01Strategy
Where to play and how to win
- Which free accounts look like enterprise buyers
- An enterprise offer that leaves self-serve intact
- The story for the new AI product, with proof
Software with a large free base, 50 to 150 people
An enterprise business inside a self-serve one
A large free base, and a new enterprise team. Somebody has to find the accounts worth selling.
An example drawn from companies at this stage, not a client story.
The situation
One enterprise seller cannot mine a small-business base and carry a quota. The best accounts already use the product.
You might recognize it
- Low public pricing and a large self-serve base.
- One or two enterprise sellers, with nobody feeding them pipeline.
- A new AI product with no named customer yet.
The number to watch
Enterprise revenue as a share of the total
Reach is proven. The next question is the enterprise slice.
How we would run it, end to end
02Design
The operating system behind the number
- Expansion signals from usage, scored and routed to sales
- Ownership rules between self-serve and sales
- An enterprise process with security and procurement stages
03Execution
Run it, measure it, keep what works
- Account research and outreach into the existing base
- The first enterprise case studies, built with customers
- Security answers ready before the questionnaire arrives
- The Monday brief: enterprise pipeline and expansion by account
The first 90 days
Weeks 1 to 2
Usage data read. The accounts worth selling to, ranked.
Weeks 3 to 6
Scoring, routing and ownership rules live. Plans for the top 50 accounts.
Weeks 7 to 12
Outreach and case studies running. Enterprise share reported weekly.
What Monday looks like
SampleMonday briefWeek 8
The number: Enterprise revenue as a share of the total
What moved
- 14 free accounts crossed 200 active users. All 14 routed to the enterprise team.
- Two security reviews opened. Standard answers covered most questions.
This week
Draft the first AI case study with a logistics customer.
What you keep
An expansion engine: signals, routing, an enterprise process and proof.
Functions it touches
Sound familiar? Tell us what's stuck and we'll bring what we found.