What signal indicates the right time for a startup to move upmarket into enterprise sales?

Stevie Case · Jan 25, 2023

Vanta moved upmarket because it was pulled there by inbound success it hadn't pursued, and the move is additive rather than a replacement for SMB

Mid-market and a few enterprise customers started arriving on their own, so she created a dedicated team on a different comp plan, ran it as an A/B test, and it worked immediately

16:10 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Noah Desai Weiss · Jun 16, 2023

The signal that an SMB-first company is ready for enterprise is independent pockets of teams inside large organizations adopting the product on their own

That organic demand proves people at large companies already get value, so you can go negotiate an enterprise agreement and let them tell you the 17 things missing, which starts the enterprise journey

Scope: even if you lack the control and administration features large companies need

28:36 20Product: Slack CPO Noah Weiss on How to Master Product-Led-Growth, The Biggest Mistakes Founders Make When Scaling Into Enterprise & What Needs to Change with your Product, Team and Processes when Scaling From PLG to Enterprise

Sean Murray · Jan 24, 2024

The signal to move upmarket should come from data — inbound interest from larger companies and how customers are actually using the product

Let the data teach you whether you are able to creep up market

42:20 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Dan Siroker · May 15, 2024

The right time to move upmarket is when you feel market pull — individuals inside large companies bypassing process to use your product — at which point salespeople should augment existing relationships rather than cold call

Signals beyond a logo mean someone feels the pain viscerally; without that, cold outbound into the Fortune 100 gets dismissed because the buyer has no intrinsic interest in what you do

20:23 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless