What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

Name: What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)
Uploaded: 2025-11-30T12:00:53.000Z
Duration: 2 h 52 min 2 s

Go to Market Strategies in the Age of AI

The Importance of Differentiation

The competitive landscape has intensified with AI, leading to a greater need for effective go-to-market strategies. Companies must differentiate themselves to succeed.

Instead of focusing solely on the problems being solved, companies should emphasize how they outperform competitors. Understanding that 80% of customers buy to avoid pain is crucial for startups.

Customer Buying Journey

The experience of purchasing can significantly influence buying decisions; thus, creating a unique customer journey is essential for differentiation.

Sales approaches should feel less like traditional sales pitches and more like genuine conversations, especially when engaging technical audiences such as engineers.

Insights from Gan Grosser

Gan Grosser, former Chief Product Officer at Stripe and current COO at Versell, shares her expertise on building successful go-to-market teams.

Discussion includes what constitutes a world-class go-to-market team and the emergence of the "go-to-market engineer" role that enhances operational efficiency.

Tactics and Tools for Success

Specific tactics are shared to improve go-to-market skills, including segmentation strategies and viewing the process as a product itself.

Recommendations on tools and insights into product-led growth (PLG), sales compensation structures, and hiring practices are also discussed.

Podcast Engagement and Resources

Listeners are encouraged to subscribe to the podcast for ongoing insights into market strategies. Annual newsletter subscribers gain access to various products beneficial for their ventures.

Sponsored segments highlight tools like Data Dog for product management analytics and Lovable for app development without extensive coding knowledge.

Understanding Go-to-Market Strategies

Defining Go-to-Market Functions

The go-to-market (GTM) strategy encompasses all functions that interact with customers or generate revenue, including marketing, sales, customer success, and support.

Specific roles within GTM include technical sales positions like sales engineers and post-sales platform architects, highlighting the diverse nature of customer engagement.

There is often a misalignment in objectives among marketing, sales, and support teams due to differing segmentation frameworks; this necessitates a more integrated approach.

Evolving Nature of Go-to-Market

The current trend indicates a shift from hyper-specialization in GTM roles towards a more holistic view that focuses on the entire customer journey from awareness to long-term retention.

Companies may start with either marketing or sales as their primary focus depending on their product type and target market; this can evolve as they grow.

Changes in Go-to-Market Over Recent Years

The rise of consumption-based business models has made GTM strategies more consultative rather than transactional, emphasizing relationship-building with customers.

With advancements in AI technology, there is an increased need for understanding customer needs deeply to align products effectively.

Role of AI in Go-to-Market Strategies

Organizations are increasingly adopting best practices akin to consulting approaches to help clients navigate changes brought about by AI integration into their workflows.

A new role emerging is the "go-to-market engineer," which combines technical expertise with GTM strategies to enhance tooling and data utilization.

Practical Applications of Go-To-Market Engineering

These engineers work closely with customers to understand their environments better and facilitate successful technology implementation while gathering insights for product development.

The introduction of AI tools aims at personalizing customer experiences at scale while optimizing internal processes within organizations.

Building a Data-Driven Sales Approach

The Genesis of Project Rosland

The speaker reflects on the challenges faced with traditional SDR approaches, noting that they would only have four SDRs instead of thirty.

Introduction of Project Rosland, inspired by the scientist who mapped DNA; it aimed to create a comprehensive database of companies with attributes useful for targeted sales.

The concept involved creating customizable email templates (Mad Libs style), where 80% of the content would be tailored based on company attributes.

Challenges and Evolution

Initial attempts in 2017 were difficult, with high false positive rates despite collaboration with data science teams.

Current efforts at Verscell are more successful due to advancements in AI technology and the inclusion of a go-to-market engineer alongside data scientists.

Role of AI in Sales Strategy

Discussion about building an agent that replicates human workflows to enhance efficiency in sales processes.

Reflecting on how much simpler it is now to map out company universes using AI compared to previous attempts without it.

Emerging Roles and Automation

Mention of Ben Salman’s work at Zoom Info and his new startup focused on automating outbound prospecting through AI-driven company-product matching.

Recognition that many individuals from past projects are now contributing to significant advancements in AI within sales strategies.

Future Directions for Go-To-Market Engineering

The emerging role focuses on automating various functions within go-to-market strategies, starting with inbound outreach before moving onto outbound efforts.

Emphasis on creating agents capable of executing tasks traditionally done by humans, enhancing productivity across different market segments.

Optimizing Sales Time Allocation

Aiming for salespeople to spend more time interacting directly with customers rather than performing repetitive tasks; current benchmarks show only 30%-40% engagement time.

Vision for achieving up to 70% customer interaction time through effective use of agents for research and follow-up activities.

AI's Impact on Sales Development

Leveraging AI for Enhanced Efficiency

The integration of AI in sales development allows companies to reduce the need for a large number of Sales Development Representatives (SDRs), enhancing efficiency and return on investment (ROI).

Concerns about receiving ineffective, AI-generated emails are common; however, maintaining a human element in the process is crucial for crafting effective communications that convert.

Human-AI Collaboration in Sales Processes

The process begins with a go-to-market engineer shadowing top-performing SDRs to understand their workflows and strategies, which informs the initial setup of AI systems.

The AI agent assesses lead qualification and response crafting, but all outputs undergo human review before being sent out to ensure quality and brand alignment.

Transitioning Roles and Responsibilities

By streamlining processes, one human can now oversee what previously required ten SDRs, allowing for reallocation of resources towards outbound efforts.

This shift not only improves efficiency but also enhances job satisfaction as SDRs engage more directly with customers rather than performing repetitive tasks.

Measuring Success Through KPIs

Key performance indicators (KPIs), such as lead-to-opportunity conversion rates and response times, were monitored throughout the implementation phase to ensure effectiveness.

The results showed that while conversion rates remained stable, the speed of responses improved significantly due to reduced delays in processing leads.

Future Implications of AI in Sales Roles

There is an ongoing debate about whether AI will fully replace SDR roles; however, it appears more likely that it will enhance their capabilities rather than eliminate them entirely.

While basic prospecting tasks may be automated by AI, complex enterprise-level interactions still require human insight and decision-making skills.

Understanding Sales Roles: SDR vs. AE

An explanation of sales roles clarifies that an SDR focuses on generating pipeline opportunities while Account Executives (AEs) typically handle closing deals.

Sales Development and Account Executives

Understanding Sales Roles

The sales process begins with talking to prospective customers, determining if they are worth investing time in for a more extensive sales process.

There are two types of Sales Development Representatives (SDRs): inbound, where customers reach out via the website, and outbound, where SDRs proactively target potential clients to generate interest.

Account Executives (AEs) are responsible for closing deals by transforming interested prospects into paying customers who believe the product is the best solution for their needs.

Sales Complexity Across Market Segments

AEs may sell to different market segments: small businesses (SMBs), mid-market companies, or enterprises. Each segment presents varying complexities in decision-making processes.

Selling to SMBs often involves a single decision-maker, while mid-market and enterprise sales require coordination among multiple stakeholders like finance and engineering teams.

The Importance of a Structured Sales Process

Transitioning from Founder Sales

Startups transitioning from founder-led sales to hiring their first salesperson must recognize that effective selling requires skills beyond just talking to people.

Effective sales involve discovery—asking questions that uncover customer challenges and willingness to pay—rather than merely presenting products.

Establishing Best Practices Early

Many startups achieve significant scale without a replicable sales process; however, having documented best practices is crucial for effective go-to-market strategies.

Founders should aim for at least 10 employees before introducing a Go-To-Market (GTM) engineer who can help formalize the sales process.

Hiring Strategies for Sales Teams

When to Hire Your First Salesperson

Founders should consider bringing in revenue operations early on as it provides analytical insights into what works within the sales process.

It’s advisable to hire your first salesperson around one million in Annual Recurring Revenue (ARR), ensuring there is some repeatability in the sales approach.

Maintaining Customer Connection

Founders need to stay connected with customers even after hiring; understanding customer profiles helps refine the ideal customer profile (ICP).

If customer bases vary significantly, it indicates an evangelist sale rather than a structured approach; establishing an ICP can lead to more consistent success.

Transitioning Knowledge in SaaS Development

Importance of Knowledge Transfer

Founders must effectively hand over responsibilities to new team members while ensuring they understand the existing processes, including content management and objection handling.

It's crucial for founders to remain connected with customers during this transition to continue R&D efforts and identify future product resonance.

Profile of an Ideal Go-To-Market Engineer

Successful go-to-market engineers often have prior experience in sales; at Verscell, initial hires were technical sales engineers who transitioned from front-end development.

Understanding good go-to-market (GTM) practices is essential, as it helps in modeling effective strategies based on experienced personnel.

Sales Experience vs. Engineering Background

The speaker emphasizes the importance of blending art and science in sales, advocating for either practical experience or extensive learning about best practices.

Transitioning from a sales role to a more technical position offers unique opportunities for individuals to engage closely with engineering teams.

Utilizing AI Tools for Market Insights

Leveraging Technology in Sales Processes

Companies like Stripe exemplify how technology can streamline operations and enhance customer experiences through tailored solutions.

Gong has become increasingly valuable by allowing agents to analyze transcripts and derive insights that inform strategic decisions.

Analyzing Lost Opportunities

Using AI tools like Dealbot enables teams to review lost opportunities comprehensively, revealing underlying issues such as failure to connect with economic buyers.

Insights gained from analyzing interactions help refine value propositions and improve overall market strategies by addressing specific shortcomings identified during loss reviews.

Sales Process Innovations and AI Integration

Transition from Lostbot to Dealbot

The sales leadership identified shortcomings in the sales process, prompting a shift from "Lostbot" to "Dealbot," which now operates in real-time.

Insights are fed into Slack channels dedicated to each customer, providing timely updates on the sales process and interactions with economic buyers.

Enhancing Sales Team Efficiency

The rapid iteration velocity in tech makes it challenging for go-to-market teams; thus, the bot helps diagnose issues in objection handling and identifies areas of improvement.

Weekly huddles allow teams to address identified weaknesses as if they were bugs in software development, leading to continuous improvement.

AI's Role in Sales Insights

The AI tool reveals insights that humans may overlook, showcasing its potential to draw different conclusions about sales effectiveness.

An example is provided where an airline uses AI not only for support queries but also analyzes call transcriptions to reduce future calls.

Building Effective Internal Bots

There’s a growing interest among companies for internal bots like Dealbots; insights on creating effective bots are shared.

Building these agents is relatively straightforward and cost-effective; examples include a lead agent developed over six weeks costing around $1,000 annually compared to traditional staffing costs.

Future of Internal Software Development

Companies may transition from purchasing software solutions to developing their own internal platforms with multiple agents tailored to specific needs.

Experimentation with internal agent development can unlock significant value, suggesting a shift towards more customized solutions within organizations.

AI Deployment Challenges and Opportunities

The Need for Integrated Tools

The speaker notes that while building custom tools can yield quick returns, there is a lack of plug-and-play solutions available in the market.

A common issue faced by customers is the proliferation of numerous tools, leading to inefficiencies as they manage multiple platforms instead of a single integrated solution.

Procurement Issues in AI Adoption

Many organizations are experiencing challenges with procurement processes due to an overwhelming number of AI initiatives, often referred to as "experimental run rate revenue" (ERR).

Companies are currently procuring various narrow-focused solutions, which may evolve over time but highlight the need for specific workflows tailored to internal needs.

Building Custom Agents

The discussion shifts towards platforms like Vercel that facilitate rapid agent development. Sales engineers leverage their coding skills to build agents directly on this platform.

Vercel provides essential features such as an AI gateway and sandbox environments that enhance the efficiency of developing these agents.

Advantages of Using Vercel

The ease of use provided by Vercel's framework allows teams to quickly bring agents into production, showcasing a competitive advantage in utilizing their own product effectively.

The culture at Vercel emphasizes continuous improvement through self-utilization, helping identify customer needs and areas for product enhancement.

Go-to-Market Strategy as a Product

Conceptualizing Go-to-Market Strategies

The speaker reflects on their early career experience with Gmail and how it shaped their understanding of technical differentiation in products.

They argue that as software commoditizes, companies must find new ways to differentiate themselves beyond just technology.

Customer Experience Focus

Emphasizing customer experience during the buying journey becomes crucial when product differences are minimal; this approach can significantly influence purchasing decisions.

At Stripe, efforts were made to create unique customer experiences during sales processes rather than relying solely on traditional discovery methods.

Building Collaborative Customer Relationships

The Importance of Whiteboarding Sessions

Stripe initiated whiteboarding sessions to help customers visualize their payment architecture, fostering collaboration and understanding.

Customers often left these sessions with a clearer mental model of their systems, gaining insights into their own stack and how it could be improved.

Creating Meaningful Customer Experiences

Building a go-to-market strategy is akin to product development; it requires mapping out customer experiences from awareness to long-term retention.

The goal is to transform interactions from transactional to personalized, enhancing the overall customer journey.

Adding Value at Every Touchpoint

At Stripe and now at Vercel, the principle of providing value regardless of purchase status was emphasized; past customers may return years later.

Sharing performance data about website speed and SEO can engage potential customers even if they are not currently in a buying cycle.

Enhancing Customer Engagement Through Insights

Providing immediate insights on website performance relative to peers can pique interest and encourage further engagement with the company.

Focusing on Experience Over Transaction

A product-oriented mindset involves ensuring every step of the customer journey is engaging, rather than feeling like a sales pitch.

Effective Go-To-Market Tactics

Leveraging Unique Insights for Engagement

Companies should invest in data that reveals unique insights about their products or identifies suboptimal states for potential customers.

Documentation as a Sales Tool

Good documentation is essential, but companies must also provide tailored best practices for larger clients who seek specific implementation guidance.

Learning from Successful Examples

Stripe's experience with marketplaces allowed them to offer specialized advice on payment setups based on extensive industry knowledge.

The Role of Discovery in Sales Conversations

Founders should prioritize discovery over pitching; effective salespeople ask questions that guide customers toward self-discovery rather than immediately proposing solutions.

How to Enhance Communication and Sales Skills

The Importance of Listening and Asking Questions

Emphasizes the value of responding to questions with further inquiries, enhancing communication skills.

Suggests sharing unique insights about personal shortcomings as a way to connect with others and improve sales techniques.

Leveraging Performance Metrics for Better Sales

Discusses using core web vitals to benchmark website performance against peers, providing actionable insights for clients.

Highlights the importance of educating customers on MCP servers, helping them understand when to utilize these technologies effectively.

Building Trust Through Insight Sharing

Explains how AEO (Answer Engine Optimization) relates to performance and SEO, positioning the company as knowledgeable in this area.

Notes that sharing valuable insights can lead potential clients to view the company as a trusted resource over time.

Shifting Focus from Pain Points to Competitive Advantage

Reflects on advice from Jenna Ael regarding sales strategies; emphasizes showcasing competitive advantages rather than just addressing pain points.

Encourages framing discussions around how clients can achieve significant improvements by choosing their service over competitors.

Understanding Customer Buying Behavior

Shares a statistic indicating that 80% of customers make purchases primarily to avoid risk rather than seeking new opportunities.

Discusses how startups often struggle with pivoting their messaging towards risk aversion, which is crucial for appealing to enterprise clients.

The Role of Segmentation in Sales Strategy

Introduces segmentation as a method for categorizing companies based on buying behaviors, essential for tailoring sales approaches.

Describes common segmentation strategies (small, medium, large), noting that understanding decision-making processes varies across different business sizes.

Understanding Business Segmentation at Stripe

Segmentation Strategy

Stripe utilized a segmentation graph with the x-axis representing company size (small, medium, large) and the y-axis indicating growth potential. This approach was crucial for targeting businesses that could drive significant revenue through consumption-based models.

The strategy involved prioritizing companies with high growth rates (e.g., 200% year-on-year) over those with lower growth rates (e.g., 8%). This informed their sales targeting and resource allocation.

Business Model Considerations

Stripe differentiated its approach based on business models: B2B, B2C, platform-based, or marketplace. Each model required tailored payment solutions—business payments for B2B and consumer payments like Apple Pay for B2C.

Understanding the specific needs of different business models allowed Stripe to create targeted sales strategies and product offerings that aligned with customer requirements.

Growth Potential Analysis

In addition to size and growth potential, Stripe incorporated observable metrics such as site traffic into their analysis. High traffic sites were considered more valuable despite being smaller in size due to their revenue-generating capabilities.

An example provided was OpenAI, which had a substantial online presence despite having a mid-sized employee count. This led to an enterprise-level engagement from Stripe due to their high traffic volume.

Tailored Sales Approaches

Different industries necessitated distinct sales approaches; e-commerce companies required specific terminologies related to product management systems compared to crypto companies that might operate on cloud services like AWS.

By segmenting businesses based on these attributes, Stripe could identify which companies were most likely to purchase their products effectively.

Data Analysis for Targeting Customers

The speaker emphasized using regression analysis to determine key attributes correlated with successful customer acquisition. Identifying three critical attributes helped narrow down target markets effectively.

For instance, understanding how website traffic correlates with pricing allowed them to refine their segmentation framework further.

Insights gained from analyzing penetration in various sectors revealed unexpected trends; while e-commerce showed strong adoption of Stripe's services, enterprise SaaS companies lagged behind due to legacy system challenges.

By structuring this information clearly and linking it back to timestamps in the transcript, readers can easily navigate through the content while gaining insights into effective business segmentation strategies employed by Stripe.

Segmentation and Go-to-Market Strategies

Importance of Segmentation

The speaker emphasizes that segmentation should ideally be limited to three categories for practical reasoning, as having too many segments complicates the process.

Segmentation is framed not just as a go-to-market strategy but as a fundamental aspect of company operations, highlighting its importance in aligning product development with customer needs.

Customer Understanding and Product Development

New product managers are encouraged to consider their target audience (e.g., enterprise vs. startup) when developing products, ensuring alignment with market strategies from the outset.

Effective communication between product teams and go-to-market organizations is crucial for successful product launches and market penetration.

Building Collaborative Sales Organizations

A former colleague praises the speaker's ability to create a sales organization that integrates seamlessly with engineering teams, emphasizing the need for salespeople to possess deep product knowledge.

The speaker suggests that account executives should be indistinguishable from product managers within ten minutes of conversation, underscoring the necessity of strong product understanding in sales roles.

Balancing Revenue Generation and R&D

The best go-to-market organizations balance revenue generation with research and development efforts, allowing them to translate customer feedback into actionable insights for product management.

Distinguishing between genuine market opportunities and mere objections is essential for effective sales strategies.

Sales Mindset Aligned with Business Goals

Sales teams should adopt a general manager mindset, focusing on building sustainable business practices rather than merely closing deals.

Recognizing when to push back on feature requests versus advocating for valuable enhancements is critical in maintaining strategic focus.

Partnership Between Sales and Product Teams

Successful collaboration between sales and product teams hinges on mutual respect; sales must act as partners rather than demanding features without context.

The integration of company strategy involves aligning both product strategy and go-to-market approaches to optimize efficiency in generating revenue.

Insights on Product-Led Growth (PLG)

The discussion hints at the evolving landscape of PLG strategies, suggesting that while they gained popularity, there remains skepticism about their exclusivity as a winning approach.

Product-Led Growth (PLG) and Its Relevance Today

Understanding PLG's Current Landscape

The speaker discusses the diminishing perception of Product-Led Growth (PLG) as a primary growth strategy, noting that while some companies still thrive through PLG, its prominence seems to be waning.

Companies targeting enterprise clients, like Sierra, may find PLG less effective since they aim for large deals from the outset rather than relying on self-service models.

Many startups initially adopt PLG to attract users but must eventually enhance their offerings to scale up market reach. Examples include Versell and Stripe, where PLG significantly contributed to their growth.

A common misconception is that PLG can sustain unlimited growth; however, it typically has a ceiling. Companies need larger deal sizes over time to maintain growth rates.

Companies often struggle when they delay integrating a sales process alongside their PLG approach. Building an outbound sales engine takes time and is crucial for sustained success.

Sales Organization Development

Every company ultimately needs a sales organization; some start with a product-led approach before transitioning into sales-driven strategies.

The speaker notes the rarity of billion-dollar companies solely relying on PLG, suggesting that such companies might miss out on potential revenue by not diversifying their growth strategies.

Pricing Strategies in Business

Key Insights on Pricing

The speaker emphasizes treating pricing as a product itself. Understanding customer value and cost alignment is essential for effective pricing strategies.

Many companies underprice their products due to fear of charging what they're worth. This can lead to missed opportunities for revenue generation.

An example from Stripe illustrates how initial premium pricing was reconsidered after recognizing integration challenges; this led to adjustments in trial offers and pricing structures.

Transitioning Pricing Models

At Versell, there was a shift from bundled pricing resembling SaaS models towards unbundling as more functionalities were added, reflecting changes in customer needs and market dynamics.

Recent substantial changes in Versell’s pricing structure aimed at better serving startups by allowing self-service purchases without human intermediaries have driven significant growth in their PLG funnel.

Sales Compensation and Hiring Practices

Perspectives on Sales Compensation

The speaker shares insights about sales compensation being tied closely to performance but acknowledges that rigid plans can limit organizational flexibility due to pre-defined values set months ahead of time.

Adapting Hiring Strategies

Flexibility in hiring practices is crucial as market conditions evolve; innovative approaches are necessary when new products or services emerge mid-year, such as the introduction of AI cloud solutions at Versell.

Sales Strategies and Personal Insights

Challenges in Sales Planning

The speaker discusses the difficulties of creating an effective sales plan, emphasizing the need for flexibility in decision-making amidst annual planning challenges faced by many companies.

Value of Diverse Backgrounds in Sales

The importance of a diversified portfolio in sales teams is highlighted. The speaker believes that while traditional sales experience is crucial, pairing it with individuals from non-traditional backgrounds (like consulting or banking) can enhance team performance.

Combining Skills for Enhanced Learning

Mixing traditional salespeople with those from analytical backgrounds fosters a richer learning environment. This collaboration allows both groups to learn valuable skills from each other, such as understanding financial metrics and effective communication with CFOs.

Life Lessons and Motivational Quotes

In response to a question about life mottos, the speaker shares two key phrases: "When the going gets tough, the tough get going" and "Where there's a will, there's a way," which serve as guiding principles during challenging times in sales.

Transferable Skills from Competitive Diving

Reflecting on their experience as a competitive diver, the speaker notes that precision and resilience learned through diving translate well into sales. They emphasize the importance of striving for excellence and handling rejection positively.

The speaker concludes that embracing 'no' as constructive feedback rather than discouragement is vital for growth in sales. This mindset helps transform setbacks into opportunities for improvement.