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, but still gives them “real world” prospects. Scheduled “Ask an Expert” Blocks Have daily or weekly times when a senior agent or manager is free for quick consults. The new hire can pop in with, “Client says they recently replaced their roof but not the plumbing—what do I do?” That immediate feedback cements knowledge better than PowerPoint slides ever could. Clear Milestones: Map out 3 months of onboarding with explicit checkboxes: Month 1: Master basic call scripting, do 5 calls/day, practice “hand-off” protocol if a lead is hot. Month 2: Increase calls to 10/day, conduct partial quoting for simpler cases, attend 2 coaching sessions/week. Month 3: Sell with minimal assistance, handle common underwriting scenarios, start building personal brand on social media. Pairing Company Marketing with Individual Agent Efforts The second big question: How do you blend your brokerage’s formal marketing activities (like brand campaigns or leads from your website) with each agent’s personal prospecting? Provide Starting Leads If you’re running ads or generating inbound leads, new hires can cut their teeth on less-coveted prospects (like “closed/lost” or older leads). Let them gain confidence responding to these, then earn the right to handle prime leads. Build Personal Brands In B2C insurance, it’s often about relationships. Encourage new reps to network in their communities, join local groups, and use social media responsibly (respecting all compliance rules). If your agency runs a local radio ad, for instance, your new hires can promote that talking point when they connect with neighbors or friends. Content Library Arm them with digital and print assets they can share on their own channels – e.g., short videos on “Top 3 Mistakes in Home Insurance,” or infographics about “Why You Need More Than Minimum Auto Coverage.” Make it easy for them to align with the company’s brand while showcasing their personal touch. Accountability and Metrics Set targets. For example, “Attend 2 local networking events each month, post weekly on social media about a relevant insurance tip, schedule 3 coffee meetups with new community contacts, etc.” Pair that with your marketing team’s leads to create a one-two punch. Reaping the Benefits of Faster Pipeline Growth When you let new agents “wait” for months before prospecting, you risk: Lost Momentum: They might lose confidence or develop call reluctance if they’re not used to consistent outreach. Zero Early Wins: Without a single success story in the first few months, new hires feel pressure, question themselves, and sometimes churn. Delayed Revenue: The longer it takes a new rep to start building pipeline, the fewer deals you close in that critical first year. On the flip side, training them to prospect earlier (even if just setting appointments for someone else) provides real sales experience right away. They see how the process works end-to-end, gain incremental confidence, and bring in revenue sooner. Final Thoughts: Onboarding for Early Success One of the biggest challenges for sales leaders and executives is getting new salespeople ramped up faster. An unproductive sales head is costly, draining the P&L. So, getting them prospecting, filling their pipeline, and making those cold calls quickly is crucial. At Sales Gravy, we believe in getting new hires on the phone as soon as possible—within their first week. By starting with a few leads and gradually increasing their call volume, we build their confidence and get them productive faster. Remember, a long onboarding process delays success. So pull that band-aid off quickly and start building pipelines from day one. If you’re serious about accelerating new rep success, don’t quarantine them in a training bubble. Integrate real-world prospecting early. Show them that pipeline building is the lifeblood of the agency—and get them excited about bridging their education with on-the-ground sales. Likewise, unify your company marketing with each agent’s personal outreach. Give them guidelines, brand assets, and expectations around networking and social media. Encourage them to talk about your brand in everyday life, and to rely on your marketing team for ongoing support. Because here’s the truth: In property and casualty insurance—or any complex field—a new hire can’t master everything in a few weeks. But if you wait until they’re “100% ready” before making calls, you’ll sabotage the ramp-up process and miss countless early opportunities. Let them start early, help them as a team, and watch as they transform into confident, quota-busting agents. Need help with your new hire sales onboarding process? Download our FREE guide: The Small Business Owner's Guide to Sales Training