😎 $30k/mo sales rep quits for AI, strategic job hopping, and how to sell to rich people

SELLER’S SECRETS

Who is Brandon Harris, and what is Stride Systems?

Brandon Harris is a sales pro turned AI-enablement founder based in Utah who helps small businesses (especially service & sales teams) weave AI into their daily workflows to boost overall efficiency, close rates, and profits.

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

Brandon’s come up (in 10 bullet points)

• Got his first taste of sales through selling mattresses

• Then went door-to-door for Vivint, got valuable D2D lessons early

• Transitioned into tech sales at BambooHR, really solidified his ability

• Co-founded a service-based SaaS and learned product/market fit

• Joined the remote high-ticket sales space and scaled income to $30k/mo

• Ended up selling for a product that he purchased himself

• Started toying around with A.I. to make his job easier

• Won first side clients by helping them automate small tasks & workflows

• Leaned into “AI guy” identity by never shutting up about it

• Now runs AI solutions + coaching for sales teams & service niches

Brandons’ (A.I.) sales alpha and best practices

Weaponize you ADHD for profit

Brandon frames his brain as “web-style thinking”. Multiple threads, fast pivots. He says AI is uniquely suited to mirror and expand that flow. He uses AI not as a crutch but as a partner; dump ideas into it, iterate, explore tangents.

That’s how he built solutions that others might have overlooked or delayed. He doesn’t expect AI to replace his role; he expects it to magnify his zone of genius.

Automate non-revenue-generating work first

Start with the question: “Which parts of your process don’t directly generate income? And then automate those. Prep, follow-ups, reminder emails, CRM hygiene. All of that and more is fair game.

The stuff that requires human-to-human persuasion (tailored follow-ups, value-based closing) stays human. That dividing line is one of his guiding lights as he designs automations and AI workflows.

Get sales training from your favorites, at scale, for free

One of his most easily adoptable tactics: Train a custom GPT as your personal sales coach, based on your favorite sales framework. Feed it your call transcripts, role plays, coaching calls, etc. Then drop conversation transcripts into it and get instant coaching.

“Here’s what you missed, next time try this.”

He frames it as capturing ~70‑80% of what a high-level human coach would do, every single time, at scale. That’s how he collapses the standard “sales coaching bottleneck.”

4 things to steal, 4 steps to implement

1. Create a Personal Context File ASAP

• Record yourself talking about your stories, values, voice, etc.

• Use AI to summarize & condense to personality + style file

• Drop that in every new chat (“Here’s how I write, think”)

• Use across all LLMs to keep voice and outputs consistent

2. Audit your processes for A.I. implementation

• Map your end-to-end sales process and it’s details

• Label each step: “revenue producing” vs “not”

• Identify 3 non-revenue tasks to eliminate or automate

• Use an LLM (like ChatGPT) to help structure the build (or hire Brandon)

3. Build an A.I. voice agent for 24/7 lead coverage

• Clone your voice via ElevenLabs (use casual recordings)

• Pick a non-critical flow (e.g. “appointment reminder call”)

• Wire it via Twilio APIs or webhook

• Monitor performance, then expand if it works to other tasks

4. Forget speed-to-lead. Build speed-to-meaning.

• Track the time between lead opt-in → meaningful pain conversation

• Prompt: “Given this lead, what’s the fastest meaningful question I can ask?”

• Use that in your first outreach (email, call, or SMS)

• Automate the “hook question” to go out immediately on lead capture

Connect with Brandon

• Hire Brandon: https://www.stridesystems.ai/

• Instagram: https://www.instagram.com/stridesystemsai/

• Youtube: https://www.youtube.com/@StrideSystems-AI

• X: https://x.com/Stridewharris