If you’re stepping into a Head of Demand Generation or Revenue Operations leadership role in a B2B SaaS company, chances are you’ve inherited a set of challenges that are far from straightforward. Unlike consumer marketing, where demand can often be manufactured with brand spend and viral reach, true B2B demand generation success is typically a long game that requires precision, alignment, and resilience.
But what happens when the engine that powers your go-to-market machine is either missing, broken, or poorly configured?
In this article, I’ll explore five of the biggest challenges B2B SaaS demand generation leaders face, why they’re so complex, and what lessons you can learn from Elon Musk’s SpaceX rocket program to navigate them successfully.
Five Core Challenges of B2B SaaS Demand Generation Leadership
1. Rebuilding After Leadership Loss
You’ve lost both your Head of Revenue Operations and Head of Demand Generation. Now you’re starting from scratch, rebuilding the engine room of your growth function.
Unlike replacing parts in a car, you can’t just slot in a new “engine” and expect things to work. Every leader comes with their own experience, style, and alignment challenges. A misstep here can set your growth trajectory back by months, quarters, or even years.
2. No Demand Generation Engine—Just Outbound Sales
Many SaaS firms rely too heavily on outbound prospecting. SDRs and AEs pound the phones, book demos, and chase the pipeline. But it’s an expensive model. “No-show” rates creep past 25%, CAC balloons, and sales morale plummets. Aggressive and inexperienced 'gun-ho' sales reps can also fatally damage your brand.
Without a demand generation engine, a scalable, predictable inbound system that attracts and nurtures ICP buyers, you’re running uphill against gravity. With outbound sales, you continually start from scratch. With a demand generation engine, you are building, improving and optimising over time.
3. Agency Dependency and Declining Returns
You hire an agency. They perform well in year one, but as time passes, performance stagnates while their integration into your processes deepens. Suddenly, you’re stuck with status quo bias, the fear that replacing them will be more painful than persisting with mediocrity.
The truth: agencies rarely innovate on your behalf after the honeymoon phase. A demand generation leader has to know when to pivot and when to insource.
But to do so requires courage, and experience - a demand generation expert that is tried and tested.
4. Broken Metrics and ICP Confusion
Lead scoring models that don’t predict conversion. A pipeline filled with the wrong personas. Confusion over customer lifetime value (CLV) and churn. A lack of clarity on your ideal customer profile (ICP).
At this stage, it’s not clear whether any single demand generation manager can “fix” the problem without broader executive buy-in and a serious reset. But again, if that person can be found, it must be a demand generation leader with sufficient 'gravitas' to persuade the C suite that he knows what he's doing - and one that can follow through and deliver.
5. Organisational Silos and Politics
Sales, marketing, product, and customer success aren’t talking. Worse, they’re competing. Information is withheld, psychological safety is low, and the people who care most about the business (and speak uncomfortable truths) get punished.
You’re left with the consummate politicians while the passionate operators—the very people you need—walk out the door. This is when a company can fall into a death spiral. It takes a skilled expert, to pull out of such a doom loop, and set the demand function on a healthy growth course again.
Replacing Demand Generation Leaders isn't like swapping out a car engine; it's like rebuilding a rocket
Why Losing Your Growth Engine Is Like Launching a Rocket
When I first thought about losing key revenue roles, I compared it to pulling an engine out of a car. But the more I thought about the analogy, the more I realised that it doesn’t do justice to the reality.
In cars, engines are standardised. You can swap them, and they’ll usually work. In B2B SaaS demand generation, leadership roles are not plug-and-play. Hiring a new Head of Demand Gen or Revenue Ops is closer to building a rocket than fixing a car.
And rockets fail—a lot—before they succeed. Whereas a brand-new car engine is pretty much guaranteed to work if inserted into another vehicle.
SpaceX and the “Known Unknowns”
Donald Rumsfeld once spoke about “known knowns, known unknowns, and unknown unknowns.” This framework applies perfectly to building a demand generation engine:
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Known challenges: Your new leaders must learn the organisation, tech stack, and products.
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Known unknowns: How will they perform as individuals? How will they work together? How will sales, SDRs, and product marketing respond?
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Unknown unknowns: What happens if the system breaks down completely? What happens if your new head of demand generation and new head of revenue operations don't get along? What happens if neither works well with sales? The list goes on....
SpaceX’s Falcon 1 and Early Failures
Elon Musk’s SpaceX faced multiple failed launches of the Falcon 1 rocket between 2006–2008. Each failure was costly, public, and demoralising. But on the fourth attempt, Falcon 1 succeeded—and from there, SpaceX iterated its way to reliability.
Falcon 9: Iteration and Reusability
With Falcon 9, SpaceX didn’t just build a bigger rocket—it built one that could be reused. That single innovation changed the economics of space travel. For demand gen leaders, the equivalent is creating repeatable, reusable, scalable campaigns—not one-off wins.
The Starship Analogy
Today, SpaceX is pushing the boundaries with Starship, a vehicle designed for Mars. It has already exploded multiple times. But each failure accelerates learning.
Similarly, in demand generation, failure is part of the job. Campaigns will flop, SDR alignment will slip, MQL-to-SQL conversions will crater. But with the right mindset, each failure becomes data that makes the system stronger.
However, confidence is built over time, as trust inside a team, and with cross-functional teams, grows. What happens if your new demand generation/revenue operations team has a big set back early on? Will the executive team and wider company support them, so they can learn from their mistakes?
Or will the C suite and team abandon them, and lose faith in the strategy, execution, and team? - This is far more likely to happen with completely new Demand Generation and Revenue Operations leaders.
You need highly skilled, experienced, courageous and tough operators to be successful in such scenarios.
The Skills of a World-Class B2B Demand Generation Leader
So, what does it take to thrive in this high-stakes environment? From working across SaaS firms and demand gen programs, I’d distil the role into five core skill areas:
1. Revenue Architecture
The ability to design go-to-market engines that align marketing, sales, and customer success around shared revenue metrics.
2. Data and Analytics Mastery
From lead scoring models to intent data (6sense, Demandbase), a modern demand gen leader must understand the signals that actually predict pipeline and revenue—not vanity metrics.
3. Full-Stack Channel Expertise
Paid media (LinkedIn Ads, Google Performance Max), SEO, content marketing, email nurture, ABM, webinars, and partnerships—demand gen leaders need range, not silos.
4. Cross-Functional Leadership
The ability to break silos, foster psychological safety, and align diverse teams behind a single growth vision.
5. Resilience and Iteration
Like SpaceX, the best demand generation leaders fail fast, learn faster, and iterate continuously.
That takes more than tactics — it requires C-suite backing, trust in your leaders, and the grit to ride out the inevitable highs and lows.
As Churchill put it, success demands “blood, sweat, and tears” — not blame or recrimination.
From Engines to Rockets: The Opportunity Ahead
Yes, the challenges in B2B SaaS demand generation leadership are immense: broken engines, siloed teams, political infighting, ICP confusion, agency inertia.
But the opportunity is equally vast. Just as SpaceX transformed the economics of space travel through persistence and iteration, the right leaders can transform SaaS demand generation into a predictable, scalable growth engine.
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