Using AI TOOLS to Work 2 Remote Jobs as a SAAS SALES REP

May 30th 2025 by Work Two Remote Jobs

Working two full time remote jobs in 2025 is not just a trend—it is a strategy. And for SaaS sales reps, it has become more possible than ever thanks to the rise of AI tools. These tools are helping sales professionals manage multiple pipelines, stay organized, and meet quota for two companies at the same time without burning out.

If you are a SaaS sales rep thinking about becoming overemployed, this guide will show you how to use AI to work smarter, close deals more efficiently, and maintain a healthy work balance.

What Does It Mean to Be Overemployed

Being overemployed means holding two full time remote jobs at the same time. In SaaS sales, this typically means managing two separate pipelines, prospecting for different companies, and handling two sets of quotas. It sounds intense—and it is—but with the right systems and tools, it can be done.

Because SaaS sales is results driven, not time tracked, many reps find that as long as they’re closing deals and staying on top of their numbers, managers are happy. That flexibility creates room for overemployment, especially when enhanced by AI.

Why AI Is a Game Changer for SaaS Sales Reps

AI tools are built to streamline repetitive tasks and increase efficiency. In sales, that includes writing emails, scheduling meetings, qualifying leads, and tracking pipeline activity. When you’re overemployed, time is your most valuable resource—and AI helps you protect it.

Using AI doesn’t mean cutting corners. It means removing friction so you can spend more time actually selling.

Best AI Tools for Overemployed SaaS Sales Reps

1. ChatGPT or Jasper for Writing Sales Emails

Whether you’re sending follow ups, cold emails, or demo recaps, using AI to draft your messages can save you hours every week. You can build a library of templates and use AI to personalize each one based on the prospect or stage of the deal.

The key is to edit and tweak the output so it still sounds like you. But for volume and speed, tools like ChatGPT or Jasper are incredibly helpful.

2. Grammarly for Polishing Communication

When you’re moving quickly between two roles, mistakes can happen. Grammarly helps clean up grammar, spelling, and tone so your emails are polished and professional—especially when switching contexts throughout the day.

3. Calendly with AI Integration

Managing calendars for two roles can get tricky fast. Calendly helps simplify meeting scheduling, and when paired with AI scheduling assistants, it can automatically suggest optimal times and even adjust your calendar based on availability or location.

This keeps your meetings from overlapping and helps you avoid unnecessary back and forth.

4. AI-Powered CRM Assistants

Some modern CRM platforms now include built-in AI assistants that can write call summaries, identify deal risks, and recommend next steps. Tools like Salesforce Einstein, HubSpot AI, and Gong’s AI features can save you from manually logging notes and help you prioritize follow ups across both jobs.

5. Automation for Task Management

Using tools like Zapier or Notion AI, you can automate reminders, track your to-dos, and organize your outreach lists. When you’re working two jobs, it is easy to let small things slip. AI can help you stay accountable without constantly checking boxes all day.

How to Keep Both Roles Sustainable

AI helps with speed and organization, but the real secret to being overemployed is having clear boundaries. Use separate laptops, email accounts, and CRMs for each job. Block time on your calendar for each company and avoid back-to-back calls that put you in a rush.

If one role is high touch, try to pair it with a role that is more independent or has a longer sales cycle. You do not want to be chasing thirty deals in two different companies at the same time unless you have strong systems in place.

What Overemployed Sales Reps Are Saying

SaaS reps who are successfully managing two jobs say AI gives them just enough leverage to make it work. They are using it to handle busywork, automate follow ups, and stay ahead of their quotas. Most importantly, they say that using AI helps them maintain energy and avoid burnout.

At the end of the day, overemployment is not about slacking off. It is about being strategic and maximizing your time. AI helps make that possible.

Final Thoughts

Using AI tools to work two remote jobs as a SaaS sales rep in 2025 is not only possible—it is happening right now. With the right mix of discipline, organization, and automation, you can manage two full time sales roles while still delivering real results.

AI will not close the deals for you. But it will help you work faster, smarter, and more efficiently. And if you are aiming to be overemployed, that kind of leverage is exactly what you need.