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😎 Deep dive with a 9-fig closer, the 5% of a cold call that matters, and making $100k with the cold facetime method

Learn how Dylan Rich is scaling multiple sales teams at once with his DFY sales agency.

IN THIS EDITION

Banger edition for you guys this week.

While we sit on the sidelines to see what happens with this whole tariff tug of war, there’s still plenty to share:

  • He’s managing 50 sales reps with his fractional sales agency - Dylan Rich

  • Learn about the 5% of the cold call that actually matters

  • The guy who made $100k through the cold facetime method

  • 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!

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OUR SPONSOR

This week’s sponsor is The Serial Sales Community.

262, 237, 215.

That’s how many open high-ticket remote appointment setting and/or closing roles were shared inside TSSC across April, May, and June.

At a crossroad with where you want to go next with your sales career?

Confident in your ability to perform, but not willing to compromise on things like being remote, uncapped commissions, etc.?

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(^into remote 1099 sales roles that is)

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Now, back to the newsletter…

SELLER’S SECRETS

Who is Dylan Rich, and what is Systemized Sales?

Dylan Rich is a Tampa-based DFY sales agency co-founder helping online businesses scale sales teams to $700K+ months, fully on a revenue share basis.

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

Dylan’s come up (in 10 bullet points)

  • Criminal justice at Rutger’s, decided he didn’t want to sit in a patrol car

  • Stacked an associate in graphic design, got first taste of client work on the side

  • Landed an internship at copier sales company; thrown into outbound sales

  • Assembled a cold call crew from his frat brothers, made some solid money

  • Broke into SaaS sales in 2015, eventually working up to enterprise level

  • A VP of Sales job was brought to him through strong networking at past roles

  • Discovered “online business” through a coaching program he joined

  • Stood up his sales agency with cold email and outbound campaigns

  • Made the jump from outbound to inbound client work with his agency

  • Scaled the agency, now managing 50+ sales reps and millions in client revenue

“Gonna be a good week” - Dylan

Dylan’s sales alpha and current best practices

You can get paid well to own the sales function for multiple businesses

Dylan’s agency doesn’t just drop in sales reps, they build and host CRM systems, write scripts, train reps, and oversee every step from lead opt-in to cash collected. This lets clients stay lean and focused while scaling fast. His team runs entire launches, including webinars, challenges, and post-event monetization, even booking upwards of 1,000+ calls in five days on behalf of their clients.

It’s hard to lose money with a low-ticket ascension funnel

Instead of giving away one-size-fits-all information in the form of PDFs (most don’t open), Dylan’s found that selling something interactive like a calculator or diagnostic at a low price-point yields far better return. A product such as a calculator creates urgency for the user without a standard sales asset or rep directly “selling” them.

Having the prospect sell themselves using a resource they paid to get access to > having the prospect be sold by someone they don’t know

You can send voice notes from the founder (without the founder)

Using ElevenLabs, Dylan’s agency can replicate a founder’s voice to send custom voice notes for pre-call, follow-ups, or no-shows. They upload the call notes from Fathom to ChatGPT, then using VA’s to feed that into Eleven Labs and send the MP3/voice note to the prospect.

Pro tip: If using a “blue message” tool like Send Blue or Linq, you can send this as a native voice message as it’d be received from one iphone to another. The only caveat is that this may contingent on them texting you first.

This is why Dylan has a VA turn it into an MP3 file that can be sent outbound via traditional SMS to anyone they want to send to.

How it feels to scale sales teams on a 100% performance-based comp structure

4 cool things you should try. 4 steps to implement. (4×4)

1. Operate as turn-key as possible for more leverage (and pay)

  • Control the entire motion of what you’re providing, not just one part

  • Build and host necessary tech in an easy-to-deploy manner

  • Treat the maintenance as an ongoing service, not an add-on

  • Aim for quick wins early to sweeten the relationship long-term

2. Try a “paid challenge” over free webinars

  • Paid = higher show rate and urgency

  • Pitch live before and during the session, not just end

  • Let hot leads "skip the line" and buy early (small %, but they exist)

  • Didn’t convert at the end? Provide a gift that guides them towards ascension

3. Treat B2B like B2B, and B2C like B2C (they’re different)

  • Your appearance on video matters as much as it does in person

  • High presentation necessary to excel in both B2B and B2C

  • Learn when to “speak up” or “speak down” when necessary

  • Every lead get’s a fair shake. You never know what’s on the other side.

4. Use AI to make custom voice notes for prospects

  • Feed the required audio amount to ElevenLabs.io

  • Use the call transcript to create a script with ChatGPT or Claude

  • Put the script into ElevenLabs for recording

  • Send via SMS to leads through your CRM

Connect with Dylan:

Check out Dylan full interview on Youtube, Spotify, or Apple Podcasts.

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