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Sales Development Representative, Outbound

September 9, 2026

Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We're trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide. Our customers (researchers, marketers, HR teams, nonprofits, and platform businesses) rave about how fast and easy Tremendous is to use. Check out our ratings on G2. Tremendous is profitable and growing without outside investors. We’re a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s. About The Role As a Sales Development Representative, your primary responsibility will be to secure meetings with top prospective companies and individuals. You'll work closely with one paired Account Executive to generate meetings from their target account list. We encourage account development through outbound prospecting, social selling, networking, attending conferences and field marketing events, and any sales activity that would contribute to expanding the Tremendous brand. You will be the first line of engagement with prospective customers and will have an impact on Tremendous’ revenue growth and future success. What You'll Do <ul><li>Work primarily to bring in new deals through Outbound prospecting. </li><li>Collaborate with Account Executives, as well as members of our Marketing and Customer Success teams, to develop new strategies to build our sales pipeline and grow our business. </li><li>Use Amplemarket, LinkedIn, your own network, and other prospecting tools to research accounts, identify key contacts and craft targeted messaging. </li><li>Learn our technology and effectively communicate our value proposition. Work to understand their goals and challenges to better understand how we can help. </li></ul>What You'll Bring <ul><li>1-3 years of prior sales experience, ideally in a similar outbound or SDR role. </li><li>Clever and creative problem solving. We're small and emphasize output and iteration over a sales handbook set in stone. </li><li>Independence. We all work together to solve tough problems here at Tremendous, but taking pride in experimenting and finding your own answers is the best way to learn. </li><li>Collaboration. When our SDRs uncover new trends and tactics that work to set meetings, they share them with their teammates so everyone can benefit. </li><li>Ability to thrive with a well-set quota. We want our goals to be fair and achievable. You should find these goals alongside your team and with your manager and use them as a benchmark for success. </li><li>Ambition. Ambition isn't a dirty word at Tremendous. We're a team of achievers collaborating on a fast-growing product and that means personal growth in both role and responsibility as well as tons of personal upside for you. </li></ul>What's Cool About The Role <ul><li>You'll work at a company growing quickly yet sustainably. We’re profitable with plenty more opportunity ahead. That’s good news for your career growth. </li><li>Competitive pay and equity. Base salary for this role: $65,000 - $70,000 plus commission. </li><li>Real benefits. 100% covered health (US), unlimited PTO, 12-16 weeks paid parental leave. </li><li>Fully remote. Work from anywhere in the Americas. </li><li>Great culture. Read more about how we work in our public handbook. </li></ul>Location This role is remote-first and you can work wherever you want in the Americas. Compensation Range: $65K - $70K

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...