Scaling Founder-led Sales on LinkedIn - #BOSTechWeek
Hosted by
ʘ‿ʘ
:◗Scaling Founder-Led Sales on LinkedIn
A practical workshop on building and operationalizing founder-led LinkedIn outreach
📅 Wednesday, May 27, 2026
⏰ 12 PM ET
📍 Virtual (Zoom)
A lot of founders are doing outbound inconsistently or are trying to automate before the messaging is actually working.
And honestly, a lot of LinkedIn outreach right now is bad... we all know why!
People are over-automating, sending generic messaging, and scaling outreach that was never positioned well to begin with.
This workshop is focused on how to actually structure founder-led outreach in a way that still feels personal while being operationally manageable long term.
I’ll walk through the systems, messaging philosophy, campaign organization, and automation workflows I use across consulting clients to manage LinkedIn prospecting and outbound.
We’ll also talk about where founders tend to get stuck, common mistakes with automation tools, and how to think about outbound as an evolving process rather than a one-time setup.
What we’ll cover
1. Founder-led sales on LinkedIn: what actually works
-Why founder outreach performs differently
-Common messaging mistakes founders make
-The mindset shift from “selling” to supporting
2. Building and organizing your prospect list
-How to curate higher-quality LinkedIn prospect lists
-Why ICP alignment matters before automating outreach
-What founders often get wrong about volume
3. Structuring scalable outreach systems
-How to operationalize LinkedIn outreach workflows
-Cadence structure and campaign organization
-Connection requests, follow-ups, and sequencing philosophy
-Why campaign maintenance matters more than people think
4. Messaging that gets responses
-Why “you-focused” messaging performs better
-How to position around the buyer’s goals and problems
-Clear calls-to-action that convert into meetings
5. Automation tools and real-world workflow examples
-How I use automation tools like Dripify within outbound systems
-Common automation mistakes that quietly hurt results
-Why bad messaging scaled is still bad outreach
6. Optimizing over time
-Why outreach systems should evolve every few weeks
-How to evaluate what’s working
-Real examples of improving outbound activity and engagement across client accounts
Who this is for:
-Founders leading their own sales efforts
-Early-stage operators building outbound systems
-Consultants and fractionals supporting GTM execution
-Anyone trying to create more consistent pipeline through LinkedIn outreach
What you’ll walk away with:
-A clearer framework for founder-led LinkedIn outreach
-A more scalable way to organize outbound efforts
-Messaging principles that improve response quality
A better understanding of how automation should support, not replace, relationship-building.
This event is a part of #BosTechWeek—a week of events hosted by VCs and startups to bring together the tech ecosystem. Learn more at www.tech-week.com
Guest List
ᵔ▿ᵔ
⚆◟⚆
•ᴥ•