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

Key Concepts

Go-to-Market (GTM): The comprehensive strategy and execution plan for bringing a product or service to market, encompassing all customer-facing functions.
GTM Engineer: A new role focused on applying technical prowess, data, and AI to optimize GTM workflows and enhance customer experiences.
AI in GTM: Leveraging artificial intelligence to automate, personalize, and scale GTM processes, from prospecting to customer support.
Customer Buying Journey: The end-to-end experience a customer has from initial awareness to becoming a loyal advocate, viewed as a product in itself.
Segmentation: The process of dividing the market into distinct groups of customers with similar needs and buying behaviors to tailor GTM strategies.
Product-Led Growth (PLG): A GTM strategy where product usage and experience drive customer acquisition, expansion, and retention, often with a self-serve model.
Value-Based Selling: Focusing on how a product or service helps customers avoid pain, reduce risk, or increase upside, rather than just listing features.
Sales Comp: Sales compensation structures, with a discussion on balancing performance incentives with organizational flexibility.
Diversified Sales Profiles: Hiring a mix of experienced salespeople and individuals with non-traditional backgrounds (e.g., consulting, banking) to bring diverse analytical and strategic skills.

Go-to-Market as a Product and the Rise of the GTM Engineer

The discussion centers on the evolving landscape of Go-to-Market (GTM) strategies, particularly in the context of AI. The speaker, Jean Grosser, emphasizes that GTM is no longer just marketing and sales but encompasses any function that touches a customer or generates revenue, including customer success, support, and partnerships. The current trend is towards a more integrated GTM lifecycle, moving away from hyper-specialization towards a holistic approach that mirrors product development.

The GTM Engineer: Revolutionizing Workflows

A significant focus is placed on the emerging role of the GTM Engineer. This role leverages technical skills and AI to re-architect GTM workflows, enabling personalized customer experiences at scale and significantly increasing operational efficiency.

Evolution of Prospecting: An illustrative example from Stripe's early days highlights the challenge of lean sales teams and the ambition to create a "company universe" database for targeted outbound prospecting. This project, "Rosalind," aimed to use company attributes to personalize email templates but was difficult to execute without AI.
AI-Powered Automation: Today, GTM engineers can build agents that automate tasks previously requiring significant human effort. For instance, at Versell, a single GTM engineer developed a lead agent that, with human oversight, can handle inbound leads with the efficiency of ten SDRs. This frees up human SDRs to focus on more complex outbound efforts.
Broader Applications: The GTM engineer's role extends beyond prospecting to areas like install-based sales, where AI can identify the next best action for existing customers based on usage data. The ultimate goal is to increase the percentage of time salespeople spend interacting with customers, reducing time spent on rote tasks like research and follow-up.
Human-in-the-Loop Approach: A critical learning is the necessity of a human-in-the-loop process for AI-driven GTM. Agents make initial calls, conduct research, and craft responses, but a human reviews and approves before sending. This ensures brand alignment and accuracy.
KPIs and Efficiency: The lead agent at Versell maintained lead-to-opportunity conversion rates while significantly condensing the time to convert, demonstrating the tangible ROI of AI in GTM.

Understanding Sales Roles: SDR vs. AE

To clarify for those less familiar with sales terminology:

Sales Development Representative (SDR): Primarily responsible for generating pipeline by engaging with prospective customers and qualifying them for the sales process. This includes inbound (responding to website inquiries) and outbound (proactively reaching out to target accounts).
Account Executive (AE): Responsible for closing deals, taking qualified leads from initial interest to a purchase decision. AEs often specialize in different market segments (SMB, Mid-Market, Enterprise), with Enterprise sales involving more complex coordination and multiple stakeholders.

When to Hire a GTM Engineer and the Importance of a Playbook

The introduction of GTM engineering forces companies to formalize their sales processes and develop a playbook early on.

Playbook Development: GTM engineering requires a documented understanding of what works and what doesn't, including content and discovery questions. This rigor is essential for AI to effectively replicate or augment human workflows.
Early Adoption: While there's no definitive scale, founders are advised to consider bringing in revenue operations (RevOps) earlier than they might think, as data and process provide crucial insights. Similarly, GTM engineering can be beneficial from the outset to optimize processes.
Hybrid Roles: A hybrid AE/GTM engineer role is also a possibility, where a technically minded salesperson develops best practices and then works to automate them.

The Ideal GTM Engineer Profile

The most effective GTM engineers often come from a GTM background themselves, such as sales engineers who are also front-end developers.

GTM Experience is Key: Understanding GTM best practices and processes is crucial. The speaker's experience shows that sales engineers with technical backgrounds have been successful in this role.
Balancing Art and Science: While AI can automate, understanding the "art and science of sales" is vital. This involves discerning signal from noise, understanding objections, and knowing when to push for a deal versus when to pivot.

Go-to-Market as a Product: Crafting the Customer Experience

A core philosophy is treating the customer buying journey as a product. This means meticulously designing each touchpoint to be a unique and valuable experience, rather than a transactional interaction.

Differentiating Through Experience

As products become more commoditized, the experience of being sold to becomes a key differentiator.

Beyond Features: The realization that technical differentiation narrows over time leads to focusing on how customers feel about their interactions with a company.
Unique Customer Journeys: Creating a customer buying journey that feels personalized and unique drives buying decisions.
Stripe's Whiteboarding Example: At Stripe, the initial discovery call was transformed into a collaborative whiteboarding session where customers drew their payment architecture. This provided value to the customer by helping them visualize their systems and positioned Stripe as a deeply interested partner.
Adding Value at Every Touchpoint: Even if a customer doesn't buy immediately, providing insights and value can lead to future engagement. Versell, for example, offers immediate insights into website performance and benchmarking relative to peers, even if the prospect doesn't convert immediately.

Effective GTM Tactics

Several tactics are highlighted for increasing attention and driving purchases:

Unique Insights: Providing unique insights about a product's value proposition or how a customer might be in a suboptimal state. This involves investing in data to uncover these insights.
Well-Architected Guides/Blueprints: For larger companies, generic documentation is insufficient. Providing specific guidance on how to implement a product within their unique setup (e.g., Stripe's marketplace payment setup) is crucial.
Deep Discovery: Founders are reminded of the importance of excellent discovery skills. Salespeople should talk less and listen more, asking probing questions to help customers arrive at conclusions themselves, rather than immediately jumping into problem-solving.
Focus on Risk Reduction: A significant statistic suggests that 80% of customers buy to avoid pain or reduce risk, rather than to increase upside. This means framing the value proposition around mitigating risks like not meeting revenue targets or falling behind competitors.

Segmentation: Carving Up the Market for Strategic Focus

Segmentation is presented as a critical tool for understanding and targeting the right customers.

The Principles of Segmentation

Segmentation involves dividing the market into groups that buy differently.

Beyond Size: While size (SMB, Mid-Market, Enterprise) is a common segmentation factor due to differing buying complexities, it's often insufficient on its own.
Multi-Dimensional Segmentation: Effective segmentation often involves multiple axes.
- Stripe's Approach:
  - Size (X-axis): SMB, Mid-Market, Enterprise.
  - Growth Potential (Y-axis): Crucial for consumption-based models, prioritizing high-growth customers.
  - Business Model: B2B, B2C, Platform, Marketplace. This dictates specific product needs (e.g., Stripe Connect for marketplaces).
- Versell's Approach:
  - Size (X-axis): Similar to Stripe.
  - Traffic/Promote (Y-axis): Using data like Chrome UX Report (CRUX) to identify high-traffic sites, even if they have fewer employees, pushing them into higher-tier segments (e.g., OpenAI).
  - Workload Type: E-commerce, crypto, enterprise SaaS. This influences language, sales approach, and product focus.
Data-Driven Insights: Segmentation helps identify winning patterns and areas of low penetration, guiding strategic focus. For example, Versell found strong e-commerce penetration but less in enterprise SaaS, leading to a focus on AI cloud for the latter.
Company-Wide Impact: Segmentation is not just a GTM function but a company-wide principle. New hires should understand the segmentation framework to ensure product development aligns with target customer needs.

Building a Collaborative GTM Org: Sales as a Partner

A key strength highlighted is building a GTM organization that works seamlessly with product and engineering.

The "Sales Org That Doesn't Feel Like a Sales Org"

The litmus test for this is that engineers within the company should struggle to distinguish a salesperson from a product manager within 10 minutes.

Product Depth and Credibility: This requires salespeople to have incredible product depth, fostering credibility with product and engineering teams.
GTM as R&D: The best GTM organizations are seen as equal parts revenue drivers and R&D extensions. They translate customer feedback into actionable signal for the product roadmap.
Discerning Signal from Noise: Sales teams need to be adept at identifying genuine market opportunities versus mere objections to be overcome.
General Manager Mindset: Salespeople should think like general managers, not just focusing on closing deals but on building the business, knowing when to say no, and identifying new market opportunities.

Sales as a Strategic Partner

Sales should feel like a true partner to product and engineering, contributing to company strategy.

Product Strategy Meets GTM Strategy: Ultimately, company strategy is a fusion of product and GTM strategies. Revenue leaders must think about pricing and product strategy to drive efficiency and market success.
Informing Company Strategy: Insights from customer interactions should inform the overall company strategy, not just sales tactics.

Product-Led Growth (PLG) and Pricing Strategy

The Relevance of PLG

PLG remains highly relevant, especially for companies targeting startups initially and then scaling upmarket.

Initial Growth Driver: PLG is a major driver for companies like Versell and Stripe, facilitating initial customer acquisition.
Ceiling Effect: PLG typically has a ceiling, as self-serve models are less effective for very large, high-value deals.
Timely Sales Integration: Companies often hit growth walls by waiting too long to integrate a sales function. A predictable outbound engine takes time to build.
Universal Sales Need: Essentially, most companies will eventually need to build a sales organization, whether they start with PLG or sales from the outset.

Pricing as a Product

Pricing should be treated as a product in itself, requiring careful consideration of value and costs.

Aligning Value and Cost: Understand where customers derive value and where costs are incurred, and align pricing accordingly.
Avoiding Underpricing: Companies often fear charging for the full value they provide.
Strategic Pricing: Premium pricing should be a deliberate strategy, not a default. Stripe's decision to remove the free trial for Stripe Billing, based on the understanding that integration effort implied commitment, is an example.
Unbundling and Rebundling: Versell's transition from a bundled SaaS-like price to an unbundled consumption-based model, and then a significant pricing change in August, demonstrates the iterative nature of pricing strategy. This included creating a self-serve enterprise skew to capture startup demand.

Hot Takes on Sales Comp and Hiring

Sales Compensation

Flexibility Challenge: Sales compensation, while performance-driven, can reduce organizational flexibility. Annual plans are set 12 months in advance, making it challenging to pivot quickly, especially in dynamic markets like AI.
Balancing Upside and Agility: The speaker is exploring ways to maintain the motivational upside of sales compensation while retaining the flexibility to adapt to changing market conditions and product offerings.

Sales Hiring

Diversified Portfolio: A diversified hiring approach is valued, combining experienced salespeople with individuals from non-traditional backgrounds like consulting or banking.
Cross-Pollination of Skills: This mix creates a richer learning environment. Consultants/bankers learn sales skills, while experienced AEs gain quantitative and analytical insights, improving their ability to discuss P&Ls and TCO.

Life Motto and Lessons from Diving

Life Motto

"When the going gets tough, the tough get going" and "Where there's a will, there's a way." These mottos emphasize resilience, perseverance, and the ability to find solutions even in challenging circumstances, highly relevant in sales and work.

Lessons from Competitive Diving

Obsession with Excellence and Replicability: Diving is a precision and repetitive sport. The forced repetition after failures (landing flat on your back) instills an obsession with excellence and the importance of replicable outcomes, crucial for driving predictable results in sales and forecasting.
Comfort with "No": Sales involves frequent rejections. The lesson from diving, where "yeses are great, nos are great, maybes kill you," highlights the importance of embracing "no" as valuable data to learn from and act upon.