Ryan Staley, CEO of Whale Boss ($150MM Rev Closed) | How To Close The Biggest Deal Of Your Life

Success Story with Scott D. Clary

➡️ About The Guest

A career revenue and sales executive. Ryan Staley had his first success in business as an inside sales representative selling cutting edge technology and training to CIO’s, CTO’s and VP’s of the largest Investment Banks and Brokerages in the world. He finished #1 nationally, was promoted to Manager and then Sr. Manager.

This experience later launched Ryan into a leadership position (at a new organization) in which he was responsible for transforming a struggling business unit into the top performing office, creating an enterprise team from scratch and in developing a recurring revenue engine.

The new business unit resulted in growth from 0-$30M Annual Recurring Revenue, $30 Million in capital revenue, over (30) $500,000 plus contracts and a $20 Million contract (with ONLY 4 Sales people and without lead generation).

Ryan codified the playbook that he’s learnt and executed over every single sales role he’s held in his career and built out his own firm, Whale Boss, working with executives, CEO's or Revenue Leaders to implement a 7-8 figure sales system in relatively short, three-month sprints.

➡️ Talking Points

00:00 - Intro

04:18 - Ryan’s origin story.

14:05 - The importance of networking.

18:57 - How to move up market and sell bigger deals.

23:11 - Find larger new customers and sell more to existing customers.

24:51 - Customer referrals.

26:23 - Dropbox’s referral system.

29:29 - Help 100 million people grow their business.

35:24 - The secret strategy to sell to enterprise.

44:15 - Reinventing yourself later on in life.

46:46 - Good books for entrepreneurs.

48:12 - Ryan’s definition of success.

➡️ Show Links

https://www.linkedin.com/in/ryan-staley/

https://bit.ly/3BmuKCl

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➡️ Success Story Podcast

Stories worth telling.

Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

On this podcast, you'll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship.

Scott will discuss some of the lessons he's learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights.

He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.

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