Sales Trainer

Reports to: Director of Training and Enablement

Location : Austin TX or Charlotte NC

In Office : M-F 8am to 5pm

About the Job

Why We Need You

At Olly Olly, we’re looking for a Sales Trainer to take full ownership of new hire onboarding for the sales organization. You’ll be the very first touchpoint for every new sales rep, delivering engaging, outcome-driven training that equips them with the skills, knowledge, and confidence to succeed on the floor.

This is a hands-on role where you'll spend your time delivering live sessions, running call simulations, and coaching 1:1 and in groups for all 3 offices. You’ll work closely with Sales Leaders, Enablement, RevOps, Product, and Marketing to ensure training is relevant, aligned, and directly tied to performance expectations.

Your impact will be measured not just by classroom satisfaction, but by how quickly and effectively new hires ramp into producing reps. You’ll be shaping the culture, pace, and expectations from day one.

About Olly Olly

Olly Olly is a profitable, fast-growing SaaS company helping small businesses get found online and grow with confidence. We’re building the all-in-one marketing and revenue engine that empowers owners to rank higher, attract better leads, and convert more jobs without getting lost in marketing fluff.

Our Vision

Small businesses power our communities, and they deserve more than cookie-cutter marketing. That’s why we’re building real tools with real ROI. From search optimization to lead management, our platform is designed to help business owners thrive in an AI-driven search world.

Key Responsibilities

New Hire Training & Onboarding

• Own all new hire training for the sales org—from day one to graduation.

• Deliver engaging, outcome-driven training sessions on our products, sales process, tools, and culture.

• Coach new hires 1:1 and in group settings to build skill, confidence, and accountability.

• Facilitate roleplays, call simulations, and script practice to ensure reps are ready for live calls.

• Provide hands-on management during “phone days” in which trainees are on the phones operating as full-time Sales Reps (approximately 10 days per month)

• Ensure strict adherence to the sales process and pitch from day one.

Continuous Improvement

• Partner with Sales Leaders and Enablement to align training with real-world performance expectations.

• Track and report on onboarding success metrics (time-to-first-call, time-to-first-sale, certification pass rates, ramp performance).

• Gather feedback through surveys, observations, and performance data to continuously improve training content and delivery.

Content & Collaboration

• Build, maintain, and update training materials (presentations, playbooks, quizzes, LMS content, etc.).

• Work cross-functionally with RevOps, Product, and Marketing to ensure content is current and aligned with GTM strategy.

• Contribute to broader learning and development initiatives as the team scales.

Requirements

• Employed with Olly Olly for at least 1+ year.

• Strong understanding of our sales methodology, pitch, process, and internal systems.

• Outstanding communication and presentation skills. You make complex ideas simple and actionable.

• Reliable in your current role with a track record of consistency and performance.

• A strong sense of ownership - you build it, fix it, and raise your hand when something’s off.

• Comfortable working cross-functionally and managing multiple priorities.

• High EQ, natural confidence, and a genuine interest in helping others succeed.

• At least 1 year experience in Sales Management or Training.

Nice-to-Haves

• Background in sales enablement, onboarding, or leadership.

• Experience with LMS platforms and training content creation.

• Familiarity with HubSpot, sales analytics, or call coaching tools.

Why This Role Matters

You will play an important part in shaping the future of our sales org. The experience you create for new hires will directly impact ramp time, retention, and team culture for years to come. You’re not just training skills—you’re setting the tone for how we sell, how we show up, and how we win.