How to Get New Sales Reps Cold Calling and Building Pipe Faster (Ask Jeb)

Gaius, who runs an insurance brokerage in Ohio wants to know how to get his new sales agents cold calling and building pipeline earlier in their training cycle, without making them feel overwhelmed and sabotaging their confidence. If you’ve ever hired a sales class or tried to ramp up new hires in an industry with complex products or strict guidelines, you’ll relate to Gaius’s dilemma. Below, you’ll find the key takeaways from our conversation on accelerating new rep success, establishing realistic expectations, and blending company marketing with individual agent prospecting efforts. The Challenge: New Hires, Big Learning Curves Gaius plans to hire new property-casualty agents in classes of four, each going through about 3–4 months of training. During that time, they have to learn multiple carriers, underwriting guidelines, and compliance rules so they don’t accidentally write poor-fit policies or lose deals over technicalities. It’s crucial they build confidence before being “thrown to the wolves.” But here’s the catch: If new hires only focus on product and system knowledge for months, their pipeline remains empty. By the time they’re “ready” to sell, they’ll be way behind on prospecting —and might even lose that DAy One enthusiasm for building relationships. The question is, how soon can they start generating leads and setting up sales conversations? Why Pipeline Activities Can’t Wait As I shared with Gaius, I’ve seen many companies assume new reps aren’t “ready” to prospect until they’ve absorbed the entire knowledge library. Yet waiting too long to do real sales activities can backfire. Early Wins Boost Confidence If new hires can set even a few appointments or pass warm leads to experienced agents, it gives them a sense of accomplishment. That momentum helps them stick with the grind of more complex training. Practical Learning Beats Textbook Learning In industries with loads of carriers and underwriting rules, real-life sales scenarios actually teach new reps faster than purely theoretical training. Once they’ve got a potential client on the hook, the rep has motivation to find the answers. Improved Onboarding Speed Companies that mix early pipeline-building with supported team selling often see new hires reach quota faster—sometimes shaving weeks or months off the usual ramp-up. And yes, there’s a risk of missteps. But that’s where a collaborative culture (“sell as a team”) ensures mistakes become teachable moments, not deal-killers. The Team-Selling Approach When new agents don’t have full carrier knowledge, they’ll naturally hit roadblocks. How do you keep them from burning deals (and morale)? Encourage “Hand-Raises” If a new rep snags an interested customer, let them wave the flag: “Hey, I have a lead who needs home and auto coverage. Here’s what they’re telling me. What do I do?” Then a veteran agent or manager steps in to guide the quote or finalize the sale, with the rookie learning through an actual client scenario. Shared Commissions Make sure new reps see a direct benefit. If they hand off a deal, they might get a partial commission or spiff for their contribution. Over time, they’ll rely less on help—but they’re still building pipeline from Day One. Hands-On Coaching Each real conversation is a goldmine for coaching. The rep sees how an experienced teammate answers tricky questions, navigates underwriting guidelines, and pivots between carriers. It’s in-the-field training, not just theoretical. Structuring Training + Prospecting Gaius is worried that his new agents need a full 3–4 months before picking up the phone. The short answer is no. They can start small while still in training. Here’s how: A Few Leads a Day Instead of waiting for them to finish product modules, drip leads early. Let them call 5 or 10 leads each morning, focusing on booking appointments (rather than doing in-depth quoting). This keeps them from drowning in complexity,