Category Archives: Directing Business

Forget What You Know About GTM: 5 Insights on Why Your Next Hire is an Engineer and Your Best Tool is a Whiteboard

In an era of rapid technological advancement, Go-To-Market (GTM) strategy has become more complex and strategically important than ever. The rise of AI is not just creating new tools; it’s forcing a fundamental re-architecture of how companies find, win, and retain customers. To navigate this new landscape, leaders are looking for proven, practical insights.

Jean Grosser is one of the world’s most respected GTM leaders. As COO at Vercel and the former Chief Product Officer at Stripe, where she built their early sales team from the ground up, she has a unique vantage point on what works. This article distills five principles from her recent conversation on Lenny’s Podcast that form the foundation of a new GTM playbook—one where AI-driven leverage and human-centered experience are not competing forces, but two sides of the same coin.

1. The “Go-To-Market Engineer” is Here, and They Have 10x Leverage

A new, high-leverage role is emerging that combines deep technical prowess with a GTM mindset: the Go-To-Market Engineer. This role is responsible for using AI and code to re-architect core GTM workflows, unlocking massive efficiency gains.

At Vercel, this is not a theoretical concept. The company’s first GTM engineers were drawn from its technical sales team—former front-end developers who had transitioned into sales engineering. One of these engineers, spending only about 30% of their time over six weeks, built an AI “lead agent.” The results were immediate and profound: the agent enabled one Sales Development Representative (SDR) to do the work of ten. The company reduced its inbound team from 10 people to a single person who now functions as a quality assurance manager for the AI agent. The ROI is staggering: an annual cost of $1,000 to run the agent, replacing over a million dollars in salary—a 99%+ reduction in cost.

This case study demonstrates not only the incredible leverage AI offers, but also the speed at which it can be deployed to solve core GTM challenges.

“before we did that move I mean the other thing that’s just incredible about this is the person who built the lead agent was a single GTM engineer he spent maybe 25 30% on his time of his time on this uh it was 6 weeks before we felt confident going from 10 to one so it wasn’t like this was a multi-quarter process it actually moved super quickly”

2. Think of Go-To-Market as a Product

As technical differentiation between products narrows, the experience of being sold to is becoming a primary factor that drives buying decisions. Grosser argues that the most effective GTM strategies are designed like a product, focusing on creating a customer journey filled with unique, human, and personalized experiences rather than flat, transactional interactions.

Grosser’s time at Stripe provides a masterclass in this product-led GTM approach. Instead of running a typical “discovery” call where a salesperson quizzes the potential customer, the first meeting was designed as a collaborative whiteboarding session. The customer would be invited to draw their payments architecture. This simple shift provided Stripe with deep insights, but more importantly, the customer left the very first meeting with a valuable, tangible asset they co-created—an architectural diagram they often hadn’t created themselves.

This approach transforms the sales process from an extractive one (getting information) to a value-creating one at every single touchpoint.

“we buy a lot of things because of how we feel about them… the experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin”

3. Your Customers Are Buying to Reduce Risk, Not Just to Gain Upside

A common mistake, especially for founders, is to get excited about selling the “art of the possible”—the grand future vision of what their product can enable. While this message resonates with other founders and visionaries, it’s not what drives most buying decisions. Grosser shared a counter-intuitive but critical statistic: “80% of customers buy to avoid pain or reduce risk as opposed to… increase upside.”

Enterprise customers, in particular, are motivated by de-risking their operations. They are trying to avoid the pain of missing revenue targets, being outcompeted, or suffering brand damage. A sales message focused on providing certainty and mitigating these risks is often far more powerful than one focused on potential future gains.

This psychological insight is a direct challenge to the visionary founder’s default pitch and a crucial reminder of what truly motivates the enterprise buyer.

“80% of customers buy to avoid pain or reduce risk as opposed to increase upside which is a good thing for startup founders to understand we all love to talk about the art of the possible… but that’s often really a sale that’s going to resonate with another founder”

4. AI Can Tell You Why You’re Really Losing Deals

Human perception is often flawed, especially when it comes to understanding why a deal was lost. Vercel’s internal “Dealbot” provides a powerful case study in using AI to find the ground truth. This custom agent analyzes Gong transcripts, emails, and Slack messages to deconstruct sales opportunities.

In one powerful example, an account executive reported that a major deal was lost on price. After the Dealbot analyzed all communications, however, it came to a different conclusion. The AI determined the real reason was an “inability to demonstrate value.” It found that the salesperson never truly connected with the economic buyer and, crucially, that “when you talked to somebody about ROI and total cost of ownership it was clear from their reaction that they didn’t really buy your math.” The insight shifted from a generic excuse to a highly actionable critique: our ROI models are not credible. The tool has since evolved from a retrospective “Lostbot” to a real-time “Dealbot” that feeds insights into Slack channels, helping reps course-correct mid-process.

This highlights a critical truth: human perception is biased, but data-driven AI can provide the objective feedback needed to debug a failing sales process.

“the biggest loss that quarter uh according to the account executive was lost on price and when you ran the agent over every Slack interaction every email every gong call it said actually you lost because you never really got in touch with economic buyer… so really the reason we lost was an inability to demonstrate value”

5. The Calculus on Build vs. Buy for GTM Tooling Is Changing

The key learning from Vercel’s experience building powerful internal AI agents is that it’s “not that hard” and “not that expensive.” This insight challenges the traditional “buy over build” mentality for GTM software.

The evidence is compelling: the initial “Lostbot” was created in just two days, and the more complex “Lead Agent” took one person only six weeks of part-time work. Grosser believes the real value—the “alpha”—lies in building your own agents. The reason is that your company’s “own esoteric context, your content, your workflow is really key to unlocking the power of the agent.” Custom-built tools can be precisely tailored to your unique data and processes in a way that off-the-shelf software cannot.

This approach signals a potential sea change in how companies source GTM technology, prioritizing bespoke advantage over off-the-shelf convenience.

“I think one of our learnings is that it’s not that hard to build these agents and they aren’t that expensive either… I think there’s real value in experimenting with your own internal agent development… because you may find that it’s meaningfully easier than you think and you get returns pretty quickly”

Conclusion

The principles of Go-To-Market are undergoing a paradigm shift. The five takeaways from Jean Grosser are not isolated tactics but interconnected pillars of a new, cohesive strategy. It creates a powerful feedback loop: the GTM Engineer (1) builds custom AI tools (5) that surface objective truths humans miss (4). This frees up the team’s capacity to move beyond transactional sales and instead design memorable, value-added experiences (2) that provide the certainty and risk reduction modern customers crave (3).

This new model is defined by the intelligent application of AI, a product-centric approach to the customer journey, and a deep understanding of the psychology that drives modern buyers. It leaves us with a critical question to consider: As AI agents become increasingly capable co-workers on our sales teams, what uniquely human skills will become the most valuable differentiators in the future of Go-To-Market?

Reference: Lenny’s Podcast–>https://www.youtube.com/watch?v=RmnWHz8HD74

Borderline Professionals and the AI-Powered Kriya Shakti

image by author and ChatGPT

Most people assume creativity belongs only to experts. But a silent category exists between amateurs and full-fledged professionals—the borderline professionals. These are individuals who have the desire to create, and just enough basic skill to understand what they want, yet they struggle to execute.

Today, AI changes that equation.


The Ancient Framework That Explains Modern AI

In the Lalita Sahasranama, creation is rooted in three forces:

  1. Ichha Shakti — the deep desire or will
  2. Jnana Shakti — the knowledge or understanding
  3. Kriya Shakti — the power to execute

In my book Directing Business, I highlighted how these three powers capture the entire arc of creation. Most people possess the first, many have some version of the second, but very few have the third.

This is where AI steps in—not as a replacement for human skill, but as the missing Kriya Shakti that unlocks execution.


Who Are Borderline Professionals?

Borderline professionals are not amateurs. They are not novices. They are people who:

  • Have a genuine desire to create
  • Possess basic foundational knowledge
  • Can articulate what they want
  • But get stuck when it’s time to execute

They often sit on ideas for years—songs they wanted to compose, books they wanted to write, companies they wanted to start, designs they always imagined but never completed.

Their limitation is almost always Kriya Shakti—the ability to translate intent and knowledge into a finished creation.


AI Completes the Creation Triangle

If you possess:

  • Ichha (desire)
  • Jnana (basic understanding)

AI now gives you:

  • Kriya (execution superpower)

This shifts the creative world in a fundamental way. AI does not magically inject expertise into you.
Instead, it amplifies your minimum viable expertise.

In other words:
If you can imagine it and understand it at a basic level, AI can help you build it.


Real Examples of Borderline Creators Becoming Real Creators

1. Writing & Storytelling

People who always wanted to write but struggled with structure or flow can now produce full essays, chapters, and scripts. AI becomes the co-author that takes their intent and shapes it into polished work.

2. Music & Composition

A person who can hum a tune or grasp rhythm but lacks musical training can now generate full compositions, lyrics, and studio-quality tracks.

3. Entrepreneurship

Someone with a startup idea but no experience in planning, pitching, or prototyping can now generate:

  • business plans
  • branding
  • pitch decks
  • landing pages
  • even early product mockups

In short, AI provides the scaffolding for company creation.

4. Multimodal Creativity

Text → Images → Video → Audio → Apps
With modern multimodal AI, the entire pipeline of creativity becomes accessible—even if the individual has never been trained formally.


The Big Insight: Skill Is Not Dead—It Is Amplified

You still need some Jnana Shakti—some grasp of your domain. AI cannot replace absolute ignorance.

But the amount of knowledge needed to start has dramatically dropped.

Earlier, you needed 100% skill to get 100% output.
Now, even with 20–30% knowledge, AI multiplies your ability to produce a finished work.

This is the true empowerment.


Why This Is the Best Time for Borderline Professionals

For the first time in history:

  • You don’t need a studio to compose.
  • You don’t need a publisher to write.
  • You don’t need a team to launch a startup.
  • You don’t need a design degree to create visuals.
  • You don’t need a production crew to make videos.

If you have deep desire (Ichha) and basic understanding (Jnana), AI gives you Kriya at a never-before scale.

This makes today the most powerful era for borderline professionals—those who were always “almost there,” waiting for a catalyst.


Conclusion

Creativity no longer belongs only to the trained elite. It belongs to anyone with the will to create and the willingness to learn just enough to guide AI.

AI completes the Ichha–Jnana–Kriya triad.
It transforms borderline professionals from dreamers into doers, and from doers into creators.

The door is open wider than ever.
And if you’ve always stood just outside it—this is your moment to walk through.


Infographic based on this article (using Nana Banana Pro)

Kanne Swami Management: What Pilgrimage Can Teach Modern Workplaces About Care, Growth, and AI


footsteps…mentorship…image by author and ChatGPT

Some traditions carry management secrets hidden inside rituals.
The Kanne Swami custom from the Ayyappa pilgrimage is one of them.
A structure so human that even the best corporate handbooks can’t quite touch it.

Every first-time pilgrim, the Kanne Swami, walks under the care of a Guru Swamy. Someone who has done the journey before. Someone who remembers the fear, the fatigue, the feeling of not knowing what lies beyond the next hill. The Guru doesn’t instruct from a distance. He walks beside the novice. Watches. Corrects. Encourages.

It’s mentorship without bureaucracy.
Discipline without coldness.
And care that doesn’t require an app.

Now imagine a company doing that.


A workplace that feels like a pilgrimage

Picture a new hire on their first day.
They’ve cleared interviews, signed forms, logged in, smiled through the icebreaker round. Then what? Usually, silence.

An inbox full of welcome messages that mean well but sound rehearsed.
A manager too busy to explain what “ownership” really means.
A team that helps politely but never deeply.

What if that person was treated as a Kanne Swami?
Guided with sincerity, not policy. Paired with someone who feels responsible for their initiation, not just their output.

Guru Swamy at work would not be another “buddy” from HR.
He or she would be a custodian of learning. The person who ensures that the first 41 days of the new member’s journey feel grounded, ethical, and alive.

Every culture that survives more than a century has some version of this.
The Japanese senpai–kohai system. The guild apprenticeships of Europe.
And here in India, the Guru–Śiṣya bond. The Ayyappa tradition simply gave it ritual clarity.

The modern company can too.


What ancient India already understood about leadership

Our texts and customs weren’t management manuals, but they carried psychological precision.
The Guru–Śiṣya paramparā wasn’t just about transferring knowledge. It was about transmitting restraint, intuition, and self-control. The mentor watched how the student moved through frustration. The real lesson wasn’t the mantra; it was how to stay still when the world tested you.

Sevā bhāva taught that service purifies ego.
A true guide serves the learner’s growth, not his own reputation.
Atithi Devo Bhava reminded communities that newcomers bring divine potential.
Even the Gītā quietly handed managers a code: Karmanye vadhikaraste ma phaleshu kadachana. Do your duty, but let go of the reward.

That line, taken seriously, can clean entire boardrooms.

We keep calling this philosophy. It’s actually process design.
A cultural operating system, written in poetry.


The science caught up later

Psychology took two thousand years to name what the sages practiced daily.
Amy Edmondson called it psychological safety.
Google made it famous through Project Aristotle.
Every study since then says the same thing. Teams thrive when people can speak without fear.

Fear is what ruins most first-time experiences.
The first code deployment. The first client call. The first on-air appearance.
One mistake, and it haunts you.
Guru Swamy neutralizes that fear. Not by removing risk, but by standing nearby.

Even AI systems—predictive ones, at least—run on something similar: feedback loops and safety nets. A team that encourages early vulnerability behaves like a well-trained model that’s constantly improving through gentle correction.

Funny how science ends up rediscovering faith with spreadsheets.


Translating pilgrimage into management practice

Let’s turn this into structure.
Every time someone in your company does something for the first time, they’re a Kanne Swami.

A new hire.
A first-time team lead.
A developer pushing production code.
A salesperson pitching a global client.
Even an executive leading their first crisis.

Each deserves a guide. Someone with enough scar tissue to teach through calm.

The company can formalize this with small rituals, not heavy frameworks.

  • The 41-Day Frame: The first six weeks are sacred. They include orientation, shadowing, and reflection. The Guru ensures rhythm, not just routine.
  • The Two-Pouch Method: Inspired by the Irumudi the pilgrim carries. One pouch for learning goals. The other for contributions made during the journey.
  • The Safety Phrase: A simple, pre-agreed sentence any member can use to pause action when things feel wrong. Something human like, “Hold. Let’s rethink.” It must be honored instantly.
  • Completion Rite: After 41 days, both the guide and the learner sit together to reflect. The learner thanks, but the guide doesn’t take credit. The circle closes quietly.

Small, human mechanics. Yet they carry deep order.


Rituals aren’t weakness

In fact, they create accountability without paperwork.
Every religion, military, and school that works well has rituals because rituals bypass bureaucracy. They create shared meaning fast.

A prayer, a salute, a morning sync-up—all function the same way: alignment through rhythm.
Corporate life tried to replace ritual with tools, but tools can’t carry reverence.

So when someone becomes a Guru Swamy inside an organization, give them that dignity.
Not a badge. Not a slide deck.
A quiet recognition that they are guardians of culture.

And culture, as Peter Drucker warned, still eats strategy for breakfast.


What movies already taught us about guidance

We’ve seen this pattern in cinema again and again.

In Chak De! India, the coach isn’t training hockey players. He’s rebuilding belief. He doesn’t reward obedience; he rewards trust.
In 3 Idiots, learning flows sideways—friend to friend, not top-down. Humor becomes pedagogy.
In Super 30, the teacher’s power lies in hunger shared with students, not distance.
Even Guru (2007) hides mentorship in ambition. Behind the swagger of business growth stands a quiet influence, a voice that asks harder questions.

Movies get it because stories remember what systems forget: that transformation is personal before it becomes organizational.


Bringing AI into the circle

Now the modern twist.
What happens when you bring AI into this human equation?

AI can’t bless you, but it can remember you.
It can keep a record of learnings, patterns, hesitations, blind spots. It can nudge both the mentor and the learner gently: “You missed two check-ins.” or “You’ve asked fewer questions this week.”

AI can play the role of the silent observer—the third pilgrim. It never sleeps, never forgets, and can hold mirrors without judgment.

Think of it as the keeper of the pilgrimage diary.
The Guru Swamy guides through emotion. The Kanne Swami learns through experience.
AI preserves their journey for the next generation.

And when done right, it doesn’t replace the bond. It deepens it.
Because now the wisdom stays even after both have moved on.

This is what intelligent mentorship could look like. A trinity of presence: Human, Learner, Machine. Each aware, each humble.


Where the system breaks (and how to keep it alive)

Of course, rituals decay fast in corporations.
Titles creep in. Ego returns. Mentorship becomes KPI. The sacred becomes symbolic.

That’s where vigilance matters.
Guru Swamy cannot be the learner’s boss.
He or she must hold space, not authority.

Feedback must travel both ways.
If the guide talks too much, the system fails. If the learner flatters too much, it fails again.
Honesty is the only incense worth burning.

And every six months, rotate roles.
Let learners become guides. Let guides return to learning.
The cycle keeps humility fresh.

Because once people start saying “I’m done learning,” decline has already started, even if numbers still look fine.


The invisible outcomes

Companies that design this consciously will notice strange results.
Meetings get quieter, but deeper.
Attrition drops, not because of perks, but because belonging becomes visible.
People start describing their managers as “protective,” not “demanding.”
Errors reduce. Reflection increases.

All this without new software, slogans, or all-hands pep talks.
Just a reintroduction of old-world care into high-speed business.

The future might actually belong to organizations that treat onboarding as initiation, not information download.


The AI parallel, again

There’s another way to see this.
Large Language Models, at their core, learn like disciples.
They absorb examples, refine responses through correction, and evolve through fine-tuning.
Their growth depends on human supervision, alignment, and calibration.

Isn’t that what mentorship really is? Fine-tuning a human through feedback until their internal model aligns with shared values.

Now imagine combining that principle consciously.
Each Guru Swamy in a company could have an AI co-pilot that records learnings, tracks questions asked by past Kanne Swamis, and generates a “wisdom log” for new ones.

The AI doesn’t command. It curates.
A digital archive of lessons from countless pilgrimages across projects, departments, and years.

That’s not science fiction. It’s good documentation with a soul.


The paradox of progress

Technology races forward.
Human depth often lags.

In a rush to automate, we risk forgetting the warmth that makes structure meaningful.
Kanne Swami framework doesn’t slow progress. It gives progress roots.
And roots are what stop speed from turning into chaos.

AI can predict, suggest, summarize. But it can’t bless effort, can’t feel another’s struggle, can’t see pride in someone’s first small win.
For that, you still need the human beside you.

Progress without mentorship is noise.
Progress with care becomes tradition.


What success looks like when done right

A few years into such a system, your company would look different.
Not in its products, but in its posture.

You’d hear stories like:
“She was my first Guru Swamy here.”
Or, “He taught me how to pause before responding.”

You’d notice people quoting lessons instead of policies.
Meetings would start later but end faster.
Trust would feel less like a word on posters and more like an atmosphere in the hallway.

That’s the test.
When behavior travels through imitation, not enforcement, you’ve created culture.


Returning to the mountain

In the end, the pilgrimage to Sabarimala is physical, emotional, communal.
Everyone carries the Irumudi, walks barefoot, sings the same chant, and reaches the same temple.
Yet every person’s journey is different.

Organizations could learn from that.
Equality in rules. Diversity in experience. Shared rhythm. Personal meaning.

Because when a team walks together that way, success stops being a race. It becomes a yatra.

And maybe that’s the secret we’ve forgotten in the age of dashboards and deadlines.
That a journey, whether to a temple or to market leadership, feels complete only when someone wiser walks beside you, reminding you to breathe, to focus, to keep faith.


The last vow

Treat every newcomer as sacred responsibility, not replaceable labor.
Let AI hold the checklist.
Let humans hold the promise.

Because true leadership isn’t measured by how far you go.
It’s measured by how many you take with you.