At one of the companies I worked for, we focused on mid-market customers because the product wasn’t enterprise-ready yet. The reporting wasn’t there, scalability was an issue, and we didn’t have the robust integrations enterprises expect. Over time, as the product matured, we expanded into enterprise—but that transition required a completely different sales motion, team, and mindset.

At another company, the product was ready for both segments from the start. Instead of picking just one, we split the sales team, with high-velocity reps focused on mid-market and experienced, relationship-driven sellers handling enterprise.

There is no one answer, but there can be wrong ones (or at least suboptimal ones).

So, how do you choose which market to target first? And if you want to do both, how do you avoid spreading yourself too thin?

Your enterprise segment is part of your ICP

The first step in deciding your market focus isn’t sales strategy—it’s your ideal customer profile (ICP). A few aspects to consider:

  • Product readiness: Your product likely needs to have enterprise-level features, such as scalability, advanced reporting, SSO, and high availability to be considered by enterprises. What features are considered table stakes for this market will depend on category maturity, competition, and minimum customer requirements.
  • Customer readiness: If you sell a cutting-edge cybersecurity product that solves the latest attacks, most mid-market companies may not be sophisticated enough to use it. Conversely, if your product simplifies an existing enterprise solution for mid-market use, the opposite may be true.
  • Business drivers: Some compliance requirements only apply to companies of a certain size, such as those processing a minimum amount of credit card transactions or being publicly traded. Enterprises may turn to big consulting firms, while mid-market firms look for a more standardized approach.
  • Financial situation: Your own company’s financial situation may also play into it - specifically if you don’t have a lot of funding. Enterprise deals are complex, unpredictable, and fewer in number. This creates a feast-and-famine scenario—high rewards but significant risks. Mid-market may provide steadier revenue, with occasional enterprise deals as a bonus. Additionally, enterprises hesitate to engage with vendors lacking financial stability.

How to define your market segments

There is no universally accepted definition of SMB (small and medium businesses), mid-market, and enterprise—it’s yours to define. Typically, these definitions drive sales team segmentation, but there’s more to it. Analyze the segments and determine where the edge cases lie.

For example:

  • SMB may be below a certain size where human-led sales aren’t cost-effective, leading to an e-commerce-only approach (or no service at all).
  • Mid-market may include companies up to a size where there is typically one technical decision-maker and one economic buyer.
  • Enterprise involves more complex buying motions with purchasing committees.

These definitions impact your average sales price (ASP), sales cycle, and go-to-market motion (e.g., inbound vs. outbound). Review and refine them annually.

The five biggest differences between mid-market and enterprise

I’d like to share some key figures from the recently published IT & Cybersecurity Buyer Insights Report by TechnologyAdvice. These insights illustrate trends I’ve observed firsthand:

1. Buying cycles: speed vs. complexity

  • Mid-market deals close faster—typically within 3-6 months.
  • Enterprise deals take longer—83% of large companies take 3+ months, and nearly 40% take over 6 months.
  • If you need revenue quickly, mid-market is more predictable.

2. Who makes the decisions?

  • Mid-market: Fewer stakeholders; often the CEO and CFO are directly involved.
  • Enterprise: Long buying committees—60% of enterprises have 6+ stakeholders, and nearly 30% involve 10+ people.
  • More stakeholders mean longer deal cycles and a greater need for sales enablement content. You’ll need enterprise account managers who can navigate these complex sales.

3. What are their top priorities this year?

  • Mid-market: Focuses on network infrastructure and cybersecurity investments.
  • Enterprise: Prioritizes cybersecurity, cloud migration, and AI adoption.
  • If your solution requires a mature security team, enterprise may be your only viable market.

4. Where do they get their information?

  • Mid-market: Trusts customer testimonials, case studies, and product reviews.
  • Enterprise: Leans on independent analyst reports and expert research.
  • These stats were close, so you should conduct your own research into the buyers’ journey.

5. Why do they buy cybersecurity solutions?

  • Mid-market: Buys to reduce risk and fill security gaps.
  • Enterprise: Focuses more on compliance, regulations, and incident response.
  • Be cautious: Mid-market compliance needs are often driven by contractual obligations from larger enterprise clients, while enterprises develop policies proactively to prevent data breaches.

Should you try to serve both?

Many cybersecurity startups are tempted to go after both mid-market and enterprise from day one. That’s an option, provided you don’t spread yourself too thin.

If you do want to sell to both:

  • Hire for mid-market first and let founders handle enterprise deals until you can hire seasoned enterprise sales reps. Mid-market reps are usually lower-cost hires, and you can train them on simpler deals before scaling up.
  • Segment your sales team—mid-market and enterprise reps require different skill sets. Mid-market sales reps operate like fast-paced bistro waiters (high volume, quick turnaround), while enterprise reps are like fine-dining servers (strategic, high-touch engagements). Choose the right profiles for each role.
  • Take inbound deals in all segments, as long as you believe your product can succeed in them. However, be wary of becoming too dependent on a single enterprise client, as they can steer your roadmap away from your long-term vision.

For more on hiring your first sales rep and structuring your team, check out my post on how to hire your first salesperson.

Final thought: Pick your focus, then commit

There’s no single right answer. If your product requires extensive customization and customer expertise, enterprise may be the better fit. If you need quicker wins and a scalable go-to-market motion, mid-market is the way to go.

But whatever you choose, commit and move forward. Half-assing both segments is a recipe for wasted resources and lost deals. Set a check-in point to take stock and adjust based on your learnings.

Are you struggling to define your ideal customer? Let’s talk.