What happens when you bring together a seasoned SVP, a couple of GTM nerds, and a mic? Real talk on what actually works in marketing, sales, and operations.

In this episode of Chat GTM, hosts Michael Beck and Chad Horn sit down with Kevin Jaskolka, SVP, Checkmate, to get tactical on:

🔸 Why CRM structure is make-or-break

🔸 Salesforce vs. HubSpot vs. Zoho: who should use what

🔸 Building data architecture for restaurant tech

🔸 Getting real ROI out of trade shows

🔸 What “marketing should do” when you’re still under $500k ARR

🔸 Why AI is only as smart as the human using it

🔸 Tips for driving adoption, cleaning up data, and personalizing at scale

Plus: Kevin drops serious wisdom on using HubSpot’s custom objects, the pros and cons of sales-marketing alignment, and where too many companies get stuck with demand gen.

🎙️ Whether you’re a marketer, founder, sales leader, or ops pro—this episode will help you stop spinning your wheels and start scaling smarter.

👀 Watch to the end for Kevin’s favorite AI tools and trade show hacks.

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🧠 Hosted by Michael Beck & Chad Horn

🎧 Subscribe for more GTM deep dives, straight from the field

Resources & Mentions

• Checkmate: https://www.checkmate.com

• Kevin Jaskolka on LinkedIn: https://www.linkedin.com/in/kevinwjaskolka/

• Inc Tank GTM: https://inctankgtm.com

• Michael Beck on LinkedIn: https://www.linkedin.com/in/michaeltbeck

• Chad Horn on LinkedIn: https://www.linkedin.com/in/chadhornboston

• HubSpot, Zoho, Salesforce, Brizo, Chain Store Guide, Ignite, Apollo, ZoomInfo, Beautiful.ai, Synthesia, and more