarkable candor about her emotional state:

She shares a recent experience that exemplifies this duality:

Yamini summarizes:

She explains her approach to managing this uncertainty:

Yamini acknowledges the rapid pace of change:

Timestamp: [44:28-45:47]

The conversation concludes with reflections on the unprecedented speed of change in the technology industry.

Jubin shares a personal anecdote:

He emphasizes the rapid pace:

Yamini responds positively:

Jubin references a historical perspective for context:

He contrasts this with today's reality:

Yamini applies this to her own experience:

She agrees with the accelerated timeframe:

Jubin adds additional layers of complexity facing Yamini's position:

Yamini concludes with a simple assessment:

Timestamp: [45:47-47:24]

• AI will significantly reduce customer support staffing needs by 20-50% or more, fundamentally changing the economic equation from seat-based fees to labor replacement
• Companies with proprietary data advantages (like Axon with police data) have strong defensive moats in specific verticals
• The complex question of data ownership creates tension in the AI ecosystem - customers own their data, but companies derive value from analyzing it
• HubSpot's strategy focuses on aggregating structured, unstructured, and external data to provide insights back to customers
• A key value proposition is identifying best practices (like top-performing sales conversations) and helping others replicate them
• Attracting top AI talent is a critical challenge when competing against exciting startups
• HubSpot counters this by creating "startup within a startup" environments and emphasizing the learning opportunity of this transformative period
• Leaders like Yamini experience the duality of being "excited and scared" during this period of intense change and competition
• Planning horizons have compressed dramatically - focus is now on 3-month increments rather than multi-year plans
• The pace of change has accelerated from reinvention every 5 years (John Chambers' era) to every 3-6 months today
• Multiple factors compound complexity: new competitors, rapidly improving models, and dramatically falling costs

Timestamp: [36:10-47:24]

Companies:

• HubSpot - Yamini's company, focused on aggregating data to provide customer insights
• Axon - $60B company with 99% market share in tasers, now building AI co-pilots for police officers
• Salesforce - Referenced in discussion about customer data ownership
• Harvey - Mentioned as an exciting AI startup that competes for talent
• Amazon - Mentioned regarding Axon's cloud usage
• Microsoft - Cited regarding Axon's cloud infrastructure
• Netflix - Used as comparison point for Axon's data scale
• Snapchat - Used as comparison point for Axon's data scale
• Cisco - Referenced through John Chambers' approach to reinvention
• Kleiner Perkins - Jubin's venture capital firm that runs a CIO group

Concepts:

• Co-pilot - AI assistant for specific roles (like police officers), automating documentation
• Structured vs. unstructured data - Distinction between traditional database information and conversational content
• 10Ks/10Qs - Financial reports that can provide external data for AI analysis
• 20-50% clip - The expected reduction in customer support staffing due to AI
• Startup within a startup - HubSpot's approach to innovation and talent attraction
• AG (Artificial General Intelligence) - Referenced regarding future uncertainty
• Risk profile - How individual talent evaluates opportunities at startups vs. established companies
• Foundational models - The base AI systems dropping in price by 10x annually
• The state of AI - Rapidly evolving landscape requiring frequent reassessment

People:

• John Chambers - Former Cisco CEO known for reinventing the company every 5 years

Timestamp: [36:10-47:24]

The conversation shifts to Yamini's unexpected journey to becoming CEO of HubSpot, beginning with Jubin asking about the timeline.

Yamini reveals:

She then begins to share the surprising story of her succession.

Yamini clarifies who Brian is for context:

She recounts the unexpected message she received:

Yamini explains that they had just one brief conversation about succession, and she didn't think much more about it until a sudden turn of events:

Timestamp: [47:30-48:31]

Yamini describes the abrupt leadership transition that occurred following Brian's accident, highlighting the unexpected nature of her ascension to the role.

The timing of this transition was particularly challenging:

Yamini recalls their initial conversation about the temporary arrangement:

She emphasizes the challenging business context:

When Yamini asked for guidance, Brian's response was characteristically blunt:

Jubin asks for clarification about her initial role:

Yamini explains:

Timestamp: [48:31-49:46]

Yamini describes how what began as a temporary leadership assignment unexpectedly became permanent, showcasing the unpredictable nature of executive succession.

She initially assumed Brian would return to his role:

Yamini recounts the surprising moment when Brian returned:

She describes her expectation versus the reality:

The transition became official:

Yamini emphasizes the challenging circumstances surrounding her permanent appointment:

Timestamp: [49:46-50:54]

Jubin and Yamini discuss the tumultuous market conditions that followed her appointment as CEO, highlighting the challenges of leading through dramatic economic shifts.

Jubin observes:

Yamini points out the even shorter timeframe of stable conditions:

She describes the rapid economic deterioration:

Yamini offers her perspective on the macroeconomic factors:

She details HubSpot's response to these changing conditions:

Yamini summarizes her experience:

Timestamp: [50:54-52:04]

When asked about her emotional reaction to becoming CEO, Yamini shares a deeply personal reflection on her journey and how the reality exceeded even her imagination of what was possible.

Jubin asks:

Yamini responds with raw emotion:

She describes her humble beginnings in the United States:

Yamini shares a touching moment with her family:

She recalls her son's concern:

Yamini reflects on how becoming CEO was beyond anything she had imagined for herself:

She articulates her original aspirations:

Yamini emphasizes her focus on growth rather than status:

She concludes with a powerful statement about exceeding the American dream:

Yamini expresses her gratitude:

Timestamp: [52:04-54:14]

• Yamini's path to becoming CEO began unexpectedly when Brian Halligan texted her on Christmas Eve that she was part of his succession plan, just one year after she joined HubSpot
• When Brian had a serious snowmobile accident in March 2021, Yamini was thrust into the interim CEO role just 15 months after joining the company
• What initially seemed like a temporary arrangement became permanent when Brian returned in July/August 2021 and confirmed she should continue as CEO
• The timing of her appointment coincided with extreme business volatility – first rapid growth during the pandemic, then a sharp market correction
• October 2021 represented the peak of the market, giving Yamini only two months of favorable conditions before the environment changed dramatically
• By April 2022, HubSpot had to "turn the whole ship around" – slowing hiring and recalibrating growth plans due to inflation and rising interest rates
• Yamini's personal journey – from a small town in India without a high school, coming to the US with just $300, to leading a public company – made the CEO appointment deeply emotional
• She describes her achievement as "more than my dream" – beyond even what she had imagined possible within the American dream narrative
• The transition exemplifies how leadership succession can happen unexpectedly, requiring flexibility and readiness
• Yamini's emotional reaction to the news (crying when telling her family) reveals the profound personal impact of her professional achievement

Timestamp: [47:30-54:14]

People:

• Brian Halligan - HubSpot co-founder and CEO for 15 years who appointed Yamini as his successor after a snowmobile accident
• Yamini's son - Asked if she got fired when he saw her crying after learning she would become CEO

Companies:

• HubSpot - The public company where Yamini unexpectedly became CEO

Concepts:

• Succession planning - Process that began informally with a text message on Christmas Eve
• Interim CEO - Yamini's initial role when Brian stepped away for recovery
• Market peak (October 2021) - Referenced as the high point before economic conditions deteriorated
• The American dream - Concept Yamini references as something her achievements exceeded
• Economic pullback (April 2022) - When HubSpot began seeing customer spending slow due to inflation and interest rates
• C-suite - Executive leadership level Yamini never expected to reach in a public company

Timestamp: [47:30-54:14]

Yamini describes how the fundamental challenge of her role changed when transitioning from Chief Customer Officer to CEO, particularly regarding the exponential increase in stakeholders.

She contrasts the relatively straightforward stakeholder prioritization of her previous go-to-market roles:

Yamini explains her previous framework for decision-making:

She details how this guided her approach:

The CEO position dramatically expanded this framework:

Yamini acknowledges the fundamental challenge this creates:

She summarizes the complexity:

Timestamp: [54:22-56:36]

Yamini reveals a persistent sense of "being behind" throughout her life and career, and how this has actually served as a powerful motivational force.

She begins by noting the perception challenges she initially faced as CEO:

This connects to a deeper pattern in her life:

Yamini traces this feeling through various life transitions:

Rather than seeing this as a disadvantage, she reframes it as fuel for growth:

Yamini reveals her mindset for handling this feeling:

Timestamp: [56:36-58:17]

Jubin shares his own feelings of inadequacy, and Yamini responds by describing how she's come to embrace the discomfort of always feeling behind, recognizing it as a driver of her greatest growth.

Jubin admits:

He describes chasing "this imaginary dragon of getting over the hill of not enough," while recognizing that this same feeling may be what drives him forward.

Yamini responds with a profound insight about her relationship with this feeling:

She illustrates with a specific example from early in her career:

Yamini candidly analyzes the challenges she faced in sales:

Timestamp: [58:17-59:55]

Yamini shares how she discovered her unique strengths by focusing on what she could do well rather than traditional approaches, illustrating how perceived disadvantages can become advantages.

She describes her meticulous preparation process:

Yamini explains how she leveraged her analytical strengths:

She came to a breakthrough realization:

This approach, while requiring significant effort, led to deeper expertise:

Yamini connects this back to her broader philosophy:

She concludes with a powerful insight:

Timestamp: [59:55-1:01:50]

Jubin asks about the widely-acknowledged loneliness of the CEO position, and Yamini confirms this reality while explaining the specific constraints that create this isolation.

Jubin poses the question:

Yamini immediately confirms:

Jubin interjects with specific limitations:

Yamini continues:

Jubin adds:

Yamini affirms:

She describes attempts to find community during COVID:

Despite having this network, she acknowledges its limitations:

Yamini explains the practical constraints:

She highlights the fundamental accountability that comes with the role:

Yamini shares how she handles this:

She concludes:

Timestamp: [1:01:50-1:03:46]

Jubin asks a probing question about Yamini's relationship with HubSpot's founder and former CEO, Brian Halligan, exploring the complex dynamics of succeeding a founder.

Jubin poses the question:

He then adds the emotional complexity:

Yamini acknowledges this tension:

She describes how these interactions can be both validating and complex:

Yamini explains how their leadership styles necessarily differ:

She concludes by emphasizing the all-encompassing nature of her role:

Timestamp: [1:03:46-1:05:28]

• The CEO role dramatically expands stakeholder management from the relatively straightforward "customer-company-rep" framework to include shareholders, board members, and founders
• Unlike other roles, being CEO makes it "almost impossible" to satisfy all stakeholders simultaneously; optimizing for one group often means delaying benefits for others
• Yamini has experienced a persistent feeling of "being behind" throughout her life – from growing up in a small town to navigating cultural transitions to shifting career paths
• Rather than seeing this as a disadvantage, she has embraced this discomfort as a powerful driver of growth and learning
• As an introverted engineer entering sales, Yamini compensated for weaknesses in small talk by developing strengths in deep business analysis and genuine problem-solving
• She used preparation (studying 10Ks, 10Qs, management statements) to identify customer challenges rather than relying on traditional relationship-building approaches
• The CEO position is uniquely lonely because you can't fully discuss challenges with your team (inappropriate), board (they evaluate you), or even other CEOs (lack context)
• A fundamental aspect of CEO loneliness is the asymmetry between delegation (necessary) and accountability (which remains 100% with the CEO)
• Even with supportive founders, successor CEOs face complex dynamics – wanting both guidance and independence, especially when strategic directions must differ
• Yamini describes the CEO role as consuming "everything you have in your life" requiring "200%" commitment – "more than a job... it's my life now"

Timestamp: [54:22-1:05:28]

People:

• Brian Halligan - HubSpot founder and former CEO who Yamini succeeded
• Dharmesh - HubSpot co-founder mentioned briefly (Dharmesh Shah)

Companies:

• HubSpot - The company Yamini leads as CEO

Concepts:

• Stakeholder management - The expanded complexity of balancing interests of multiple groups as CEO
• Customer-company-rep framework - Yamini's previous decision-making approach in go-to-market roles
• 10Ks/10Qs - Financial reports Yamini studied to prepare for sales calls
• Startup-to-scale-up vs. scale-up-to-grown-up - Different CEO roles and styles described by Brian
• The feeling of being behind - Persistent sense Yamini has experienced throughout her life and career
• CEO loneliness - The isolation that comes from having ultimate accountability without peers to fully discuss challenges
• Engineer's approach to sales - Yamini's analytical method that compensated for traditional relationship-building weaknesses

Timestamp: [54:22-1:05:28]

Jubin asks Yamini about the stakeholders she feels she's let down most in her role, leading to a candid discussion about the painful realities of leadership during difficult times.

Yamini's response is both surprising and deeply honest:

She describes the operational challenges this created:

Yamini then addresses the most difficult decision of her tenure:

Jubin interjects, emphasizing the necessity:

Timestamp: [1:05:35-1:06:33]

Yamini provides a thoughtful analysis of the layoff decision, its timing, and the personal impact it had on her as a leader.

She describes the emotional weight of the decision:

Yamini acknowledges the shared responsibility while taking personal ownership:

Jubin directly asks about the impact on her leadership standing:

Yamini responds without hesitation:

Jubin notes the broader impact on organizational confidence:

Yamini confirms this perception while describing her approach to rebuilding trust:

She shares a personal philosophy that guides her through mistakes:

Yamini concludes with the ongoing challenge:

Timestamp: [1:06:33-1:08:13]

Yamini describes the compounding challenges of simultaneously managing economic downturn, technological disruption, and workplace transformation.

She summarizes the cumulative effect:

Despite these challenges, Yamini emphasizes their core focus:

Timestamp: [1:08:13-1:08:46]

The conversation shifts to Yamini's personal relationship with rest and relaxation, revealing her intense drive and difficulty disconnecting from work.

Jubin asks:

Yamini responds emphatically:

Jubin probes further:

Yamini's answer is definitive:

When Jubin asks why, Yamini explains:

Jubin expresses disbelief:

Yamini insists:

She connects this to her passion for the industry:

Yamini reveals how this connects to her deeper motivations:

Timestamp: [1:08:46-1:10:28]

Jubin pushes Yamini on her relationship with rest, and she reveals the careful balance she's created to sustain her energy and creativity without burning out.

Jubin observes:

Yamini confirms:

Jubin then asks about the concept of slowing down:

After Yamini acknowledges that slowing down is possible, Jubin refines his question:

Yamini reveals that she has developed a system for balance:

She also describes her approach to vacations:

Jubin asks a pointed question about her ability to disconnect:

Yamini explains that she's developed this discipline out of necessity:

She connects rest to creative capacity:

Yamini describes her structured approach to daily rejuvenation:

She concludes by noting that even her relaxation tends to be mentally engaging:

Timestamp: [1:10:28-1:12:26]

• Yamini identifies employees as the stakeholders she feels she let down most, particularly through the January 2023 layoffs
• Though she acted relatively quickly to slow hiring in June 2022 (just two months after seeing warning signs), the action "was not hard enough" given previous hiring
• She acknowledges losing credibility with employees after breaking the implicit promise that HubSpot would be "a great place for them, their families, their careers"
• Yamini's leadership philosophy includes "make new mistakes" - learning deeply from errors but not repeating them
• The layoffs occurred during a period of "tumultuous" change that included economic downturn, AI pivot, roadmap changes, and remote work productivity challenges
• Yamini has not "sat on the couch without my laptop in 20 years" - illustrating her difficulty disconnecting from work
• Her difficulty resting connects to a deeper anxiety about "being behind" - if she's not constantly learning, she feels she's falling further behind
• After experiencing burnout ("by June, July... I'm so exhausted I can't function"), she developed a structured approach to breaks
• Her system includes daily breaks (yoga, workout, walking, music), protected Saturdays (no email checking), and longer vacations
• Even during relaxation, Yamini tends toward mentally engaging activities like reading, rather than fully "vegging out"
• She recognizes that creativity suffers without proper breaks, creating a practical incentive for maintaining balance

Timestamp: [1:05:35-1:12:26]

People:

• Yamini's son - Mentioned as asking her to shut down her computer to talk for 5 minutes at 11 PM before leaving for college
• Yamini's husband - Mentioned as her walking companion on Saturdays
• Brian - Referenced as agreeing with the layoff decision (Brian Halligan, former CEO)
• Dharmesh - Referenced as agreeing with the layoff decision (Dharmesh Shah, co-founder)

Companies:

• HubSpot - The company where Yamini is CEO and implemented layoffs in January 2023

Concepts:

• Pull forward demand - The pandemic phenomenon where future growth was compressed into a shorter timeframe
• Losing credibility - The leadership impact of making difficult decisions that affect employees' lives and careers
• "Make new mistakes" - Yamini's philosophy about learning from errors without repeating them
• Burn out - The exhaustion that Yamini experienced when not taking proper breaks
• The three phases of vacation - Yamini's description of the adjustment period (3-4 days), immersion (7 days), and anticipatory return (last 3 days)
• "Sitting still" - The challenge of truly disconnecting from work and productivity

Timestamp: [1:05:35-1:12:26]

The conversation shifts to Yamini's unusual reading habits, revealing another dimension of her multitasking tendencies and intellectual curiosity.

Yamini reveals a surprising approach to reading:

Jubin expresses disbelief:

He asks for clarification about her method:

She confirms her preference for physical books:

Jubin seems amazed by her approach:

Yamini confirms:

Jubin tries to understand her process:

Yamini acknowledges:

Timestamp: [1:12:31-1:13:08]

Yamini shares insights about her eclectic reading choices, from dense intellectual works to popular non-fiction, demonstrating the breadth of her curiosity.

Jubin offers a theory about business books:

Yamini acknowledges this point:

When asked about her book selection, she reveals:

Jubin responds humorously:

Yamini admits her own challenge with the book:

She contrasts this with another current read:

Timestamp: [1:13:08-1:14:08]

Jubin and Yamini discuss the psychology of reading and how giving oneself permission to abandon books can actually encourage more reading.

Jubin shares his own evolving approach:

He mentions a perspective that changed his thinking:

Jubin explains the rationale:

Yamini enthusiastically agrees:

Timestamp: [1:14:08-1:14:51]

Yamini shares a touching childhood memory about her relationship with books, revealing how reading shaped her worldview and nurtured her curiosity from an early age.

She explains how this habit reflected her personality:

Yamini recounts a memorable interaction:

She explains what books meant to her:

Yamini concludes by describing her ideal day of relaxation:

Timestamp: [1:14:51-1:15:39]

As the interview winds down, Jubin asks about HubSpot's current hiring priorities, revealing the company's ongoing focus areas.

Jubin expresses appreciation for the conversation:

Yamini responds warmly:

Jubin then asks about HubSpot's hiring status:

Yamini enthusiastically confirms:

When asked about specific roles, she identifies two key areas:

Timestamp: [1:15:39-1:15:54]

In the final question, Jubin asks Yamini to define "grit," leading to a powerful reflection on intentional choices and resilience that encapsulates her life philosophy.

Jubin asks:

Yamini responds with a thoughtful definition that connects to her life journey:

She illustrates with examples from her own path:

Yamini articulates her philosophy:

She acknowledges the universal pattern of challenges:

Yamini concludes:

Timestamp: [1:15:54-1:16:45]

Jubin closes the interview with gratitude and information about the podcast.

Yamini responds graciously:

Jubin provides closing information about the podcast:

Timestamp: [1:16:45-1:17:08]

• Yamini reads four books simultaneously, demonstrating her multitasking approach to learning and intellectual curiosity
• She prefers physical books over digital formats, despite consuming online articles and magazines
• Her reading spans from dense, intellectual works (Gödel, Escher, Bach) to popular non-fiction (Sapiens), showing the breadth of her interests
• Yamini has given herself "permission" to read books in a non-linear way, following Naval Ravikant's philosophy that this approach encourages more reading
• Books were her "window to the world" from childhood, to the point where she had "read every book in the library" in her small town
• Her introverted nature as a child manifested in having her mother retrieve library books rather than going herself
• Yamini's ideal relaxation includes a long walk, yoga, and reading just one chapter of a book
• HubSpot is actively hiring in two key areas: R&D (product building) and sales (product selling)
• Yamini defines "grit" as "the intentional choices I have made and the resilience to follow through"
• She sees her major life decisions (coming to America, becoming an engineer, shifting to sales) as intentional choices that went against conventional wisdom
• Yamini's philosophy acknowledges that all worthwhile pursuits include "good days and bad days" and require resilience to achieve meaningful goals

Timestamp: [1:12:31-1:17:08]

Books:

• Gödel, Escher, Bach - A dense intellectual work about math, architecture and music that Yamini reads 10 pages at a time
• Sapiens - Book by Yuval Noah Harari that Yamini is reading one chapter at a time

People:

• Naval - Referenced by Jubin as someone who advocates not feeling obligated to finish books (Naval Ravikant)
• Yamini's mother - Mentioned as retrieving library books for Yamini as a child
• Librarian - Person who told Yamini's mother that her daughter had "read every book in this library"

Companies:

• HubSpot - Yamini's company, currently hiring in R&D and sales
• Kleiner Perkins - Venture capital firm producing the podcast, where Jubin is a partner

Concepts:

• Parallel reading - Yamini's approach of reading multiple books simultaneously
• Grit - Defined by Yamini as making intentional choices and having resilience to follow through
• "Window into the world" - How Yamini describes what books represented to her growing up
• Intentional choices - Major life decisions that may go against conventional wisdom
• Physical vs. digital books - Yamini's preference for traditional book format

Timestamp: [1:12:31-1:17:08]