Your Board wants a CRO, Here's What They're Missing...

Hey ,

You might have noticed we've been a bit quiet lately. And if you know us, you know we're not typically the quiet type. But we've been heads down working on something we’re genuinely pumped to share with you – our completely “reimagined” website and brand identity at Revenue Reimagined.

If you're thinking "Jake, it's just a website," I get it. But this isn't just about a fresh coat of paint. This is about creating a home that truly reflects the deep work we do with founders and the results we help them achieve. We've poured everything we've learned from working with companies from $2M to $200M into this new platform.

Check it out at https://www.revenue-reimagined.com/ and let me know what you think – We'd love your feedback.

Speaking of the deep work we do with founders, there's a conversation that's been coming up so frequently lately, I knew I had to address it. Just recently, a founder dropped this on me:

"Board meeting coming up and our Chairman wants to start discussing hiring our first Head of Sales. We're at $1.8M ARR, growing about 15% MoM, but it's mostly been me and two AEs doing all the selling. Board thinks we need someone more experienced to build out the team and processes so I can focus on other parts of the business that have been neglected, like product. Our chairman has a seasoned candidate he wants to introduce me to who has led large teams and had a couple of exits. Trying to figure out if this is the right move or if we should keep running lean for a bit. Thoughts?"

I've seen this movie before. And while the question seems straightforward, it opens up a much bigger conversation about what kind of revenue leadership you actually need at this stage.

Estimated reading time is 4 minutes—feel free to hit reply and share your takeaways or questions.

On Deck:

• Ready for a CRO? The Question Every Founder Needs to Answer

• Why Traditional Revenue Leadership Might Be Holding You Back

• Marketing Tip of the Week - Powered by Decoded Strategies

• Episode #83 The Brutal Truth About Startups

Ready for a CRO? The Question Every Founder Needs to Answer

Think of building your revenue organization like constructing a house. Most founders I work with get pressured into hiring a general contractor (your Head of Sales or CRO) before they've even finalized the blueprint. Here's the hard truth: at this stage, you don't need someone to manage construction; you need an architect to design the foundation.

This is where a fractional CRO comes in. But before we dive deeper, let's clarify what this actually means for your business.

First, let's bust a myth that's probably bouncing around your head right now: a fractional CRO isn't just a part-time sales leader. If that's all you're looking for, stop reading and go hire that Head of Sales. A true fractional CRO is your strategic revenue architect who looks at the entire picture. From your go-to-market strategy to your customer success playbook.

"But Jake, my board wants a proven leader who's going to be in it with us full-time."

Trust me, I get it. That "seasoned executive with multiple exits" looks great on paper. But here's what most founders (and boards) miss: at your stage, you don't need someone spending 40 hours a week managing a team of two. You need someone spending 10-20 hours a week answering questions like:

• How do we design a sales process that won't break when we triple the team?

• Where are we leaving money on the table in our customer journey?

• What metrics should we actually be tracking to show we're ready to scale?

Here's When You Know It's Time for a Fractional CRO

Let me paint you a picture of three scenarios we see all the time:

1. You're in the Product-Market Fit Dance: You've got some early customers, maybe even hit that coveted $1M ARR mark. But something feels off. Your sales process is more art than science, your marketing team is shooting in the dark, and your customer success? Well, let's just say it's reactive at best. This is where a fractional CRO becomes your revenue architect, helping you build the foundation for scalable growth before you pour concrete on processes that won't hold up.

2. You're Hitting a Growth Ceiling: Your revenue has plateaued, and throwing more sales reps at the problem isn't moving the needle. Whether you're at $2M or $200M, these plateaus are often less about your sales team's execution and more about your revenue architecture. A fractional CRO can dive deep into your revenue engine, identifying those hidden bottlenecks that are keeping you stuck. I saw this recently with a $100M company that thought they had a sales leadership problem – turns out their entire go-to-market strategy needed a reset to reach the next level.

3. You're Gearing Up for a Transition: Maybe you're preparing for a funding round, or you're a larger organization looking to make the leap from $100M to $250M. Your board is pushing for "experienced revenue leadership," but you need to get your house in order first. This is where a fractional CRO can be your secret weapon – helping you build the systems, processes, and metrics that will make your next phase of growth not just possible, but predictable.

When Does Fractional Leadership Make Less Sense?

Let's be real – while a fractional CRO can add value at any stage (we work with companies from $2M to $200M in revenue), there are situations where it might not be the best fit. If you've got a well-oiled revenue machine that's hitting all its numbers, your sales leaders are executing flawlessly on your vision, and you have complete confidence in your growth trajectory – you probably don’t need the strategic reset that fractional leadership provides.

But here's what's interesting: we often see larger companies bringing in fractional leadership precisely when they're ready for their next big leap. Maybe they're hitting a revenue ceiling at $100M and need fresh eyes on their go-to-market strategy. Or they're not sure if their current sales leadership can take them to $250M. In these cases, a fractional CRO can help assess the gaps, stabilize the foundation, and build a framework for that next phase of growth.

The bottom line? Your revenue strategy is too important to get wrong. Whether you're stuck in the messy middle of scaling or preparing for your next growth phase, bringing in fractional leadership can be the difference between building a revenue engine that purrs and one that just makes expensive noises.

You might be thinking, "That all sounds great, but how do I know if this is right for my specific situation?" And you're right to ask. Every company's growth journey is unique, which is exactly why we start every engagement with a deep dive into your current reality and future vision.

Want to explore whether a fractional CRO is right for your business? Let's talk. Book a free strategy call and we'll help you figure out your next best move.

When Traditional Revenue Leadership Might Be Holding You Back

Here's a pattern I keep seeing that drives me crazy: A company hits $2M, $20M, or even $100M in revenue, and immediately everyone pushes them to hire "seasoned revenue leadership." You know the type – the exec who's "been there, done that" at big companies. Sounds great on paper, right?

But here's what nobody talks about: these traditional revenue leaders often bring baggage that can actually slow your growth. Let me share a recent example that might hit close to home.

We just started working with a company that had hired a rockstar CRO from a $500M company to help them scale from $50M to $100M. Impressive resume, multiple exits, the whole package. Six months in, growth had slowed to a crawl. Why? Because he was trying to implement the same playbook that worked at his last company – complete with heavy processes, complex tech stacks, and a bloated org chart.

Here's what we've learned from working with companies across every growth stage: The skills that made someone successful at a $500M company aren't necessarily the skills you need to get from $50M to $100M, let alone from $2M to $10M.

Think about it. When you're scaling, you need someone who can:

• Design systems that scale with you, not systems designed for where you want to be in three years

• Make decisions based on your current reality, not their past experiences

• Build processes that enable growth rather than control it

• Focus on revenue architecture, not just revenue execution

The thing about traditional revenue leadership is that it often comes with what I call the "big company hangover." These leaders are used to having established processes, large teams, and robust systems already in place. When they step into a growth-stage company, they're like a master chef walking into a food truck – all their usual tools and ingredients aren't there, and they struggle to adapt.

Let me share another story that might sound familiar. We recently worked with a founder who hired a VP of Sales from a publicly traded SaaS company. Great hire on paper – had scaled teams from 20 to 200 reps, managed $100M+ territories, the works. But three months in, the founder was pulling his hair out because this VP spent $300K building out a tech stack before they even had their ICP nailed down.

Think of it like this: hiring traditional revenue leadership too early is like buying a Ferrari before you've learned to drive stick. Sure, it looks impressive in your driveway, but without the right foundation, you're more likely to crash than to win the race.

So what's the alternative?

This is where fractional leadership shines. Instead of committing to a full-time executive who might be stuck in their big-company ways, you get a revenue architect who:

• Has built multiple engines from scratch

• Knows when to use duct tape and when to use titanium

• Can design systems that grow with you, not hold you back

• Isn't afraid to roll up their sleeves and get their hands dirty

The best part? When you do eventually hire that full-time revenue leader, you'll have a blueprint for success that's been battle-tested in your business, not someone else's.

You might be thinking, "Jake, this all makes sense, but my board is still pushing for that big-name hire." Trust me, I get it. Let's talk about how to navigate that conversation. Book a free strategy call and we'll help you build a case for what your business actually needs right now.

Marketing Tip of the Week - Powered by Decoded Strategies

Want to know why most marketing messages fail? They talk about solutions before establishing credibility.

Think about the last time you got advice from someone you didn't trust. Didn't matter how good the advice was, did it?

Your prospects are the same way. Before they care about your solution, they need to believe you understand their world.

This is why most marketing copy follows this (broken) pattern: "We help companies [achieve result] through our [solution/platform/service]"

But great marketing flips the script: "We've helped [specific type of company] overcome [specific challenge] when [specific situation]"

See the difference? The first talks about what you do. The second proves you've done it before.

Remember: Credibility before capability. Always.

Episode #83 The Brutal Truth About Startups, VC Pressure & Scaling to $3M ARR with Max Greenwald

In this week's episode of Bridge the Gap, I sat down with Max Greenwald, Founder & CEO of Warmly, for what turned into one of the most brutally honest conversations about startup growth I've had in a while. If you're tired of the sugar-coated "overnight success" stories, this one's for you.

Key Takeaways:

1. The VC-Founder Tightrope

• The hidden tension between VC timelines and sustainable growth

• Why chasing the wrong metrics can kill your company

• How to maintain control while keeping investors happy

2. The Real Definition of Product-Market Fit

• Why PMF isn't what most founders think it is

• The "nose-yanking" moment that tells you you've found it

• How to tell if you're actually solving a real problem

3. The "Lettuce vs. Supermarket" Strategy

• Why trying to be everything to everyone kills startups

• How to find your niche and dominate it

• The power of saying "no" to good opportunities

4. Rethinking Cold Outreach

• Why traditional cold outreach is broken

• How AI is transforming lead generation

• Building a warm-first approach that actually works

5. The Ultra-Marathon Mindset

• Why most founders burn out before finding success

• Building for the long game, not the quick exit

• Creating sustainable growth in a pressure-cooker environment

Ready for some real talk about what it takes to build a multi-million dollar company?

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Agree? Disagree? Have Questions?

We love engaging with our community—reply to this email with your thoughts, and let’s chat!

Talk soon,

Jake Reni
Revenue Reimagined
Helping founders scale, lead, and build elite teams—without burning out.