AI Practice Sessions: Prospecting Methods 2025 • 
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AMA session
16 Oct, 10:00 АM PT

Gerry Hill

RVP, EMEA at ConnectAndSell
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Meet Gerry Hill

Gerry Hill is an expert in C-Level communication, doing 6 and 7-figure deals in complex, matrixed accounts. Because he’s brokered some of the biggest ConnectAndSell deals in the world by cold-calling himself, there’s no one better as a practitioner to teach you the stratetgy & tactics that get these outsized revenue results.

Gerry’s Hard Skills

Cold Calling

Objection Handling

Negotiation

Top Funnel

Closing

C-Level Comms

Enterprise Selling

You asked, Gerry answered

Here are the most upvoted questions from the AMA and Akio answered them all. In case you missed it, scroll down to watch the recording.

How do you get CEOs to stay engaged in your deal?

Walk us through the last 6-figure deal you closed soup to nuts.

Why don’t you believe in using email as an outbound channel?

What are some of your repeatable techniques to get to the root objection - the real objection under a smokescreen - and keep the deal moving forward with the next steps and decision-makers?

How I can spend less time drafting personalized email?

How many times should one call a c level executive?

Couple of real examples if he can share

"You get forwarded to whom you sound like". Myth or truth in enterprise land?

How do you keep CEOs engaged?

How have marketing teams supported your deals (if any)?

How would Gerry go on about finding a job where you can actually learn something nowadays?

How do you time block your prospecting activities?

If you could highlight one mistake you were consistently doing in the earlier stages of your career, that was having a detrimental affect on your career what would it be, and why was it so detrimental?

Understanding cro better, curious about the email statement

How will connect and sell compete with the likes of science? (AI cold calling software)

What is the most effective script that can scale across industries and callers?

Open or closed questions when starting call?

What levers do you utilise to negotiate?

What would you put in a 30/60/90 VP Sales plan that most people don't?

What other ways than phone can effectively get you a meeting with the C-Suite?

Can I land a remote SDR role from Africa working for a USA based company?

How long would it take for an SDR to be up and running to sell a new tech if they already have your skills?

Walk us through the last 6-figure deal you closed soup to nuts.

Why don’t you believe in using email as an outbound channel?

How do you get CEOs to stay engaged in your deal?

How do you convince a CEO of your vision?

If email only converts at 1% why is it still the favorite hunter channel for SDRs to AEs?

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