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March 18, 2025 15 mins
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,
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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:05):
This is the Sales Gravy Podcast. Hi. I'm
Jeb Blunt, best selling author of fanatical prospecting,
objections, sales EQ, and inked, and I'm here
to help you open more doors, close bigger
deals, and rock your commission check.
Alright. It is wisdom Wednesday where you drive

(00:26):
the agenda. On this segment of the sales
review podcast, you bring me your biggest questions,
and I give you my best answers.
Answers, by the way, that comes straight from
the trenches. Because just like you, I'm out
there prospecting, selling, closing deals, and leading my
sales team every single day.
Before I get started, I've got some fantastic
news.
We're gonna be announcing the date and location

(00:46):
of the next outbound conference very soon.
Now outbound is the biggest, baddest conference in
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Now tickets are extremely limited, and we sell
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outboundconference.com.

(01:08):
That's outboundconference.com.
Alright. Let's take the next caller.
Alright. Next up on the show is, Gaius
from North Royalton,
Ohio.
Gaius, how you doing? I am doing excellent,
Judd.
How are you doing? I'm doing good. I'm
doing good. It's a, a good day to

(01:29):
spend some time with some sales folks like
you.
Tell me what's happening in your world.
Well, Judd, first of all, I wanted to
thank you for your work.
Thank you for your especially for your book,
Fanatical Prospecting. I have it right here on
on my desk.
It's, it's an inspiring book, very helpful.
Well, thank you so much for reading. I
appreciate that. We had everybody in the company
read it. Wow. I thought That's how much

(01:51):
we believed in him, man. It was a
it was a game changer for us, so
thank you for that. Awesome. Very good. Thank
you so much. I'm truly grateful.
Jeb, we are a property and casualty insurance
agency.
Our agents primarily work from home remotely.
And then my question I say two two
questions that I had.
We want to essentially hire sales agents in

(02:12):
classes of four agents at a time. These
are new agents to the industry.
And what recommendations would you have for helping
them start their lead generation activities? And whatever
specific examples from your experience that you could
share, that would be great. And I have
a follow-up question
to the first one.
How do we blend
our company's

(02:33):
marketing efforts
with the individual agents'
prospecting efforts?
K. Good. I'll get you to remind me
of the second question as we move forward
if I forget that one. That's a great
question. Really good question.
Okay. So let me make sure I understand.
So you're bringing in new agents,
and you're bringing them in as classes of
four. So they're going through training together?

(02:53):
Yes. And how long is the training?
Three to four months approximately. Okay. And they're
new to the industry. So they just got
licensed before I started working with us. They
got a license. They're training.
They're straight commission?
No. No. Base plus salary. Base plus salary.
And
you want them
to begin
building pipeline
as soon as they get there, or is

(03:14):
there a period of time where you don't
want them building any pipe?
We want them to build their pipelines
sooner rather than later, but we realize there's
a quite a bit of training incurred that
needs to take place.
So we wanna find that right balance. Maybe
after a couple months, they can start working
on their pipeline. What's the easiest thing for
them to sell?
Auto and home. Okay. Auto and home. What

(03:35):
they're gonna be focusing primarily on. And so
primarily b to c auto and home? Correct.
Okay. How much training would you have to
give me to be able to go have
a conversation with a person who has a
house and a car
and sell home and auto insurance?
As I said, between three to four months.
Really? I would take three to four months
for me to go sell I mean, I
have a house and a home, and I

(03:56):
have insurance.
And I talked to my agent.
I'm trying to figure out how complicated that
really is just to go sell house and
home.
Well, you have to know the guidelines. You
have to know your carriers. We don't wanna
rush people into it because what happens,
if they don't master
the knowledge of the carriers, the underwriting guidelines
Right. Their confidence level just tanks when they're

(04:18):
in front of the client. Okay. So Gotcha.
Could technically do it in a month or
two, but their confidence level is not where
it needs to be. Okay. Gotcha. So you
deal with a lot of carriers.
You they need to be able to to
recommend the right carrier for that homeowner,
the person who owns auto based on what
they're learning as they're having a conversation with
them. And they need to understand the underwriting
rules so that they don't put deals in

(04:39):
the pipe, and then they get back, hey.
We're not gonna cover this particular
homeowner. So then they've inconvenienced the homeowner.
They're inconveniencing themselves. They're losing deals along the
way. They lose their confidence, and everything falls
apart. Correct. Okay. Great. We don't wanna be
penny wise and dollar foolish
especially upfront. Okay. So quick story. I was
working with a company, and they were taking,

(05:01):
like, six weeks to train people.
And they wanted to move faster. So they
wanted people selling faster,
building pipe faster.
I challenged them that I thought they could
do it faster if they could just get
people selling earlier.
And they said, well, they need to have
all this information because if they don't, then
we got problems, and they get their heart
broken.
And I said, okay. Well, I've never sold

(05:22):
your product before, but I'll do this for
you. I'll work in your business for a
week as a salesperson.
I don't know anything about this at all.
At the end of the week, let's talk
about what I've learned and whether or not
it makes sense for you to change what
you're doing.
Well, by the end of the week, I'm
the number one salesperson in the company,
and I don't know anything about it.
But here's what I did. I'm really good

(05:44):
at having conversations with people. I mean, I
can call people, talk to them, get them
in. I didn't know a lot about the
company's product. I didn't really understand, you know,
what they were doing, and I could seriously
make some mistakes. But there were a lot
of people in that company. So when I
got someone on the hook, I just went
and got someone who was experienced to help
me. And I would say, hey. I've got
this person. Here's the situation.

(06:05):
What do I do? And they would jump
in and help me. Now by the end
of the week, I knew a whole lot
more about the product, and I probably needed
three or four more weeks of learning so
that I could do it on my own.
But what I was good at was getting
someone into the pipe. And once I got
them into the pipe, there were other people
that could help me. Now I'll move you
forward into my business. If you look at

(06:25):
the array of products that we sell and
the different businesses we sells to, it's almost
impossible for someone to really understand it. I
would argue that it takes years for a
person to come in and be able to
have a conversation with a customer and map
a solution to them,
based on where they are knowing everything we've
got. But we still gotta bring people in.
So what we say to our folks is

(06:46):
you get them on the hook. Like, you
bring them in and get them interested,
we will help you sell it. We have
this motto in our company called sell as
a team. Because the whole point is if
I've got someone and it's taken them, like,
nine months to sell anything,
that to me is way more heartbreaking
than if I can get them a win
early because we all jump in and help
them. And the fact that we're jumping in

(07:07):
and helping them, that's how they begin to
learn because now they're actually experiencing it in
real life versus in a book. Now I
don't know how that works for your business,
but my my point here is that how
do you get them to start building their
pipe earlier
is they have to start building pipe earlier.
But if they're building pipe and they call
someone and the person says, hey. Yeah. I
wanna learn more about this,
And they don't know how to sell it.

(07:28):
If they can't bring someone in to help
them, there's no reason for them to do
any pipeline building until you say it's ready
for them to go. And now they're, you
know, they're two, three months into the job.
You've paid them a salary for two or
three months, and the hardest thing that they're
gonna do is go out and prospect. So
you're having to wind them up at that
point versus
bring them in, get them acclimated,

(07:49):
and, like, every day for the first month,
give them a list of five leads to
call
and have them call those leads. And even
if they just set an appointment for one
of your veteran agents who brought them in
and took them along on the call, throw
them a spiff if you close it. Like,
I'm gonna pay a commission on it, but
you're gonna start getting this going.
That and that process, they can begin to

(08:09):
at least build pipe.
Does that make sense? Yes. That's that's how
you can go faster. It's hard work because
as leaders, you've gotta build a culture that's
willing to do that for them. But I
can tell you from experience,
one of
our wheelhouses as an organization
at Sales Gravy is
we're freaking good at helping companies

(08:30):
improve their sales onboarding.
We take companies that are taking a year
to onboard people, and we solve the problem
in ninety days. We took a a company
recently, a software company out in the Silicon
Valley, and it was taking them ninety days
to get new SDRs up to speed. We
were able to do it in ten days.
And all it was was understanding that we
need to teach people the things that they
need to know when they need to know

(08:51):
it as soon as they need to know
it. But the number one thing they need
to do is start building pipe. So I
would just suggest that look at what you
could do in your system
to get them
prospecting earlier, then pair them with veteran agents
who can also benefit for bringing them along.
But these people are learning how to have
the conversations, ask the questions,

(09:12):
learn the things that they don't know. If
a person comes in and says, hey, boss.
I'm dealing with the customer. Here's the situation.
Here's what's happening. What do I do? In
a situation like that, you can, like, really
teach them what to do versus a hypothetical
situation.
That leads me into the second question, which
is how do you marry
their efforts with your marketing efforts?

(09:34):
Correct. And and and an idea of building
the pipe for someone brand new. First of
all, what I would say to you is
you get new people, you're gonna have to,
as a business, provide them with some prospects
to call. These could be closed lost deals,
not your Glengarry leads. These are the worst
leads. Give them the give them the things
that nobody can sell. Have them go out

(09:54):
and build their own list. But at the
same time, what are they doing to build
out their personal brand on social media, building
out their relationships in the marketplace?
So you start thinking about what are your
top agents doing
to create the awareness that they're out there
and start taking those practices
and put them into a playbook. So if

(10:15):
I get somebody who's brand new coming on,
I need to be able to say, I
need you to, a, do this, do this,
do this, do this, do this. Whether it's,
like, especially with p and c since they're
in, a b to c space, they're probably
gonna be on Meta and TikTok and things
like that. You've got regulatory issues that you
have to deal with, so you have to
teach them to be compliant.

(10:35):
But I would not waste a day
giving them training on here's what you need
to do, and then I would begin setting
up metrics around it. Like, what are you
doing every single day to create awareness that
this is who you are, this is what
you're doing? I don't have time to, like,
get into, like, a full marketing
campaign, but how are they introducing
them themselves to all of their family and

(10:58):
friends? Like, one of the biggest issues that
I see with people that are in b
to c is that they think that their
family and friends know what they're doing. They
believe that everybody suddenly gets it. Right. But
if you don't tell your family and friends
often what you do, you wake up one
day and you're, you know, at a family
reunion, and uncle Joe goes, yeah. You know,
I just had a friend. He was getting
some auto insurance. I sent him over to
my buddy. And you're like, what? Why did

(11:18):
you I'm I'm your nephew. What's wrong with
you?
And uncle Joe goes, oh, I forgot that
you did that. So giving them those mechanisms
for individual marketing essentially,
and that should be paired with what you're
doing as an agency, and you should be
able to give them assets that they can
use. Think about what are they doing to
network in their community, and I would set

(11:39):
up expectations that you're gonna go to some
of these networking events. Like, you're gonna go
to your Chamber of Commerce networking event or
wherever your top agents are hanging out. These
are expectations, and you're gonna come back and
report about what you found out, what you
learned, and make that part of your onboarding
process over three months with clear milestones
about what you're expecting from them. You're paying

(11:59):
them a salary, so you can tell them
what you want them to do. I would
meld those two things together and then make
sure that your marketing team has the expertise
to guide
and train and coach and lead that process
with them so all of the onus isn't
on your shoulders
or the shoulders of your leaders. I hear
what you're saying, but I would say you
pair
that work

(12:19):
with actually talking with people and having conversations
and then have a team selling focus where
if they get somebody on the hook, we're
not letting them go out there all by
themselves and fail. You're absolutely right about that.
You break their soul in the process of
bringing them on board. They're not gonna be
very good salespeople. But if you do all
that together, what'll happen is you can accelerate

(12:39):
ramp up. And if you accelerate ramp up,
if you get them selling faster,
Katie bar the door. It will change your
entire business.
I love it. Thank you, man. I appreciate
it very much. Thank you. With them. God
bless you. Carry on. Thank you, sir. Have
a good one.
That was a great question from Gaius.
And I have a few final thoughts on

(13:01):
ramping new salespeople up fast. But before we
dive into that, a quick shout out to
Jessica Schilling who posted this comment on LinkedIn
about this week's Money Monday episode called failure
is not a tattoo.
She writes, this Money Monday really spoke to
me today. Thank you for always helping shift
the mindset.
I also wanna say thank you to Grace

(13:22):
Yawn, who's a senior at the University of
Tampa, majoring in international business marketing and who
was in the advanced sales and selling class
for sharing the Sales Gravy Podcast on LinkedIn
with her followers. Thank you, Grace. Appreciate that.
And finally, a shout out to user g
seven six six zero eight nine one, that's
a mouthful, who posted this five star review

(13:42):
on Apple. They write awesome podcast with real
tangible ideas to hit your goals. Jeb is
so uplifting and inspiring. Listen to this every
week, especially like Money Mondays and Wisdom Wednesdays.
If you enjoy this podcast, if you're getting
value from our message, please take three seconds
to post a five star review rating on
your favorite podcast app. It really helps us

(14:04):
out, and it helps us move up in
the algorithms so that other people can find
us.
One of the biggest challenges for sales leaders
and executives
is getting new salespeople ramped up faster.
An unproductive sales head is costly. It drains
the p and l. So getting them prospecting,
filling their pipeline, and making those cold calls
quickly is crucial.

(14:25):
Now at SalesGravy, 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 we get them
productive faster.
Remember, a long onboarding process delays success.
So pull the band aid off quickly and

(14:45):
start building pipelines with your new reps from
day one.
And teach your new reps from the get
go that when it's time to go home
and they're ready to quit for today, always
make one more call. I'll see you next
time on the Sales Gravy Podcast.
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