Closing Time

Flipping the Script: How to Get Started with Cold Calling & Enjoy it!

How can you be creative, have fun, and let your personality shine in sales?

Would you believe it’s by cold calling more?

In this episode of Closing Time, we welcome Daisy Chung from Orum, who is on a quest to make outbound sellers love cold calling (yeah, you heard that right). 

Daisy maps out for new outbound sellers how to get started with cold calling, build confidence while doing it, and leverage those valuable skills to advance their sales career.

Get ready to change your whole perspective on every salesperson’s least favorite task…cold calling!

Watch the video:
Key Moments:
Reframing Rejections — From Personal Attacks to Positive Outcomes

Cold calling, often dreaded for its association with rejection, can actually be a gateway to humor, confidence-building, and fun. Daisy says that the key lies in reframing how we perceive rejection.

It’s natural to view cold calling as a series of rejections, but it’s important to remember that even the most successful individuals have faced numerous rejections. Rather than seeing rejection as a setback, consider it a stepping stone.

Each ‘no’ is an opportunity to develop resilience and confidence. As you become more accustomed to rejection, its impact lessens, allowing you to approach calls with a lighter, more creative attitude. You can even start infusing humor into your conversations, making the process more enjoyable.

That said, Daisy emphasizes that it’s crucial to separate yourself from the rejection – it’s not an attack on you, but a part of the business process.

Understanding that rejection is not a personal affront but rather a natural part of searching for a mutually beneficial business arrangement can significantly ease its sting. When you detach the personal element from cold calling, it becomes easier to handle rejection.

Daisy explains that your role as a salesperson is to explore various methods of persuasion and communication to help others see different perspectives. When you focus on being creative and thoughtful in your approach, cold calling becomes a less personal and more enjoyable experience.

This mindset shift transforms the cycle of rejection into a cycle of positivity, where each challenge is an opportunity for growth and improvement.

Leveraging New Technologies — Intent Data, Velocity Acceleration, Call Coaching

Gone are the days when sellers relied solely on cell phones, binders, and pen and paper to make calls. Daisy recalls her time as an outbound seller and how the manual process was time-consuming and often inefficient, with hours spent to reach only a handful of potential customers.

Today, outbound sellers are equipped with a variety of tools that make the process more efficient and effective. Here are just a few that Daisy recommends:


One key advancement is the use of intent data through platforms like 6sense. This technology helps identify leads who are more likely to be interested in your product, ensuring that calls are targeted and more likely to be successful.

Another vital tool is what’s known as a velocity acceleration tool, like Orum. This technology significantly increases the number of live conversations a seller can have in a day, reducing the time wasted on unanswered calls. It allows sellers to focus on their pitch rather than the manual labor of dialing numbers.

Finally, coaching software such as Gong plays a crucial role. It helps sellers analyze their calls, providing insights and feedback that enable continuous improvement in their approach and technique.

Bonus: Integrating these tools with your CRM to reduce manual data entry, streamline processes even further, and expedite your sales process.

In essence, the integration of these technologies into the cold-calling process has revolutionized outbound selling. Sellers can now focus more on the quality of their pitches and conversations, talking to the right people, rather than getting bogged down in the manual, labor-intensive aspects of the process.

New Email Regulations and Their Impact on Outbound

Starting in 2024, new regulations from Google, Yahoo, and likely other email providers, are going to change the landscape for outbound sellers significantly. These regulations will impose stricter controls on bulk emailing, with a particular focus on the quality of emails. Daisy explains that as a result, sending generic, mass emails will become more challenging. This shift necessitates a change in strategy for sales representatives.

In light of these changes, personalization in emails is more crucial than ever. Outbound sellers will need to invest more time in crafting customized emails tailored to each recipient.

This approach, while time-consuming, will increase the likelihood of the email being read and responded to, rather than being dismissed or deleted. The downside is that even after spending hours on research and customization for a perfect email, there’s still a risk it might not get the attention it deserves.

Meanwhile, phone communication is emerging as a viable alternative. One of the key advantages of phone calls is the ability to cut through the digital noise. Once a call is answered, it provides an immediate, direct line of communication. Even in cases where calls are not answered, modern software and tools can save time by streamlining the calling process, reducing the time spent on unsuccessful attempts.

Daisy suggests a multi-channel strategy of combining emails and phone calls to prospects. For instance, after sending a well-researched, custom email, a follow-up phone call can direct the recipient’s attention back to that email. If the email was initially overlooked or deleted, the phone conversation could prompt the recipient to revisit and reconsider it. This integrated approach could potentially enhance the effectiveness of outbound selling efforts in the face of the new email regulations.

Building Confidence & Negotiating a Higher Comp Plan

Cold calling teaches resilience. Every time you dial, you’re exercising control. You choose to make the call, handle rejection, and keep going. Daisy explains how this process instills a powerful sense of empowerment. You learn to view rejections positively and not take them personally. This mindset, cultivated over time, builds immense confidence.

This confidence and empowerment are not just abstract concepts—they translate into real career progression. In Daisy’s decade-long experience in sales, this self-belief propelled her from one promotion to another. When you believe you can control outcomes, you’re more likely to take initiative and demonstrate the skills that lead to career growth.

You can also leverage these skills for higher pay. Here are a few talking points Daisy shares:

Outbound vs. Inbound Value. Outbound sales reps, especially proficient cold callers, are often more valuable than their inbound counterparts. This is because outbound efforts drive revenue independently of market fluctuations and marketing spends.

Economic Impact. A skilled outbound salesperson can articulate their value to potential employers. For instance, if you’re interviewing, you can point out how your ability to generate outbound revenue can save the company money on marketing and provide a more reliable revenue stream, even in uncertain economic times.

By demonstrating how your skills contribute to the company’s bottom line, you can make a strong case for higher compensation. This isn’t just about the revenue you bring in; it’s about showcasing the reliability and consistency of your performance, regardless of external factors like inbound leads.

Preparing for the Interview

When preparing for an interview as an outbound seller, Daisy emphasizes how important it is to showcase your cold-calling skills effectively.

Hiring managers, like those at Orum, often use mock cold calls as a key part of the interview process. These mock calls might involve scenarios where you’re asked to pitch as if you’re a representative of the company you’re interviewing with. This tests your ability to handle common objections and demonstrates how quickly you can adapt to a new product or service.

You should also be prepared to pitch the products or services of your current company. This method allows the interviewer to see how candidates perform in a more familiar context, showcasing their natural selling abilities and how they navigate objections they’re already comfortable with.

It’s not just about the technical skills in cold calling; it’s also about your approach. One crucial tip for those aspiring to excel in cold calling is to make it enjoyable. View cold calling as a collaborative and fun team sport, rather than a solitary challenge. Embracing the fun aspect can help alleviate the stress of rejection and motivate you to engage more actively.

Remember, successful cold calling can lead to significant deals, and it’s an excellent way to improve your skills, earn promotions, and potentially increase your earnings.

So, approach it with a positive attitude, focus on honing your skills, and enjoy the process. This mindset not only helps in the interview but also in your overall career in sales. Good luck!


What activity in sales is creative, humorous and a confidence builder?
What if I told you that activity is cold calling?
Let’s break it down in this episode of Closing Time.
Thanks for tuning in to Closing Time the show for Go to Market leaders.
Val Riley, head of Content and Digital marketing at Insightly CRM.
Today, I’m joined by Daisy Chung.
She is the director of sales at Orum, an outbound calling platform.
Welcome to the show, Daisy. Thanks, Val.
Great to be here today. Excited to chat. Awesome.
So when most people think of cold calling, they don’t associate it with
humor., building confidence or something fun.
They really associate it with rejection.
And I want to hear how you flip that script.
Yes. So I think it’s very common to think about cold calling as rejection
because you do get rejected on calls more often than not.
But the most successful people I know are folks that have gone through a lot
of rejections.
So when you reframe the thought of rejection from bad to good,
that will empower you to start thinking of it as a good thing.
Because with each rejection,
you’re building the grit and the confidence to get better and better.
That rejection impacts you less and less.
And so
a lot of times once you get past that, you’ll start having the strong mindset
where every rejection is just empowering you
to have a better and better conversation and can start laughing about it, adding
jokes, being creative, relaxing and not being so scared of this rejection
piece of it.
And with that, it becomes a vicious cycle of positivity
because you’re excited for the rejection, you’re excited for the next challenge,
you’re excited to get better.
And that’s how cold calling can be a lot more fun than thinking about it as a
negative thing.
Is there a specific way you
talk to people about not taking it personally?
Yes. A lot of it is really mental.
You have to really take away the the personal part of the cold calling
where you think that they’re attacking you or it’s directly at you
when they’re rejecting you.
If you can take that away and know it’s not personal, that this is strictly
business, it’s strictly trying to find the win win between the two of you guys.
And if you can’t come to agreement and it’s your job
as a sales rep to find different ways to consult,
to persuade, to get people, to see other perspectives.
And so when you take out the personal from it,
I think the rejection is a lot easier to take.
And when you spin it
so that, it’s your job to get creative, to get thoughtful,
to think of different ways of talking about it,
that way it becomes a lot more fun, a lot less personal, too.
Got it. Okay.
So you say that cold calling has changed a lot in recent years
for the better based on a few factors.
The first one is that maybe tech is making it a little bit easier. Yes.
So when I started cold calling about,. I’d say almost ten years ago,
we would use an actual cell phone.
We have a binder with pieces of paper and I would just call one by one.
If someone picks up, we write the conversation,
if they don’t pick up. I put, left voicemail, etc., etc.,
literally pen, paper, binder and a cell phone.
And it will take me hours.
I kid you not 8 hours plus day to call a hundred people,
talk to maybe six or seven and make sure everything’s recorded here.
Fast forward ten years now.
I think we’re very blessed with so much technology on the market.
Typically, when folks are thinking about cold calling,
I think in today’s world we have a trifecta effect.
So there’s three technology that comes to mind
whenever you cold call you always want to have some sort of intent data.
So software like 6sense, which will tell you which leads
are more likely to be part of your ICP, which leads are more likely to have
a stronger relation to what you’re selling so that you’re calling smart.
From there we recommend some sort of velocity acceleration tool,
something like Orum, where our goal here is to drive more live conversations.
You know, it’s not fun
when you’re calling all day and no one is picking up
and you spend a lot of time on that manual work.
But what if there’s technology that can plug you in to conversation
after conversation after conversation
and your only job is to pitch versus all the manual labor?
The last piece is some type of coaching software, such as a Gong,
where you’re able to really take the live conversations at high
velocity and get better and better.
So gone are the days where you’re doing everything manually.
There’s no data, there’s no insight, there’s no direction, essentially.
Now, there’s technology
that can do all that for you so all you’re left
with is pitching and getting better and talking to the right people.
Yeah, I mean, definitely big advantages there.
Another aspect that you say that is changing is the remote workplace, right?
Post-Pandemic and the fact that a lot of phone numbers are actually cell numbers.
So in today’s world, a lot of times what we’re seeing is
we always want to target as many mobile numbers as possible.
Because since the pandemic, a lot of folks have now turned remote
or partially remote
and we’re seeing a big uptick in people picking up because people are working
at home because it’s, one a lot quieter and easier to pick up your cell phone.
Two, A lot of times, meetings can either run late, start early, all that fun stuff.
And so you usually have five, 10 minutes between the top of the hour or meetings
like that.
And so if someone’s calling you.. It’s quiet.
You have a higher chance of picking up versus in the office,
if someone’s calling you
even if you’re done with the meeting earlier,
you have a coworker grabbing you, someone saying this
someone saying that, and it’s very easy to ignore your calls.
So I say in today’s world, generally speaking, it’s been
we’ve seen a big uptick in people picking up their mobile numbers.
So as a remote worker,. I can tell you some days,
if I’ve just spoken to my cats all day,. I might actually pick up a cold call.
So I think there’s value there. Yeah.
So another
factor we want to talk about is what’s going on with email.
And in case anybody watching this does not know, starting in 2024,
there are just additional regulations coming from Google and Yahoo!
And I’m certain other vendors will follow suit where there’s going to be heavier
restrictions on bulk emailing and
and just email quality will be scrutinized.
So maybe in that case the phone is looking like a better option as well.
So with emails being scrutinized right now,
I think it’s more important than ever to send very customized emails.
We’re a big fan of doing everything, but now that it’s harder
to send high volumes of emails without super customizing them,
it gets really tough because a good rep can spend hours doing the research,
doing the customization, writing one stellar email.
But more often than not,
senior leadership will just click delete, and all that work will be for naught.
And so with phone, what’s great is you can cut through the noise.
Once you get that pick up, you can have that conversation.
If you don’t have it picked up, you have the software and tools
that will save your time,
not spending a bunch of time calling and not talking to anyone.
I think it also gives you the advantage that if you do put together
the time and effort for that very custom email, once you get a pick up,
you can have them refer back to the email that you deleted. It.
They’ll go ahead and flag it back open because you’re asking
them to on that call too.
Got it.
Okay, so maybe a tiny bit easier now, but in general,
cold calling really is a skill that salespeople need to hone.
Can you maybe talk about your own experience
with cold calling and how it maybe helped you move up the ranks a little bit?
Yeah, I know.
Earlier we talked a little bit about how
cold calling can drive confidence and creativity.
Just through the repetition and reframing how rejections is a positive thing.
I think the biggest thing that has helped me personally through over ten years
of cold calling is that that empowering piece,
when you’re cold calling, you really become empowered
because it enables you to believe that everything’s within your control.
You decide to pick up your phone, you decide to have a call.
You decide that after you get rejected, someone tears
you apart, you’re gonna pick up the phone again.
You decide that someone says something that doesn’t make you feel great, that
you’re going to pick up the pieces, not take it personally and continue going.
Because of that and because that improves your skill set.
It gives you that confidence and that empowerment
that you could pretty much do anything you set your mind to.
I think that has always given me the confidence
throughout my entire sales career to go from promotion after promotion
because I feel
very empowered that everything’s within my control.
What I want.
And I think cold calling gives you that confidence and that empowerment to do so.
Wow, So maybe a highway up the career ladder,
kind of riffing off of that in terms of a comp plan,
if you have experience in cold calling and success, proven success
in cold calling, it seems like if you’ve mastered that,
you might be able to attract or earn a better comp plan
just because of the economics of working
inbound leads versus doing outbound.
So a lot of times it might not be obvious on why if you’re a strong outbound rep,
someone who can cold call and drive outbound revenue,
deserve a higher compensation plan.
However, if you’re interviewing, you’re a candidate, and you’re able to articulate
that your skill set to drive outbound, to drive more revenue,
and you can articulate back,
if you do your research and share with that company that, hey,
I notice on your quarterly earnings report, you guys are spending X, Y, Z
dollars on marketing and that can be very, very expensive.
And with the ups and downs of the economy, marketing and inbound leads
aren’t always guaranteed.
With your outbound expertise and how you’re confident
you can bring in revenue and pipeline throughout outbounding
that should equal to X, y, z more savings for the company
x, y, z, more revenue x, y, z, more reliability that I’m going to be
a rep that’s consistent regardless of inbounds come or not,
and that should be able to command X, y, z, percent more pay
because of the confidence. I’m giving you in my abilities here. So
a rep that can connect the dots essentially
should be able to command a higher comp, compensation plan here.
Can you talk through, in your experience as a hiring manager,
how you really test or validate someone’s cold calling skills?
A couple of things.
When we’re interviewing for, let’s say, sales development reps
who really focus on cold calling, we do do mock cold calls.
We have them do actual cold calls in a couple of scenarios.
I think one, the scenario is having them pitch as if they’re a rep at our company,
Orum, and see how they go through some of the common objections.
But we also do another mock where we have them pitch their current company
because a lot of times you can see people get a little uncomfortable.
They don’t know what to say, they don’t know the competitors.
All that fun stuff,
but you really see them in their realm, their world when they’re pitching
what they’re selling today.
And that will give you a lot of insights on how they navigate objections
that they are currently comfortable with.
I love that idea.
I think it’s great to put them in the place where they are comfortable
and then you can really see their actual sales skills shine versus
how much they have managed to learn about your company
in that very short period of time when they’ve been interviewing.
Yep, exactly.
And you really want to see how they sell
when they’re the most comfortable and the most confident too.
Got it.
Daisy, any other tips for our potential budding cold callers out there?
I think the biggest tip is have fun.
A lot of times. I think the rejection piece,
and you feel like you’re kind of alone in this bubble.
Makes it very hard for you to have the, have the urgency to pick up the phone
and start calling.
But if you make it more fun, you make it more collaborative,
you make it a team sport with other colleagues,
and you create an environment where it’s just a lot more fun.
I think you get a lot of results from there and know that end of the day,
you know, big, big deals are closed from cold calling.
And so if if you’re motivated by money, you’re motivated by promotions,
you’re motivated to just get better yourself as the skill set.
I think cold calling is a great way to really up level those skills sets.
Well, I hope everybody out
there is inspired to pick up the phone after listening to this episode.
Daisy, thanks so much for joining us. Of course.
Thank you, Val.
All right. And thanks to all of you for tuning in out there.
Remember, you want to like this video, subscribe
to the channel and click the bell so you don’t miss an episode.
We will see you next week.

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