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Looking to break into tech sales, or level up quickly?
Next Sales Start Date: June 1st, 2026
At Olly Olly, we’re hiring driven, competitive individuals who want a clear path to six figures, hands-on training, and the opportunity to own deals within months—not years.
You won’t be stuck shadowing forever. You’ll start by generating opportunities for senior reps, then quickly transition into running your own full sales cycle in a high-performance environment.
What you can expect:
- $45,000 base salary (paid weekly)
- Uncapped monthly commission (earn up to 170% of revenue sold)
- Realistic first-year earnings: $80K–$120K+
- Top performers earned $295K+ in 2025
- Clear promotion path from ramp → full-cycle Account Executive
If you’re coachable, competitive, and ready to bet on yourself—this is where you build real income and real career momentum.
About Olly Olly
We’re on a mission to help small businesses grow—without the complexity.
Olly Olly combines hands-on marketing expertise with powerful, easy-to-use software to help business owners generate leads, get more calls and reviews, and grow sustainably.
We’ve already helped thousands of businesses succeed, and as we evolve into a human-centric SaaS company, our sales team is at the center of that growth.
Named one of Built In’s 2026 Best Places to Work in Charlotte
Why This Role Exists
We’re continuing to invest in our sales team by bringing in individuals who want to develop real sales skills and earn based on performance.
This isn’t a “sit back and manage accounts” role. This is a high-output, new business sales environment where effort directly drives income.
If you’re looking for a place to build discipline, sharpen your sales skills, and be rewarded for results—this is that environment.
What You’ll Be Doing
- Learn and execute a proven outbound sales process
- Generate new business pipeline via outbound prospecting (70–80 cold calls/day)
- Set appointments for senior reps during your first month (ramp period)
- Transition into full-cycle sales (prospect → close) as early as your second month
- Sell digital marketing and SaaS solutions to small business owners
- Handle objections, think on your feet, and create urgency
- Participate in daily huddles, call reviews, and ongoing training
What Success Looks Like
- You show up consistently and execute the process
- You improve quickly through coaching and repetition
- You hit activity targets and build pipeline daily
- You earn the opportunity to run your own deals—and close them
Who This Is For
- Competitive and motivated by performance-based income
- Coachable and quick to apply feedback
- Brings energy, discipline, and consistency every day
- Excited to help small businesses grow
Who This Is NOT For
- You prefer account management or inbound-only roles
- You’re uncomfortable with high call volume or outbound sales
- You’re looking for a low-pressure or low-activity environment
Compensation & Growth
We believe performance should be rewarded—without limits.
- $45,000 base salary (paid weekly)
- Uncapped commission (up to 170% of revenue sold)
- Base increases tied to performance milestones (up to $85K)
- Top performers: $295K+
Perks & Benefits
- In-office: Monday–Friday, 8AM–5PM CST
- High-energy, competitive sales floor (music, contests, daily wins)
- Medical, dental, vision, and mental wellness benefits
- 3 weeks PTO + 10 paid holidays
- 401(k) with company match
- Future Leader Development Program (path into leadership)
What We’re Looking For
- Comfortable making high-volume outbound calls
- Competitive, coachable, and performance-driven
- Strong communication and objection-handling skills
- Experience with CRM tools (HubSpot preferred)
Diversity, Inclusion & Work Eligibility
Candidates must be authorized to work in the United States and able to complete I-9 documentation. We are unable to provide visa sponsorship at this time.
At Olly Olly, we believe diverse backgrounds, perspectives, and experiences make our team stronger. We’re committed to building an environment where individuals are respected, supported, and given the opportunity to succeed based on performance and potential.
