Moving upmarket, the right way

When should a startup go from SMB to enterprise - and when should you not?

I break this down with a former revenue leader at Box, SurveyMonkey, Asana, etc - Matt Harmon (ex‑Box, Asana, SurveyMonkey). We discuss the real signals for enterprise readiness, why security/compliance readiness matters, and why “we’ll build it if you buy it” kills confidence. We also compare playbooks for existing vs. new categories, the land→expand reality, and how to balance self‑serve revenue with enterprise ambitions.

In Today's Episode We Discuss:
1:42 Why the “go upmarket” conversation starts early
4:53 Company readiness: security, compliance, SEs, forecasting shifts
10:57 Signals it’s curiosity-only vs. a real enterprise opportunity
16:45 “Is it someone’s KPI?” and the need for true pain/need
18:36 Existing category = one path to buy (ripping/replacing)
22:52 New category upmarket: shared services & proving uniqueness
28:28 Land→expand and product-led reality
33:08 Don’t force a model—map the customer journey first
37:57 Positioning and intellectual honesty at ~$1M ARR
40:00 Category creation vs. innovating in an existing one
45:07 Why not to fear SMB/self-serve revenue
47:15 Don’t over-index on “sell to pain” for new categories
50:15 Founder advice: embrace ambiguity and EQ
52:25 What great VCs do: back leaders who can hire leaders