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  • 😎 Sales rep builds a $250k/mo business, AI workflows to save hours, and the highest paid sales roles in 2025

😎 Sales rep builds a $250k/mo business, AI workflows to save hours, and the highest paid sales roles in 2025

Learn how Austin built his dream life working 4 days per week.

IN THIS EDITION

GM and happy Wednesday team. We’ve got a treat of an edition coming to you this week.

  • How this remote sales rep built a $250k/mo online business - Austin Medlin

  • AI workflows that’ll save you hours every week

  • Five of the highest paid sales roles in 2025

  • And more…

Want to be featured in BOS? Know somebody that we should feature? Please submit your information here for consideration. You don’t have to be making one billion dollars per year so long as sales has enabled you to live a pretty cool life. Thanks!

LIVE FROM THE SALES FLOOR

Cool Links to Help You Sell More (news, tools, trainings)

  • $150k+/yr sales reps share their secrets for newer reps (Nutmeg_37)

  • The government’s guide on how to sell to them (GSA)

  • LeadFi let’s you see a prospect’s buying power before a sales call

  • Use these AI workflows to save hours every week (Connor Murray)

  • Podcast: How Russell Brunson closes millions (Next Level Podcast)

  • Guarantee you haven’t taken a sales call like this (Hendrik Johannsen)

  • Five of the highest paid sales roles in 2025 (Sales Tips)

  • Use Splitit when other financing options fail to close more (Whop)

  • Workshop: Think Fast, Talk Smart (Stanford Grad. School of Business)

  • Here are 430 free sales courses (LinkedIn)

OUR SPONSOR

This week’s sponsor is The Serial Sales Community.

If you’ve ever looked into the world of 1099 remote sales jobs, you’ve probably run into this bottleneck: The best jobs are hard to find.

The ones blasted far and wide on LinkedIn, Indeed, or Glassdoor are almost always dead ends.

MLM’s, pay-to-play, requiring licenses, or just small ball opportunities.

The biggest and best teams in the remote appointment setting and closing industry are using “back door” hiring channels (such as TSSC) to find the best talent.

They aren’t posting to an audience of 100k+.

They aren’t hiring via LinkedIn’s Easy Apply feature.

They are going where the top 5% of sales reps hang out.

Private groups and networks.

That’s just the way this industry operates.

And to clearly define this “industry” we’re talking about:

High ticket sales, remote closing, remote contracted sales, etc.

Basically being an inbound commission-based sales rep for high cashflow businesses that generate leads but need sales talent to convert them.

Think coaching, consulting, agency services, masterminds, bootcamps, seminars, memberships, masterminds, and even some software.

If you’re ready be put into the epicenter of opportunity, you can apply to join TSSC here.

Mention “Because of Sales” for a 5% discount on 6 months or lifetime access.

Now, back to the newsletter…

SELLER’S SECRETS

Who is Austin Medlin, and what is CloseSales.com?

Austin Medlin, based in Tampa, Florida, owns ClosesSales.com. He works with online coaches and sales professionals to upgrade their closing abilities, improve their sales metrics, and overall just sell more of their services so they can earn well and live better.

Check out Austin’s full interview on Youtube, Spotify, or Apple Podcasts.

Austin and Dylan while recording the podcast (which you should totally watch)

Austin’s Come Up (in 10 bullet points)

  • Started sales hustling candy and door-to-door in high school.

  • Entered network marketing at 18, built a 1,500-member international team.

  • Girlfriend's death and business collapse pushed him to entrepreneurship.

  • Took over Dad’s landscaping business, scaled from $300k/yr to multi 7-figures.

  • Quit landscaping abruptly to explore more optimal opportunities (remote sales)

  • Got into “high-ticket sales”, went from failing to $20k/mo by month 3.

  • Scaled a YouTube ads company from $300k to $1.7mm in monthly in revenue.

  • Broke off to work with other businesses to do the same as a consultant.

  • Took his case studies and launched ClosesSales.com to help more people.

  • Recently expanded into helping train and connect sales pros with businesses.

Proof that Austin has been at it for a while now. His biceps are maybe twice as big now.

Austin’s Sales Alpha and Best Practices:

1. Learn how to align a buyer’s head and heart to close more.

One of Austin’s biggest sales unlocks was discovering that you need to close both the head (logic) and the heart (emotion). Most reps only pitch to the head, and they’re pretty decent at it. "Here's the process, here's the ROI." But Austin trains clients to live in deep discovery for 20–30 minutes, asking sharp, layered questions that get prospects to voice their own emotional drivers.

2. Make millions with strategic partnerships.

CloseSales.com scaled from $0 to $700K in revenue off one affiliate channel in year #1. Austin offered free weekly coaching inside of a marketing program, helped clients crush it, then paid the host referral fees. Instead of cold traffic, he embedded into ecosystems with aligned but non-competing offers. He met his perfect prospects, for free, right as they needed him.

3. Stop trying to be liked by your prospects, be trusted instead.

Most reps think being friendly leads to conversions. Austin says that’s wrong: people buy from those they trust, not those they like. Rapport doesn’t replace clarity. His strategy? Start every call neutral and direct, short intro, then deep into discovery. No fluff. Most of his clients don’t like him when they sign, but they believe he’s the exact guy for the job. Once they get the result they came for, they love him.

Austin and Jeremy (his biggest strategic partnership)

Action Items: Consider implementing some of these takeaways from Austin

#1: When alignment is present, selling is a service.

  • People don’t need to like you, they need to trust you

  • Be neutral and direct, not overly friendly

  • Pushy isn’t bad if you will truly help them

  • Not closing them is a disservice if they’re a good fit

#2: Don’t pitch until you diagnose their unique situation

  • Most reps skip real discovery (20-30 mins)

  • Align the prospect’s head (logic) and heart (emotion)

  • Deep questions beat clever statements (people judge by quality of questions)

  • Stop using a one-sized fits all pitch, tailor it to their needs

#3: Implement active call reviews with predictions

  • Make sure you’re getting feedback from competent source

  • Schedule a structured call review cadence with a partner

  • Predict what each party will say as far as questions, objections, etc.

  • Refine scripts through this practice to build more confidence

#4: How to sell to creative types better

  • Creatives (musicians, artists, etc) ramble on calls, you must not allow this

  • Set clear frames and kindly cut off stories when necessary

  • Prioritize shaping the convo without seeming rude

  • Ensure you leave time for a proper pitch, otherwise book another call

Check out Austin’s full interview on Youtube, Spotify, or Apple Podcasts.

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