• Mapping B2B Sales with Buyer Job Priorities

    There comes a stage early on in the B2B founder’s journey where they ask themselves: “Why aren’t people buying?”.

    This usually happens after they have exhausted their base of industry friends and contacts. The ones who are happily running pilots and demos, even gushing about how good the product is. This is the initial traction that every founder so desperately wants by this point—that glimpse of validation, telling them that there is after all a market of buyers who only need to be told about the product. Anyone who fits the profile of their first users.

    Which is exactly the kind of sales approach that a founder should be following at this point. As long as they remember the huge caveat that the customers they are going after at this stage can’t and won’t fit the profile of their first users, for the simple reason that they aren’t personal contacts to begin with. What happens at this stage now may well feel like having to start all over again, dashing all the enthusiasm which had kicked in after that first flavour of success with early users.

    (Of course, there can be the scenario that you have a large enough ocean of friends and industry contacts to keep giving you a steady stream of revenue and growth, along with product validation, that you don’t need to worry about reaching out to the open market. I can only say two things to you—you have my unreserved envy and that you probably don’t need to read any further from here. You have already put in the hard work over the years of cultivating the right kind of network that’s needed to build a business.)

    For the rest of us, let’s figure out what happens next.

    The Four Stages of Startup Reality

    When an early-stage B2B startup hits this wall, there are typically four possibilities at play:

    Non-existent problem: The problem exists in the founder’s mind alone. No real fix for this, except talking to people and starting afresh.

    Problem exists, product is crap: Not a bad place to be in. That’s where the best businesses have been born out of. Just hang out there, talk talk talk and work on the product.

    Problem exists, product does the job, wrong customer: Congratulations, you have reached a stage most founders only dream of. You’re just talking to the wrong folks.

    Problem exists, product works, right customer, wrong priority: This is the trickiest spot. The product works, it solves a problem, and the customer profile is correct too. So why aren’t they buying?

    If you’re in that fourth category – and frankly, that’s where most promising startups get stuck – the issue isn’t your product or your market. It’s timing and priority.

    The Priority Problem: When Good Products Meet Bad Timing

    Here’s the thing about business problems: they don’t all carry the same weight in your customer’s world. Any business needs to get dozens of jobs done to function properly. These jobs are performed by the very people who should be using your product. But they’ll only prioritize your solution when the problem you solve becomes urgent enough to demand their immediate attention.

    This is where most founders get it wrong. They assume that having a real problem and a working solution equals inevitable sales. But there’s a crucial missing piece: understanding where your customer’s problem sits on their priority ladder.

    Eisenhower Matrix: The Unlikely B2B Sales Weapon

    You’ve probably heard of the Eisenhower Matrix – that simple 2×2 grid that divides tasks by Urgency and Importance. What you might not have considered is how it can transform your approach to B2B sales.

    When you map your prospect’s problems to this matrix, buying behavior becomes remarkably predictable:

    Quadrant I (Urgent + Important): High probability of purchase, short decision cycles, willingness to pay premium prices for speed and risk reduction. These prospects have budget authority and executive attention.

    Quadrant II (Important, Not Urgent): Moderate-to-high probability with longer evaluation periods. They focus on ROI, require multi-stage procurement, and involve strategic stakeholders.

    Quadrant III (Urgent, Not Important): Quick tactical purchases, preference for cheap solutions or internal workarounds. Lower spend, faster decisions.

    Quadrant IV (Not Urgent, Not Important): Near-zero purchase probability. Your time will be better spent in another quadrant at this stage.

    What this translates into for the customer

    Quadrant I (Urgent, Important)“We have a burning issue. We need a solution now.”
    Quadrant II (Important, Not Urgent)“This matters strategically, but we can wait.”
    Quadrant III (Urgent, Not Important)“This is a recurring problem that needs fixing without asking for too much.“
    Quadrant IV (Not Urgent, Not Important)“Nice to have, but no time or money.”

    Where Should You Aim?

    Q1 is where you would ideally like to be, but getting there requires a combination of the right timing and event triggers. During early stages, the best place to target is Q3. Once there, you can start building your move towards Q2, the place to be for B2B legend status.

    Here are a few examples of businesses in each of these quadrants to give you a better sense.

    Quadrant I (Urgent + Important): This is where you want to be when prospects have budget and authority. Think PagerDuty during system outages, Zoom during COVID lockdowns, or Slack when email became unbearable. But you can’t manufacture these moments – you can only be ready when they happen.

    Quadrant II (Important, Not Urgent): This is the sweet spot that SaaS startups should aim for. The place where they achieve nirvana. Salesforce owns Q2 for CRM, HubSpot for marketing automation, Notion for team productivity. These companies built sustainable, predictable revenue by making themselves essential to long-term strategy. The challenge? It takes time and perfect product-market fit to get here.

    Quadrant III (Urgent, Not Important): This is often where you’ll start and get initial traction. Calendly began solving the “urgent but small” problem of scheduling conflicts. Loom started as a quick way to record screens instead of typing long explanations. Typeform tackled the immediate pain of ugly surveys. The key is using Q3 as your wedge into Q2.

    The interesting thing about problems is that they don’t remain confined to any quadrant, but keep moving between them. This can be seen in how some businesses have achieved greater success as their customers transitioned.

    • Slack: Started as a gaming company’s internal tool (Q3) → became essential team communication (Q2) → now critical business infrastructure (Q1 during outages)
    • Zoom: Video calls were “nice to have” (Q3) → strategic remote work enabler (Q2) → mission-critical during pandemic (Q1)
    • Intercom: Simple customer chat widget (Q3) → comprehensive customer engagement platform (Q2)

    Actions

    Take your recent calls and assess where their problem sits. If most are in Q4, you’re wasting time. If they’re mostly Q3, you might have a business. This exercise will change how you qualify leads.

    Keep a simple spreadsheet with columns for Prospect, Problem Quadrant, Trigger Events to Watch, and Last Priority Ranking. Review it weekly. You’ll start seeing patterns that transform your hit rate.

    The beauty of this approach is its simplicity. It doesn’t ask for anything dramatic, while giving you greater insight into your buyer’s mindset to align it to your product and sales approach. That’s usually all you need at this stage.

  • The Founder as the First Sales Rep

    Sales is tough. And it is toughest for the first sales rep at any startup. Which in most cases, or at least those B2B startups which manage to get somewhere, happens to be the founder.

    The B2B founder as the first sales rep may sound intuitive. After all, there are many good reasons for this to be a naturally compelling proposition.

    1. Belief: Nobody can believe in the product if the founder doesn’t have sufficient conviction in it. When it comes to convincing customers about the value which the product offers, the founder should be the one doing it. Their passion and conviction create the emotional foundation that transforms skeptical prospects into loyal customers. 

    2. Problem understanding: Most founders have lived experience of the problem which they have developed a product for. This gives them an insight into the user’s pain that can be effectively articulated such that it resonates deeply with prospects. Nothing can help build trust faster than the knowledge of this shared struggle.

    3. Technical understanding: Developing the product gives the founder an edge about explaining the technical aspects as well as handling any technical objections. They can dive deep into architecture discussions, explain why certain design decisions were made, and pivot the conversation when technical concerns arise. 

    4. Product development: Customer conversations provide feedback regarding the product viability as well as performance and features, which are useful for product refinement. Every sales conversation becomes a product research session. It’s not just selling what exists — it’s about discovering what should exist. This direct feedback loop between customer needs and product evolution is invaluable during the early stages when product-market fit is still being refined.

    5. Skin in the game: Sales reps are exceptional at a later stage of the business when the product has matured to find PMF, the sales playbook is ready and the cycle has become predictable. Early on, they can be an overkill, especially since they may not be as invested in the business. On the contrary, the founder has everything to lose. And if they don’t stake it out for themselves, nobody else is. 

    The Reality Check

    In practice, this isn’t the easiest thing to do. Sales doesn’t come naturally to most people. I know this, because it didn’t come naturally to me. There were parts of it which came naturally, but there were parts which I had to learn, work on and develop. It hasn’t been very different for some of the best performing salespersons I know. The natural salesperson is a rare creature.

    Most founders are builders, problem-solvers, or domain experts—not sales professionals. The transition from creating something in isolation to convincing strangers to pay for it can feel jarring. You might find yourself uncomfortable with rejection, uncertain about pricing conversations, or struggling to balance confidence with humility. This discomfort is normal, but it’s not an excuse to delegate sales too early.

    The key insight is that founder-led sales isn’t about becoming a slick salesperson overnight. It’s about leveraging your unique advantages while systematically developing the skills you lack. Your authenticity and deep product knowledge will carry you further than polished sales techniques in the early days.

    The Marathon Approach

    Sales at an early stage startup is like preparing yourself to run a marathon in short bursts of sprints before settling into a regular cadence. Here’s how to build that endurance:

    1. Routine: Develop one. Set aside a block of time for sales. Treat sales activities with the same seriousness as product development or fundraising. Block out specific hours for prospecting, follow-ups, and customer calls. Make it non-negotiable. The biggest trap founders fall into is treating sales as something they’ll do “when they have time.” 

    2. Analyse: Keep a record of as much as you can of customer conversations. Don’t worry if you don’t see any patterns immediately. Over time, they will start emerging. Use them to settle on a handful of key metrics which can be used consistently, eventually laying the foundation of your sales playbook.

    3. Improve: Try to do more, have more conversations, each week. When you can’t have more conversations, try to have better conversations. Continuously refine your messaging, improve your demo flow, and get better at handling objections.

    4. Grind: The number one rule of sales. Go after more, every day. Keep going after people. Take rejection on the chin. There will always be someone who will want to talk to you. As long as you keep casting a wide net, day after day. It is brutal, but it builds the much needed resilience that a founder needs to excel in their role.

    5. Belief: Know that it is only a question of finding the right person who has that problem you are solving, and then the next person, and then the next. As long as you are really solving a problem that exists and is important enough for someone to pay to solve. This belief isn’t blind optimism—it’s based on the fundamental assumption that your startup exists because you’ve identified a real problem worth solving. Trust that assumption, but validate it ruthlessly through every customer conversation.

    Your Path Forward

    The transition from founder to founder-salesperson isn’t just about learning sales techniques—it’s about evolving your relationship with your own creation. You’re not just building a product anymore; you’re building a business. And businesses are built one customer conversation at a time.

  • The Blurry Lines Between Sales, Marketing, Customer Success & Product in Early-Stage Startups

    The classic tension between Sales and Marketing teams makes each view the other as putting the cart before the horse that’s them. But if all you have is a hammer, which is all that a startup does, just nail a horseshoe and ride the horse yourself.  

    At early stages, you don’t have the luxury of large budgets, siloed teams, or seasoned experts specialising in narrow roles. This is the reality for early-stage B2B startups. Messy, unorganised and far more interesting. You don’t have the luxury to choose one over the other. Instead, you need a composite machine which brings them together. A lean, high-performance engine that generates revenue, informs product development and delights early customers. 

    This is where the lines blur—between sales, marketing, customer success, and even product—and where founders need to think differently.

    The Unified Revenue Engine

    In any startup, Sales, Marketing and Customer Success begin as an integrated function with two simple goals. Revenue and Product Market Fit. 

    Clubbing these functions together isn’t purely driven by resource constraint, but by a natural relationship they enjoy because of an overlap between their tasks and outcomes, and the way each feeds into the other. 

    Product teams, while often treated as separate, are deeply intertwined. In fact, your early sales and marketing activity is your product research. Every conversation with a customer should influence the roadmap.

    Let’s take a quick look at the traditional roles of Sales and Marketing and where they now overlap in a startup context:

    Sales vs. Marketing in Startups: A Quick Comparison

    FunctionMarketingSalesOverlap
    OutreachCampaigns (email, social, ads) to drive top-of-funnel awarenessDirect emails, cold calls, prospectingMessaging, audience targeting
    LeadsAttracts leads through content, SEO, webinars, etc.Converts leads into opportunities and customersQualification criteria, ICP discovery
    FrontlineEngages prospects through content, brand presenceEngages prospects through 1:1 conversationsCustomer engagement
    NarrativeDevelops brand, voice, positioningTailors pitch and objection handling based on real-time feedbackMessaging alignment
    RevenueIndirect driver: creates demandDirect driver: closes dealsAttribution and performance tracking
    BudgetSpends on tools, campaigns, and creativesSpends on reps, CRM, commissionsROI analysis
    Feedback LoopCaptures top-funnel feedback on content and channelsCaptures mid-to-bottom funnel feedback on objections, pricing, etc.Insight to product and positioning
    Human TouchScaled via content and automationHigh-touch human interactionPersonalization at different stages

    Building a Lean Revenue Engine

    Instead of obsessing over where sales ends and marketing begins, focus on building a single, agile system that loops together learning, revenue, and product validation.

    Here’s how:

    1. Evaluate Your Goals

    Start by defining what success means right now. Is it validating your ICP? Booking 10 discovery calls a week? Converting your first 10 paying customers? Avoid vanity metrics—focus on learnings and traction.

    2. Build Processes Around Those Goals

    Design simple, repeatable workflows: outreach cadences, demo scripts, onboarding templates. Don’t over-engineer. You’re aiming for speed, not scale—yet.

    3. Run Small Experiments

    Test different value propositions, channels (LinkedIn, cold email, webinars), pricing models, or onboarding flows. Keep each experiment focused, and short in duration.

    4. Evaluate Success and Enable Automation

    Did the cold outreach campaign convert? Did your webinar generate leads? Automate what works—email sequences, follow-ups, qualification criteria—so you can double down.

    5. Develop Process Around Success

    Once something works, build a lightweight process or playbook around it. This is the start of your scalable GTM motion.

    Early Revenue Experiments: What to Focus On

    Your first sales and marketing efforts should focus on three core outcomes:

    • ICP (Ideal Customer Profile): Who is your buyer? What are their pain points, job titles, and industries? How do they describe their challenges?
    • Product Feedback: What features matter most? Where does the pricing feel off? What objections keep coming up?
    • Sales Cycle Mechanics: What’s working in outreach? What messaging resonates? How long does it take to go from conversation to conversion?

    Treat each of these as a mini-research project. Every response, rejection, or closed deal is data.

    Make Feedback Loops Your Superpower

    What binds Sales, Marketing, CS, and Product together isn’t headcount—it’s feedback. Every customer touchpoint is an opportunity to learn:

    • Marketing sees what brings attention
    • Sales hears what makes people buy (or not)
    • CS hears what makes customers stay (or churn)
    • Product builds what solves the actual problem

    The real power is when these learnings are shared across the team in real time. That’s your startup’s competitive advantage.

    Final Thoughts: Embrace the Blur

    As a founder, your job isn’t to draw hard lines between departments. Your job is to build the revenue engine that informs product, builds brand, and closes deals. This engine thrives on overlap, feedback, and iteration.

    So embrace the blur. That’s where your growth lies.

  • The Founder’s Sales Advantage: Five Evidence-Based Strategies for B2B Tech Success

    Conventional wisdom suggests founders should step back from sales as quickly as possible. This approach misses a fundamental dynamic: the founder’s unique advantages in B2B sales environments.

    Academic research demonstrates that founder-led companies consistently outperform their peers, particularly in the critical early-stage sales process. Not necessarily because of superior sales technique, but because of their position as a problem-solver invested in customer success.

    Strategy 1: Leverage Authentic Passion as Social Proof

    Research on emotional contagion reveals that genuine enthusiasm spreads unconsciously between people. Founders communicate with what’s “authentic credibility”—prospects perceive reduced agency risk when a CEO stakes their reputation on a solution.

    This dynamic becomes particularly powerful in B2B environments where buyers must justify decisions internally. The founder’s presence inherently validates the purchase decision, providing social proof that extends beyond product features to encompass organisational credibility.

    Strategy 2: Master the Consultative Paradox

    Founders possess a unique advantage: they can afford to be genuinely consultative, even when it means walking away from revenue. This “costly signaling” demonstrates trustworthiness through actions that appear contrary to immediate self-interest. Research shows prospects develop deeper trust when salespeople acknowledge limitations or suggest competitors might be better fits.

    This authenticity paradoxically increases close rates by positioning the founder as trusted advisor rather than vendor, fundamentally altering the buyer-seller dynamic.

    Strategy 3: Transform Product Roadmap Discussions into Strategic Partnerships

    Customer co-creation research reveals that involving buyers in product development significantly increases purchase likelihood and retention. This approach creates “psychological ownership” through the IKEA effect—people value things more highly when they’ve contributed to their creation. When founders invite prospects into product development discussions, they’re creating this psychological ownership that significantly influences purchase decisions.

    Strategy 4: Weaponise Intellectual Humility

    Social psychology research reveals that admitting uncertainty in non-expertise areas actually increases credibility in expertise areas. Founders who acknowledge gaps in their sales process or market understanding create “authentic leadership presence” that paradoxically strengthens their authority when discussing technical solutions.

    Research on founder personality suggests successful entrepreneurs exhibit high intellectual humility, adapting strategies based on market feedback. This translates to more effective discovery conversations and stronger prospect relationships built on mutual learning rather than one-way pitches.

    Strategy 5: Create Asymmetric Value Through Vision Sharing

    Transformational leadership research shows vision-driven narratives create stronger emotional connections than feature-focused presentations. Founders possess exclusive access to the origin story—the authentic “why” behind their solution that hired salespeople can only approximate.

    Research on entrepreneurial narratives demonstrates that founder-led stories about company purpose create “meaning-making” for prospects—connecting solutions to broader organisational goals. When founders share their authentic problem-solving journey, they provide prospects with compelling stories to champion internally, creating advocates within the buyer organisation.

    The Founder’s Competitive Edge

    These strategies work because they leverage inherent founder advantages. Each strategy represents a foundation for deeper exploration—from emotional contagion neuroscience to consultative selling behavioural economics providing a robust framework for understanding why founders can excel as chief sales officers. Much of which comes down to understanding founder weaknesses and using them counter-intuitively as sources of strength.

  • Eid and Lessons in Sales Leadership

    Over the weekend, we observed Eid ul-Adha, honouring Prophet Ibrahim and the spirit of sacrifice he displayed in obeying Allah’s command.

    Religion isn’t considered the best place to derive business inspiration, especially in sales. Yet for believers, it provides a framework guiding their actions. Our beliefs—whether religious or secular—profoundly influence how we act professionally, affecting business outcomes.

    Academic research supports this. Weber’s Protestant work ethic showed how religious values influenced capitalist behaviour. Weaver and Agle demonstrated that ethical foundations lead to greater business integrity. Thornton and Ocasio’s institutional logics research reveals how belief systems shape organisational practices. Of course, not all who act religious are ethical in business. The idea is to learn from where we can.

    Can we learn from Eid ul-Adha for business? Honestly, not directly. What matters is learning from how Prophet Ibrahim lived. 

    I can think of three lessons for B2B sales leadership.

    1. Take Full Ownership

    For modern sales leaders, accountability extends far beyond hitting quarterly numbers. Yes, meeting quotas matters, but how you achieve those targets matters even more.

    Too often, sales teams resort to questionable practices to close deals—overselling features that don’t exist, making promises the company can’t keep, or pressuring clients into decisions they’re not ready for. These shortcuts might deliver short-term wins, but they invariably backfire. Clients discover the truth, relationships sour, and the long-term cost far exceeds any immediate gain.

    True accountability means taking responsibility not just for the numbers on your dashboard, but for the methods you use to achieve them. It means having the courage to walk away from deals that require compromising your integrity. It means being transparent with your team about what’s working and what isn’t, and owning your mistakes rather than deflecting blame.

    2. Invest in Your Team

    Creating a culture where your team knows you have their back isn’t about being their friend or avoiding difficult conversations. It’s about being genuinely invested in their growth and success. It means providing them with the resources they need to succeed, shielding them from unnecessary organisational politics, and advocating for them when they deserve recognition or advancement.

    When sales representatives know their leader will support them through challenges, they’re more likely to take calculated risks, pursue ambitious targets, and maintain their integrity even when facing pressure. They’ll also be more honest about pipeline challenges, client concerns, and personal development needs because they trust that this information will be used to help them improve, not to penalise them.

    This approach builds loyalty that transcends compensation packages and job titles. Team members who feel genuinely cared for become advocates for your leadership and the organisation’s mission.

    3. Never Compromise

    In B2B sales, the temptation to take shortcuts is constant. When deals stall, when competition intensifies, when pressure from above mounts, the easy path often seems attractive. True success comes from staying the course with integrity intact.

    This means continuing to provide value to prospects even when they’re not ready to buy immediately. It means being honest about timelines and capabilities even when it might cost you a deal. It means investing in long-term relationships rather than optimising for quick wins.

    The sales leaders who build lasting success are those who understand that every shortcut carries a hidden cost. They persist through difficult quarters, maintain their standards during challenging negotiations, and never compromise their values for temporary gains.

    The Compound Effect

    These three principles work together to create something powerful: trust. 

    When you demonstrate accountability, genuinely care for your team, and persevere with integrity, you build trust with clients, colleagues, and team members alike. 

    And in B2B sales, trust is the ultimate currency.

    In a world where quarterly pressures often overshadow long-term thinking, these timeless principles offer a foundation for sustainable success that transcends any individual deal or sales cycle.

  • The Builder.ai Collapse: Sales vs Reality

    Following the collapse of Builder.ai, one of the most commonly mentioned quotes by its founder is where he said about wanting to make building an app as easy as ordering pizza. 

    Could it really become that? Possibly so, for there is no dearth of “make your own pizza” options around the corner of any London high street. Or a lack of imagination among pizza aficionados when thinking of pizza toppings. 

    You can’t fault a startup founder for building a vision. Outrageous as it may be. On the contrary, the more the better. There are numerous examples throughout startup history. We thrive on, enable and reward a “fake it till you make it” culture.

    The product is being pulled apart for being more human than AI, as was being claimed. The approach in itself isn’t wrong to begin with – how else does a startup validate, build and refine its value proposition? But a line needs to be drawn where the MVP needs to become the product it set out to become. A few hundred million in investor money later, and you can’t still be cranking up the machine by adding more horses to pull the cart. It needs to transform into the swanky car that was promised.

    That’s not what I want to talk about though. Because what brought the company down was its sales function. It had to correct its sales figures, with last year’s number being revised to less than 25% of what had been claimed.

    The Recurring Nightmare: Five Ways Sales Culture Destroys Startups

    Builder.ai’s implosion isn’t some freak accident. It’s a pattern repeated across the startup landscape, driven by the same systemic failures that infect companies like a virus. 

    Leadership Skills

    Founders, many of whom come from purely technical backgrounds, often lack the understanding of building a sales org. Sales ends up becoming a black box which should magically conjure sustainable revenue. Unrealistic revenue targets become the norm. The processes aren’t supportive, and feedback to and communication with various teams like product and customer success doesn’t happen.

    Misaligned Incentives

    Sales teams get bonuses for closing deals, not creating customers who’ll stick around. This creates a perverse dynamic where success is measured by signatures rather than value delivered. The rep who overpromises gets promoted while the one who sets realistic expectations gets questioned about their “hunger.”

    Investor Pressure

    Venture capital has turned exponential growth from nice-to-have into must-have-or-die. The pressure becomes so intense that sustainable practices get sacrificed on the altar of hockey stick projections.

    Product Hype

    Startups market products as revolutionary breakthroughs without sufficient proof they actually work. The gap between marketing copy and product reality becomes so wide, an elephant could walk through. Everyone becomes complicit in maintaining the illusion because admitting the truth feels like defeat.

    Toxic Culture

    A culture that prioritises revenue above all else inevitably becomes one that justifies cutting corners, bending truths, and burning people out. What gets called “high performance” is often just dysfunction operating at scale.

    The Question That Matters

    Any company’s sales organisation is the most visible manifestation of what a company actually believes about itself. When sales culture is grounded in reality and focused on genuine customer value, it becomes a force for sustainable growth. But when it becomes corrupted by hype and misaligned incentives, it metastasises and kills everything else.

    The question every founder, investor, and operator should be asking isn’t “How fast can we scale?”

    Instead, it should be: “Are we selling something that actually exists, delivers real value, and can be delivered as promised?”

    You can promise the world’s greatest pizza, but if what you deliver is cardboard with ketchup, no amount of wizardry will save you.

    The Builder.ai story isn’t just about one company’s failure. It’s about an entire ecosystem that has lost sight of the difference between ambition and delusion, between growth and sustainability. Until we acknowledge that difference, we’ll keep creating conditions for the next Builder.ai to rise and fall in exactly the same way.

  • Two Startups: B2B Sales Strategy as Determinant of Fate

    Two rockets going in two different directions

    In the summer of 2021, two B2B SaaS startups launched within weeks of each other. The world had started emerging from the global pandemic, but its effects were still reshaping how we work. Remote work had become the new default, and companies were scrambling to adapt to this fundamental shift.

    Sensing opportunity, countless startups began building solutions for remote workforce management and employee well-being. Among them were RemoteAB* and TeamXY*—both founded by driven teams of consultants and technologists who saw the same market gap and had similar visions for filling it.

    The timing seemed perfect. The economy was rebounding, funding was flowing, and both teams easily secured seed rounds. They built solid MVPs that gained early traction and hired their first sales reps within three months of launch.

    By the end of Year 2, one had hit $4M ARR and closed a Series A.

    The other folded quietly after burning through its seed capital.

    This is the story of how two seemingly identical startups took radically different paths—and what every B2B founder and sales leader can learn from their journeys.

    1. Strategic Focus vs. The “Everyone is Our Customer” Trap

    RemoteAB’s Approach: Cast the widest possible net. Software, manufacturing, healthcare, financial services—if they had remote workers, they were a prospect. Size didn’t matter. Geography didn’t matter. Industry vertical didn’t matter. The philosophy was simple: more leads equal more revenue.

    TeamXY’s Approach: Ruthless focus. They targeted software and IT services companies with 100-200 employees and operations across exactly three countries. This wasn’t arbitrary—it was the sweet spot where their solution delivered maximum value and where buyers had both the pain and purchasing power to act quickly.

    The Results:

    RemoteAB generated 3x more demos but struggled with conversions. When deals did close, customer fit was poor and churn was brutal.

    TeamXY had fewer leads but achieved a 40% higher close rate and 60% lower churn in their first year.

    The Strategic Principle:

    This reflects Michael Porter’s concept of strategic positioning—the idea that competitive advantage comes from choosing to perform different activities than rivals, or performing similar activities in different ways. TeamXY chose differentiation through focus on a narrow niche, while RemoteAB fell into the trap of trying to be everything to everyone.

    Lesson: A tighter ICP doesn’t shrink your addressable market—it sharpens your go-to-market motion and amplifies your value proposition.

    2. Building Systems vs. Being the System

    Both founders were natural salespeople who could close deals through sheer force of personality and market knowledge. But they approached scaling in fundamentally different ways.

    RemoteAB’s Founder: Became addicted to the rush of closing deals personally. Every important prospect call included the founder. When the first sales reps were hired, he continued leading most conversations, believing his presence gave prospects confidence in the company.

    This approach worked initially—deals closed faster when he was involved. But it created an unsustainable bottleneck and prevented the development of repeatable processes that others could execute.

    TeamXY’s Founder: Used early sales conversations as a laboratory for building institutional knowledge. Rather than dominating every call, they meticulously documented each interaction, analysing what messaging resonated, which objections surfaced, and how successful deals progressed.

    Over six months, this research became a comprehensive sales playbook that enabled consistent rep onboarding and performance.

    The Results:

    RemoteAB’s revenue plateaued at $500K ARR as the founder became the constraint.

    TeamXY scaled from founder-led sales to a five-rep team generating $300K monthly.

    The Strategic Principle:

    This reflects Henry Mintzberg’s research on effective managerial roles—specifically the tension between operational involvement and strategic system-building. TeamXY’s founder understood that scaling requires transitioning from performing operational tasks to designing the organisational capabilities that enable others to perform those tasks effectively.

    Lesson: Your early sales success should generate processes, not dependencies. Build a machine that works without you.

    3. Intelligence-Driven Optimisation vs. Activity Theatre

    RemoteAB: Operated on volume assumptions. More emails, more calls, more LinkedIn connections would inevitably lead to more revenue. Success was measured in activity metrics, not outcome insights.

    TeamXY: Approached sales as a hypothesis-testing exercise. They tracked granular data: which personas responded to specific messaging, which objections consistently stalled deals, which CTAs drove engagement. Weekly reviews focused on pattern recognition and continuous optimisation.

    The Results:

    RemoteAB exhausted themselves and their prospects with spray-and-pray tactics that generated noise, not signal.

    TeamXY achieved compound improvements by turning small insights into systematic advantages.

    The Strategic Principle:

    This reflects the lean startup methodology’s Build-Measure-Learn cycle, applied to sales operations. TeamXY treated their sales process as a product that required continuous iteration based on data-driven feedback.

    Lesson: You can’t improve what you don’t measure, and you can’t scale what doesn’t work consistently.

    4. Customer Success as Revenue Insurance vs. “Set It and Forget It”

    RemoteAB: Treated the signed contract as the finish line. New customers received login credentials, a PDF user guide, and reactive support when they reached out. No structured onboarding, no success milestones, no proactive engagement. Within 60 days, 40% of customers had churned or gone completely silent.

    TeamXY: Recognised that the sale was actually the beginning of the revenue relationship. Every new customer received a customised 30-60-90 day success plan. Customer Success Managers joined hand-off calls. Usage patterns were monitored proactively, and outreach was triggered by both positive and negative behavioural signals.

    The Results:

    – RemoteAB haemorrhaged customers before they could realise value, creating a leaky bucket that no amount of new sales could fill.

    – TeamXY achieved 90%+ activation within 30 days and expanded 25% of accounts within six months.

    The Strategic Principle:

    This aligns with the concept of Customer Lifetime Value (CLV) optimisation. TeamXY understood that retention and expansion revenue from existing customers is significantly more profitable than acquiring new ones—typically 5-25x more cost-effective according to research by Bain & Company.

    Lesson: Revenue doesn’t end at signature—it begins there. Design your onboarding as carefully as your sales process.

    5. Building Winning Culture vs. Grinding Through Dysfunction

    By Year 2, the cultural differences between the teams were stark.

    RemoteAB: Sales reps were burned out and demoralised. Without a clear ICP, they chased unqualified leads. Without proven processes, they couldn’t replicate the founder’s success. Without proper onboarding support, their deals often fell apart post-signature. Compensation plans were confusing, career progression was unclear, and morale was toxic.

    TeamXY: Cultivated a tight, collaborative culture. Reps shared insights from their calls, celebrated both individual wins and team milestones, and had clear guidelines for success. The sales organisation felt like a learning laboratory rather than a pressure cooker.

    The Results:

    RemoteAB experienced 80% sales team turnover, creating constant disruption and knowledge loss.

    TeamXY promoted two SDRs into AE roles and maintained zero attrition while consistently hitting team targets.

    The Strategic Principle:

    This reflects Daniel Pink’s research in “Drive” about intrinsic motivation: autonomy, mastery, and purpose drive performance more effectively than external pressures alone. TeamXY created an environment where reps could develop mastery within clear boundaries and see how their work contributed to customer success.

    Lesson: The sales culture you build early becomes your competitive moat. Invest in it deliberately.

    The Strategic Framework: Your Two Playbooks

    Sales success in B2B startups isn’t about luck, charisma, or market timing—it’s the result of intentional, strategic decisions compounding over time.

    The TeamXY Playbook (Do These):

    1. Define and defend a tight ICP early—specificity creates clarity and competitive advantage

    2. Build repeatable, coachable processes—systems scale, heroes don’t

    3. Track outcomes and patterns, not just activities—intelligence beats intensity

    4. Design proactive customer success as revenue insurance—retention amplifies acquisition

    5. Cultivate a culture of learning and growth—great reps attract great reps

    The RemoteAB Playbook (Avoid These):

    1. Chasing every lead—bad-fit customers kill momentum and morale

    2. Founder dependency beyond seed stage—you become the bottleneck

    3. Measuring motion instead of progress—activity without insight is waste

    4. Treating signature as finish line—revenue starts with successful onboarding

    5. Neglecting team culture—dysfunction compounds faster than growth

    What This Means for You

    If you’re building or scaling a B2B sales organisation, the path forward is clear. The difference between RemoteAB and TeamXY wasn’t talent, timing, or luck—it was strategic discipline applied consistently over time.

    The question isn’t whether you’ll face these decisions—you will. The question is whether you’ll recognise them as strategic inflection points and choose the path that builds sustainable competitive advantage.

    Further Reading

    To deepen your understanding of the strategic principles underlying successful B2B sales organisations:

    “The Nature of Managerial Work” by Henry Mintzberg – Understanding the evolution from operational to strategic roles

    “Competitive Strategy” by Michael Porter – Understanding strategic positioning and competitive advantage

    “The Lean Startup” by Eric Ries – Applying Build-Measure-Learn to sales processes

    – “Drive” by Daniel Pink – Creating motivation and culture that scales

    *Company names are purely fictional