Enterprise Sales, SMB, or Mid-Market: Which One Is Right for You?

In past blogs, we've covered what questions to ask in sales interviews and how to break into a sales career. But once you're in, another question quickly follows: How do you grow?

Sales is a world of its own when it comes to career growth. There’s no one-size-fits-all path. One of the biggest decisions you'll make is choosing the type of customer you want to sell to and also what type of sales you will enjoy doing—because it directly shapes your day-to-day, your income potential, and your career trajectory.

In order to understand how you want to grow once you break into sales, we must first understand the difference between the different sales cycles in companies: SMB, Mid-Market, and Enterprise—and help you figure out which is the right fit for you.

⚡ SMB Sales

SMB (Small and Medium Business): Depending on the company you work for, SMB sales reps typically target businesses with 1–50 employees. Once you move beyond that, the accounts are generally considered mid-market. In SMB sales, the sales cycle is usually very short—often just 3 to 5 days. You’ll be working through high volumes of leads and are expected to move fast and close quickly.

Typical SMB Role:

• Fast-paced, transactional, often phone/email-heavy

• You might close multiple deals per week (or even per day)

• If you do not have a BDR team helping you generate leads, you will have to

Is this for you?

✅ Yes, if you:

• Thrive in a high-energy, competitive environment

• Like shorter sales cycles and quick wins

• Are early in your career and want to build reps fast (Typically business development reps get promoted into SMBs, also if you made a career move into tech sales but have enough experience, you could jump to an SMB role).

🛑 Maybe not, if you:

• Want to sell more strategic/consultative

• Prefer building long-term, deep customer relationships

⚖️ Mid-Market Sales

Mid-market sits between SMB and Enterprise. Deals are larger (though not too large), cycles are longer 2-3 months, and there’s usually more structure. Typical Mid-Market target companies would range from 100-1,000 employees. Depending on the company you work for, a mid-market rep would typically have a BDR help with generating leads so the rep can focus on closing the deals, though some companies have the mid-market rep also generating their own leads due to the demand/fast paced nature of the role.

Typical Mid-Market Role:

• Selling to companies with 100–1,000 employees

• Typically one to three months sales cycle

• Involves some stakeholder management

Is this for you?

✅ Yes, if you:

• Enjoy consultative selling but don’t want 6–12 month cycles

• Want to earn higher commissions

• This is the career trajectory that would follow if you want to move from BDR > SMB > Mid Market

  
  

🛑 Maybe not, if you:

• Crave either high-velocity deals or complex strategic accounts

• Want instant gratification - fast deals

  
  

🏢 Enterprise Sales

Enterprise sales is more of a complex sales. Here you would be selling to large corporations, think 1,000+ employees, multiple stakeholders and a lot of wine and dine. You can think of an Enterprise Sales account like targeting HSBC, Walmart, or Microsoft - these are large companies and the average deal size can reach the thousands, often millions. Think of this as are you a farmer or a hunter? Reason we use these comparison in sales is that a farmer takes their time and in enterprise sales, you can't rush the deal - not when there are millions at stake.

Typical Enterprise Role:

• At least 6-12 months, could exceed depending on the deal size/agreement

• Selling into organizations with 1,000+ employees

• Often involves multiple stakeholders to make a decision as well as multiple conversations/site visits/meetings

• Average deal sizes: $100K+—sometimes in the millions

Is this for you?

✅ Yes, if you:

• Love solving complex business problems

• Are patient, strategic, and thrive on long-term relationships

• Want to close fewer but much larger deals

🛑 Maybe not, if you:

• Need instant gratification

• Dislike politics/ long cycles without feedback

• Prefer inbound, high-volume pipelines

It’s important to note that you typically can’t jump straight into an Enterprise Sales role without prior experience. These roles involve complex sales cycles, multiple stakeholders, and large deal sizes—so employers usually look for reps who have already sold into large accounts or have a proven track record of handling complex deals.

If you're just starting out in sales or currently in an SMB or Mid-Market role, it's worth thinking ahead. If Enterprise Sales is your goal, start mapping out the skills and milestones you’ll need to get there. 

What Kind of Salesperson Are You?

Your Style/Preference	Best Fit
You want quick wins & variety	SMB
You enjoy consultative selling/bit longer cycles	Mid-Market
You're strategic, patient, and love big deals	Enterprise
You’re early in your career	SMB or Mid-Market
You’re looking to specialize and maximize earnings	Mid-Market or Enterprise

Are you looking for a new challenge and seeking your next sales opportunity? Get in touch with us at hello@optimyze1.com