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.
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.
The Impact You’ll Have
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.
What We Really Need From You
- 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.
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.
What You’ll Love About Working at Olly Olly
- Salary + Variable
- In office; Monday through Friday, 8AM-5PM
- Medical, Dental, and Vision Insurance
- 401(k) Retirement Plan
- Mental Health & Wellness plans
- Growth-oriented culture: Join an inclusive, international and innovative team where your contributions make a tangible difference.
Why Choose Us?
Join us during this pivotal transition as we transform from an agency to a human-centric SaaS provider. Your ideas, strategies and solutions will directly impact the success of small businesses. And our own growth!
Let’s shape the future of small business growth together! Apply now to join a team that’s as committed as they are supportive of each other.
Diversity and Inclusion at Olly Olly
At Olly Olly, we celebrate differences in background, culture, abilities and perspectives because diversity drives innovation and creativity. Your voice matters here, it really does! And your unique perspective will help us shape the future of small business growth.
