Elan Jones and Bradley Robinson are two of the best MSP salespeople in the country — and they work at the same company. Elan sold beer and cannabis before walking into IT sales the month the world locked down, then won MSP Salesperson of the Year. Bradley came from operations and project management, had never really sold, and became a two-time national Sales Champion finalist. Neither came from tech.

This one's a first for the show: two sellers from the same shop, eCreek IT in Denver, breaking down a sales process repeatable enough to mint champions out of totally different people. We get into selling with confidence, why price objections are usually a value problem, how they keep a discovery call conversational without abandoning the checklist, the camaraderie of a two-person sales team, and where AI actually helps versus where it's just noise. If you're an MSP owner trying to build a sales engine that doesn't depend on you, this is the playbook.

What You'll Learn

• Why most price objections are really value problems from a weak discovery call

• How to keep a discovery call conversational without abandoning the checklist

• What it actually takes for an MSP owner to replace themselves in sales

• Why drive beats credentials every time (and the camping story that proves it)

• Where AI genuinely helps in sales — and where the human-first approach still wins

Books & Resources Referenced

• Myers-Briggs Type Indicator — Elan and Bradley both tested as ENTJ despite their different backgrounds. - https://www.myersbriggs.org/my-mbti-personality-type/mbti-basics/

• Calendly (referenced as "Calum"/scheduling tool) — automated meeting reminders and follow-ups. - https://calendly.com

GEO (Generative Engine Optimization) — the emerging practice of optimizing to be recommended by AI search, discussed re: getting surfaced by ChatGPT for "IT providers in Denver."

Art Sobczak has been selling on the phone since he was 14 — starting with tickets to the Omaha police fundraising circus. Forty-plus years later: founder of Business By Phone, author of Smart Calling (three editions), host of The Art of Sales, 1,500+ trainings — including one for my first inside sales team at the US Chamber of Commerce twenty years ago.

We get into what AI actually does for prospecting, why he'll never say "this is a cold call," the Salesperson's Oath, turning gatekeepers into allies, and the four pillars that separate salespeople who execute from those who collect training. If you or your team make outbound calls, this is the masterclass.

What You'll Learn

• Why AI is the greatest assistant — and worst replacement — salespeople have ever had

• Why personalization without relevance is just spam

• The Possible Value Proposition: the opener formula that replaces "this is a cold call"

• Why permission-based openers trigger fight-or-flight in your prospect's brain

• The Salesperson's Oath: first, create no resistance

• The social engineering approach that turns gatekeepers into allies who prep your prospect before you call

• "If the music is still playing, stay on the dance floor" — why rushing to book the meeting kills live conversations

• The four pillars of top performers — and why identity beats discipline (Be-Do-Have, shades of Atomic Habits)

• The backwards math: why 6-8 meetings a month might take 8 dream prospects and a handwritten note, not 14,000 dials

▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox

▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com

---------------------------

Books & Resources Referenced

• Smart Calling: Eliminate the Fear, Failure, and Rejection from Cold Calling (3rd Edition) by Art Sobczak - https://www.amazon.com/Smart-Calling-Eliminate-Failure-Rejection/dp/111967672X

• How to Get a Meeting with Anyone by Stu Heinecke - https://www.amazon.com/s?k=how+to+get+a+meeting+with+anyone+stu+heinecke

• Get the Meeting!: An Illustrative Contact Marketing Playbook by Stu Heinecke - https://www.amazon.com/Get-Meeting-Illustrative-Marketing-Playbook/dp/1948836440

• Atomic Habits by James Clear - https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

• Art's First 20 Seconds Formula masterclass — smartcalling.com

• The Smart Calling Report newsletter — via smartcalling.com

• The Art of Sales podcast — theartofsales.com

• Dale Dupree Podcast Episode - https://www.youtube.com/watch?v=DotK-CSfWOI

• Chris Walker Podcast Episode - https://www.youtube.com/watch?v=2o5mLPdJp2E

▸ Slides + every prompt from this talk (free): mspsalestoolbox.com

▸ Work with us: mspsalespartners.com

AI has changed how companies prospect, research, and communicate, but many of the world's largest technology companies continue investing heavily in human sales teams. This episode explores what AI can automate, what it still struggles to do, and why trust, judgment, and complex buying decisions continue to require skilled people.

• Why automation hasn't eliminated the need for human sales conversations
• Which parts of the sales process AI handles well—and which parts it doesn't
• What the hiring decisions of major technology companies suggest about the future of sales

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

A high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates that are 68% — a the lowest rate — and why consistency in process matters more than most sales teams realize.

• The qualification mistake that causes many MSPs to leave deals on the table
• Why strong discovery creates higher close rates later in the process
• The structure top performers use instead of overwhelming prospects with proposals and quotes

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

A lot of people feel stuck because they think they need more information, another strategy, or outside guidance. But often, the real problem is execution avoidance. This episode explores the growing gap between the things we know we should do and the things we actually complete — and how that gap quietly impacts business growth, health, relationships, and momentum.

• Why most people already know the decisions that would improve their lives
• The hidden psychological cost of carrying an unfinished “should list”
• How scheduling difficult tasks shifts the brain into execution mode

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

When difficult decisions start showing up everywhere at once — business, marriage, parenting, finances, health — it’s easy to assume life is breaking down. But often, those seasons are actually periods of transition and recalibration. In this episode, Ray explains why hard conversations and uncomfortable decisions are usually the entry point to meaningful progress, and how avoidance quietly creates long-term dissatisfaction.

• Why periods of intense pressure often happen right before major growth
• The hidden long-term cost of avoiding uncomfortable decisions
• How to reframe difficult seasons as leverage points instead of warning signs

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

A high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates as high as 76% — and why consistency in process matters more than most sales teams realize.

• The qualification mistake that causes many MSPs to leave deals on the table
• Why strong discovery creates higher close rates later in the process
• The structure top performers use instead of overwhelming prospects with proposals and quotes

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Dale Dupree sold copiers for 13 years and outsold his industry average by 11x — using a crumpled piece of paper instead of a thousand cold calls. After losing his father to cancer, he founded The Sales Rebellion.

We got into why he thinks AI is making sales worse, how 20 letters outperformed a 4-person SDR team, why he'd hire a grocery bagger over a polished resume, and what servant leadership looks like when nobody's watching.

What You'll Learn

• Why a crumpled letter consistently outperforms thousands of cold emails
• How an Australian SDR booked 12 meetings with 20 letters — and got written up for it
• The one interview question Dale uses to identify coachable hires
• Why the SDR model fundamentally breaks relationship-first selling
• What Dale's father taught him about leadership at 5 AM without knowing anyone was watching

Resources

• thesalesrebellion.com
• Dale on LinkedIn: linkedin.com/in/copierwarrior

//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram