Startup CXO by Matt Blumberg A Field Guide to Scaling Up Your Company’s Critical Components
What's it about?
Startup CXO (2021) serves as a comprehensive tactical manual for scaling the specialized leadership roles that drive a growing company’s most vital departments. With contributions from several co-authors, it details how various executive functions – from finance and marketing to product and people operations – must evolve and integrate to ensure a business survives the transition from a small team to a mature organization.
Starting a company is one thing. But scaling it? That’s an entirely different challenge. In the early days of a new venture, you can get by on hustle, improvisation, and sheer force of will. But, as your startup grows, the scrappy approach that got you to product-market fit becomes the bottleneck – and it starts preventing you from reaching the next level. It’s at that point that you start needing structure and specialized expertise. And, perhaps most importantly, you need leaders who can build the systems and teams that turn a promising idea into a sustainable business.
The problem is that most founders are learning on the job – and often making expensive mistakes that compound over time. What seemed like a small shortcut in year one becomes a major liability when you’re trying to raise your Series B or scale to a hundred employees.
Well, that’s where this lesson comes in. In it, you’ll learn how to build and scale five critical functions in your startup. You’ll discover how finance, people, marketing, revenue, and customer success leaders should approach their roles differently as the company evolves – and what decisions in the early days will either support or sabotage your growth trajectory years down the line.
Let’s start with your CFO, or Chief Financial Officer. Their role in a startup demands an uncomfortable balancing act from day one. Every decision forces a choice between doing things properly – with full diligence, adequate time, and appropriate resources – or taking the scrappy, fast, cheap route. These early choices echo far longer than most founders expect.
Consider for a moment something as mundane as board meeting minutes. When your board consists of three people sitting around a kitchen table, meticulous record-keeping feels excessive. But five years later, when you’re courting serious financing, those same minutes become artifacts under intense scrutiny. Lawyers representing potential investors will examine them closely, and your early diligence – or lack thereof – suddenly matters enormously. The seemingly trivial documentation decisions made in year one become the foundation that either supports or undermines your growth trajectory.
Before those lawyers ever open your files, though, you need to capture investor attention. This brings us to fundraising, perhaps the most fundamental process in any scaling business. As CFO, supporting your CEO through this vital process means becoming a master storyteller with data.
Which brings us to the pitch deck – that carefully crafted document designed to pique investor interest before a call or crystallize key takeaways afterward. This isn’t merely a financial document that the CFO runs numbers for. You’re collecting and synthesizing information from across the entire organization, weaving it into a compelling investment narrative.
So, what information does an effective pitch deck contain? Most start with the opportunity and business – they articulate your core value propositions clearly and explain your approach and business model. Then comes your product, including relevant screenshots and a development roadmap that demonstrates forward momentum.
The fourth element is about market size, specifically what’s known as your Total Addressable Market. You can calculate this two ways. The top-down approach starts with macro indicators – say, the size of the national real-estate segment – then estimates growth rates and the percentage you can realistically capture. The bottom-up method starts with specifics: you might take your average product price and then multiply it by your total potential customer base.
Element number five in your pitch deck is your current business status. Present existing partners and clients, highlight key performance indicators, and include anything that validates your progress. Next are your financials – current numbers paired with credible projections. Finally, your seventh element is introducing your senior team, emphasizing both their roles and the specific experiences that qualify them to execute your vision.
These practices represent just the beginning of what it takes to scale successfully as a CFO. Get these fundamentals right, and you create the infrastructure that makes sustainable growth possible.
The role of HR has undergone a fundamental transformation in the last couple decades. What once centered on compliance, transactions, and administrative paperwork has evolved into something far more strategic – work that touches every corner of an organization and drives real business outcomes. This new approach earns a new title: People. And if you’re leading it, you’re the Chief People Officer, or CPO.
Your primary mission as CPO starts with building an inclusive culture. Culture can be defined as the sum of everyday behaviors your employees exhibit. These behaviors flow directly from your values, but only when you actively align actions with principles. The gap between stated values and lived reality determines whether your culture thrives or withers.
Your early hires carry disproportionate weight in shaping your culture. When they don’t share the CEO’s and company’s core values, they inject tension and conflict into the system. This misalignment drains resources, kills productivity, and burns time nobody can afford to waste. Prevention starts with clarity.
To gain this clarity, as CPO you’ll need to spark what the authors call the culture conversation. This involves pushing your fellow leaders with concrete questions: How do they view hierarchy and decision-making? Do they embrace remote work or resist it? Where do they stand on work-life balance? Together, these questions act as diagnostic tools that reveal where your leadership team actually aligns.
So, once you can articulate your culture clearly, it’s time to start focusing on codifying your values. Research possibilities, compile a list, then guide your leadership team through the hard work of narrowing it down. With culture and values established, your job then shifts to maintaining what’s known as alignment. This means periodic evaluation, personal championing, and course-correction when behavior drifts from principle.
Sometimes, however, a course cannot be correct – and you’ll need to let people go. This can become necessary at any stage, whether performance stalls or strategy pivots. And how you handle departures matters enormously. So, instead of making decisions behind closed doors, bring transparency to the process. Where possible, discuss with your employee to see if they might fit a different role or choose voluntary redundancy. When termination becomes necessary, offer transition time and a meaningful severance package. Consider adding career placement assistance and extended severance for those struggling to land their next role.
The payoff for treating employees well compounds over time. That person you’re letting go today might be exactly who you need tomorrow. When you’ve handled their departure with dignity and support, they’ll actually consider coming back. Burn that bridge, and you’ve closed a door you can’t reopen.
Everyone thinks they understand marketing. Your CEO has opinions. Your engineers have opinions. Your investors definitely have opinions. But as Chief Marketing Officer or CMO of a startup, you face an endless buffet of approaches, techniques, and tools – which creates both opportunity and paralysis. Your real job is deciding what actually matters.
Marketing boils down to three core priorities: building and maintaining your company brand, generating demand that sales can convert, and supporting the culture that makes everything else possible.
Start with your brand. After all, if you can’t articulate what your company stands for, selling becomes impossible. But brand isn’t just your logo, name, or messaging – it’s the sum of conversations people have about you. It’s dynamic, evolving with every interaction someone has with your company.
It all starts with a conversation. Ask yourself and your colleagues fundamental questions: Who are we? What do we do – and why does it matter? What’s our brand’s personality? Collaborate across the entire organization here. The more diverse perspectives you gather, the more likely you’ll uncover creative, recurring themes that crystallize into something authentic. Brand built in isolation rarely connects with anyone beyond the person who built it.
Next comes demand generation – the machinery that converts prospects into customers and keeps them engaged over time. This work starts with market research. If that phrase triggers flashbacks to dense academic papers, relax. Market research spans everything from formal studies to customer interviews to analyzing competitor websites. Specialist agencies exist if you need them, and countless accessible books cover the fundamentals. The crucial move is simply starting.
Once you’re deep in demand generation, you’ll encounter an overwhelming array of technology solutions. The trick here is to start simple and expand your tech stack as genuine needs emerge. Begin with a solid Customer Relationship Management system. Many CRM tools now include built-in features covering essentials like search engine optimization and social media management, giving you a surprising range from a single platform.
But when it comes to CRM goals, don’t overthink the metrics. Set a few goals and stick to them – whether they are leads, marketing return on investment, customer acquisition cost – each measures something valuable. So, pick the metrics that map to your current business priorities and start tracking them. You can always refine, combine, or change your measurements as you learn what actually predicts success.
Finally, remember the People team we talked about in the last section? You’ll need to build a close relationship with them too, all to help support the company culture. Marketing brings invaluable creative insight to employee engagement, recruiting efforts, and internal communications. This ensures your company isn’t just great to work with, it’s also great to work for.
Revenue is oxygen for a company. Without it, you can’t survive. As Chief Revenue Officer or CRO, you’re in charge of this lifeline.
The first lesson every CRO needs to hear hits hard: it doesn’t matter how much work and sacrifice you’ve poured into your product, or how deeply you love it. The only thing that matters is whether people want to buy it. And whether you can actually sell it. This distinction between building something beautiful and building something sellable separates successful startups from expensive hobbies.
In the very early days, the whiteboard becomes your best friend. You should literally go to your prospects’ offices with a whiteboard and draw graphs and arrows and circles to discover what problem of theirs needs solving – and how you might solve it. As you grow, you’ll graduate from the whiteboard to a polished sales deck and pitch, because by then you’ll have a refined and tested understanding of your customers’ actual needs.
All the while, don’t forget that a CRO is the company’s first salesman. You should only hire additional salespeople once you have crystal clarity about what you’re offering. Hiring before that point just multiplies confusion.
When the time does come to hire, who you should look for might surprise you: people who’ve been through adversity in their lives. These individuals tend to emerge more empathetic, and empathy is the key ingredient for sales success. They know how to listen – and how to tell a compelling narrative that resonates with real human concerns. Your sales hires should also get along with other departments, and those departments should participate in the interview process. Sales staff will work across the organization constantly, and friction there kills deals.
When it comes to setting their compensation, it’s advisable to start with a base salary at or above market rate. As you’re building toward your first major revenue milestone, pay commission on every single dollar salespeople generate. As the company matures, shift to a system where commission rates increase as salespeople approach annual targets, broken down quarterly. This ensures they’re thinking about the current quarter while simultaneously keeping the longer-term picture in view.
Beyond evolving compensation, you need to evolve your sales pipeline as you scale. Start with the basics: learn about your buyers’ decision-making processes, their timing, and how they evaluate different products. Figure out not just what you’re doing, but how what you’re doing affects the buyer’s journey at each stage.
Combine these elements – empathetic sellers, aligned compensation, and refined pipelines – and you’ll be positioned to scale with real momentum behind you.
Every business exists to complete a job the customer is hiring them to do. Your task as a company is to do that job better than competitors and make it as frictionless as possible for the customer. This is where the Chief Customer Officer or CCO enters the picture.
As CCO, it’s your job to coordinate across departments and leadership to keep the entire company laser-focused on customer priorities. This means working with sales to ensure they’re targeting the right client types, collaborating with product teams to streamline onboarding, and partnering with marketing to communicate features clearly. The role is fundamentally about orchestration – making sure every department’s work aligns toward delivering customer value.
Many startups assume they don’t need a CCO yet. But this can prove costly. Customer success matters intensely at the beginning. Ongoing feedback from early clients helps you smooth the rough edges of the customer journey before they calcify into permanent problems. Get it right early and scaling becomes exponentially smoother. You don’t need to call the position “Chief Customer Officer” – something like “Head of Services” works just as well. What matters is that someone owns this responsibility from day one.
One common misconception companies make about the service department is that it alone controls customer retention and churn reduction. The truth is that churn has roots everywhere. How customers were sold to matters. How intuitive the product feels matters. The responsibility spreads across teams. The CCO’s job is coordinating these teams for the customer’s benefit, which in turn drives down churn naturally.
Another crucial element for creating exceptional customer experiences is segmentation. A customer paying one hundred dollars cannot receive the same attention as one paying ten thousand dollars – the economics don’t support it and attempting to do so burns resources without delivering proportional value. For lower-paying segments, employ a “tech touch” approach where most service flows through less personalized channels like automated messaging and a support team handling volume. For higher-paying segments, design human-backed “moments of truth” unique to each client. These are breakthrough “aha” moments that dramatically accelerate the value clients extract from your product.
Ultimately, a strong customer success strategy transforms your client base from a simple revenue source into a sustainable growth engine. By aligning every internal department around the client's actual needs, you ensure the value promised during the sales process is the value they actually receive. That's the key to securing long-term retention – and turning satisfied users into vocal advocates for your brand.
In this lesson to Startup CXO by Matt Blumberg, you’ve learned that scaling a startup requires making decisions today that will echo for years.
Your early choices create either foundations or friction as you grow. Finance leaders must balance scrappy speed with proper diligence, while People leaders need to build inclusive cultures by hiring for shared values and treating departures with dignity. Marketing then starts with conversations that define your brand before you chase metrics. This leads into revenue, which depends on empathetic salespeople and evolving pipelines that match customer maturity.
Finally, customer success requires coordinating across every department to prioritize the customer and deliver value. Get these fundamentals right early, and you create the infrastructure that makes sustainable growth possible instead of constantly playing catch-up to fix yesterday’s shortcuts.
Startup CXO (2021) serves as a comprehensive tactical manual for scaling the specialized leadership roles that drive a growing company’s most vital departments. With contributions from several co-authors, it details how various executive functions – from finance and marketing to product and people operations – must evolve and integrate to ensure a business survives the transition from a small team to a mature organization.
Starting a company is one thing. But scaling it? That’s an entirely different challenge. In the early days of a new venture, you can get by on hustle, improvisation, and sheer force of will. But, as your startup grows, the scrappy approach that got you to product-market fit becomes the bottleneck – and it starts preventing you from reaching the next level. It’s at that point that you start needing structure and specialized expertise. And, perhaps most importantly, you need leaders who can build the systems and teams that turn a promising idea into a sustainable business.
The problem is that most founders are learning on the job – and often making expensive mistakes that compound over time. What seemed like a small shortcut in year one becomes a major liability when you’re trying to raise your Series B or scale to a hundred employees.
Well, that’s where this lesson comes in. In it, you’ll learn how to build and scale five critical functions in your startup. You’ll discover how finance, people, marketing, revenue, and customer success leaders should approach their roles differently as the company evolves – and what decisions in the early days will either support or sabotage your growth trajectory years down the line.
Let’s start with your CFO, or Chief Financial Officer. Their role in a startup demands an uncomfortable balancing act from day one. Every decision forces a choice between doing things properly – with full diligence, adequate time, and appropriate resources – or taking the scrappy, fast, cheap route. These early choices echo far longer than most founders expect.
Consider for a moment something as mundane as board meeting minutes. When your board consists of three people sitting around a kitchen table, meticulous record-keeping feels excessive. But five years later, when you’re courting serious financing, those same minutes become artifacts under intense scrutiny. Lawyers representing potential investors will examine them closely, and your early diligence – or lack thereof – suddenly matters enormously. The seemingly trivial documentation decisions made in year one become the foundation that either supports or undermines your growth trajectory.
Before those lawyers ever open your files, though, you need to capture investor attention. This brings us to fundraising, perhaps the most fundamental process in any scaling business. As CFO, supporting your CEO through this vital process means becoming a master storyteller with data.
Which brings us to the pitch deck – that carefully crafted document designed to pique investor interest before a call or crystallize key takeaways afterward. This isn’t merely a financial document that the CFO runs numbers for. You’re collecting and synthesizing information from across the entire organization, weaving it into a compelling investment narrative.
So, what information does an effective pitch deck contain? Most start with the opportunity and business – they articulate your core value propositions clearly and explain your approach and business model. Then comes your product, including relevant screenshots and a development roadmap that demonstrates forward momentum.
The fourth element is about market size, specifically what’s known as your Total Addressable Market. You can calculate this two ways. The top-down approach starts with macro indicators – say, the size of the national real-estate segment – then estimates growth rates and the percentage you can realistically capture. The bottom-up method starts with specifics: you might take your average product price and then multiply it by your total potential customer base.
Element number five in your pitch deck is your current business status. Present existing partners and clients, highlight key performance indicators, and include anything that validates your progress. Next are your financials – current numbers paired with credible projections. Finally, your seventh element is introducing your senior team, emphasizing both their roles and the specific experiences that qualify them to execute your vision.
These practices represent just the beginning of what it takes to scale successfully as a CFO. Get these fundamentals right, and you create the infrastructure that makes sustainable growth possible.
The role of HR has undergone a fundamental transformation in the last couple decades. What once centered on compliance, transactions, and administrative paperwork has evolved into something far more strategic – work that touches every corner of an organization and drives real business outcomes. This new approach earns a new title: People. And if you’re leading it, you’re the Chief People Officer, or CPO.
Your primary mission as CPO starts with building an inclusive culture. Culture can be defined as the sum of everyday behaviors your employees exhibit. These behaviors flow directly from your values, but only when you actively align actions with principles. The gap between stated values and lived reality determines whether your culture thrives or withers.
Your early hires carry disproportionate weight in shaping your culture. When they don’t share the CEO’s and company’s core values, they inject tension and conflict into the system. This misalignment drains resources, kills productivity, and burns time nobody can afford to waste. Prevention starts with clarity.
To gain this clarity, as CPO you’ll need to spark what the authors call the culture conversation. This involves pushing your fellow leaders with concrete questions: How do they view hierarchy and decision-making? Do they embrace remote work or resist it? Where do they stand on work-life balance? Together, these questions act as diagnostic tools that reveal where your leadership team actually aligns.
So, once you can articulate your culture clearly, it’s time to start focusing on codifying your values. Research possibilities, compile a list, then guide your leadership team through the hard work of narrowing it down. With culture and values established, your job then shifts to maintaining what’s known as alignment. This means periodic evaluation, personal championing, and course-correction when behavior drifts from principle.
Sometimes, however, a course cannot be correct – and you’ll need to let people go. This can become necessary at any stage, whether performance stalls or strategy pivots. And how you handle departures matters enormously. So, instead of making decisions behind closed doors, bring transparency to the process. Where possible, discuss with your employee to see if they might fit a different role or choose voluntary redundancy. When termination becomes necessary, offer transition time and a meaningful severance package. Consider adding career placement assistance and extended severance for those struggling to land their next role.
The payoff for treating employees well compounds over time. That person you’re letting go today might be exactly who you need tomorrow. When you’ve handled their departure with dignity and support, they’ll actually consider coming back. Burn that bridge, and you’ve closed a door you can’t reopen.
Everyone thinks they understand marketing. Your CEO has opinions. Your engineers have opinions. Your investors definitely have opinions. But as Chief Marketing Officer or CMO of a startup, you face an endless buffet of approaches, techniques, and tools – which creates both opportunity and paralysis. Your real job is deciding what actually matters.
Marketing boils down to three core priorities: building and maintaining your company brand, generating demand that sales can convert, and supporting the culture that makes everything else possible.
Start with your brand. After all, if you can’t articulate what your company stands for, selling becomes impossible. But brand isn’t just your logo, name, or messaging – it’s the sum of conversations people have about you. It’s dynamic, evolving with every interaction someone has with your company.
It all starts with a conversation. Ask yourself and your colleagues fundamental questions: Who are we? What do we do – and why does it matter? What’s our brand’s personality? Collaborate across the entire organization here. The more diverse perspectives you gather, the more likely you’ll uncover creative, recurring themes that crystallize into something authentic. Brand built in isolation rarely connects with anyone beyond the person who built it.
Next comes demand generation – the machinery that converts prospects into customers and keeps them engaged over time. This work starts with market research. If that phrase triggers flashbacks to dense academic papers, relax. Market research spans everything from formal studies to customer interviews to analyzing competitor websites. Specialist agencies exist if you need them, and countless accessible books cover the fundamentals. The crucial move is simply starting.
Once you’re deep in demand generation, you’ll encounter an overwhelming array of technology solutions. The trick here is to start simple and expand your tech stack as genuine needs emerge. Begin with a solid Customer Relationship Management system. Many CRM tools now include built-in features covering essentials like search engine optimization and social media management, giving you a surprising range from a single platform.
But when it comes to CRM goals, don’t overthink the metrics. Set a few goals and stick to them – whether they are leads, marketing return on investment, customer acquisition cost – each measures something valuable. So, pick the metrics that map to your current business priorities and start tracking them. You can always refine, combine, or change your measurements as you learn what actually predicts success.
Finally, remember the People team we talked about in the last section? You’ll need to build a close relationship with them too, all to help support the company culture. Marketing brings invaluable creative insight to employee engagement, recruiting efforts, and internal communications. This ensures your company isn’t just great to work with, it’s also great to work for.
Revenue is oxygen for a company. Without it, you can’t survive. As Chief Revenue Officer or CRO, you’re in charge of this lifeline.
The first lesson every CRO needs to hear hits hard: it doesn’t matter how much work and sacrifice you’ve poured into your product, or how deeply you love it. The only thing that matters is whether people want to buy it. And whether you can actually sell it. This distinction between building something beautiful and building something sellable separates successful startups from expensive hobbies.
In the very early days, the whiteboard becomes your best friend. You should literally go to your prospects’ offices with a whiteboard and draw graphs and arrows and circles to discover what problem of theirs needs solving – and how you might solve it. As you grow, you’ll graduate from the whiteboard to a polished sales deck and pitch, because by then you’ll have a refined and tested understanding of your customers’ actual needs.
All the while, don’t forget that a CRO is the company’s first salesman. You should only hire additional salespeople once you have crystal clarity about what you’re offering. Hiring before that point just multiplies confusion.
When the time does come to hire, who you should look for might surprise you: people who’ve been through adversity in their lives. These individuals tend to emerge more empathetic, and empathy is the key ingredient for sales success. They know how to listen – and how to tell a compelling narrative that resonates with real human concerns. Your sales hires should also get along with other departments, and those departments should participate in the interview process. Sales staff will work across the organization constantly, and friction there kills deals.
When it comes to setting their compensation, it’s advisable to start with a base salary at or above market rate. As you’re building toward your first major revenue milestone, pay commission on every single dollar salespeople generate. As the company matures, shift to a system where commission rates increase as salespeople approach annual targets, broken down quarterly. This ensures they’re thinking about the current quarter while simultaneously keeping the longer-term picture in view.
Beyond evolving compensation, you need to evolve your sales pipeline as you scale. Start with the basics: learn about your buyers’ decision-making processes, their timing, and how they evaluate different products. Figure out not just what you’re doing, but how what you’re doing affects the buyer’s journey at each stage.
Combine these elements – empathetic sellers, aligned compensation, and refined pipelines – and you’ll be positioned to scale with real momentum behind you.
Every business exists to complete a job the customer is hiring them to do. Your task as a company is to do that job better than competitors and make it as frictionless as possible for the customer. This is where the Chief Customer Officer or CCO enters the picture.
As CCO, it’s your job to coordinate across departments and leadership to keep the entire company laser-focused on customer priorities. This means working with sales to ensure they’re targeting the right client types, collaborating with product teams to streamline onboarding, and partnering with marketing to communicate features clearly. The role is fundamentally about orchestration – making sure every department’s work aligns toward delivering customer value.
Many startups assume they don’t need a CCO yet. But this can prove costly. Customer success matters intensely at the beginning. Ongoing feedback from early clients helps you smooth the rough edges of the customer journey before they calcify into permanent problems. Get it right early and scaling becomes exponentially smoother. You don’t need to call the position “Chief Customer Officer” – something like “Head of Services” works just as well. What matters is that someone owns this responsibility from day one.
One common misconception companies make about the service department is that it alone controls customer retention and churn reduction. The truth is that churn has roots everywhere. How customers were sold to matters. How intuitive the product feels matters. The responsibility spreads across teams. The CCO’s job is coordinating these teams for the customer’s benefit, which in turn drives down churn naturally.
Another crucial element for creating exceptional customer experiences is segmentation. A customer paying one hundred dollars cannot receive the same attention as one paying ten thousand dollars – the economics don’t support it and attempting to do so burns resources without delivering proportional value. For lower-paying segments, employ a “tech touch” approach where most service flows through less personalized channels like automated messaging and a support team handling volume. For higher-paying segments, design human-backed “moments of truth” unique to each client. These are breakthrough “aha” moments that dramatically accelerate the value clients extract from your product.
Ultimately, a strong customer success strategy transforms your client base from a simple revenue source into a sustainable growth engine. By aligning every internal department around the client's actual needs, you ensure the value promised during the sales process is the value they actually receive. That's the key to securing long-term retention – and turning satisfied users into vocal advocates for your brand.
In this lesson to Startup CXO by Matt Blumberg, you’ve learned that scaling a startup requires making decisions today that will echo for years.
Your early choices create either foundations or friction as you grow. Finance leaders must balance scrappy speed with proper diligence, while People leaders need to build inclusive cultures by hiring for shared values and treating departures with dignity. Marketing then starts with conversations that define your brand before you chase metrics. This leads into revenue, which depends on empathetic salespeople and evolving pipelines that match customer maturity.
Finally, customer success requires coordinating across every department to prioritize the customer and deliver value. Get these fundamentals right early, and you create the infrastructure that makes sustainable growth possible instead of constantly playing catch-up to fix yesterday’s shortcuts.
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