OK19: The Outbound Playbook That Made This SDR #1 at Twilio Segment - Jesse Leong, #1 SDR at Twillio Segment
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Discover how Jesse Leong, a classical musician turned #1 Global SDR at Twilio (Segment), 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.
Key Topics from the Episode:
Rapid Career Progression in Tech Sales
Jesse's journey from classical musician to #1 Global SDR at Twilio (Segment) in just six months, including Rookie of the Quarter and 164% quota attainment.
Account Selection and Prioritization
How to identify high-value accounts using intent signals, ICP fit, compelling events, and strategic initiatives.
Omnichannel Prospecting Strategies
Leveraging multiple channels like email, phone, LinkedIn, voicemails, digital gifting (e.g., Sendoso), and even unconventional approaches like Google Calendar invites to increase engagement.
Scalable Workflow for Outbound Outreach
Jesse’s three-step process for scaling outreach without compromising personalization or quality, including compiling account data, segmenting personas, and bulk sequencing emails.
Selling to Multiple Buyer Personas
Tailoring messaging for different personas, marketing, engineering, data/analytics, product teams, and adapting strategies for technical vs. non-technical buyers.
Finding and Using Compelling Events
Researching triggers like mergers, international expansions, product rollouts, or executive interviews to craft timely and relevant outreach.
Essential Tools for SDR Success
Tools like Outreach, SalesLoft, ZoomInfo, LinkedIn Sales Navigator, Koala (for intent), and dialers to optimize prospecting efforts.
Transferable Skills from Non-Traditional Backgrounds
How Jesse leveraged skills from classical music, like performing under pressure and memorization, for success in tech sales.
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Who is Jesse Leong (They/them)?
#1 SDR at Twillio Segment
More context about the Jesse's SDR team:
- 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:
- On LinkedIn: https://www.linkedin.com/in/jessemoyleong
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Chapters:
(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
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