Healthcare (Senior Living) with Jonathan Dobrovich

In this episode, Stephen Saberin sits down with Jonathan Dobrovich, Principal Services Consultant at HubSpot, to unpack a complex enterprise deal for a senior living organization operating across B2B and B2C models.

Jonathan shares how he helped the client replace custom-built tech and scale beyond their Twilio-based infrastructure—navigating multiple stakeholders, tight timelines, and a high-pressure, multi-hub rollout with over 200 sales seats.

Hear how Jonathan leveraged deep implementation expertise to scope custom calling integrations, balance stakeholder priorities, and deliver a future-proof solution across marketing, sales, and service teams.

Plus:

• Why project management skills are underrated in pre-sales
• How to identify and support strong champions
• When to say “MVP now, roadmap later”
• And why a great sales rep makes all the difference in the room

Key Takeaways from the Episode:

Custom Integrations Are the New Normal – Especially with legacy infrastructure

mplementation Strategy Is a Selling Tool – Not just a post-sale necessity

Champions Drive Alignment – But they need enablement, not just enthusiasm

Connect with us:

Stephen Saberin (Host): 

https://www.linkedin.com/in/stephen-saberin/

Jonathan Dobrovich: 

https://www.linkedin.com/in/jonathan-dobrovich

Aptitude 8: 

https://www.aptitude8.com

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