Chicago, Illinois

Sales training built for how Chicago does business.

Face-to-face coaching, training and consulting for sales teams across the Chicago metro — no big stage, no script, just real conversations that close.

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Also serving Naperville · Schaumburg · Oak Brook · Evanston · Aurora

The orange octopus leaning over a table, talking with a group of business people.
The orange octopus at a whiteboard, mid-lesson, with a small team watching.

Chicago runs on relationships, not slide decks. We build sales teams that win the room — one real conversation at a time.

Where are you at?

Pick your role.

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New to Sales

You have a super-power.

You have an opportunity to learn the top techniques untainted by biases and old habits. You can quickly catch and surpass your peers. Ask about ‘weaponized ignorance’.

We’re excited for you. The world is yours.

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Sales Professional

The best career in the world.

Nobody has as much control over their success and fulfillment than a career sales professional.

Master your craft. Master your career.

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Owner or Manager

Your sales team.

Some months it runs like a Swiss watch. Some months it’s herding cats. Either way, every win and every loss lands on your desk.

Every win. Every loss. Your desk.

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OOSA also runs sales training in Milwaukee and is actively building relationships with clients and strategic partners across Canada and the USA. See the full list of areas we serve.

Let’s talk about your Chicago sales team.

Start with a no-charge, no-obligation chat about what would be most impactful.

Book a Consult Become a Partner