The "Messy Middle" of Scaling
Identifying why GTM stalls at $5M–$10M ARR.
40% growth 🚀
20% 👏
5% 🤦♀️
Stalling growth is scary for founders who are used to double-digit numbers.
You risk disappointed investors and frustrated employees who are worried that their exit window is closing.
The problem is that the go-to-market strategies that got you to $3M-$5M in ARR won’t get you to $10M-$25M.
In today’s GTM playbook, I’ve got 8 reasons that this happens and 5 things you can do about it to correct course.
8 Reasons your Growth is Stalling
Founder-led sales isn’t viable any more: Beyond $1M+ ARR its simply logistically improbable that a founder can lead every sales effort. Unfortunately, those that do outperform others. Hiring others to lead sales is tricky. They may have been a top salesperson at an enterprise company, but selling for a startup, one you didn’t create and don’t have as much passion for, is different.
Your ICP has changed: You probably hit the $1M ARR mark because you knew your ICP intimately. Sometimes, to scale, companies need to attack new markets and new ICPs. Or, the ICP evolves what it is demanding. Whether for market conditions, new entrants, or new expectations.
Distribution expansion: Since you knew your ICP intimately, you knew where they hung out looking for solutions to their pain points. But, those distribution channels can change and finding new ones takes money and time.
Merging GTM motions: Merging two different go-to-market motions adds complexity. You may have started out using PLG go-to-market motions but are now adding in, or shifting to, SLG motions.
ICP/Message dilution: I mentioned that ICPs change. What changes with that is the messaging needed to reach the new ICP.
Team growth: Operating as a scrappy 10 person team is a lot different than managing how a 100+ person team maneuvers.
Technical debt/feature fatigue: This has killed more startups than anything. Founders, especially technical founders, love to build. Hitting the next level of growth requires a product that can grow to suite demand. But, adding more features isn’t always the answers. More features equates to more technical debt and the chances are high that even your top users aren’t leveraging the full feature suite.
Managing churn: Keeping a customer is infinitely more profitable, in most cases, than landing a new one. The longer you keep a customer, the better your CAC to LTV ratio looks and the less time your team is spending trying to replace revenue.
If you look for the common thread, most of the eight reasons point to one thing - added complexity.
Sometimes the product that got you to $1M ARR isn’t the one that will get you to 10x that.
Sometimes the founding team is great at 0 to 1, but terrible at 1+.
If you have one, or more, of the above challenges, first, it’s great you are acknowledging it. Now, let’s look at some fixes.
How to Fix Stalling Growth
These are in no particular order. But, its possible that you will need to engage multiple of these fixes to address your stalling growth 🚂.
Formalize Processes: With small teams, it’s easier to keep everyone informed and operating from the same playbook. As your venture grows you need to document how things are done. That means you need to formalize, i.e. document 📝, your processes and procedures.
Better segmentation: Since your ICP is evolving you are going to need to segment better. That way you don’t leave your original ICP behind, but you don’t lump new ICPs in with the original fans.
ARRto NRR: It feels good to a founder’s ego to promote their annual revenue. People do it all the time. But $1M in ARR doesn’t equal $1M in NRR (Net Revenue Retention), and, as you grow, NRR is a much more important number. Retaining revenue is what gets you to $10M.Avoid over hiring: Every top founder and CEO has made this mistake. Just look at how many tech firms needed to do layoffs to right size for the over hiring they did during the COVID pandemic. As you venture scales, its going to be natural to want to add people. That’s not always the best solution. Nikita Bier, Head of Product at X, recently shared that their engineering team has just 87 people. <insert image>
Data and measurement: As you scale its critical your processes allow for data gathering and measurement. Think of it as transitioning from an amateur athlete to a professional. Professional teams measure everything. To measure you must have the data. Use that data to establish KPI/OKRs that you can use to a) warn you when things are wrong; b) point you in the right direction.
2 GTM Playbooks
One of the toughest challenges I listed was merging GTM motions.
I’m going to share excerpts from separate GTM playbooks/comparisons I’ve developed for clients.
The 90-day SLG Transition Plan
This plan works for companies who are moving towards a sales-led growth engine. That is often when you are a B2B company and/or selling to enterprise-level clients.
Goal: Transition from Founder-Led Sales to a VP of Sales/Director model without crashing the pipeline.
Phase 1: Days 1–30 (The “Shadow & Audit” Phase)
The new sales leader should not be closing deals yet. They are there to “extract” the founder’s brain.
Audit the Pipeline: Clean out the “hope” deals. If a lead hasn’t moved in 45 days, it’s dead.
Shadowing: The VP shadows every founder call to document the “unwritten” talk tracks, common objections, and the “why now” triggers that close deals.
Tech Stack Hygiene: Ensure the CRM is the single source of truth. If it isn’t in the CRM, it didn’t happen (solution #1 above; Formalize Processes)
Phase 2: Days 31–60 (The Playbook & “First Rep” Success)
Draft the Playbook: Create a 10-page “Battle Card” for the AEs (by the way, I instituted this at the fintech where I led Product GTM; the sales staff is in love with those Battle Cards/FAQs). It must include the Ideal Customer Profile (ICP), competitor landmines, and pricing levers.
Founder as “Executive Sponsor”: The founder moves from “Primary Closer” to “Executive Closer.” They only join calls in the final 20% of the deal to provide “social proof” and authority.
Sales Enablement: Set up a weekly “Film Review” where the team listens to call recordings (e.g., Gong or Chorus) to align on messaging.
Phase 3: Days 61–90 (Quota Carrying & Scale)
The “Clean Hand-off”: Marketing and SDRs now hand off leads directly to the VP/AEs. The founder is removed from the initial discovery process entirely.
Quota Setting: Establish realistic ramp-up periods for new AEs. A common mistake is expecting 100% quota attainment in Month 1.
Predictability Check: By Day 90, the VP should be able to forecast the next quarter’s revenue within a 10% margin of error.
PLG vs. Enterprise
I developed this brief for a client who was considering a dual GTM motion approach that included PLG (their former method) and SLG with enterprise-level prospects.
Product-Led Growth (PLG)
The Philosophy: The product sells itself. The user finds value before they pay.
Key Metric: Time to Value (TTV). If it takes more than 5 minutes for a user to see a “wow” moment, PLG will fail.
The Team: Product Managers and Engineers are your “Sales” team. Marketing focuses on “Top of Funnel” (SEO, viral loops).
The $5M–$10M Challenge: Moving from “Individual Users” to “Team/Company-wide” accounts. This usually requires adding a “Product-Led Sales” (PLS) layer where AEs reach out to power users to sell them an Enterprise plan.
Enterprise (Sales-Led)
The Philosophy: You solve complex, high-stakes problems for large organizations. The buyer is often different from the user (this is critical).
Key Metric: LTV:CAC and Sales Velocity. How much does it cost to acquire a $50k+ seat, and how long is the cycle (typically 6–9 months)? (note - see solution #5 above; Data and Measurement)
The Team: Heavily weighted toward AEs, Sales Engineers, and “High-Touch” Customer Success, but organized as one collective GTM team.
The $5M–$10M Challenge: Shortening the sales cycle and preventing “Feature Requests” from individual big clients from hijacking the entire product roadmap.
The Growth Strategy Takeaway
What got you here won’t get you there. Stalling at $5M isn’t a sign of failure. It’s a sign that your “unscalable” manual efforts have reached their limit. To break through to $25M, you have to trade founder intuition for documented systems, and prioritize retention (NRR) over the ego-boost of raw acquisition
Curious how your existing go-to-market strategies measure up? Take my free GTM Readiness Assessment. In 5-minutes you’ll know where you stand and how to improve.