About The Position

Olly Olly is seeking driven, competitive individuals for an Inside Sales B2B Account Executive role. This position offers a clear path to high earnings, hands-on training, and the opportunity to manage full sales cycles within months. The role involves generating opportunities for senior representatives, with a quick transition to running one's own sales cycle in a high-performance environment. Olly Olly's mission is to help small businesses grow through marketing expertise and user-friendly software, focusing on lead generation, customer engagement, and sustainable growth. The sales team is central to the company's evolution into a human-centric SaaS company. This role is designed for individuals who want to develop real sales skills and earn based on performance in a high-output, new business sales environment where effort directly impacts income. It's an opportunity to build discipline, sharpen sales skills, and be rewarded for results.

Requirements

  • Comfortable making high-volume outbound calls
  • Competitive, coachable, and performance-driven
  • Strong communication and objection-handling skills
  • Experience with CRM tools (HubSpot preferred)
  • Authorized to work in the United States and able to complete I-9 documentation

Nice To Haves

  • Looking to break into tech sales, or level up quickly
  • Coachable and quick to apply feedback
  • Brings energy, discipline, and consistency every day
  • Excited to help small businesses grow

Responsibilities

  • 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 the first month (ramp period)
  • Transition into full-cycle sales (prospect → close) as early as the 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

Benefits

  • $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
  • Base increases tied to performance milestones (up to $85K)
  • 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)
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