Stockton 2.0

Intentionally trained for Runway ML.

Case Study

How we trained our model

Stockton has been specifically trained across various roles to excel at Runway ML.

Brex: MidMarket Account Exec | Embedded Finance & Partnerships

Experience:

  • Co-sell with Brex's strategic partners to find the mutual win: upselling Brex's base, helping partners upsell theirs, growing GMV and making clients stickier on a fully integrated stack.
  • Selling to C-level, VP and Director stakeholders in Finance and Procurement at companies from 250 to 2,500 employees.
  • Coordinate daily with partner AEs and AMs on overlapping deals, using Crossbeam to surface accounts where Brex can be leveraged. That partner overlap is my outbound.
  • Roll out brand-new product features and take them back to the existing base as upsells. On a recent launch I ran early-tester transcripts through the AE team to surface feedback and show developers where to spend their time.
  • Monitor payment performance so realized revenue and spend migration actually land. I'm not a closer who hands the account off; I implement the integrations myself.

Attainment:

  • Q1 2026: 101%
  • Q2 2026: 178%

Rippling: MidMarket Account Exec | Spend

Experience:

  • Ten months at Rippling helping grow their corporate card, expense management and spend management products.
  • Sold the spend management suite into brand-new logos regardless of whether they already used Rippling, then upsold them on the rest of the ecosystem.
  • Worked cross-functionally to land and expand quickly, drive stickiness with the product, and grow deal size and ARR out of every account.
  • Rippling is where I learned the methodology: how to genuinely de-risk a deal and ask the hard questions. I ran a crisp cycle against competitors with more reputation and more mature product.
  • Left with the highest attainment on the team and as 1 of 2 reps on a team of 10 tracking to President's Club for FY 2025. I went back to Brex to sell partnerships and the product that was the company's bread and butter.

Brex: Variety of Roles

AE II: Feb 2024 – Nov 2024

  • Ten months as an Account Executive on Brex's Commercial team, consistently one of the team's top performers.
  • Closed 27 deals worth more than $765K in ARR.

Global Strategic Accounts: Jun 2023 – Feb 2024

  • Sole SDR on Brex's 10-month Fortune 100 initiative, generating meetings and pipeline for two Strategic Account Executives.
  • Successfully outbounded and set meetings with Tesla, SpaceX, Block, Coca-Cola, Electronic Arts, Pinterest, Rivian, Target and Twilio.

Enterprise SDR Manager: Dec 2021 – Jan 2024

  • Promoted into management after eight months as an SDR and stayed 2.5 years, building Brex's first enterprise SDR team for larger, more complex accounts.
  • Led hiring, coaching, playbook development, outbound strategy, sequencing and messaging.

About me

Stockton 2.0 Natural Data Set

1

Natural obsession for AI & robotics

I have a natural obsession for robotics. I'm a massive Tesla FSD nerd and known to spend my free time watching YouTube videos on machine learning and the training of autonomous systems.

2

Out of the box thinker

Consistently known for creative thinking and a willingness to stand out, just like this website. You can't rely on sending in an application. Not enough.

3

AI fluency

In my free time I love exploring the latest and greatest. I work in the terminal and with MCPs, have spent 6B lifetime tokens in Codex and 97M in Claude, and have built apps past 250K lines with a fully functional back-end, third-party API integrations and image generation endpoints. That acumen gets used in my day-to-day in sales too.

Benchmarks

Stockton 2.0 Evaluation Results

1

Sales experience

5+ years in sales, including 2.5 years leading SDR teams of up to 10 reps. I've built new teams and segments from scratch and closed and negotiated my way to consistent 100%+ performance across both AE and partnership roles.

2

More than just a closer

I'm usually the person on the team surfacing a new technique, process or AI automation and handing it to everyone else. I'd rather find a better way to work and share it than run the playbook I was given and leave it there.

3

100%+ attainment

I find a way to hit the number, whether that comes from leading the team, closing the deal, staying aggressive, or negotiating properly.

AI in my day-to-day

Stockton 2.0 Inference Capabilities

1

Improve close rates

AI isn't just a way to automate emails. I've built systems with Claude that run my call transcripts and email threads against MEDDPICC and flag the risks, gaps and pains I haven't vetted thoroughly enough.

2

Coaching

I use AI to sharpen my own playbook and to see which features didn't land, drilling into the value props that actually resonate. It keeps me pulling feedback out of real transcripts so the next conversation focuses on the right things.

3

Efficiency

Through MCP connectors and automations I use AI to speed up deck creation, follow-ups, Salesforce tasks and pipeline hygiene. It also surfaces upsell opportunities I would otherwise miss.

Why Runway

Three reasons, and I mean all three.

  1. 01

    A different industry.

    Six years in finance and spend management. I'm good at it. But it's time to point that experience somewhere new, and Runway is about as far from an expense report as you can get.

  2. 02

    The AI wave, from the inside.

    I'm all the way in on AI. I think it's the biggest unlock for productivity, ease of life and plain happiness the world has seen, and I want to spend my days at a company that is AI-native through and through rather than one bolting it on. Watching this decade happen from the outside would be a waste of the moment.

  3. 03

    It's what I actually have taste for.

    I have an eye for design, marketing and branding. I love AI-generated video and imagery, and getting to live in that world every day is something I would genuinely love doing. This page is the evidence.

How this page got made

  1. 01 Drafted by hand, in Canva.
  2. 02 Built with Claude Code.
  3. 03 Video generated with Veo 3.