B2B cold outreach that books meetings, even in December

Key takeaways

• A trigger is necessary and not sufficient. Two months in a new role is a great signal. Without a constructed reason to meet, it produces “why would I catch up?”

• Meet the objection head-on and flip it. During COVID, the line was “with no one travelling, it’s the perfect time to redesign your travel process.” The December version: “start now and your strategy is ready to deploy in the new year.”

• December starts you 30 seconds ahead in the race. Decisions progress over summer and land in February and March, exactly when enterprise budgets open.

• Multi-threading is the credibility filter for senior buyers. Regan takes meetings when someone has visibly tried across channels. One generic email means you’re one of a thousand in a sequence.

• One personalised, urgent, relevant text booked a meeting at a major organisation in 15 minutes. No call, no email.

• The same message to the same finance leader in February would have got “call me in three months.” The stall was never about Christmas.

If the purpose isn’t strong enough, if it’s not relevant, the other person just won’t see benefit. That’s the biggest takeaway for making any call or any email.

Luigi Prestinenzi, co-founder, Ricavi

If you’re in a running race and you get to start 30 seconds before anyone else, which is essentially the month of December.

Regan Barker, co-founder, Ricavi

What went wrong on the call that stalled?

Luigi Prestinenzi owns it. A chief financial officer at a very large organisation, two months into the role, which is a textbook trigger. He got excited, picked up the phone, and went straight in. He hadn’t thought hard about the purpose. The finance leader couldn’t see why a meeting made sense, so he said what everyone says in late November: too busy, try me in the new year. On the same day, four other finance leaders got a call with a clear reason attached to a specific upcoming event. Two booked. One asked for more information. The purpose, not the timing, decided the outcome.

Why do sellers create the December stall themselves?

By believing in it. Luigi has watched this every Christmas, Easter, and end of financial year for decades. Sellers assume buyers have stopped and slow down to match, and the buyer’s reflex confirms the assumption. Regan Barker’s counter is that she’s taking cold meetings right now, in the same fortnight, from people selling into her firm, because the messages have value. David Fastuca admits the phone is harder than an email because the rejection is immediate, and that a strong enough message is what makes the phone feel possible.

Luigi’s example of flipping the objection comes from David’s travel company during the pandemic. Nobody’s travelling, so why talk about travel? Because nobody’s travelling, it’s the perfect moment to fix the process. Take the objection off the table, then present the reason the objection is the reason.

What does a good December message look like?

Regan’s version is a race. Start now and you’re 30 seconds ahead. Enterprise budgets get planned in February and March, so a conversation that begins in December is further along when the money is decided. Luigi builds the message from a live prospect: right ideal customer profile, a persona who started four weeks ago, and intent data showing several people in the business searching for exactly what Ricavi does. The message acknowledges the new role and names what people in that position typically want to change. It notes the internal interest. Then it asks whether it makes sense to get the strategy right now so it deploys in January. Regan, meanwhile, booked a meeting at a major organisation with a single text. Fifteen minutes, one point on the board.

Questions this episode answers

Does cold outreach work before the holidays?

Yes, when the reason to meet is strong and framed around being ready for the new year. The seasonal stall is usually a message problem in a calendar costume.

How do you handle “call me in the new year”?

Acknowledge it, take it off the table, and give the reason meeting now serves them: their decision is further along when budgets open in February and March.

Why do senior buyers ignore single-channel outreach?

Because one generic email signals a sequence. Regan Barker takes meetings when a seller has visibly tried across phone, email, and LinkedIn, because effort is the first proof of relevance.