Read Craig T. Watkins' Blog Posts

Most companies approach annual planning as a math exercise. They pick a target, divide it into quotas, and start assigning numbers. That may be enough to produce a plan on paper, but it rarely builds the alignment or visibility needed to drive consistent growth. This is where the difference between

Humans are wired for dialogue. From our earliest survival instincts to today’s digital boardrooms, progress has always depended on understanding one another. Yet in sales, especially in the complex sale, dialogue often gives way to dictation. Too many reps still default to telling instead of discovering, pitching instead of exploring.

The Ambition Trap Every founder wants growth. Investors expect it. Teams need it. And in SaaS, ambition often gets translated into overly aggressive quotas and early hires. But here’s the problem: most SaaS reps never hit quota. Industry data shows that fully ramped SaaS sales reps hit only about 50–60%

Early churn is one of the most painful experiences for founders of B2B tech startups. You worked hard to close those first few deals, only to watch customers walk away. It feels like failure. And when cash flow is tight, it can feel like disaster. But here’s the truth: churn

When you’re running a startup, every sales conversation carries weight. One deal can shape your runway, your credibility in the market, and even your ability to raise the next round. The product matters, but what buyers are really testing is you. They are asking: Can I trust this founder and

The Quiet Reason Go-to-Market Plans Collapse A startup can have a groundbreaking product, a brilliant sales team, and a marketing plan that looks bulletproof on paper, and still watch its go-to-market (GTM) strategy implode. It happens more often than founders admit, especially in B2B tech startups. The common culprit isn’t

Two B2B Tech Marketing Teams Both have the same budget, tech stack, and target market. One steadily grows. The other stalls. The difference isn’t the tools they use or the number of campaigns they run. It’s how they think. The outperforming team treats marketing not as a checklist of tactics,

The SaaS Growth Pattern You’re Not Seeing A growing SaaS company we ran into had all the right ingredients. The product solved a real problem. Sales leadership was experienced. Marketing was generating leads. Customer success was responsive and professional. Yet growth slowed to a crawl. The leadership team spent months

Why Smart Startups Treat Alignment as a System, Not a Slogan The marketing team hits its lead quota, but sales says they’re unqualified. Sales exceeds bookings, but customer success struggles with churn. Everyone’s working hard. Everyone’s doing their job. And yet revenue growth stalls…or becomes painfully unpredictable. Why? Because individual

Growth is rarely a straight line. It is also rarely achieved alone. For many companies, the biggest roadblock to revenue growth is not market conditions or product fit; it is the strained relationship between two functions tasked with generating that growth: marketing and sales. Marketing complains about sales follow-through. Sales

Want a Smarter Revenue Team? Make Them Disagree Most conversations about building a high‑performing revenue team focus on tools, processes, and metrics. But there’s a deeper, often overlooked truth: your team’s ability to challenge customers with fresh insight depends directly on how well they challenge each other internally. Complex sales

It’s a False Binary Founder-led or outsourced sales. Pick one. The common wisdom says only the founder can sell early on. This idea gets passed around so often, it feels like gospel. And for good reason. Founders are often the most compelling advocates for their vision. They speak with conviction

Startups live and die by feedback. Your early revenue team must learn faster than the market shifts, and feedback is how you close that gap. The best sales plays come not from theory but from rapid iteration: watching what worked, what didn’t, and why. But here’s the catch: the very

Hidden truths are expensive Founders can believe that shielding their teams from messy realities like product weaknesses, onboarding gaps, or strategic uncertainty, protects morale and keeps everyone focused. But in truth, the cost of selective secrecy is trust. And when trust breaks inside your revenue team, it doesn’t just slow

Growth Breaks When Trust Disappears Startups are quick to diagnose the visible issues: a broken funnel, a weak message, inconsistent follow-up, or misaligned targets. But sometimes the real problem isn’t any of those. It’s something quieter—something that doesn’t show up in dashboards or reports. Mistrust. It creeps in slowly. A

All Features, No Focus. You built something powerful. But no one understands what it does—or why they should care. Here’s why that’s your fault. Most early-stage B2B software companies don’t have a product problem. They have a clarity problem. Founders build sophisticated platforms filled with edge-case workflows, toggles, and logic

Your Revenue Plan is a Straight Line. Real Growth Isn’t. Revenue projections climb steadily quarter over quarter. Sales targets increase with each new hire. Marketing funnels are mapped with care. The whole system is sketched out like a well-engineered bridge: linear, logical, clean. The assumption is clear: progress will follow

Successful revenue systems emerge from the collision of bold creativity and disciplined iteration. That’s the fusion of art and science—and it’s how real sales innovation happens. This tension isn’t just philosophical—it’s practical. Founders feel it when they try to scale sales beyond their own voice. Revenue leaders face it when

You’d think passion wins deals. That caring more would close more. But in sales, the opposite is often true. The reps who don’t need the deal often win it. The founders who push hardest often repel prospects. The more emotionally invested you are, the more likely you are to confuse

What’s Built Without Empathy Breaks Without Warning Empathy isn’t sentimentality. It’s system design. In early-stage startups, leaders often rush to build processes that scale—but forget to consider the human layer inside those systems. Revenue teams become machines: efficient, repeatable, but ultimately fragile. And when stress hits? The system snaps. Marketing

Most founders don’t hand out sales playbooks because they love process. They do it because they’re overwhelmed. In the chaos of early-stage growth, a good playbook promises relief. It reduces confusion. It creates structure. It feels like you’re finally doing things “right.” But structure without adaptability doesn’t solve problems—it creates

Founders are builders. It’s what sets them apart. They obsess over quality, scalability, and long-term technical vision. They know their product or service inside out. But here’s the paradox: that very depth—the commitment to crafting something exceptional—can quietly sabotage their ability to scale. Not because the product is wrong, but

Great Ideas Need More Than Enthusiasm Creativity fuels most startups. New products, disruptive ideas, and fresh ways of thinking are often the spark that launches a company. But without a solid startup structure to channel that creativity, even the best ideas struggle to survive. Ideas alone are not enough; execution

The allure of a massive customer deal is hard to resist. A single contract that could double revenue, transform the growth curve, and create immediate market credibility sounds like the perfect opportunity. It’s no surprise that many revenue teams prioritize whale hunting—pouring disproportionate time, energy, and resources into securing a

Why Founders Need a Fractional Revenue Team to Scale Complex Sales When Vision Becomes a Bottleneck Most founders start with a vision so clear they can see it fully formed: the solution, the impact, the people it serves. That clarity powers the early stage—conversations with investors, first hires, early customers.

Most companies don’t set out to create a misaligned revenue team. They say all the right things—“We put the customer first,” “We value long-term relationships,” “We believe in solving real problems.” But the truth of what a company values isn’t found in its brand manifesto. It’s written in its systems.

Leaking Money Imagine this: You’ve successfully landed your first few sales, single-handedly. Your startup is gaining traction. Revenue—the lifeblood of your business—is flowing. Recognizing it’s time to scale, you hire a dedicated sales team and marketing experts. Yet months later, you find yourself still deeply involved in every decision—not because

1. “I Just Need Leads” — The Startup Trap Every founder hits that moment. Pipeline’s thin. Cash flow’s tight. Investors, if you have any, are asking for updates. And the internal monologue begins: “I can close. I just need more leads.” It’s understandable. You’ve likely closed your earliest deals personally.

Is Your Revenue Target Just a Suggestion? Yet, too many startups treat it like one—setting aggressive goals without ensuring the revenue team is structured to hit them. Alignment isn’t just a nice-to-have. It’s the difference between a revenue team that scales efficiently and one that burns time, money, and market

Why Teams Drift Apart (Even When They Start Strong) Imagine a group of explorers setting out together on a journey. At the start, they move as one, but as time passes, entropy sets in. Some take different paths, others slow down, and before long, the group fragments—not because they weren’t

Leaking Money Imagine pouring water into a bucket full of holes—no matter how much you add, it keeps leaking out. That’s what happens when your revenue team is fragmented. Marketing, sales, and customer success should work together seamlessly, yet too often, they operate in silos, leading to lost revenue, frustrated

The Startup Revenue Web: Everything is Connected Many founders think of revenue growth as a straightforward process: Marketing generates leads. Sales closes deals. Customer Success retains customers. But revenue isn’t a linear pipeline—it’s a complex, interconnected web of internal and external systems, each dependent on and influencing the others. Imagine

Why Aren’t Your Sales Growing? If your revenue growth isn’t where you want it to be, the answer isn’t in hiring more sales reps, increasing outreach, or investing in the latest sales enablement tools. The real problem? Your revenue system is working exactly as designed. Every business outcome—whether it’s hitting

Balancing Vision and Execution: A Leadership Imperative In the world of B2B tech marketing, revenue leaders face a constant challenge: navigating the delicate balance between creativity and structure. The Creativity Craving Structure Paradox—a concept that describes the tension between the freedom to innovate and the need for frameworks to execute—captures

Introduction: The Complex Dance of B2B Sales in a High-Tech World Selling in the world of B2B is anything but simple. Complex Sales involve long decision-making cycles, multiple stakeholders, and significant risk for both buyer and seller. For sellers, a lost deal doesn’t just mean missing a revenue target—it could

In B2B complex sales, your sales reps are the driving force behind your company’s growth, making it critical to structure compensation plans that motivate them effectively. However, with today’s workforce spanning multiple generations—from Baby Boomers to Gen Z—a one-size-fits-all approach no longer works. While this guide offers general insights into

Buyers Are Smarter, But Are They Seeing the Full Picture? In today’s world of endless information, B2B customers arrive at the sales conversation more prepared than ever before—or so it seems. In the complex (or difficult) sales world, they’ve spent hours researching their problem online and in social media, narrowing

As the New Year dawns, many businesses set their sights on growth—bigger revenues, larger teams, expanded markets. But growth isn’t just about adding more. Sustained growth is about building a foundation that can support progress for the long haul, not chasing fleeting moments of success that fade as quickly as

The Revenue River Ever feel like your revenue is flowing — but not always in the right direction? The ARR Waterfall Chart is the tool you need to visualize how your Annual Recurring Revenue (ARR) evolves over time. This chart lets you see where revenue growth and loss occur, providing

Achieving sustainable growth in the B2B startup space requires more than just market-savvy moves; it demands strategic foresight and flexibility. Startups with limited resources are especially positioned to benefit from innovative approaches that lay the foundation for scalable, long-term success. Here, we explore critical strategies to support sustainable growth, including

The Key to SaaS Growth: Putting the Customer First In the ever-evolving SaaS landscape, growth hinges on one vital principle: customer centricity. The companies that scale sustainably are those that place their existing customers at the core of their operations. Rather than solely chasing new acquisitions, successful SaaS businesses understand

Ditch the Pitch: The New Role of the B2B Sales Elevator Pitch You’ve heard it a hundred times – the classic elevator pitch. It’s been drilled into every professional’s head as a “must-have” for networking events, job seekers, and introductions with that next big client. But in B2B sales, especially

I. Startups: Why a Full-Time Marketer is Overkill For startups, resources are tight, priorities shift constantly, and scaling operations without ballooning overhead is critical. Hiring a full-time marketing resource may seem like a natural step as your business grows, but for many startups, it’s overkill. Startups need lean teams that

Hiring a full-time sales leader might seem like the logical step for startups and small businesses eager to drive revenue. However, in reality, many founders find themselves on a hamster wheel—constantly hiring, training, and losing unqualified salespeople who fail to deliver results. This cycle wastes time, money, and resources, leaving

How to Limit Your Growth It’s a common pitfall in many B2B tech startups: Customer Success (CS) functions are often an afterthought, stepping in only after the sale is made and the relationship is already in motion. Sales teams close deals, hand them off, and move on to the next

What Are Sales Motions and Sales Plays? Sales motions refer to the overarching approach your sales team takes to move prospects through the sales funnel. A sales motion outlines how to engage with potential customers, from the first point of contact to closing the deal. A well-crafted sales motion aligns

Three-Way Tug-of-War The effectiveness of a company often hinges on how well its Revenue Team—comprising marketing, sales, and customer success—functions as a cohesive unit. There is inherent friction between these groups in many companies, leading them to operate in silos. This separation can lead to misaligned goals, inefficient processes, and

Complex phone calls? Isn’t that all a sales rep does? Complex sales are the lifeblood of many B2B companies, representing high-stakes transactions that can significantly impact a business’s growth and success. These sophisticated sales require navigating intricate decision-making processes, involving multiple stakeholders and often extending over several months or even

Introduction In the B2B tech startup space, free software trials are often seen as an effective way to attract and convert customers. The common belief is that by offering a no-cost trial, companies can showcase the value of their software, build trust, and eventually turn trial users into paying customers.

The Founder-Sized Hamster Wheel In the early stages of a startup, founders often find themselves wearing multiple hats, with sales being one of the most crucial. Many founders enjoy the opportunity to go out and proselytize their idea. However, after a while, the excitement of potential deals can quickly turn

Put Your Money Where Your Mouth Is.. For B2B tech startups anxious for revenue growth, the search for reliable revenue generation services can be fraught with skepticism and high expectations. A recent LinkedIn conversation between me, and a potential client, (let’s call him Simon) sheds light on the complexities of

Say it, Don’t Spray it: Spam Karma Edition Effective sales communication has seen profound transformations over the last few years. Gone are the days when businesses could rely solely on high-volume tactics such as cold calling and mass emailing to capture the attention of potential customers. Today, as digital platforms

Red Rover, Red Rover… Would you buy software from, say, Africa? As globalization and technological advancement continue their rapid stride, lesser-developed countries step up as new hubs of innovation. These regions are not only increasing their capacity for innovation but are also developing unique solutions tailored to address both local

Introduction Market segmentation is a fundamental aspect of business strategy, especially for B2B tech startups looking to carve out a niche. Effective segmentation allows startups to focus their sales and marketing, and to tailor their products and services to the needs of specific groups. This enhances marketing efforts and improves

Introduction When you’re ready to hire your first sales rep at a startup, it’s a step that signals readiness for growth and a crucial milestone in your journey to generate substantial revenue. The urgency to bring revenue in the door—to fund product development, scale operations, and accelerate growth—is palpable and

Focus First, Worry About the Rest Later Here at Reditus, we engage with dozens of startups every week, and almost all of them have the same goal: achieving sustainable revenue growth. For these companies, revenue generation is more than just making money; it’s about survival, scalability, and ensuring their mission

Growth on a Budget: Why Outsourcing is the Key to Scaling Small B2B tech startups often find themselves at the forefront of innovation, crafting groundbreaking solutions to disrupt industries. However, despite their potential, many struggle with establishing a foothold in competitive markets. The challenges are substantial: limited resources, small budgets,

Introduction I’m dating myself, but I got my IMBA and re-entered the workforce in 1998—into the software industry. I experienced first-hand how the lead-up to Y2K coupled with the advent of widespread internet usage created a huge boom of irrational behavior in the tech sector in the late 90’s. Today,