Build Your AI Sales OS in Cursor

Dennis Zavolock

Enterprise AE turned AI Sales Coach

Most sellers don't know how to use coding agents. The ones who do have an edge.

Selling is hard.

Every deal requires attention, thought, effort, and persistence. Every objection is a problem to be solved.

Founders have it even harder. You built something great. Now you have to sell it. Nobody gave you a playbook.

Most sellers reach for ChatGPT. It's fine for a first draft. But it doesn't know your accounts, your product, or what was said across the last three calls. Every conversation resets and work doesn't compound. That's missed opportunity.

AI agents like Cursor are different. Your context lives there permanently and you can codify what's working. It connects to your other tools through MCPs (Salesforce, Slack, Google Drive).

That's what you want. Systems that compound over time. One input does the work of an hour.

Most AI courses teach frameworks through slides. In this course, you build in session and use it on real deals that day.

Pre-loaded with Challenger, MEDDPICC, NEPQ, Command the Message, Chris Voss negotiation, and more.

This isn't using AI just to work faster. It's using it as a strategic partner you actually trust.

By the end of this cohort, you have an AI Sales OS. More pipeline, faster close, and no more relying on gut feel.

What you’ll learn

Build an AI Sales OS that coaches you through every deal; so you close more, lose fewer, and stop running on gut and scattered notes.

  • Build the brain of your AI Sales OS with your product context, methodology, and trigger preferences

  • Install pre-built skills then build your own: MEDDPICC, Challenger, NEPQ, negotiation, proposal fork. You're not starting from scratch

  • Build a client folder structure that stores transcripts, notes, and stakeholder maps in one place, and can be shared with your team

  • Set up your live sales call coach in under 5 min

  • Your Cursor OS flags when to go deeper on an objection, when to ask about decision process, how to develop a champion, how to find the pain

  • Post-call debrief scores you on control, diagnosis, missed blind spots, and Challenger moments. Update deal context automatically

  • Integrate skills to automatically run MEDDPICC on live deals and surface the top blind spots.

  • Learn how to strategize with your agent to get clear on actionable next steps needed to drive to a successful close at the highest price.

  • Build proposals with strong business ROI, multi-thread, get executive buy-in.

  • Your OS picks the sales methodology that fits the account and builds the sequence

  • Capture what your best reps, top sellers, and favorite books do differently and encode them as reusable skills and markdowns

  • An outbound OS plugin included as part of the package

  • Chris Voss-style calibrated questions and tactical empathy skills baked into the system

  • Know what to say when legal goes quiet or procurement adds three new stakeholders

  • Encode top rep tribal knowledge so your best moves stay in the system, not just in your head

Learn directly from Dennis

Dennis Zavolock

Dennis Zavolock

6 years enterprise SaaS sales. Built an AI Sales OS that changed how I sell.

Iterable
Chooch AI
alwaysAI
New York Angels
See all products from Dennis

Who this course is for

  • Enterprise sellers managing complex, multi-stakeholder deals who want to have more clarity, better outcomes and less stress.

  • Founders and consultants who find themselves needing to sell and don't have the time to ramp.

  • B2B AEs who know their frameworks, want to improve their close rates, and build a sales system with coding agents.

What's included

Dennis Zavolock

Live sessions

Learn directly from Dennis Zavolock in a real-time, interactive format.

Lifetime access

Go back to course content and recordings whenever you need to.

Community of peers

Stay accountable and share insights with like-minded professionals.

Certificate of completion

Share your new skills with your employer or on LinkedIn.

AI Sales OS with built out markdown files

The full system Dennis built, tested and ran on live deals. Ready to make your own. Includes your AGENTS.md, client folder structure, deal templates, and methodology files - all pre-loaded. You don't start from scratch. You start from a working system and customize it to your product, your voice, and your active pipeline.

Outreach Plugin

A pre-built outreach system trained on your voice and the methodologies that get C-suite to reply. Dennis used this to 4x his pipeline in 30 days and land a CMO reply that brought a $1.2M deal into pipeline.

Skills Plugin

Pre-built agent skills you invoke with a single command. Live call prep, MEDDPICC deal diagnosis, Chris Voss negotiation, proposal forking, transcript intake, and more. Each skill knows what to ask, what to look for, and what to output. You don't prompt from scratch. You run the skill and get a result.

Maven Guarantee

Your purchase is backed by the Maven Guarantee.

Course syllabus

6 live sessions • 6 lessons

Week 1

Jun 8—Jun 14

    Jun

    8

    From 'What Is Cursor?' to running it on a Live Deal

    Mon 6/84:00 PM—6:00 PM (UTC)

    From 'What Is Cursor?' to running it on a Live Deal

    1 item

    Jun

    10

    Your OS now has Skills. Run them on real deals.

    Wed 6/104:00 PM—6:00 PM (UTC)

    Your OS now has Skills. Run them on real deals.

    1 item

    Jun

    12

    Optional: Office Hours

    Fri 6/126:00 PM—7:00 PM (UTC)
    Optional

    Office Hours

    1 item

Week 2

Jun 15—Jun 19

    Jun

    15

    Set up your live sales call coach in under 5 minutes

    Mon 6/154:00 PM—6:00 PM (UTC)

    Set up your live sales call coach in under 5 minutes

    1 item

    Jun

    17

    Your best moves, encoded. Your hardest deal, solved.

    Wed 6/174:00 PM—6:30 PM (UTC)

    Your best moves, encoded. Your hardest deal, solved.

    1 item

    Jun

    19

    Optional: Office Hours

    Fri 6/196:00 PM—7:00 PM (UTC)
    Optional

    Office Hours

    1 item

Schedule

Live sessions

4-5 hrs / week

    • Mon, Jun 8

      4:00 PM—6:00 PM (UTC)

    • Wed, Jun 10

      4:00 PM—6:00 PM (UTC)

    • Fri, Jun 12

      6:00 PM—7:00 PM (UTC)

A fully built, personalized Sales OS in Cursor

1 hr / week

An Sales OS loaded with your deals, your voice, your methodology. Not a framework you'll forget by Thursday. Something you use in your next meeting.

Async content

1 hr / week

Frequently asked questions