How to be OVEREMPLOYED as a SAAS SALES REP in 2025

May 30th 2025 by Work Two Remote Jobs

If you work in tech sales and have ever wondered whether it is possible to hold down two full time jobs at once, you are not alone. In 2025, being overemployed has become a real, practical option for high performing SaaS sales reps. The growth of remote work, flexible schedules, and results driven roles has created the perfect environment for sales professionals to double their income without doubling their stress.

This article will walk you through what overemployment looks like in SaaS sales, how to do it the right way, and what you should know before diving in.

What Does Overemployed Mean

Being overemployed means holding two full time remote jobs at the same time. It is not a side hustle. It is two separate employers, two pipelines, and two sets of responsibilities. And yes, people are doing it. Successfully.

The reason this is possible in SaaS sales is because your value is measured by one thing—results. If you are closing deals and hitting your quota, most companies are not asking how you spent your afternoon. This opens the door for motivated reps to work a second job, assuming they can balance both roles.

Why SaaS Sales Works for Overemployment

SaaS sales is one of the few career paths where time spent does not equal value delivered. That flexibility makes it ideal for overemployment strategies. You spend your day prospecting, running demos, and following up with leads. And most of it can be done independently with the help of a solid CRM and a well-organized workflow.

You also benefit from different sales cycles. Some companies have long enterprise cycles, while others are focused on fast moving SMB sales. Pairing those two together can create a natural rhythm where you are not constantly competing for your own time.

How to Be Overemployed in SaaS Sales

1. Start With the Right Roles

Before you jump into two jobs, pick the right ones. Look for roles with clear expectations and minimal micromanagement. Avoid jobs that require constant daily check ins, camera-on meetings, or strict call quotas.

Jobs with asynchronous communication and goal based performance reviews are best. You want managers who care about your pipeline, not your Slack activity.

2. Separate Your Tools and Workflows

One of the most common mistakes overemployed reps make is mixing tools. Never use the same laptop, email, or CRM for both jobs. Keep everything separate so you do not accidentally send a follow up to the wrong prospect.

This is not just about professionalism—it is about protecting yourself and the companies you work for.

3. Organize Your Calendar and Block Time

When working two jobs, your calendar is your best friend. Block out dedicated time for each company. Set regular windows for outbound work, follow ups, and internal meetings.

It helps to have one job that leans more heavily on mornings and another that is lighter or more flexible in the afternoons. You want to avoid conflicts and create breathing room between responsibilities.

4. Use Templates and Automation

You do not need to reinvent the wheel every time you write an email. Create templates for common objections, follow up sequences, and demo confirmations. Use automation inside your CRM to streamline your follow up process and reduce manual work.

Working smarter—not harder—is how you stay on top of both jobs without losing your mind.

5. Keep an Eye on Performance

The key to staying overemployed is not flying under the radar. It is consistently delivering results. Monitor your own metrics closely. If your pipeline starts to slip or you miss a forecast, it can trigger red flags with your manager.

Being overemployed only works if you can consistently hit or exceed your targets in both roles.

What Overemployed Sales Reps Say

Most SaaS sales reps who are overemployed say the same thing. It is not about greed. It is about freedom. Having a second job gives you financial security, a stronger safety net, and the ability to walk away from a toxic environment if needed.

But it is not easy. You need strong systems, clear boundaries, and the discipline to manage your time effectively. The reps who succeed are the ones who treat both jobs like real jobs and hold themselves to a high standard.

Final Thoughts

If you are in SaaS sales in 2025, becoming overemployed is more than just a possibility—it is a smart strategy if you are intentional about it. The key is not to hustle endlessly. It is to work efficiently, stay organized, and focus on results.

Being overemployed can help you double your income, build long term stability, and take control of your career. But only if you do it the right way.