I want to double the business.
I hear that sentence all the time. Sometimes it’s said confidently. Sometimes it’s said cautiously, like the speaker is testing how realistic it sounds once it’s out in the air. Either way, it usually comes from a good place: ambition, momentum, belief in the team.
Then I ask the next question:
How, specifically, are you going to do that?
And that’s where the energy shifts.
Because doubling from $20 million to $40 million isn’t just about selling more. It’s about becoming a different kind of organization.
I’m not talking about acquisitions. Buying growth is a different discussion. I’m talking about organic growth, AKA building the engine that can produce twice the output with consistency and control.
That’s where most companies run into trouble.
Challenge #1: Strategy That’s Too Comfortable
Most $10M–$20M companies grow through relationships, reputation, and hustle. Founders know buyers. Reps have long-standing connections. Opportunities surface because trust already exists.
That’s not a weakness — it’s often the reason they succeeded in the first place.
But when leadership says, “Let’s double,” the question becomes: where does the next $20 million actually come from?
I was working with a $20M company recently that had done everything right operationally. Strong customer loyalty. Solid product. High close rates.
But when we mapped out their growth plan, it became clear they were relying on momentum, not direction.
When you’re scaling intentionally, you need clarity around:
- The balance between new logos and expansion revenue
- Which markets are truly core vs. adjacent
- Whether new products are driving growth or just existing
- Whether geographic expansion is strategic or reactive
- How accounts are segmented (strategic, growth, transactional)
This is where strategy stops being conceptual and becomes mathematical.
Because the truth is: if you can’t articulate exactly where growth will come from, you can’t build capacity around it.
And that leads directly to the next constraint.
Challenge #2: When Everyone Does Everything
In many growth-stage companies, sales reps often wear 10 hats.
They hunt.
They farm.
They onboard.
They negotiate pricing.
They smooth over service issues.
It’s admirable. It’s also a scaling constraint.
And heroics don’t scale.
I worked with a $200M company that had multiple sales roles serving different markets, yet everyone was measured almost the same way. Ramp time varied wildly. Accountability was inconsistent.
We built separate sales playbooks, clarified responsibilities, and tightened manager spans of control.
Not because we love org charts. Because clarity increases output.
When doubling becomes the objective, structure typically evolves into:
- Dedicated hunters for net-new acquisition
- Dedicated farmers for account expansion
- Sales managers managing no more than 6–8 reps
- A revenue leader who has actually scaled before
And let me be frank: doubling doesn’t come cheap. If you want to play in the $40M arena, you will likely need to invest in leadership depth and capacity ahead of revenue.
Bootstrapping gets you to a point. Scaling requires design.
And once you start designing structure, you expose the next issue.
Challenge #3: The Process Lives in People’s Heads
Most leadership teams tell me, “We have a sales process.”
Then I look in the CRM.
What they really have is a collection of individual habits loosely tied together by software.
At $15M, that may not hurt you. At $40M, it absolutely will.
Forecasting becomes unreliable. Pipeline reviews become debates. Stage definitions mean different things to different reps.
And here’s something I’ve learned over the years: Optimism is not a forecast.
When you scale, process discipline becomes non-negotiable:
- Clear entry and exit criteria per stage
- Forecast categories based on evidence
- CRM hygiene that’s enforced, not suggested
- Forward-looking metrics
One metric I consistently recommend is pipeline velocity, because it forces clarity around:
- Average deal size
- Win rate
- Opportunity volume
- Sales cycle length
When doubling becomes real, instinct gives way to math. And once process tightens, you discover something else.
You don’t have enough capacity.
Challenge #4: Hiring Without a Ramp System
Here’s a pattern I see repeatedly:
Leadership commits to growth.
They hire aggressively.
Then they wait.
Hope is not a ramp strategy.
When scaling, you must hire ahead of revenue. That means ramp time becomes a strategic variable, not an HR detail.
You need:
- Role-specific 30-60-90 day plans
- Defined revenue parity milestones
- Coaching systems that accelerate development
- Playbooks aligned to each sales function
With one client, we built detailed playbooks for multiple sales roles because each had unique product depth and market focus. It required time and investment, but it dramatically reduced ramp inconsistency.
And that brings us to a bigger realization: if hiring becomes more intentional, marketing must as well.
Challenge #5: Marketing Still Acting Like “Support”
At smaller companies, marketing often plays a supporting role:
- Collateral creation
- Trade show coordination
- Website updates
There’s nothing wrong with that — at a certain size. But if you expect to double and marketing remains a support function, you are placing all the lift on sales.
That math rarely works.
Marketing must evolve into a demand engine:
- Consistent content strategy
- Account-based campaigns
- Campaign-level ROI tracking
- Alignment with sales capacity
Push alone doesn’t scale. Pull does. And as demand increases, another factor determines whether growth sticks.
Culture.
Challenge #6: Culture Shock
Growth changes behavior.
I’m currently working with a client that implemented a stronger sales operating system. Clearer forecasting rules. Defined metrics. Increased accountability.
Some team members thrived. Others struggled.
Why?
Because scaling introduces structure. Structure introduces measurement. Measurement introduces accountability.
Growth requires:
- Compensation aligned to specific objectives
- Clear performance expectations
- Consistent coaching
- A shared belief in disciplined execution
Let me say this clearly: not everyone who thrives in a loosely structured environment thrives in a scaled one.
That’s not personal. It’s structural.
It’s not about talent. It’s about fit for the next chapter.
And that leads to the final constraint most teams overlook
Challenge #7: Infrastructure That Doesn’t Scale
As revenue grows, small inefficiencies become large constraints.
Proposal creation delays. Pricing ambiguity. Discount authority confusion. CRM workflow gaps. Onboarding handoffs that depend on individual heroics.
At $20M, a salesperson might personally manage onboarding.
At $40M, that model collapses.
Scaling requires tightening:
- Proposal automation
- Pricing governance
- Approval thresholds
- CRM workflow integrity
- Defined post-sale handoffs
Growth exposes weak seams. The higher you climb, the less forgiving those seams become.
Craft Shop vs. Factory
If you step back, the transition from $20M to $40M is less about revenue and more about identity.
Here’s an analogy I use frequently:
At $20M, you’re a craft shop:
- Relationship-driven
- Highly personalized
- Dependent on key individuals
- Flexible but inconsistent
At $40M, you need a factory:
- Repeatable
- Measurable
- Structured
- Continuously improving
Factories are not less human. They are simply built to produce predictable outcomes at scale.
So…Can You Double?
Yes. I’ve seen it done.
But doubling organically requires more than ambition. It requires deliberate strategy, specialized roles, process rigor, data discipline, marketing alignment, cultural evolution, and operational infrastructure.
The real question isn’t whether doubling sounds ambitious (it is).
It’s whether you’re prepared to build the organization capable of sustaining it.
Because what got you here — as good as it was — will not automatically get you there.
And that’s where leadership either gets serious…
Or stays comfortable.