What genuinely changes for a company as it moves upmarket from SMB toward enterprise?

Kaz Nejatian · Aug 14, 2024 · hedged

Serving enterprise clients requires SOC 2, compliance, permissioning, customer success and other features small businesses never need, which effectively makes you a different company

Scope: speaker flags his own naivety and invites correction

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AJ Tennant · Oct 23, 2024

Security is the biggest challenge in going upmarket, and people—especially R&D organizations—underestimate how to navigate security, deployment, POCs and pilots

Large enterprises, especially R&D organizations, go extremely deep on data protection and security questions; one Glean co-founder spent twenty hours of calls on the same security conversation for a single account

Scope: especially with R&D organizations

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Ben Fiechtner · Aug 2, 2024

The selling motion should be the same from commercial to enterprise — solution selling, understanding the client's problems, giving a point of view, creative deal construction — but resourcing must scale up with the internal and external stakeholder complexity of the largest accounts.

Enterprise is the same game with higher stakes and far more stakeholders, so you need more people, capacity and yield on the biggest companies while the long tail should be pushed to self-serve for cost-of-sale reasons.

Scope: motion identical, resource allocation not; long tail should be self-serve

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Yamini Rangan · Mar 18, 2025

It is a myth that moving upmarket requires an entirely different company and motion; hiring a wave of enterprise-class reps would break the system and the culture, whereas incrementally fitting product and upskilling existing reps and partners segment by segment is the better way to scale upmarket

They went 200 to 500 to 1,000 to 2,000 employees, making the product a perfect fit for the next segment and up-leveling the sales and support organization each year, which let them bring along reps and the partner ecosystem while continuing product innovation

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Stevie Case · Jan 25, 2023

Moving upmarket is a fundamental shift in the story of the problems you solve, not necessarily a change to the product

At Vanta the underlying automated compliance product is identical, but SMBs are solving getting their first SOC 2 while mid-market and enterprise want a single pane of glass for compliance, and they measure success differently — speed to compliance versus time saved and risk reduced

14:50 Shift is in the story of problems solved not the product itself

Harry Stebbings · Oct 23, 2024

Moving upmarket is not an easy transition — the whole company has to move, including product requirements like SOC 2, compliance and permissioning

You cannot simply decide overnight to also be an enterprise company

12:06 Whole company not just sales must move upmarket together

AJ Tennant · Oct 23, 2024 · hedged

It is possible to move fast upmarket, at least from a sales segmentation standpoint

12:26 Sales segmentation alone can move fast upmarket

Dave Kellogg · Jan 31, 2024

The biggest mistake founders make expanding into enterprise is assuming their product will work in enterprise without understanding enterprise requirements

A big company is not a large small company — enterprise requirements are qualitatively different

65:43 Assuming product works in enterprise without meeting enterprise requirements is the top mistake

Aman Narang · Aug 21, 2024

Across restaurant segments the sales model differs materially while the service model differs only somewhat, so SMB and enterprise are not fundamentally different companies

Franchise customers can feel a lot like SMB, blurring the service distinction

38:10 Sales model differs materially by segment while service model differs only somewhat

Yamini Rangan · Mar 18, 2025 · hedged

The point where moving upmarket genuinely feels different is when the buying process shifts from a single budget owner to a committee including IT, procurement, security and sometimes the board

Selling to a committee requires different skills and a different process than selling to a sole proprietor or a VP of marketing, so the sales team has to be upskilled

25:19 Shift from single buyer to buying committee marks the real upmarket transition