The Evolution of Sales: How Technology and AI are Reshaping the Game with Jill from HubSpot

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Welcome to the NextGen GTM Podcast! In this episode, we sit down with Jill, a top-performing sales rep at HubSpot, who has been with the company for over 14 years. She’s seen firsthand how go-to-market motions have evolved, how sales reps have adapted, and how technology—especially AI—is changing the game.

From a Startup to a 7,000+ Person Company: What Has Changed?

Jill walks us through what it was like when HubSpot was a scrappy startup—when sales reps sat shoulder-to-shoulder in a small office, and even the executives were taking sales calls. Now, HubSpot is a fully remote-first company, with global operations and thousands of employees. But one thing has stayed constant: the relentless pace of innovation.

“Every January, it feels like HubSpot reinvents itself.”

How Sales Has Shifted: From Notebooks to Digital Selling

Jill reflects on how sales used to be pen-and-paper, face-to-face, and highly manual. Now, the game has changed:

• Sales reps rarely meet customers in person.
• The job now requires managing multiple screens, CRMs, Slack, LinkedIn, AI tools, and automation—all at once.
• AI and automation have made speed-to-lead and digital sales efficiency more critical than ever.

"If you're not leveraging AI, a CRM, and automation, you're going to get left behind. Your competition will be having twice as many meetings as you."

The Role of AI: What Should Be Automated vs. Human-Led?

Jill breaks down where technology should take over vs. where human reps are irreplaceable.

✅ Automate:

• Follow-ups, sequencing, scheduling, CRM logging, and basic prospecting tasks. If a sales rep is still manually logging emails or setting reminders, they’re moving too slowly.
• AI can help generate reports, draft emails, and analyze sales conversations, freeing up time for more customer interactions.

❌ Human-Led:

• Personalized messaging: AI can surface insights, but a great rep makes connections AI can’t.
• Sales conversations: Closing deals still requires empathy, active listening, and tailored problem-solving.
• Multi-threading & stakeholder management: Knowing how to navigate complex sales cycles is still a human skill.

"The best sales reps today are like command center operators. They manage all these tools, but when it comes time to talk to a buyer, they shut off distractions and engage deeply."

The Future of AI in Sales

Jill sees AI as the biggest transformation since the internet, but she emphasizes that it’s not replacing great salespeople—it’s amplifying them.

• AI will continue to remove busywork, allowing reps to spend more time selling.
• The future is “describe and done”—where sales reps can ask their CRM for a report instead of manually building one.
• The best reps will be those who embrace AI to get more at-bats while mastering the human side of selling.

"AI isn't going anywhere. The reps who lean into it will dominate. The ones who resist? They'll get left behind."

Key Takeaways

1. Sales has radically changed—from face-to-face, pen-and-paper to fully digital, AI-powered selling.
2. Speed matters. If you’re still manually handling tasks that AI can do, you’re losing.
3. The best sales reps act as command centers, leveraging AI while bringing deep human insight to buyer conversations.
4. AI doesn’t replace salespeople—it makes them more efficient.
5. Sales success still comes down to human connection. No AI can replace the ability to actively listen, navigate complex deals, and add real value.

🔥 Final Thought: AI won’t replace sales reps. But sales reps who use AI will replace those who don’t.

This episode was packed with insights on how to navigate the evolving world of sales, how AI is shaping the future, and what sales reps need to do to stay ahead. Huge thanks to Jill for sharing her experiences and wisdom! 🚀

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