From $12M to $30M ARR: How a GTM Sparring Partner Helped Cloud Academy Scale Smarter

Only a fraction of tech startups reach $10M in ARR. Even fewer manage the leap beyond. Growth stalls. What worked starts breaking. And what once felt like a rocket ship suddenly feels… stuck.

I’ve learned from experience that companies can grow fast up to the $10M ARR mark and still miss basic Go-To-Market fundamentals. Overcoming these gaps when the business has grown substantially can be painful and put future growth at risk.

This is the story of how I worked with Cloud Academy, a San Francisco-based Enterprise SaaS company, to do just that. It’s a real-world example of what I call a GTM Sparring Partner engagement.

The CEO, Stefano Bellasio, didn’t need a full-time “superhero” CRO to replace him. He was a brilliant, hands-on founder who was still the primary driver of the GTM strategy. What he needed was a strategic partner to challenge his assumptions, bring in battle-tested frameworks, and help him and his team navigate the complexities of scaling beyond the $10M mark.

We ended up working hand-in-hand for more than a year, week after week. Here’s the playbook we used to get Cloud Academy back on track towards its $30M ARR milestone.

The Situation: A Solid Business Facing Scaling Pains

When Stefano got in touch with me towards the end of 2020, Cloud Academy was already a solid SaaS business.

• 15M$ in bookings (12M in ARR)

• Growing 50% YoY, with over 90% of revenue from the US.

• Growing deal sizes, moving towards six-digit contracts with great logos.

• Recently acquired by QA (owned by PE firm CVC Capital Partners) with an ambitious 3-year earn-out target of reaching $30M ARR.

Despite this success, Stefano was concerned. He was seeing the classic signs of GTM challenges that could put that earn-out at risk:

• Pipeline was lower than expected.

• Closing rates were declining.

• He was losing trust in the sales team’s forecasts.

• He had recently let his VP of Sales go.

The initial diagnosis pointed towards sales team performance. But, as is often the case, this was just a symptom of deeper, more foundational issues.

The Fix: Rebuilding the GTM Fundamentals, Posture by Posture

After a few weeks of discovery, we agreed to focus on four key areas of work.

From Inbound-Only to Pipeline Discipline

The inbound engine had powered early growth, but it wasn’t enough anymore to get to $30M.

We discovered the Account Executives’ calendars weren’t as busy as you’d expect. The focus was only on the existing pipeline, not on creating new opportunities.

• The Action: We built granular Salesforce dashboards to track not just pipeline, but prospecting activities (accounts prospected, first meetings, etc.). This brought a new level of clarity and accountability to outbound efforts. We also split the pipeline view to distinguish New Business from Renewals. This simple change created a sense of urgency around new logo acquisition.

From “Happy Ears” to Predictable Forecasting with MEDDPIC

The CEO was frustrated with deals that were promised at “99% sold” only to vanish at the last minute. The root cause? A deal qualification framework that was too basic and subjective for the company’s current stage.

• The Action: In two weeks, we designed and deployed a customized version of the MEDDPIC framework in Salesforce. We trained the team and reclassified the entire pipeline based on these new, objective criteria. This process immediately provided a much clearer, more realistic view of the pipeline and dramatically improved the quality and predictability of forecasts.

From Unstructured Meetings to Aligned Execution

With better data and processes, we focused on making the sales team’s routines more productive. The weekly one-to-many meeting became a mix of three goals: Align, Inspire, and Educate (30 mins pipeline review, 30 mins learning). The one-on-one meetings were redesigned to be deep-dive coaching sessions, focusing on hot deals, priorities, and how I could help. This created a rhythm of continuous improvement and alignment.

From “Big Name” Hires to Stage-Fit Talent

This was the toughest, yet most critical, challenge. The previous VP had hired AEs from large, established competitors. In my experience, these “corporate titan” profiles often struggle to open doors and build markets for a scaleup that doesn’t yet have a globally recognized brand.

Brand recognition can’t replace startup muscle memory. In a scaleup, you need people who can hunt — not just farm.

• The Action: We redefined the AE job spec. The priority shifted from “domain experience” to a proven track record of selling similar-sized deals at B2B SaaS scaleups in the 5M-50M ARR range. The ability to build pipeline from scratch became a must-have. I worked hand-in-hand with the CEO and HR to rebuild the team over six months, including hiring a new VP for North America. Changing the people was the hardest part, but it was essential.

Conclusion: Key Lessons for Founders Navigating the $10M+ Hurdle

In the end, it all worked. Stefano and his co-founder secured their earn-out and have since moved on to build another successful company. The Cloud Academy story offers a powerful set of lessons for any founder facing similar scaling pains.

1. Look Beyond the Symptoms: A decline in closing rates or pipeline isn’t just a “sales problem.” It’s often a symptom of deeper, foundational GTM issues. As a founder, you have to dig deeper.

2. Data & Frameworks Bring Clarity: You can’t manage what you don’t measure. Granular dashboards on activities (not just outcomes) and a robust qualification framework like MEDDPIC are non-negotiable for achieving predictability.

3. Hire for Your Stage, Not Just Your Industry: The skills needed to thrive at a 1000-person company are vastly different from those needed at a 100-person scaleup. Prioritize stage-appropriate experience, especially the proven ability to build, not just manage.

4. A “Sparring Partner” Can Be More Valuable Than a “Superhero”: Sometimes, the right help isn’t a full-time hire to replace you, but a strategic partner to empower you. As a hands-on founder, having an external expert to challenge your thinking and provide proven frameworks can be the key to unlocking the next stage of growth.

In today’s AI-driven world, where product development is accelerating, getting these GTM fundamentals right is more critical than ever. AI won’t fix a broken GTM engine; it will only help you scale your mistakes faster. Building a solid, repeatable GTM machine is the only way to ensure you’re building a truly resilient and valuable company.

 

 

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