a single source, nothing corroborates it · contested
Weigh the enterprise motion against what it costs
Count the demo hours, the close rate and the annual revenue actually added before committing to selling upmarket, and price the staff, process, legal work and product demands that come with it. Some markets can be built to real scale without ever signing a custom contract.
Where this splits
The same set argues both ways: enterprise pays where seats and contract values are large and big buyers refuse to self-serve, yet measured against founder hours one bootstrapper found 26 demos worth roughly ten thousand a year and dropped the motion.
side 01 · 5 claims
Count the founder hours and drop the motion
Justin Jackson
- 1If you genuinely choose the enterprise route, accept the whole package: salespeople, long cycles and contract-by-contract negotiation for organisations with procurement teams and layered approvals.
- 2Before committing to enterprise sales, cost the calls: count the hours spent on demos, the close rate, and the actual annual revenue added.
- 3Let the shape of your market decide: where accounts are small, self-serve and low-ARPU, a large business can be built without ever signing an enterprise contract.
- 4Price the whole cost of going upmarket, not just the sales time - more staff, process, compliance, legal and meetings, plus the product work those buyers demand like mobile apps and single sign-on.
- 5Keep taking calls with prospects who match your actual customer profile even while you stop selling to the ones who don't.
side 02 · 3 claims
Big buyers pay well and will not self-serve
Jason Cohen · Justin Jackson
- 1Enterprise sales pays off mainly where billing is per-seat and contract values are large, so check that high-priced demand exists in volume before building the process.
- 2Expect large prospects to refuse self-serve: even with live chat, demo videos and an FAQ, many will insist on a video call with a founder before buying.
- 3When a procurement gatekeeper claims they can kill your deal, get your real buying contact onto the same call, because the gatekeeper often has no such power.
What it returned
- 1,000
Enterprise is defined here as 1,000 or more employees.
- 26
26 pre-qualified enterprise demos since 1 January at about an hour each, so 26 hours of founder time; half converted; the largest account was $1,990/year and the average $730/year, adding roughly $10,000 of ARR.
- 40%
40% of Slack's revenue was reported to come from contracts above $100k a year; in podcasting, uStudio and Storyboard reportedly charge up to $250k a year but the author doubted total demand justified the process.
Transistor saw this repeatedly, especially around its private podcasting feature.
Sources
- It's not just B2C vs B2B anymoreJustin Jackson · justinjackson.ca · Business-to-Enterprise (B2E) · undated · dissenting
- Should my SaaS try to get enterprise customers?Justin Jackson · justinjackson.ca · Is it worth doing enterprise sales calls? Let's do the math. · undated · dissenting
- When you want to quit because it’s just not worth itJason Cohen · longform.asmartbear.com · When you want to quit because it’s just not worth it · 2011-02-28 · dissenting
the second source
Three plays a week, for the phase you are in
No roundup of links, no news. Three tactics more than one builder arrived at separately, with the numbers each one returned and the disagreements left in.
More in sales
- Charge for it before it exists6 unconnected
- Book the buyer calls before you write any code6 unconnected
- Package more of what you own into sellable slots6 unconnected
- Interview customers when sales stall, not buy traffic5 unconnected
- Borrow credibility from the customers you have5 unconnected
- Keep a named list of dream accounts and work it5 unconnected