Overemployed Tips for SAAS SALES REP \\ Working 2 Remote Jobs in 2025

May 30th, 2025, by Work Two Remote Jobs

Overemployment is no longer a secret. In 2025, more and more SaaS sales reps are exploring the idea of working two remote jobs at the same time. With companies embracing remote work and digital tools keeping everyone connected, this setup is more possible than ever before. But while the opportunity is real, it comes with real responsibilities.

If you are a software sales rep thinking about becoming overemployed, here is what you need to know, including practical tips to help you navigate it all.

What Does It Mean to Be Overemployed

Overemployment is the act of holding two full time jobs at once. For most people, this is only possible with remote work. In sales, particularly SaaS sales, it is increasingly common for high performing reps to explore this lifestyle.

Sales is unique. Your performance is measured by your results, not how many hours you are sitting at your desk. If you are closing deals, no one is asking questions. That makes SaaS sales one of the most flexible and realistic career paths for working two jobs at once.

Why SaaS Sales Makes Overemployment Possible

SaaS sales is quota driven. If you are meeting or beating your numbers, your manager is usually happy. This creates a results first environment where reps can manage their own time, especially if your territory or accounts do not require daily hand holding.

Another factor is that many SaaS companies operate asynchronously. You might have a weekly pipeline review or forecast call, but most of your day is spent emailing prospects, jumping on demos, and moving deals forward. That flexibility makes it easier to run two pipelines at once if you are strategic.

Tips for Working Two Remote SaaS Sales Jobs

1. Choose Roles That Are Structured for Autonomy

Not all sales jobs are created equal. Some companies will micromanage your daily activity, while others give you freedom as long as the numbers look good. You want the second type.

Look for companies with flexible schedules, low meeting loads, and realistic quotas. Avoid companies that require call recordings, daily standups, or long onboarding timelines. Those will eat up too much bandwidth.

2. Know Your Metrics Cold

In SaaS sales, you live and die by the numbers. When you are working two jobs, it is even more important to keep tight control over your metrics.

Track your activities, demos, closes, and pipeline in both roles. Use a spreadsheet or CRM export if needed. The worst thing that can happen is losing visibility into your progress and getting caught off guard by a manager asking for updates.

3. Keep Systems and Devices Separate

Use different laptops, browsers, or virtual desktops to manage your work. Never mix tools. You do not want to accidentally email a prospect from the wrong job or confuse calendar invites.

Keeping everything, separate helps avoid costly mistakes, protects confidential data, and makes it easier to switch gears between roles.

4. Master Your Calendar

Time blocking is essential. Schedule outbound time, demo time, follow ups, and internal meetings for each job. Set recurring blocks on your calendar to make sure both roles get the attention they need.

Try to stagger responsibilities if you can. Maybe one role is more enterprise focused and slower paced, while the other is transactional and fast moving. That can help balance your workload.

5. Protect Your Reputation

Being overemployed is not about cutting corners. You still need to deliver results. Dropping the ball in one job just to protect the other defeats the point.

If you take on two roles, it is your responsibility to maintain performance in both. Be honest with yourself. If your deals are stalling or your follow ups are slipping, it may be time to reassess.

Lessons from the Field

Plenty of overemployed SaaS reps say this lifestyle has helped them build financial freedom, reduce dependence on any one employer, and even escape toxic work environments. But they all say the same thing. It only works if you stay disciplined.

You will be juggling multiple CRMs, different sales processes, and possibly competing goals. That can create stress if you are not organized. But with the right systems in place, it is possible to succeed in both roles without burning out.

Final Thoughts

Being overemployed as a SaaS sales rep in 2025 is not a pipe dream. It is happening right now. With the right roles, the right mindset, and the right habits, you can work two remote jobs and thrive.

Just remember that the goal is not to hustle constantly. The goal is to work smarter, create leverage in your life, and build something sustainable on your own terms.

Whether you call it working two full time jobs, becoming overemployed, or just taking control of your career, one thing is clear. Results matter more than hours. And in SaaS sales, results are your superpower.