Are You Better Off in Sales at a Startup or an Established Company? It Depends

Are You Better Off in Sales at a Startup or an Established Company? It Depends

Greg McBeth

Salespeople are in demand. According to LinkedIn research, sales experts have risen to the top of recruiters’ "most wanted" lists, and sales jobs are two of the three most recruited roles at tech companies. But not all sales jobs are the same.

Sales jobs at startup companies are volatile and exciting. But emerging companies can quickly go out of business, leaving salespeople (and everyone else) high and dry. Corporate sales can be risky for other reasons, especially if a top performer doesn’t gel with the culture or wants to explore other opportunities.

What’s the best choice for you? As is usually the case, it depends. Talented sales professionals have a lot of options available, but they need to determine whether their strengths, personal objectives and penchants lean toward putting down roots with a fledgling firebrand or a steadfast, known commodity.

Established Brand or New Possibilities?

Sales has a basic rhythm: attract prospects, convert prospects, renew customers, cross-sell or up-sell customers, repeat. Within that basic rhythm, the corporate selling environment affects the tempo and style used by the sales team.

Let's look at legacy brand selling first. In general, successful sales at a large company requires the willingness to follow an established and proven method of success. Behemoths already have street cred; sales professionals who are operationally competent and can represent the name well will generally meet or exceed expectations.

Sales talent with low risk tolerance tend to gravitate toward historically successful companies where they can rely on resources galore, established methods and unending support. There, they can hone their skills without worrying about the next paycheck or introducing a novel product or service to skeptical clients. As long as salespeople are willing to follow their employer’s internal rules and protocols, mesh with the culture of the team and work hard, they can expect a reasonably stable working environment and quota attainment.

Of course, not everyone thrives in consistency. It can be tough to launch an innovative selling technique or build a bespoke career path at a Fortune 500 company. And sellers who do well at corporate jobs might become pigeonholed by their own success and reputation. So when they want to make a lateral move or jump to something different, they can encounter resistance from the rest of the company.

That's why salespeople who prefer a fast-paced and uncertain environment can find startup sales invigorating. Small businesses rarely have consistent routines, complex sales processes, or tons of red tape. Startups require a high degree of self-reliance and autonomy.

Those who crave variety or the chance to shift between a range of responsibilities can prosper in incredibly disruptive businesses because they don't mind the stress. This means salespeople working for early-stage organizations have the opportunity to create new experiences every day, leaning on their nimbleness to adapt to market complexities.

But the downside to jumping into a "Shark Tank" special is the constant uncertainty. Job hunters considering upstart sales roles must be ready to set their own schedules in a fast-paced scramble, not to mention accept the reality of lower pay scales and higher risk. Factors outside the salesperson’s control can lead to damaging results or shockingly low paychecks. Even the most phenomenal sales superstar can’t save an already-sinking ship.

All Sales Roads Should Be Paved With Data

Are you interested in carving out a career in sales that leaves you feeling satisfied and leverages your strongest skills? With so many choices on the horizon, you can pick and choose between a variety of company types. Yet no matter which type of sales atmosphere you prefer, resist the temptation to forge ahead solely on gut instinct.

In our tech-savvy world, data is available to inform career decision-making across the board. Sales forums and sites like Glassdoor can provide insight into the culture, sales environment and compensation at companies ranging from early-stage startups to the Fortune 500.

So are you better off at a startup or a large company? It all depends on your personality and priorities. Think about whether you would do best selling in a world of security or a realm of untapped possibilities. Always look at data before you leap. Then, pursue the path that is going to be the best fit for you.

Greg McBeth is the head of revenue at, the first turnkey AI platform that enables businesses to embed artificial intelligence into their own products, customer databases and external systems of record, all via a standard API.

After graduating from Stanford University in 2004 with an engineering degree and a focus in behavioral psychology, Greg was a professional poker player and card counter. From that experience, he developed a multidisciplinary approach to problem-solving that starts with asking, "Why?" He still uses this approach to coach companies and business professionals on how they can improve their performance. When he isn’t working, Greg can be found playing poker, attending baseball games, enjoying wine and traveling with friends and family.

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