Software Sales
I joined a small start-up that's developed a strong shift-work scheduling tool.
The founder was a waiter who bootstrapped the project, and and put together a strong tool which solves the problem.
His idea is to market it to the masses, $5/month/location. Bars, restaurants, mom and pop shif-work.
I see a much bigger value proposition marketing it for enterprise clients. Shift workers who work in manufacturing and logistics. The value the tool brings is there, and enterprise clients are spending 4-6hrs/week making and maintaining the schedules.
How do I price it and what's the best way to get our foot in the door of large enterprise organizations?
1 Reply
I joined a small start-up that's developed a strong shift-work scheduling tool.The founder was a waiter who bootstrapped the project, and and put together a strong tool which solves the problem.His idea is to market it to the masses, $5/month/location. Bars, restaurants, mom and pop shif-work.I see a much bigger value proposition marketing it for enterprise clients. Shift worke
You’re basically looking at two very different go-to-market motions, and they behave quite differently in practice.
The $5/month/location model is classic SMB SaaS: low friction, fast adoption, high volume, but limited ACV and a lot of churn sensitivity. That path works well when the product is self-serve and can spread organically through small businesses.
Enterprise is a different game entirely. The upside is real — manufacturing and logistics companies absolutely do spend a lot of time on shift planning — but the sales cycle, procurement process, and integration requirements change everything. At that point you’re no longer just selling “a tool”, you’re selling:
reliability (uptime, support, SLA)
integration (HR systems, payroll, identity)
compliance and reporting
and often customization
On pricing, enterprise usually won’t map cleanly to “per location at $5”. It becomes more like:
per employee / per active user, or
per site tiered pricing, or
contract-based annual licensing
Trying to keep SMB pricing logic in enterprise sales often leads to underpricing and a lot of support burden.
As for getting in the door, the usual realistic path is not “big enterprise first”, but:
land SMB or mid-market clients in operationally heavy sectors (multi-location hospitality, small logistics firms)
prove ROI in hours saved / scheduling efficiency
then use those case studies to justify enterprise conversations
Enterprise buyers rarely adopt first; they validate based on existing traction.
So in short: your instinct about enterprise value is probably correct, but the sequencing matters more than the idea. If you jump straight to enterprise without proof points, it tends to stall quickly.
