🎤 Kasey Devine Left a Top Sales Job to Fix the Problem He’d Watched the Industry Ignore for Years

Kasey Devine, founder and CEO of Entravia, spent over a decade mastering the workflows inside some of the biggest names in HR outsourcing — then left a top five national sales ranking at ADP to build the platform the industry never bothered to create. Six months in, Entravia has raised $2.6 million, won the Evergreen Award for Best PEO Shopping Platform, and is already threatening legacy workflows across a $414 billion industry.

✨ Key Insights You’ll Learn:

• Cardinals ticket sales as the moment sales stopped being a dirty word

• ADP training as a total transformation — from territory management to pipeline structure

• The chamber of commerce moment that turned near-failure into a relationship-first sales philosophy

• How to ask the one sidebar question at the end of every meeting that changes everything

• The mortgage application that showed Kasey how far the PEO industry had fallen behind

• Why Entravia pivoted from B2C shopping platform to white-labeled B2B infrastructure overnight

• The general agency model and how it made brokers partners instead of competitors

• Getting rejected by every VC, then getting a second look through one unexpected relationship

• Why the cost of building software dropped enough to make this startup possible now

• Browser-based bots that could compress a 9-week PEO evaluation into a single day — once the threats stop

🌟 Kasey’s Key Mentors:

• His ADP manager and training program: built the entire foundation for how he thinks about territory, pipeline, relationships, and value creation

• TriNet founder and ProCare HR founder: showed him what it looks like to lead a sales and marketing org with accountability and discipline

• M25 and Cambrian Ventures: gave him the capital and credibility to move fast on a problem he already understood better than anyone

• His mother: showed him what self-determination looks like when you have no safety net — and that nobody’s coming to save you

👉 Don’t miss this conversation about why helping people is the only sales strategy that actually scales, how a $414 billion industry forgot to make its product easy to buy, and what it looks like to bet everything on a problem you’ve spent your whole career watching go unsolved.

🔗 Connect with Kasey Devine:

Website: entravia.co

📤 Transcript Available: Kasey Devine Left a Top Sales Job to Fix the Problem He’d Watched the Industry Ignore for Years

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📤 Special Thanks to Anthony Codispoti & AddBack Benefits Agency: AddBack Benefits Agency - Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line Website: addbackbenefits.com