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OK19: The Outbound Recipe That Made This SDR #1 at Twilio Segment

Jesse Leong, #1 SDR at Twillio Segment

Listen now on Spotify, YouTube, Apple, and Snipd (AI-powered app that takes notes for you).

Today, I'm joined by Jesse Leong, a classical musician turned #1 Global SDR at Twilio (Segment), who skyrocketed to the top in just 6 months. Learn their killer workflow for scaling prospects, unconventional omnichannel strategies, and the secret sauce for standing out in a crowded tech sales landscape.

From compelling events to AI-powered research, Jesse reveals the tools and tactics that propelled them to 164% quota attainment.

This episode is a must-listen for aspiring and seasoned SDRs alike.


Who is Jesse Leong (They/them)?

#1 SDR at Twillio Segment

More context about Jesse's SDR team:

  • Segment: Commercial (100-2000 employees)

  • ACV: $50k

  • Industries:  B2B SaaS, retail, financial services, and healthcare

  • Buyer personas: Marketing, dev, data, and product teams

  • Markets: USA, and Canada

Connect with Jesse:

Some takeaways

1. Focus on the Right Accounts (Not Just More Accounts)

Most SDRs waste time on random outreach. Jesse didn’t. They prioritized accounts using intent signals, closed-lost deals, strategic initiatives, and compelling events, focusing only on the ones most likely to buy.

2. Multi-Channel Prospecting (Not Just Emails & Calls)

Jesse used every channel possible to stand out: Email, Phone, LinkedIn, Voicenotes, Voicemails, Digital gifting (Sendoso). Even Google Calendar invites (yes, really)

3. Learn Fast from Top Performers

Jesse shadowed the best SDRs, listened to their calls, copied their workflows, and iterated fast. They weren’t afraid to make mistakes early, they just learned from them faster than most people.

4. Efficient Workflows = More Outreach, Less Effort

Jesse built a simple but scalable three-step workflow:

  1. Compile account data in one place

  2. Segment personas into targeted lists

  3. Use Outreach to automate sequences while keeping messaging relevant

This let them reach dozens of prospects efficiently, without sounding robotic.

5. Messaging That Actually Speaks to Buyers

Jesse sold to marketing, engineering, product, and data teams, very different personas with different pain points. Instead of sending the same message to everyone, they tailored every outreach to the persona.

6. Using Real-World Events to Get Responses

Most SDRs send generic outreach. Jesse used compelling events like:

  • Mergers & acquisitions

  • New product launches

  • Executives making public statements

This made their outreach timely, relevant, and impossible to ignore.

7. Sales Skills from Outside Sales

Jesse didn’t come from sales, they were a classical musician. But skills like performing on stage, under pressure, memorization, and active listening gave them an edge in sales conversations.

8. Choosing the Right Company Matters More Than You Think

Jesse made one thing very clear: Even the best SDRs will fail at a company with weak product-market fit. They picked a company where the product actually sells, instead of trying to force-fit a bad offer into the market.

In this episode, with Jesse, we cover:

(00:00) - Intro: Hacking the SDR Code

(00:59) – Rapid Immersion: Jesse's Tech Sales Experiment

(02:50) – Shadowing and Cloning: The Art of Imitation and Iteration

(04:46) – Startup vs. Market Leader: Tailoring Your Outbound Strategy

(05:28) – Challenge Accepted: Account Selection Mastery

(08:05) – Jesse's Toolkit for Identifying the "Right" Accounts

(10:03) – Data Consolidation and the "One Word Doc" Strategy

(11:13) – Scaling Outbound Without Sacrificing Quality

(12:25) – Compelling Events and the M&A Trigger

(13:23) – Segmenting for Hyper-Personalization at Scale

(15:52) – Finding the Signal in the Noise: Compiling Events, ChatGPT, and Perplexity

(21:26) – POV Outbounding and Building Confidence

(23:00) – Getting Insights From the Accounts

(25:00) – Jesse's Non-Negotiable Prospecting Stack

(27:09) – The SDR Trinity

(29:59) – Prospecting Deep Dive: Jesse's Step-by-Step Process

(32:57) – Non-Scalable Channels: High-Value and Scalable Channels

(37:57) – Jesse's Roadmap To Success in Six Months