Why Going Up Market Too Early Kills Startups | Why New Categories Cannot Do Traditional Sales | Why "Sell to Pain" is Terrible Advice for New Categories | The Hidden Truth About Box, Asana & HubSpot's Growth | Matt Harmon, GTM Advisor & Former Box/Asana
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
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
Creators and Guests
Host
Pascal Unger
Co-founder / Managing Partner at focal.vc We lead pre-seeds in North America with up to $1M: We exclusively back AI native software startups at the very start. Thereafter, we help them get off the ground better and faster, supported by a network > 200 GTM executives. That's our singular, unwavering focus.