For a long time, building products was something only engineers could do. If you had an idea, you had to wait for a developer to build it. Prototyping could take weeks or months. Product leaders had to wait. Entrepreneurs had to wait. Teams had to wait.

That world is changing quickly.

I started (vibe) coding again last year after a long gap on Replit, the AI-powered software development platform that allows users to write, build, test, and deploy applications within minutes. When they introduced their builder certification levels, I was roughly at Level 2 (Core Builder) in January’26. In two months, I have moved to Level 4 (Advanced Builder). It feels amazing!

More importantly, I have built a lot of things along the way.

Some examples:

• Nira, a math tutoring app inspired by my 7 year old’s learning journey

• Agentic customer success platform for a fictional company

• My portfolio website – ishangupta.me

Each of these started as a quick prototype. None required a large engineering team to get started.

This is why I believe being a builder is becoming an essential skill today.

A builder is someone who can take an idea and quickly turn it into something working. Not necessarily a polished product, but something real enough to test, iterate and learn from. Product managers, operators, founders, leaders and individual contributors can all benefit from this skill. And partner with the amazing technical partners to make stuff production ready.

Recently, Aakash Gupta shared a great framework on how top product managers use rapid prototyping to move from many ideas to one shippable feature. I found this particularly useful because it shows how fast experimentation can work in practice.

The idea is simple and yet powerful. Build multiple prototypes quickly, test them, eliminate the ones that do not work, and move forward with the strongest idea.

Today, many tools make this possible. The one I personally use and deeply admire is Replit, and it has been a great experience for me. Check it out here.

My advice is simple. Start small. Build something. Experiment.

Whether you are a leader or an individual contributor, the ability to turn ideas into working prototypes quickly is a skill worth developing.

I have been thinking a lot about how deals are won, especially when you are a perceived challenger in the category versus a leader.

When you are not the default option or the perceived category leader, pressure shows up early. Buyers want comparisons. Features enter the conversation faster than planned. Pricing gets examined sooner. This is not because challenger teams do not care about outcomes. Everyone wants outcomes. However, the focus often shifts to outshining the category leader in the competitive process.

That focus can create risk for the future. Deals may close on features or price, but without explicit clarity on goals, the foundation is weak. Later, when priorities shift or adoption slows, these deals struggle. The reality is that market leaders often get more patience, while challengers do not.

This is why outcome-led deal design becomes critical when you are not leading the category.

The strongest teams slow the conversation down early. They make customer goals explicit. They define what success looks like before leaning into features. Features then reinforce the outcome instead of carrying the deal on their own.

Features help you win attention. Outcomes help you earn durability.

Earlier this week, I spent time in San Francisco with customer success and post sales leaders from across the ecosystem. Conversations at events like these are useful because patterns surface quickly. Different companies. Different stages. Same problems.

At the same time, over the last few months, I have been thinking deeply about why customer success feels harder than it should for so many teams. So, when I presented some of my thoughts at the event, they resonated deeply with the attendees.

Headcount stays flat while expectations rise. Leaders assumed AI will absorb the load. The best CSMs are stretched thin, carrying accounts and context in their heads. Escalations become the default operating model. Dashboards increase, but decisions slow down.

They are system problems.

Customer success breaks when it is treated as a team that reacts, rather than a system that operates. Hero CSMs become single points of failure. Knowledge stays trapped with individuals. Every edge case requires a manager. Alignment meetings replace ownership. The organization stays busy but outcomes do not improve.

What actually scales customer success is much simpler, and much harder.

Clear signals that demand action instead of noise. Defined decision rights so trade-offs happen fast and at the right level. Repeatable motions tied to lifecycle moments, not individual style. Incentives that reward the behaviors you want, not the activity you can measure.

These are operating choices. Tools come later.

AI deployment is a good example of this. It does not fix customer success. It amplifies whatever structure already exists. A broken system with AI just creates faster chaos. A designed system creates leverage.

If you are leading customer success or post sales today, the real work is not hiring harder or buying better software. It is stepping back and designing the system your team operates in. When the system works, people can do their best work. When it does not, no amount of heroics will save you.

For those interested, I am sharing the presentation that I made for the event.
Customer Success is a System, Not a Team (Expand, San Francisco)

Your First Six Months as a CS Leader: From Foundation to Scale

Once you decide to invest in Customer Success (check out Part 1), the first six months matter a lot. This is when you set the rhythm. How your team works. How you measure progress. And how you build habits that will eventually help you scale confidently.

Your goal is simple. Build velocity, but never lose sight of value.

Here is a practical roadmap to shape those first six months.

Month 1 to 2: Diagnose and Define

Start by understanding where you stand today.

• Audit the entire customer journey. Look at onboarding, adoption patterns, renewals, and churn data.

• Define what “value realization” means for each type of customer. For some, value shows up in usage depth. For others, it shows up in how quickly they go live or how much business impact they see.

• Segment customers in a meaningful way and look for patterns in why they stay or why they leave.

This is not the time to jump into solutions. Focus on clarity. You need to understand the terrain before you start building the road.

Month 3 to 4: Design and Pilot

With clarity in place, design the first version of your Customer Success operating model.

• Connect the dots between onboarding, adoption, expansion, and renewal.

• Create two or three simple playbooks to start with. An onboarding checklist. A renewal prep guide. An executive business review format.

• Test these with a few customer segments and observe what creates movement.

• Hire your early Customer Success Managers and align them by customer segment or vertical.

Think of this phase as your MVP. Move fast. Test often. Collect feedback. Refine.

Month 5 to 6: Operationalize and Scale

By this stage, you will have a sense of what truly drives impact. Now it is time to put structure behind it.

• Set up your systems: CRM, CS platform, and basic health scoring.

• Continue to build your Customer Success Managers’ team as you build a clear picture of whats working

• Build a reporting rhythm. Bring in regular success reviews with Product and Sales.

This is when your team starts developing muscle memory. Every dashboard. Every customer conversation. Every internal alignment meeting. All of it helps you scale with confidence.

What Actually Makes This Work

From my experience, the strongest CS teams stay grounded in a few simple principles.

• Build for speed first; scale next. Start with lightweight processes. Improve with data as you go.

• Hire builders, not managers. Early CS hires should be comfortable being player-coaches who can jump into onboarding, renewals, insights and operations.

• Stay very close to the customer. Talk to them often. Listen carefully. Most of your future playbooks will come from these conversations.

Building Customer Success in a fast-growing company is not only about protecting revenue. It is about creating a culture where customer value compounds over time.

When you get this right, CS becomes far more than a retention function. It becomes the engine that fuels your next phase of growth.

While growth is hard, sustaining it is just as hard.

If your company has crossed its first few million dollars in revenue and is scaling fast, the renewals cycle will arrive sooner than you think. That’s usually when things start to strain. Cracks begin to show in retention and post-sales, not because customers stop liking your product, but because your systems haven’t kept pace with your growth.

This is where Customer Success steps in. It’s the function that keeps growth and value aligned. It ensures that as you move fast, your customers continue to see impact.

Here’s how you can start building a strong, scalable Customer Success motion. Think of this as the practical playbook that every post-sales leader needs to build early.

Start with the journey, not the org chart

Before you create roles or hire people, take time to map the full customer journey. Look at what the experience really feels like from onboarding to renewal. Identify where customers drop off or where value breaks down.

In most startups, the biggest gaps lie between handoffs: from sales to onboarding, onboarding to adoption, adoption to renewal. Fixing these early can save you time, customers, and reputation later.

Segment by value, not just revenue

Many CS teams begin by segmenting customers by ARR. That works in the early stages, but as you scale, segmenting by value and growth potential matters more.

For instance:

• Strategic customers: build joint success plans and engage with their leadership teams.

• Growth customers: design scalable programs with clear adoption milestones.

• Long-tail customers: rely on tech-touch models, health scores, and automation.

This allows you to allocate your energy where it drives the most meaningful results.

Build motions, not moments

A good CS team doesn’t react; it moves with rhythm and structure. Create repeatable motions that drive predictable outcomes.

• Onboarding: set clear success metrics and define what time to value looks like.

• Adoption: drive product usage through nudges and insights.

• Expansion: highlight new use cases tied directly to ROI.

• Renewal: focus on reinforcing the value delivered, not just discounts or pricing.

Make these motions repeatable and supported by systems and data, rather than relying on individual heroics.

Partner across the company from the start

Customer Success cannot thrive in isolation. The best CS teams work hand-in-hand with:

• Sales: align on retention goals, expansion triggers, and clean handoffs. Check out what I wrote earlier about deals getting to “Closed Done” stage and how you need to partner with Sales on that.

• Product: feed structured customer insights into the roadmap.

• Marketing: turn customer wins into advocacy and case studies.

Cross-functional collaboration keeps customer value consistent across every touchpoint.

Track the right metrics early

Net Dollar Retention is important, but it’s a lagging metric. By the time it drops, it’s often too late. Focus instead on leading indicators of customer health:

• Activation rates and time to first value

• Weekly active usage across roles

• Executive engagement and sentiment

• Support patterns and ticket trends

Build visibility into these early. It helps you act before churn risk surfaces. Because growth is great, but sustainable growth comes from helping your customers win first.

Check out Part 2, where I share how to set up your first six months when building CS from scratch- from early wins to scalable systems.

Taking over a team is one of the most important transitions a leader can go through. The instinct in those first few days is often to “step in and show leadership.” But sometimes, what a team needs most is space—to share, to be heard, and to let you in at their pace.

When inheriting a team, especially one shaped by a warm, trusted leader, the focus should be less on making a strong impression and more on building trust. The early days are the time to:

• Listen generously. Observe how people work together. Ask questions that invite perspectives. Let the team’s stories surface before sharing your own.

• Show warmth without overwhelm. Moving back to in-person workplaces means our presence feels more immediate than it did on Zoom. For leaders with big energy, it’s important to be mindful—your enthusiasm should feel inclusive, not exhausting.

• Respect team rhythms. Every team has its own pace, norms, and history. Honoring that creates the foundation for future alignment.

Of course, no transition is flawless. Sometimes our eagerness to contribute is received well, and other times it isn’t. That’s natural. What matters is how we respond. Staying open to feedback, being willing to adjust, and showing vulnerability are all part of earning long-term trust.

For leaders stepping into new roles, the invitation is clear: let your presence reassure, not pressure. Listening first doesn’t mean delaying leadership—it means setting the stage so when you do act, the team is ready to act with you.

There’s a great saying that “good fences make good neighbors.” It applies perfectly to sales and post-sales. Both functions need clearly defined KPIs so that everyone knows exactly what they are accountable for. At the same time they should feel comfortable stepping into each other’s world to provide support when needed. The key is that everyone stays clear on their own metric. That balance of clarity and collaboration only works when you have the right people in the right seats. And it only sticks when the incentives encourage partnership instead of silos.

As a GTM executive I’ve lived both situations. I’ve worked with sales colleagues where we’ve been the best of colleagues and everything clicked and worked where the partnership just didn’t land . The difference was culture. There is truth to the line “culture eats strategy for breakfast.” You can create the best-designed sales to post-sales strategy. But without trust and collaboration it simply will not work.

Here’s what I’ve learned works:

• Clear KPIs. Shared Incentives. An example of this would be “Sales owning new business and expansions while Post-sales owning time to value and renewals.” However, shared incentives align behavior. For example part of sales commission linked to successful onboarding could ensure accountability beyond closed won.

• Redefine Closed Won. A deal is not really done until the customer is live and on the path to value. Linking compensation to deployment shifts the focus from signing contracts to delivering outcomes.

• Overlap Not Drop Off. Think of it as a transition period where both teams are actively involved before one fully steps back. That overlap builds confidence for the customer.

I once had the chance to design this structure from scratch and it worked beautifully. Why. Because the sales and post-sales leaders were genuinely invested in each other’s success.

In the end playbooks, handoff meetings and CRMs all matter. But what really powers a smooth transition is the culture of collaboration at the leadership level. When sales and post-sales see themselves as partners. Not neighbors behind fences. Customers win. And growth compounds.

I wasn't at Hubspot INBOUND 2025 earlier this week in person, but I was impatiently waiting for Hubspot CTO Dharmesh Shah’s keynote. I got a chance to hear it yesterday and his framing of AI as a collaborative partner, not a competitor, deeply resonated with me. He put it simply: don’t think about competing against AI. Think about competing with AI. The goal is not a zero-sum battle. The goal is to create a positive-sum collaboration. That framing hit me hard because I see how quickly the narrative is shifting to “AI will do my job.” The real opportunity is, “AI can help me do my job better, faster, smarter.”

Dharmesh reminded us that AI has no lived experience. It has never tried to fold a fitted sheet, negotiate with a toddler, or rebuild trust after a tough miss. It does not know the weight of silence in a room after a difficult decision. That is the human moat. AI can generate, automate, and even surprise us, but it cannot replicate lived experience, empathy, or conviction.

Take the post-sales world as an example. Customer success teams managing a large number of accounts often wake up each morning wondering which account to prioritize and where to spend time. On its own, that is overwhelming. But AI as a partner can help. Imagine combining human engagement signals, telemetry, and activation data into a health score by leveraging AI. Suddenly, teams know where to focus their energy. AI can also draft MBRs, QBRs, and activation plans for clients automatically. And that is when humans can step in to decide which conversations to lead, where to apply empathy, and how to build trust. This is not AI competing with customer success managers. It is AI helping them scale their impact. And examples like this exist across every function in our professional lives.

Here’s how I see it. I encourage my team to use AI. It is a powerful accelerator. But when you come to me, bring material that you can own. Bring your judgment, your context, and your understanding. Any material without your own thinking will always be weaker. The real value is what you bring- your intelligence, your emotional quotient, and your lived experience as a professional.

The leaders and teams who truly scale are the ones who use AI as leverage while still showing up fully human. AI can help generate, automate, and even surprise us, but it cannot replicate lived experience, empathy, or conviction.

So how do we make AI a real partner in our journey. Three things to focus on:

Use AI to accelerate, not to decide. Let AI take care of the heavy lifting, but keep the ownership of decisions and trade-offs with yourself.

Show your intelligence and EQ in the final outcome. Edit, adapt, and contextualize what AI produces so that it reflects your thinking.

Turn individual usage into team habits. Make AI part of workflows, measure the lift, and build confidence across the team.

The future is not AI replacing us. It is AI amplifying us. And the paradox is beautiful. The better AI gets, the more important it becomes to bring our human-ness to the table. When we do that, we do not just scale our businesses. We scale ourselves.

AI-native startups are breaking all the old rules of building companies—and doing it with shockingly small teams.

At a recent Operator Guild Summit, Henri Shi, co-founder of Super.com, shared how a new wave of startups is scaling to millions in revenue with fewer than 30 employees. That’s not a typo. Startups like Midjourney, Replit, and Eleven Labs are proving that lean doesn’t mean less—it means sharper, faster, and focused.

Want proof? Take a look at Henri’s Lean AI Leaderboard—a snapshot of top-performing AI startups with revenue-per-employee numbers that would make any SaaS founder do a double take.

So what are they doing differently?

They start with the assumption that people are NOT the first solution. Automation is. They build products that are so well-crafted, distribution is built-in—users sell to other users. They avoid bloat by hiring generalist senior talent who can do more with less. And they measure success not by team size, but by output and revenue per person.

Here’s what you can borrow from their playbook:

• Automate ruthlessly. From customer support to hiring workflows, every repeatable task is automated. If you’re still relying on human hours for basic admin, you’re behind.

• Hire generalists who ship. A small team of 10 high-performing doers will outperform 50 average specialists.

• Experiment fast, iterate faster. Speed wins. Small teams with tight feedback loops build better products.

• Own your revenue early. These companies monetize fast, often bootstrapping growth instead of chasing VC money.

Founders and leaders often think they need to scale headcount to scale impact. This new generation proves otherwise.

The game is quickly away from how many people you employ—it's becoming about how few you need to make something people love.

So ask yourself: Are you scaling your team or your impact?

As someone who’s built BizOps teams more than once, her talk reaffirmed what I’ve long believed: BizOps isn’t just a support function—it’s a strategic lever that helps a company scale with clarity instead of chaos.

1. From Knowledge to Adaptability

Rachel started by challenging something most of us take for granted—deep expertise as a moat. Her take: functional expertise has a short shelf life in today’s world. What matters more is your team’s ability to learn fast and adapt faster.

We’re not just in a knowledge economy anymore—we’re operating in an adaptive economy. For BizOps, that means hiring for range, not just depth. Think systems thinkers who can jump across finance, GTM, and product — and connect dots in high-ambiguity situations. It reminded me of a hiring lesson I learned early: passion + learning agility > textbook expertise.

2. BizOps Should Evolve with the Company

Rachel offered a great stage-wise breakdown:

• Early stage? BizOps is glue. Filling gaps, stitching together insights, and helping teams make sense of the chaos.

• Mid-stage? BizOps starts laying tracks—building processes and bringing repeatability to how things run.

• Late stage? It becomes the orchestrator—aligning teams, informing strategic bets, and helping the company scale smart.

The takeaway? Don’t copy-paste a BizOps structure from another company. Build for the stage you’re in.

3. Structure Reflects the Pain You’re Solving

Where BizOps reports in your org says a lot about what you expect from them. Under the CEO? You’re solving for change. Under the CFO? Efficiency. Under the CRO? GTM acceleration.

One other thing that struck a chord—Rachel’s reminder that BizOps is not project management. That was a déjà vu moment for me. I’ve had to explain the same before: project management is about executing a known solution, while BizOps is about uncovering the problem and defining the path forward. It’s a subtle but critical distinction.

4. The BizOps Superpowers

Rachel laid out four competencies I loved:

• Clarify what really matters

• Align cross-functional priorities

• Anticipate issues before they escalate

• Optimize systems without slowing things down

Yes, they may sound familiar—these are the same muscles we expect from high-performing teams. But here’s the difference: BizOps operationalizes them across the organization. That’s what sets it apart. BizOps doesn’t just support execution—it designs how the company executes at scale.

Final Thought

Rachel’s talk was a reminder that BizOps isn’t about having all the answers. It’s about creating the systems, habits, and conversations that help you ask better questions—and scale smarter.

If you’re navigating your next stage of growth, a well-structured BizOps team might just be your best investment.

Once upon a time, CS was all about relationships and QBRs. Nice to have? Sure. But now, CS is being asked to do something far more strategic—drive revenue, reduce churn, and power expansion. And here’s the kicker: it has to do that at scale, without throwing more people at the problem.

Here’s a stat that really stayed with me: according to Bain & Company, post-sales headcount has more than doubled over the past seven years. But despite that, over 75% of companies have seen their Net Revenue Retention go down. More than half saw drops of over 10%. That’s not just a red flag—it’s a flashing neon sign telling us that the old model isn’t working.

The model of the future? It’s digital-first, automation-led, and outcome-obsessed. Tools like Agentic AI are redefining what scale actually looks like. No longer about how many CSMs you have—it’s about how intelligently your workflows run, how seamlessly your touchpoints trigger, and how you embed guidance right where the customer needs it.

Another insight that stood out: customers don’t want more “alignment meetings”—they want deployment help, outcomes, and fast wins. And guess what? Most CS teams are stuck playing project manager when customers are actually looking for a trusted guide.

Let’s also not ignore the global angle. If you’re running a global CS team, it’s critical to align on metrics and dashboards—but give teams room to maintain regional nuance. Automation here doesn’t replace the human touch—it amplifies it.

One provocative question someone asked was, “If you were designing post-sales from scratch today—what would it look like?” And honestly, we may not have the luxury of starting over, but we do have the power—and the urgency—to re-architect.

This is where we are now. But it will keep evolving. As AI gets smarter and CFOs get tighter with budgets, our playbooks must keep shifting too.

But one thing is clear—we’re not just scaling Customer Success anymore. We’re designing it for impact.

Over the past few weeks, I’ve been asking myself: how can Scale It Up reach more people? That led me down the path of AI-driven tools. And one thing became clear—people absorb content differently. Some like to read, others prefer to listen, and more and more now want to watch. That’s where tools like HeyGen come in. I’ve started converting blog posts into videos using AI avatars and voice.

It’s been fun to experiment—trying out different avatars and voices, tweaking scripts, and testing formats. I’ll keep refining it, but here’s what I’ve realized: perfection doesn’t matter. Presence does. What matters is showing up consistently, in different ways, to connect with a wider audience. Check out my fiirst AI Avatar video above!

So over the next few months, expect more than just written blogs. You’ll see video articles, new content formats, and fresh takes on past posts—all designed to meet people where they are.

And if you’re in a go-to-market or customer-facing role, there’s a takeaway here. AI tools are no longer just toys. You can explore AI-led onboarding, customer support, even training. The results might not be instant, but they’re worth experimenting with.

So here’s to scaling not just the business—but you. Your story. Your voice. Your impact.

Let’s keep scaling it up.

As leaders, especially in GTM and customer-facing roles, we constantly encounter challenges that seem insurmountable. Customers voice concerns, complaints pile up, and teams scramble for solutions. While it’s easy to treat these as roadblocks, the seasoned leaders recognize them as opportunities to drive engagement, retention, and loyalty.

However, solving complex customer challenges effectively requires more than quick fixes—it demands first principles thinking. The toughest problems often persist because conventional solutions have already been exhausted. When traditional approaches stop yielding results, it’s time to deconstruct the problem and rebuild a fresh solution from the ground up.

Update - AI generated podcast style video at the bottom of the blog, if you would prefer to listen to this blog instead!

Applying First Principles Thinking

1. Ask Clarifying Questions Start by breaking down the problem to its fundamental elements. What is the core issue? Is it a symptom of a larger challenge? Keep asking “Why?” until you reach the root cause. Many times, what appears to be the problem is just a surface-level manifestation of something deeper.

2. Break It Down Once you identify the root cause, dissect the challenge into smaller, manageable components. This helps in understanding which elements are controllable and where new approaches can be introduced.

3. Challenge Assumptions Many solutions fail because they are built on flawed assumptions. Ask yourself: What do we believe to be true about this problem? What if those beliefs were wrong? Could there be another way to approach the situation?

4. Rebuild a Solution from the Ground Up Now that the challenge has been deconstructed, think creatively. What new strategies can be applied? Are there insights from other industries or disciplines that could be leveraged? This step requires thinking beyond conventional frameworks.

5. Execute, Measure, and Iterate No solution is complete without execution and iteration. Deploy your approach, track its effectiveness, and refine it based on real-world feedback. The key is to remain adaptable and continue questioning the process.

Why This Matters

First principles thinking transforms customer challenges into strategic advantages. By focusing on the core issue rather than patchwork fixes, leaders can craft innovative, lasting solutions that drive real impact. This mindset doesn’t just solve problems—it reshapes how organizations approach growth, customer satisfaction, and long-term success.

The next time you encounter a persistent challenge, take a step back and strip it down to its essentials. You may just uncover a breakthrough opportunity hidden in plain sight.

Additional content - I've been experimenting with Heygen to create AI-powered videos and podcasts for Scale It Up. If you enjoyed the article and prefer a podcast-style format, take a look at the video below.

When you bring a new team member on board, you’re making a fundamental decision—you trust them. You believe in their capabilities, their intent, and their potential to contribute. That’s why I’ve always believed that trust should be the starting point, not something earned over time.

Too often, leaders hold back, waiting for proof that a new hire will deliver. But imagine starting a new job with the underlying message: “We’ll see if you’re good enough.” It creates hesitation instead of ownership. On the other hand, when a leader communicates trust from day one, it signals confidence and accountability.

Many years back, I had a very high-potential team member join me. He had offers from multiple companies, but something clicked about the mission of the company I was working at, and he decided to join us. A few days later, when I checked in with him, he said he was doing okay. But then, interestingly, when I checked in again a few days later, he said, “Ishan, I have seen you in action, and I don't trust you a lot.” I was surprised, but I immediately responded, “That's okay. I don’t expect you to trust me. I would love to earn your trust as we work together. But at the same time, I want to let you know that I trust you.” Over the next few months, we worked on many projects together, building trust through actions, not just words. Fast forward to today, and this person remains one of my most trusted professional relationships.

Trust is not static. It’s a bank account that gets built up with every credible delivery or eroded with each misstep. Some employees will continually reinforce that trust, showing reliability, ownership, and growth. Others may struggle, and over time, that trust can fade. But the key is to start from a place of trust rather than skepticism.

Think of your own career—when did you do your best work? Likely when someone believed in you, gave you space to execute, and supported your growth. As a leader, that’s the culture you need to build. Trust isn’t just a nice-to-have—it’s the most important currency in building high-performing teams.

So, next time a new hire joins, let them know: “I trust you.” Then, see how they rise to the challenge.

Culture isn’t shaped by grand speeches or company-wide memos. It’s built in micro-moments—the countless small interactions that, over time, create an environment where people feel connected, valued, and safe.

I learned this firsthand when I inherited a team that had gone through multiple rounds of layoffs. The team was exhausted, disengaged, and disconnected from the company. There was a clear lack of psychological safety, and as a result, people weren’t sure if they should give their best. It was one of the most challenging situations I had ever faced as a leader.

At first, I did what most leaders do—I met with people, listened, set a vision, and established team values. We even brought people together in person after long stretches of remote work. But while these were important steps, they were big, structural changes. They weren’t the micro-moments that truly shift culture.

So, I shifted my focus. I started building trust one person at a time.

I remember one team member who was hesitant to let me join a client meeting. They were worried I might form a negative opinion about their work. Instead of insisting, I asked questions, reassured them, and showed up consistently. Over time, they saw that I was there to support, not judge. Eventually, I earned their trust, and they started inviting me to meetings on their own.

Another time, I noticed conversations would stop when I entered the room. Instead of ignoring it, I acknowledged it—sometimes with humor, sometimes with vulnerability. Slowly, people realized I wasn’t there to micromanage, but to be part of the team.

These micro-moments—small conversations, gestures of trust, and follow-through on commitments—stacked up. Over time, the team’s culture shifted. People started feeling safer, more engaged, and more willing to contribute.

If you’re leading cultural change, know this: You have to show up every day. It’s exhausting at times, but stopping isn’t an option. Change happens through relentless commitment to the little things—because in the end, culture is built in the micro-moments.

The evolution of SaaS pricing models has been fascinating. Back in the day, companies started with enterprise licenses, moved to per-seat pricing, and now we're seeing a growing wave of consumption-based models. Some even predict a shift toward outcome-based models in the future. But in all these models, one thing remains critical—deeply understanding customer goals.

Why Goal Clarity is Essential

In a consumption or outcome-driven contract, goal clarity isn't a "nice to have"—it's fundamental. The conversation around goals should start in the sales process, ensuring that by the time a contract is signed, both the customer and the provider are aligned. Even in more traditional models, knowing what success looks like for the customer is key to long-term retention and growth.

Measuring the Right Kind of Usage

When it comes to consumption-based models, usage metrics can be misleading. A constantly rising usage graph might seem exciting, but a more telling sign of success is an upward trend with fluctuations. Why? Because it signals that the customer is experimenting, learning, and adapting—figuring out which features drive real value. This kind of engagement is healthier than blind, unchecked usage.

Consumption Models Shine in Downturns

One of the biggest advantages of consumption-based models is their flexibility. In economic downturns, customers can scale down spending rather than churn completely. When the market picks up, they can scale back up. This adaptability makes the model attractive for both customers and providers.

The Challenge of Forecasting

That said, one major challenge with consumption models is predictability. Customers want to budget, and businesses want reliable revenue projections. To bridge this gap, leveraging past data and cohort analysis is crucial. Providing customers with estimates based on similar profiles can help them plan better, making the model more approachable.

Doing Right by the Customer

At the core of all go-to-market strategies, one principle holds: doing right by the customer. Consumption-based models align well with this philosophy, ensuring customers pay for what they use and see direct value. As SaaS companies refine these models, keeping customer success at the forefront will be the key to long-term growth.

Last week, I saw a competitor shut down. No matter the reasons behind it, moments like these shake up an industry. They impact teams, customers, and even competitors. How a company responds in such times speaks volumes about its values, leadership, and long-term vision.

When a competitor folds, it’s easy to react with either anxiety or opportunism. But the right approach is a thoughtful, balanced one—where we lead with empathy, communicate clearly, and remain focused on our priorities. Here’s how:

1. Supporting Your Internal Team First

The first thing to address is your own team. News of a competitor shutting down can cause unease—people might wonder if it's an industry-wide trend or an isolated case. Clear, transparent communication is key. If your company is in a strong position, reassure your team. If there are challenges to navigate, acknowledge them and share the plan forward. A confident, informed team performs better and fosters trust.

2. Extending a Hand to Affected Employees Of the Competitor

For those suddenly out of work, this is a tough time. If you're hiring, it's an opportunity to step up and offer roles to talented professionals. Even if you’re not actively hiring, sharing openings within your network, making introductions, or offering guidance can go a long way. Being a responsible industry player builds goodwill that lasts beyond just one moment.

3. Showing Up for Clients Left in the Lurch

Customers of the folding company might be scrambling for alternatives. This is a moment to lead with support, not aggressive sales tactics. Can you offer guidance? Can you create a smooth transition plan if they need a new provider? By focusing on their needs first, you build trust—and trust builds long-term relationships.

4. Aligning Your Team’s Focus

While responding to the situation is important, it’s equally crucial not to get distracted. It’s easy for teams to get caught up in the industry buzz, but leadership needs to ensure that core priorities remain on track. Set clear expectations: address the immediate needs, but don’t let the entire organization lose sight of its long-term goals.

5. And Mostly Importantly, Leading with Empathy and Respect

It’s tempting to see a competitor’s shutdown as a business opportunity, but how you approach it matters. A respectful and empathetic stance—towards their employees, customers, and even their leadership—reflects your company’s integrity. Industries evolve, and today’s competitors can be tomorrow’s partners or allies in different ways.

At the end of the day, moments like these test leadership. The best response? Stay steady, be thoughtful, and show up with both strategy and heart. Because in the long run, companies that lead with empathy and focus are the ones that truly stand out

Leading during a company turnaround is one of the most challenging tasks a leader can face. It’s a test of vision, resilience, and adaptability. When everything feels uncertain, the way leaders act, think, and manage their teams has the power to steer the organization toward recovery—or further into crisis.

Here are some guiding principles for leadership that I have found useful during a turnaround:

1. Set a Clear Vision and Communicate It Relentlessly

In times of uncertainty, people crave direction. As a leader, your role is to provide clarity. Define a vision that is realistic yet inspiring. Outline the steps the organization must take to reach stability, and communicate this vision consistently across teams. Transparency builds trust, even when the news isn’t favorable.

Example: Instead of saying, “We’re in trouble,” articulate, “Here’s where we stand, what we’re working on, and how we’ll get through it together.”

2. Act Decisively, But Stay Empathetic

Turnarounds often require tough decisions—cost-cutting, restructuring, or even layoffs. The key is balancing execution with humanity. Make decisions based on data and priorities, but acknowledge the emotional weight they carry. Your team will remember how you treated them during difficult times.

Tip: Involve your team in problem-solving. When people feel heard, they’re more likely to stay engaged and committed.

3. Rebuild the Culture Intentionally

Company culture can take a hit during a turnaround, but it’s also an opportunity to reshape it. Revisit your core values and ensure they align with the new direction. Encourage behaviors that support collaboration, adaptability, and accountability.

Action Plan: Celebrate small wins to rebuild morale and foster optimism. Recognize individuals who embody the desired culture.

4. Focus on Teams, Not Just Individuals

Turnaround success isn’t achieved in isolation; it requires a collective effort. Evaluate team dynamics, not just individual performance. Are the right people in the right roles? Are teams aligned and working cohesively toward shared goals?

Strategy: Cross-functional collaboration becomes essential in turnarounds. Break down silos and create opportunities for teams to learn from one another.

5. Strengthen Relationships with Peers

Your leadership team is your most important asset during a turnaround. Build trust and alignment with your peers to create a unified front. Disagreements will happen, but handling them constructively is critical to maintaining credibility and focus.

Mindset: Prioritize collaboration over competition. A turnaround is no time for egos or hidden agendas.

6. Lead by Example

During a turnaround, everyone is watching you. Your actions set the tone for how others behave. Model resilience, adaptability, and a willingness to do what it takes to succeed. Show up with energy, even on hard days, and your team will follow suit.

Conclusion: Steer with Conviction and Care

Turnarounds are moments of transformation. While they bring immense challenges, they also create opportunities to redefine the company’s purpose and culture. As a leader, your ability to act decisively, communicate transparently, and care deeply for your people can make all the difference.

Remember, leadership during a turnaround isn’t about perfection—it’s about progress. Show your team the path forward, one step at a time, and lead with both your head and your heart.

As leaders, we often find ourselves caught up in the planning, strategic discussions, and structured decision-making. However, sometimes the best opportunities come knocking at our door when we least expect them. That’s serendipity! 

Serendipity is the ability to find interesting or valuable things by chance. But it actually goes beyond the wonderful blend of chance and destiny. It involves being open to innovative ideas and information, while also being an objective observer of reality.

Last week I was at a Stanford alumni meet up where one such occurrence happened with me. I met Milan, a long time friend of mine, whom I had not spoken to for many years.  Guess what, my conversation with him ended in him giving me some advice on a tricky conversation I was about to have with someone else. This advice elevated my other conversation. It was then that both of us started to talk about serendipity and why leaders should be open to it. 

Just a few minutes later, I bumped into Prof Sridhar Narayanan, one of my marketing professors at Stanford Graduate School of Business. I couldn’t help but go back to the day in 2009, when during a serendipitous conversation, he had suggested to me that I should talk to Vijay Shekhar Sharma, then a  founder of an early stage company (Paytm) in India, for exploring opportunities for myself as I was planning to return to India, post my grad school.  It was purely by chance but I acted on it and the rest, as they say, is history. Vijay not only hired me twice, but also became an investor, advisor and later acqui-hired my startup, EduKart. And I got a chance to work with a leader, who built Paytm, from the ground up leading to an IPO in India of over $15Bn. 

So, how can we as leaders harness the power of serendipity? 

Stay Curious: Curiosity is the compass that points us towards serendipitous encounters. Always be open to learning, exploring, and trying new things. You never know what new doors it may open. 

Network and Connect: Meaningful connections are often the breeding ground for serendipitous moments. Attend industry events, engage with fellow professionals, and strike up conversations. The next game-changing partnership or idea might just come from a chance encounter. 

Be Adaptable: Flexibility is key in the world of serendipity. Embrace change and be ready to pivot when unexpected opportunities present themselves. An unexpected turn of events could lead to a breakthrough you never imagined. 

Listen and Learn: Actively listen to others, even if their ideas don’t align with your initial thoughts. Serendipity often whispers through the words of others, offering insights that can be transformative. 

Trust Your Instincts: Sometimes, that gut feeling is serendipity trying to catch your attention. Trust your instincts and be open to following those inklings that guide you towards the unknown.

In this ever-evolving landscape of business, scaling up is not merely about numbers; it's about nurturing a thriving ecosystem of talent, innovation, and collaboration. Wonderful things can happen if we are open, curious, and willing to let a little magic in. Embrace these unexpected turns of events as valuable learning experiences. The agility and quick thinking developed through serendipitous encounters can significantly enhance your decision-making process. 

Incorporating serendipity into your leadership approach can transform your team and business in an amazing manner.  Stay open to the unexpected, celebrate chance encounters, and let serendipity be your trusted ally on the exciting road to scaling it up!

As an employee, it's not always easy to speak up to your manager when you have concerns, complaints, or ideas. Having difficult conversations with your manager can be intimidating, but it's important to learn how to do so effectively. 

Types of Difficult Conversations with Your Manager

There are several types of conversations that can be difficult to have with your manager. Some of the common ones are-

1. Discussing a promotion or raise

2. Raising concerns about workload or work-life balance

3. Feeling unhappy about the current role

4. Feeling unsatisfied by how the manager behaves

5. Manager stakeholders, be your peers or your manager’s peers

6. Addressing your own poor performance or other gaps you may see

These conversations can be challenging because they require you to be vulnerable and open with your manager. Additionally, there may be power dynamics at play that make it difficult for you to speak up.

Tips for Having Difficult Conversations with Your Manager

As a leader and as an employee, I have been on both sides of the table enough times during such conversations. Here are a few practices that have helped me time and again. 

1. Prepare yourself mentally and emotionally.

Before you have the conversation, take some time to reflect on your thoughts and emotions. Think about what you want to say, and how you want to say it. Consider how you might feel if your manager responds negatively, and plan ways to cope with those emotions.

2. Choose a time and place that is private and conducive to a productive conversation.

Set up a meeting with your manager in a private space where you won't be interrupted. This will help you feel more comfortable and give you the space you need to have a productive conversation.

3. Explain what you think could be the solution.

Think of an ideal state and also be clear about why it makes sense. You have to have a solution oriented approach during these conversations. For example, instead of saying "You never give me enough feedback," say "I would appreciate more feedback on my work."

Discuss whether the solution is only beneficial for you or is it beneficial for your manager’s goals as a whole.

4. Stay focused on the issue at hand.

Don't let the conversation get sidetracked by unrelated topics. Stay focused on the issue you want to address, and avoid bringing up other grievances or complaints. Let your manager know why this issue is important. Being vulnerable and clear is critical here. 

5. Be open to feedback and willing to work with your manager to find a solution.

Remember that the conversation should be a two-way dialogue. Be open to feedback from your manager, and be willing to work with them to find a solution that works for everyone. If there is a pushback, then take it in the right stride. 

Having difficult conversations with your manager is never easy, but it's an important skill to learn. Communication is key to a healthy working relationship, so don't be afraid to speak up when you need to.

If you have any tips or experiences to share, feel free to leave them in the comments. Good luck with those conversations!