Founder Mode: Kashish Gupta, Founder and co-CEO of Hightouch

Data and AI Platform for Enterprise Marketing

Hightouch is a specialized platform that bridges a critical gap in enterprise marketing by helping companies actually use their customer data effectively.

Core Services:

1. Customer Data Access - Enables marketers to access and utilize their existing customer data for advertising and lifecycle marketing campaigns
2. AI Agent Deployment - Provides intelligent agents that help run marketing campaigns more effectively and build campaigns from scratch
3. Personalized Content Creation - AI agents write highly personalized content tailored to specific customer interests (like separate basketball vs tennis campaigns for different audiences)

Key Innovation:

• Bring Your Own Database Architecture - Unlike competitors, Hightouch doesn't store any customer data
• Enterprise-First Approach - Designed specifically for large companies using data warehouses like Snowflake and Databricks
• Universal SaaS Integration - Makes all marketing tools reflect the company's existing database

Notable Enterprise Clients:

• PetSmart - Uses the platform's UI daily for marketing operations
• Spotify - Leverages the data connection capabilities
• Men's Wearhouse - Implements personalized marketing campaigns
• Warner Music - Utilizes the marketer-friendly interface

Timestamp: [0:34-1:26]

Strategic Decision Against Conventional Wisdom

Despite advice from Y Combinator and others to start with smaller companies for easier sales cycles and faster feedback, Hightouch made a deliberate choice to focus on enterprise from day one.

The Conventional Advice They Rejected:

• Shorter Sales Cycles - Small businesses typically make decisions faster
• Easier Feedback Collection - Smaller companies provide quicker iteration opportunities
• Gradual Scaling Strategy - Get initial wins, then graduate to larger enterprises

Why They Went Enterprise Instead:

1. Architecture Advantage - Their product was perfectly suited for enterprise needs and didn't make sense for smaller businesses
2. Customer-Driven Decision - Enterprise customers clearly articulated the value and need for their solution
3. Product-Market Fit Clarity - The gap between having data and using it productively was much larger in enterprise environments

Customer-Centric Philosophy:

• Strict Customer Validation - "If the customer didn't say something, it's just not true until the customer says it"
• Internal Accountability - Co-founders challenge each other: "Did the customer say that or is that your thoughts?"
• Ideas Don't Count Until Validated - Personal opinions hold no weight without customer confirmation

Timestamp: [1:28-2:36]

From ChatGPT for Travel to Enterprise Data Platform

Hightouch's journey began with a completely different business model before COVID forced a strategic pivot that led to their current success.

Original Business (2019):

• Travel Focus - Built "ChatGPT for travel" during Y Combinator Summer 2019
• Natural Language Processing - Used pre-GPT technology to book travel through messaging
• COVID Impact - Pandemic made travel business unsustainable in 2020

The Pivot Process:

1. Multiple Business Ideas - Explored various concepts after abandoning travel
2. Customer Validation Method - Asked potential customers: "Do you want this product?"
3. The Critical Follow-Up Question - "What are your top priorities other than this?"
4. Reality Check - Customers would "suddenly relax" and reveal their actual important priorities

Discovery of the Data Gap:

• Core Problem Identified - Huge gap between "having data" and "using it in production for sales and marketing"
• Enterprise-Specific Challenge - Gap was much larger for companies using data warehouses like Snowflake and Databricks
• Market Opportunity - No existing tools bridged databases and marketing platforms effectively

Segment Connection:

• Co-founder Background - Two co-founders were early engineers at Segment (YC company)
• Segment Limitation Discovery - Found that Segment's approach didn't work for enterprise needs
• Key Innovation - Enterprise customers wanted to "bring their own database" rather than send data to another platform

Timestamp: [2:45-4:52]

The Complex Challenge of Enterprise Data Utilization

Despite having vast amounts of customer data, large enterprises face significant technical and organizational barriers when trying to use that data for sales and marketing activities.

Primary Challenges:

1. Data Complexity and Governance:

• Volume Overwhelm - Enterprises have massive amounts of data requiring guidance on what's relevant and usable
• Data Governance - Complex enterprise "red tape" around data usage, compliance, and permissions
• Quality Assurance - Determining if data is properly governed and suitable for marketing purposes

2. Tooling Gap:

• Missing Infrastructure - No existing tools to execute marketing campaigns using enterprise data warehouses
• Platform Resistance - Marketing platforms prefer to own customer data rather than integrate with external databases
• Integration Complexity - Difficulty connecting data warehouses (Snowflake, Databricks) to marketing tools

Hightouch's Unique Solution:

• Zero Data Storage - Only SaaS tool that stores no customer data whatsoever
• Universal Integration - Makes all marketing platforms reflect the customer's existing database
• Enterprise Architecture - Designed specifically for companies using modern data warehouse infrastructure

Market Reality:

• Intentional Gap - Marketing platforms deliberately avoided creating these connections to maintain data ownership
• Competitive Advantage - Hightouch broke this paradigm by refusing to store any data

Timestamp: [4:54-5:46]

Stair-Step Growth Through Biennial Product Evolution

Rather than following a smooth growth curve, Hightouch has achieved success through strategic reinvention every two years, launching new products that create demand surges.

Current Scale:

• Team Size - Approximately 250 employees
• Customer Base - 2,000-3,000 customers
• Enterprise Penetration - 25 Fortune 500 companies

Growth Pattern - Product Evolution Cycles:

Phase 1: Data Connections Product

• Foundation - Basic data integration capabilities
• Market Response - Initial traction with enterprise customers

Phase 2: Marketer-Friendly UI (2-Year Mark)

• Innovation - User interface that marketers love and use daily
• Customer Impact - Companies like PetSmart and Warner Music became daily active users
• Result - Significant demand surge from improved usability

Phase 3: AI Decisioning Platform (Current)

• Technology - Reinforcement learning to optimize marketing on per-customer basis
• Customer Benefit - Reduced message frequency (one per week) while increasing relevance
• Market Problem Solved - Helping B2C brands reduce unsubscribes while increasing engagement

Strategic Approach:

• Biennial Reinvention - Major product launches every two years
• Demand-Driven Growth - Each new product creates "huge surge of demand"
• Continuous Innovation - Rather than incremental improvements, focuses on breakthrough capabilities

Timestamp: [5:50-7:13]

Proactive Communication Strategy for Leadership Transitions

Kashish has developed a systematic approach to prepare his executive team and sales leaders for when he and his co-founders need to operate in founder mode.

Team Preparation Strategy:

1. Advance Warning System - Explicitly tells exec team and sales leaders that founder mode will happen
2. Expectation Setting - Frames founder mode as something to "be engaged and excited by rather than scared"
3. Character Consistency - Prevents team from thinking founders are "acting out of character"

Key Leadership Principle:

Predictive Communication - "If you tell people that you're going to do something in advance, then when you do it, they're not surprised"

Benefits of This Approach:

• Reduces Team Anxiety - Eliminates confusion when leadership style shifts
• Maintains Trust - Team understands the behavior is intentional, not reactive
• Encourages Engagement - Positions founder mode as positive rather than concerning
• Preserves Relationships - Prevents misinterpretation of founder behavior

Broader Application:

This approach demonstrates how founders can maintain team cohesion while preserving their ability to take decisive action when necessary, making founder mode a tool rather than a disruption.

Timestamp: [7:30-7:59]

Essential Insights:

1. Customer-Centric Validation - Hightouch's extreme focus on customer feedback over internal opinions drives all major decisions, including rejecting conventional wisdom about targeting smaller businesses first
2. Strategic Reinvention - The company achieves growth through biennial product evolution rather than incremental improvements, creating demand surges with breakthrough capabilities
3. Founder Mode Preparation - Proactive communication with teams about when founder mode will be used prevents confusion and maintains trust during leadership transitions

Actionable Insights:

• Enterprise-First Strategy - When product-market fit clearly favors enterprise customers, resist pressure to start with smaller businesses for easier sales cycles
• Zero Data Storage Innovation - Differentiate by refusing to store customer data, instead integrating with existing enterprise data warehouses
• Predictive Leadership Communication - Warn teams in advance about leadership style changes to maintain engagement and prevent misinterpretation

Timestamp: [0:00-7:59]

People Mentioned:

• Kashish Gupta - Founder & Co-CEO of Hightouch, featured guest discussing founder mode and enterprise data marketing
• Jessica Livingston - Y Combinator Partner and podcast host
• Carolynn Levy - Y Combinator Partner and podcast host

Companies & Products:

• Hightouch - Data and AI platform for enterprise marketers, helps companies use customer data for marketing campaigns
• Y Combinator - Startup accelerator that Hightouch participated in during Summer 2019
• Segment - Customer data platform where two of Hightouch's co-founders previously worked as engineers
• PetSmart - Major retail client using Hightouch's marketing platform daily
• Spotify - Music streaming service client leveraging Hightouch's data capabilities
• Men's Wearhouse - Retail client implementing personalized marketing campaigns
• Warner Music - Music company client utilizing Hightouch's marketer-friendly interface

Technologies & Tools:

• Snowflake - Cloud data warehouse platform commonly used by Hightouch's enterprise clients
• Databricks - Data analytics platform used by enterprise customers as their primary database

Concepts & Frameworks:

• Founder Mode - Leadership approach where founders take direct control during critical business moments, discussed as core topic
• Customer-Centric Validation - Methodology of only accepting ideas and strategies explicitly validated by customer feedback
• Bring Your Own Database Architecture - Hightouch's core innovation allowing enterprises to use existing data warehouses rather than migrating data

Timestamp: [0:00-7:59]

Core Philosophy of Leadership

Kashish Gupta defines founder mode as fundamentally about making the company successful rather than making everyone happy. This represents a shift from consensus-building to conviction-driven leadership.

Key Components of Founder Mode:

1. Results-Oriented Leadership - The primary job is to deliver company success, not individual satisfaction
2. Stop Negotiating - When you have strong conviction, execute fully rather than accepting compromised versions
3. Vision-Aligned Team Building - People committed to the mission will prefer successful decisions over personal comfort

The Transformation Process:

• Early Stage: Tried to listen to everyone, build consensus democratically
• 2024 Breakthrough: Stopped negotiating and started executing with full conviction
• Current Approach: Provide clear direction based on founder perspective and market context

Why This Works:

• Mission-Driven Employees prefer company success over personal accommodation
• Clear Boundaries create psychological safety (similar to parenting dynamics)
• Decisive Leadership eliminates uncertainty and builds confidence

Timestamp: [8:18-9:32]

Daily Writing Practice for Leadership Clarity

Kashish has developed a systematic approach to decision-making through continuous writing and reflection.

The Writing System:

1. Constant Documentation - Writes down almost every thought throughout each day
2. Weekly Filter Process - Reviews all thoughts to identify what remains true by week's end
3. Conviction Testing - Ideas that survive the week get shared with leadership team
4. Transparency Timeline - Anything still relevant after a week must be disclosed

The Philosophy Behind Sharing:

• Information Hoarding = Lying - Withholding insights from executives is considered deceptive
• Intuition Validation - Good team members often sense the same issues
• Collaborative Problem-Solving - Sharing concerns leads to joint solutions rather than fear

Practical Benefits:

• Volatility Management - Daily writing captures emotional fluctuations without immediate action
• Pattern Recognition - Persistent thoughts reveal genuine insights vs. temporary reactions
• Team Alignment - Transparent communication builds trust and collective intelligence

Timestamp: [11:11-12:29]

The Unique Risk-Taking Advantage of Founders

According to leadership coach David Clemens' teaching, founders have a structural advantage in risk-taking that employees fundamentally cannot match.

The Founder Risk Advantage:

1. Job Security Difference - Founders can't easily be fired, while employees face termination risk
2. Risk Tolerance Gap - Most people are naturally risk-averse due to job vulnerability
3. Decision Authority - Founders can execute without seeking permission or consensus

The Risk-Taking Imperative:

• 100% Success Rate = Failure - If you're always right, you didn't take enough risks
• Unique Founder Responsibility - Risk-taking is the one thing only founders can do that others struggle with
• Employee Limitations - Staff will seek permission, tone down ideas, or take half-measures

How Others Hedge Their Bets:

• Permission Seeking - Employees want founder approval before big moves
• Risk Dilution - They'll take partial risks rather than full commitment
• Conservative Execution - Natural tendency to hedge and play it safe

The Practical Result:

Founders must embrace being wrong sometimes as proof they're taking appropriately large risks for company growth.

Timestamp: [12:30-13:28]

A Founder Mode Risk-Taking Case Study

Mid-2023, Kashish made a massive hiring bet that contradicted all existing metrics but proved transformational for Hightouch.

The Risky Decision:

• Bold Commitment: Decided to double sales team headcount
• Ambitious Targets: Projected hitting current year's revenue plan AND next year's plan
• No Data Support: Historical metrics didn't justify the expansion
• High Stakes: Hiring is risky because firing is demoralizing and expensive

The Market Signal Detection:

1. Direct Management Approach - Started personally managing 4 sales managers and 20 reps
2. Customer Interaction Increase - Direct contact revealed unmet demand patterns
3. Forward-Looking Metrics - Sensed pipeline growth that wasn't showing in historical data
4. Capacity Constraint Realization - Discovered demand was limited by headcount, not market size

The Opposition Landscape:

• Executive Level: Significant pushback from leadership team
• Ground Level: Strong support from sales reps and managers
• Rep Feedback: "I'm going to close 2-3x of quota"
• Manager Insights: "I'll hit 4 million more than you think"

The Learning Process:

Taking on the sales role directly was preparation for hiring a Chief Revenue Officer - learning the job firsthand to make better hiring decisions.

Timestamp: [13:30-15:29]

The Challenge of Leading Equals

Kashish identifies coordinating with co-founders as the most difficult but potentially most rewarding aspect of founder mode leadership.

Why Co-Founder Coordination is Uniquely Difficult:

• Hierarchical vs. Peer Relationships - Easy to direct reports, challenging to influence equals
• Decision-Making Complexity - No clear authority structure for resolving disagreements
• Highest Stress Scenarios - Most emotionally and strategically demanding situations

The Potential Upside:

• Aligned Co-Founders = Mountain Moving - When coordination works, execution becomes exponentially powerful
• Shared Vision Amplification - Multiple founders aligned can drive unprecedented company momentum
• Strategic Multiplication - Combined founder conviction creates unstoppable forward motion

The Coordination Challenge:

Unlike managing direct reports where authority is clear, co-founder relationships require:

• Influence Without Authority - Persuasion and alignment rather than direction
• Mutual Respect for Expertise - Recognizing each founder's unique strengths and perspectives
• Consensus on Vision - Shared commitment to company direction and values

Timestamp: [15:41-15:59]

Essential Insights:

1. Founder Mode Definition - Making the company successful rather than making everyone happy, with conviction-driven execution over consensus-building
2. Risk-Taking Advantage - Founders uniquely can take big risks because they can't easily be fired, while employees naturally hedge and seek permission
3. Decision-Making System - Daily writing practice with weekly filtering to identify persistent insights worth sharing with leadership team

Actionable Insights:

• Stop negotiating when you have strong conviction - execute fully rather than accepting compromised versions
• Write down every significant thought and share anything that remains true after a week with your leadership team
• Take direct operational roles temporarily to gain firsthand insights before making major hiring decisions
• Listen to ground-level feedback from sales reps and managers, not just executive-level data and opinions
• Embrace being wrong sometimes as proof you're taking appropriately large risks for company growth

Timestamp: [8:00-15:59]

People Mentioned:

• David Clemens - Leadership coach who taught Kashish that founders are uniquely positioned to take risks because they can't easily be fired

Companies & Products:

• Hightouch - Data activation platform where Kashish serves as Founder and Co-CEO, mentioned in context of sales team expansion and founder mode implementation

Concepts & Frameworks:

• Founder Mode - Leadership philosophy focused on company success over individual happiness, emphasizing conviction-driven decisions and unique founder risk-taking abilities
• Risk-Taking Framework - The principle that if you're right 100% of the time, you didn't take enough risks as a founder
• Writing-Based Decision Making - Daily documentation of thoughts with weekly filtering to identify persistent insights worth sharing with leadership

Timestamp: [8:00-15:59]

Strategic Product Pivot and Market Opportunity

The Original AI Product:

• Reinforcement Learning Focus: Built an AI product that predominantly didn't use LLMs while other companies focused on LLM-based solutions
• Market Timing: CMOs were scared of LLMs and averse to content generation throughout H2 last year and most of H1 this year
• Strategic Choice: Used reinforcement learning to choose the best content rather than generate it
• Market Response: Excitement but slow adoption from customers

The Pivot Decision Process:

1. Current State Assessment: Company had 4 main products with 50 engineers - understaffed for large surface area
2. Growth Projection: On track to double this year and likely double next year
3. Bigger Opportunity Recognition: Identified a much larger opportunity that no one had cracked yet
4. Risk Assessment: Realized the team could hit current numbers without founders' direct involvement

The New Vision:

• Market Research: Asked customers and top CMOs how they would build marketing teams from scratch with today's technologies
• Customer Feedback: CMOs said they wouldn't do anything they're currently doing - too much trial and error, writing briefs, "stabbing in the dark"
• Solution Direction: Enable data-informed decisions with LLMs analyzing campaigns and data to make decisions collaboratively
• Development Approach: Offered free product to customers in exchange for collaborative development

Timestamp: [16:00-18:25]

Co-Founder Alignment and Decision-Making Process

Timeline and Challenges:

• Duration: 2-3 months of convincing each other
• Decision Complexity: No clear proposal initially - more exploratory than binary yes/no decision
• Uncertainty Factor: None of the three co-founders knew exactly what to do at the start

Decision Framework:

1. Opportunity Recognition: Technical shift in the market that competitors couldn't capitalize on
2. Unique Advantage: Exclusive access to marketers that other companies didn't have
3. Collaborative Approach: "Let's do something, let's figure out together what to do"
4. Iterative Process: Gradual alignment rather than immediate consensus

Team Structure:

• Three Co-Founders Total: Shared decision-making responsibility
• Collective Uncertainty: All founders acknowledged they didn't have a clear roadmap initially
• Mutual Convincing: Process involved convincing each other rather than one founder persuading others

Timestamp: [18:25-18:58]

Essential Insights:

1. Strategic Pivot Timing - Hightouch moved from reinforcement learning AI to a bigger opportunity when they realized their current success was sustainable without founder involvement
2. Market Research Validation - Direct customer feedback from top CMOs revealed fundamental dissatisfaction with current marketing approaches and openness to AI-driven solutions
3. Co-Founder Alignment Process - Major strategic decisions require extended discussion periods (2-3 months) when exploring undefined opportunities rather than clear proposals

Actionable Insights:

• Assess whether your current business can succeed without your direct involvement before pursuing bigger opportunities
• Validate new directions by asking customers how they would rebuild their operations from scratch with current technology
• Allow sufficient time for co-founder alignment when exploring undefined opportunities rather than rushing binary decisions
• Leverage unique market access and relationships as competitive advantages when identifying new opportunities

Timestamp: [16:00-19:28]

Companies & Products:

• Hightouch - The company discussed in the interview, focusing on AI-powered marketing solutions

Technologies & Tools:

• Large Language Models (LLMs) - AI technology that CMOs were initially scared of for content generation
• Reinforcement Learning - AI approach used by Hightouch as an alternative to LLM-based solutions for marketing optimization

Concepts & Frameworks:

• Founder Mode Decision Making - Strategic approach where founders take calculated risks on undefined opportunities
• Customer Development - Process of working directly with customers to co-develop new products and validate market needs
• Technical Market Shifts - Recognition of fundamental technology changes that create new business opportunities

Timestamp: [16:00-19:28]