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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.
What is focal podcast?
Pivotal early lessons of today's best startups.
Welcome to the focal podcast where we go deep with some of today's best founders and operators on ONE crucial lessons from their early days.
This podcast is not the usual "highlight reel" startup podcast that goes one inch deep across 20+ topics. Rather, we ask the questions you’d ask if you were sitting across from them. No fluff, just the real, actionable insights you’d get if these founders were mentoring you 1on1.
We cover topics including:
- What worked and why.
- Costly mistakes and how they fixed them.
- Frameworks that truly made a difference.
- Tactics to move faster.
- What they wish they’d known sooner.
- And much more!
"Only a fool learns from their own mistakes. The wise learn from the mistakes of others."