Should you sell for a startup or big company?

Ryan Walsh, CEO and Founder
Ryan Walsh, CEO and FounderSep 15, 2022

Many times in your career you will probably have to make a decision to work for new startup, or go the safer route (maybe), and sell for a large company instead. Each have their advantages and disadvantages, especially when working in the sales industry. We’ll break some of them down below.

Startup advantages:

Visibility – you’ll have regular all hands, CEO updates, deeper understanding of the biz, which is exciting and fun
Making an impact – every deal matters, and you’ll be closing some of them
Growth opportunities – as the team grows, you’ll be in a position to take advantage
Start-up MBA – you’ll learn a ton about marketing, growth, product, etc
— Maybe a bit more upside on equity (but don’t factor this too heavily)

Startup disadvantages:

Lack of formal training / onboarding – don’t expect them to have really anything
Business stage risk (burn rate?)
Lack of extensive ecosystem to support you (tech stack, built out SDR org, solution consultants)
Senior leadership figuring it out (have they done this before?)
Initial comp (OTE) may be a tad lower

Big company advantages:

They’ll train you up
They’ll have a full ecosystem (tech stack, SCs, SDRs, etc)
Senior leadership likely has vast experience
Typical at or above market comp

Big company disadvantages:

Your contributions, no matter how well you do, will likely be inconsequential in the grand scheme of things
— Much of your success will be at the mercy of the territory you are assigned
Bureaucracy at every turn internally (process, process, process, process)
Nobody really cares about anything tbh

Dive deep into the early stage product-market fit. It’s way more important than any other factor (comp plans, who the manager is, etc).

If you want to see the highest rated companies for product market fit, go here and sort by product market fit.

We hope this helps when deciding to work for a well established company, or roll the dice with a startup.

If you are in the market for a new sales role, you can view jobs at startups and big orgs here.

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