Closing Time

Self-Sourcing Pipeline: How to Empower & Enable AEs to do More Outbound

Sure, getting leads from marketing is great. Leads served up from your SDR team? We love it! But real revenue growth happens when AEs are also self-sourcing pipeline.

Sales leaders, if you want your AEs to get excited about outbound, it’s up to you to explain the “why” and enable them with fresh tactics for success.

In this episode of Closing Time, Jason Bay of Outbound Squad helps reps and their leaders really get outbound going by setting realistic activity targets, employing a solid contact strategy, and leveraging situation-based personalization.

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Key Moments:
The Challenge of Outbound Prospecting

When account executives take charge of sourcing their own leads, it boosts their motivation and performance because they’re driving their own success. This hands-on approach also means the sales funnel isn’t just relying on marketing, making it stronger and more versatile. Plus, it speeds up the sales cycle since AEs can build real connections and tailor their pitches right from the get-go.

If it’s so beneficial, why are reps so reluctant to put in the work?

According to Jason, one of the main reasons outbound prospecting is so challenging is the high rejection rate. In typical sales scenarios, win rates can be around 10-20%, meaning salespeople lose over 80% of the deals they work on. However, in outbound prospecting, facing a 95-98% rejection rate is considered normal. Dealing with this level of rejection requires a strong mindset and tough skin.

Jason highlights that this constant rejection can be extremely demoralizing. If any professional faced such rejection daily, it would be unhealthy and unsustainable.

Sales organizations that expect their teams to make calls and send emails without sufficient support, direction, or enablement are setting them up for constant resistance and rejection, which discourages continued effort.

To improve the situation, Jason advocates for a shift towards a more customer-centric approach. This involves moving away from aggressive product pitching and focusing instead on strategies that reduce rejection and center on the customer’s needs and interests. This change can make outbound prospecting more effective and less discouraging for sales teams. Keep reading to learn how.

Sales Leader's Role in Enablement

If you want your reps to be motivated to self-source pipeline, you first have to get them excited about it and give them the tools and tactics they need to succeed.

Step 1: Jason recommends sitting down with account executives to explain the “why” behind self-sourcing pipeline. He does this by calculating the necessary activities needed to achieve their commission goals, or what he calls “sales math.”

For instance, if an AE wants to earn a certain amount, they need to understand how much revenue they must close, factoring in their commission rate. This helps identify the gap that self-sourced efforts need to fill. For example, if 70% of the pipeline comes from inbound leads and SDRs, the remaining 30%—potentially worth $60,000—must be self-sourced.

Sales math calculator

Managers must have individual conversations with their reps to ensure they understand their specific targets. Instead of setting arbitrary activity goals, managers should help AEs reverse-engineer their numbers. For instance, if an AE needs to make 26 calls daily based on their pickup and conversion rates to set one meeting per day, this detailed breakdown makes the goal tangible and achievable.

Step 2: Jason employs “The Outbound Equation,” which is split between quality and quantity. He emphasizes the importance of quality in outbound efforts, which he breaks down into three components: fit, message, and delivery.

First, identifying the right prospects (fit) is crucial. Rather than working through a list in your CRM from top to bottom, AEs should focus on the most promising accounts. For example, if healthcare is a high-performing industry, AEs should prioritize healthcare accounts and target key decision-makers like VPs of IT.

Next, the message must be compelling and relevant to the prospects. And finally, delivery involves the AE’s soft skills—executing calls, writing persuasive emails, handling objections, and securing meetings. By focusing on these elements, sales leaders can help their reps concentrate their efforts effectively and increase their success rates in outbound prospecting.

Importance of Multi-Channel & Multi-Day Outreach Strategy

Effective outbound prospecting requires persistence, strategic targeting, and a well-structured outreach plan to achieve the best results. Jason offers several key tips to help reps optimize their impact. 

Tip 1: Multi-channel. It often takes 12 to 15 touchpoints to reach most prospects, which is why persistence is key. Jason explains that the contact strategy should integrate multiple channels—phone, email, and social media—as using three channels instead of one can triple contact rates.

Tip 2: Multi-day. For outreach to be effective, touchpoints should be spread over 2 to 4 weeks, not crammed into a single day. Jason suggests a structured weekly pattern: a triple touch (phone, email, LinkedIn) on, for example, a Tuesday should be followed by an email and phone call on Thursday. This sequence, repeated over three weeks, achieves the necessary 15 touches and is a great starting point.

Outbound contact sequence strategy

Tip 3: Prioritizing targets. Jason advises focusing more effort on high-value contacts, like VPs of Sales, who can significantly impact the decision-making process. For such key contacts, the full 15-touch sequence is warranted. In contrast, for lower-priority contacts, like sales managers, it may be efficient to reduce the effort slightly, tapering off on more time-consuming activities like phone calls.

Setting Activity Targets Without Historical Data

Activity targets are crucial for motivating sales reps because they provide clear, measurable goals that guide daily efforts and focus. These targets help reps understand what is expected of them and how their activities contribute to overall success.

Jason offers practical advice for setting activity targets, especially when there’s no historical data to rely on. He emphasizes the importance of avoiding arbitrary numbers. Instead, sales leaders should start with industry benchmarks and work backward from known metrics like win rates and the percentage of intro calls that convert into qualified opportunities.

Jason provides specific benchmarks to guide initial targets. For example, a good starting point is aiming to book meetings with 5-10% of contacts reached. Channel-specific benchmarks include a 5% average pickup rate for cold calls, with 10% of those calls converting to meetings, though top reps might achieve 25-30%. For emails, a 35% open rate and a 1-3% reply rate are reasonable targets, though Jason notes that the average reply rate is typically around 1%.

It’s crucial for sales leaders to explain the reasoning behind these targets. Jason points out that younger sales reps, particularly from Gen Z, are less likely to follow directives blindly. Instead, they respond better when they understand the logic and see an objective analysis behind the numbers. By clearly explaining the “why” behind activity targets, sales leaders can gain more buy-in and enthusiasm from their teams, fostering a more motivated and informed workforce.

Situation-Based Prospecting "At-Scale"

Personalization is no longer a nice to have in sales. In a competitive market, personalized communication is the only way to stand out and cut through the noise. It not only demonstrates that you understand and value the prospect, which builds trust and credibility, but it also increases the effectiveness of outreach efforts and improves conversion rates. 

Rather than debating whether to personalize, Jason suggests focusing on how to personalize efficiently. He introduces the concept of identifying common patterns among prospects. For instance, when reaching out to DevOps leaders, reps should look for specific triggers like hiring engineers, recent product releases, or mergers and acquisitions. These common situations can be used to create pre-prepared email sequences that require only slight customization.

Jason calls this approach “situation-based outreach.” By preparing for the most common scenarios, reps can have a repeatable game plan, allowing them to personalize at scale without sacrificing productivity. This method involves sorting through account lists to find prospects that fit these typical situations, reducing the need for extensive customization and making the outreach process more streamlined and effective.




If you enjoyed this episode, you’ll love the content Jason posts on LinkedIn. Give him a follow there and/or check out his podcast, The Outbound Squad podcast


Outbound prospecting is one of the most talked about topics in the industry today.
If you’re sales leader like me,
you’re asking the same question over and over, How’s outbound going?
Let’s talk about ways to get reps excited about self-service pipeline.
In this episode of Closing Time.
Hi I’m Dave. Osborne, chief Sales officer at Insightly.
Welcome to Closing Time. The show for. Go to Market Leaders.
I’m joined today by Jason Bay, founder and CEO of Outbound Squad.
Welcome, Jason.
What’s up?. Good to jam here with you, David.
Yeah, absolutely.
So, Jason, you and I were talking a little bit before the session, right?
Like, I think outbound is almost
the holy grail of building pipeline and has been for a long time.
And I know a lot of folks out there are deadly focused on either
adding that to their skillset or to their, you know,
their pipe gen strategy or they’re trying to just amplify it.
So I think this is going to be a really, really relevant topic for a lot of folks.
But, you know, looking at your past, you’ve always some big, big brands
at Outbound Squad, right?
You’ve worked with Zoom, Gong, CBRE.
The list goes on. Right.
So by that list, I mean, I assume that that means that the challenges
with building self-source pipeline isn’t just limited to small startups.
Is that fair?
Definitely not.
If you kind of step back
and think about, you know, why is this so hard and why do so
few people do it.
I mean, it’s filled with rejection.
I mean, worse than selling, you know, the average win rates,
you know what, ten or 20%, depending on your industry,
that means you lose 80% plus of the deals that you work.
Well with outbound, It’s one of those things where, hey,
if you have a 95 to 98% rejection
rate, you’re actually doing okay.
Yet, The mindset behind
dealing with that amount of rejection is crazy.
You know, when you apply for an Ivy League school,
the rejection rate is not 95% usually, Right?
You know, there’s all kinds of rejection that an individual faces
in sales with prospecting, that if anyone had that in their daily job,
it would be so unhealthy for them.
You know, I think that’s a really big part that as a sales organization,
if you’re treating outbound like,. Hey David and team, just go make calls
and go send emails and you provide very little enablement or direction
or guidance, you’re going to have people that pick up the phone and get met
with a lot of rejection and resistance and who would want to continue doing that.
So I think shifting into an approach that’s more customer centric,
that isn’t talking all about my product and pitching people who I have
not met before, like shifting to something that has less rejection
and is more customer centric is a start in the right direction.
So let’s talk about like how we kicked this off.
So let’s kind of pretend that,
you know, I’m a sales leader, I’m just getting started.
We’re about to do a stand up to do a an outbound motion, right?
So we have a meeting to get everyone pumped up about outbound, right?
And everyone is being hyped.
And then you check in a few weeks later and there’s absolutely no movement.
Like, yeah, what is the disconnect that happens there
between like an AE’s desire to self source
and build their own pipeline to them actually executing and getting it done?
Yes, I think that’s step number one is sitting down
with your account executives, and I call it the sales math.
So we have a sales math calculator that we use and we say, Hey,
you want to make X amount of dollars in commissions?
Let’s backtrack that into the revenue that you need to close
with your commission rate and say, hey, based on how inbound and SDRs
like that portion of your pipeline, you’re going to get 70% of the way there.
So that 30% that you need to self
source is worth $60,000 in your pocket, let’s say.
And then why is that number important?
You need to have that whole why conversation and that needs to be done
with a manager individually with each of their reps
so that you’re not about to do step number two and pull out an
arbitrary activity target and say,. All right, David and team,
everyone needs to make 30 cold calls a day.
No, you want that to be.
Hey, David, based on your number, if we back, you know, reverse engineer the math.
It looks like you need to make 26 of these calls
every single day because your pick up rate is 10%.
That’s going to give you two or three conversations.
And we know with your conversion rate, that’s going to be one meeting per day.
So that’s five meetings
a week of which you’re probably going to close one of those deals.
So if you can make it very real, that’s step number one.
Step number two, the kind of framework,. I call it
the outbound equation, there’s three kind of components to it
on the quality side of the equation.
So there’s a quality and then quantity side.
So I need to have activity no different
than if I’m working out and trying to lose weight.
I need to exercise for a certain number of minutes, right?
There has to be an activity.
I focus a lot on the quality side of the equation,
so there’s three parts on the quality side.
It’s fit, So who am I reaching out to?
Message, What am I saying?
Three is delivery, which is. I know the what the message should be.
What are my soft skills and my ability
to When the prospect says hello, execute a great call?
To write a compelling email, to handle an objection,
to secure our meeting, to get them to show up, etc.
So where I would start is the fit piece.
I think the number one mistake.
I was just on a call right before this with a sales leader
and we were joking around because he just joined a new team around
how the worst way to approach a set of accounts is to just go top
to bottom in your Salesforce or Insightly or your whatever.
What you want to do is you want to say that 100 accounts that you’re going after,
how do we say, hey, we know that health
care is the industry where we’re closing the most work right now.
We know that VPs of IT
Are the best place to get a meeting started.
Now let’s cherry pick and look at all the health care accounts.
Let’s get on LinkedIn SalesNav and look for newly appointed IT leaders.
Let’s see if there’s anyone
that used to be a previous customer that moved to one of these places.
Like let’s go through that exercise of the fit component
and say outbound is really hard.
It’s a lot of work.
Let’s make sure our effort is focused in the right direction.
So I’ll pause there.
That’s the most critical thing to nail first is where is my effort
going to be directed and at what?
How much of that?
Also, Jason is like a factor of, you know,. I don’t have the stats in front of me,
but there’s always a certain amount of touchpoints before you potentially do
get a response, right?
So I think conceptually, if this is your fourth or fifth or sixth
call or email or touch point, whatever that looks like versus the first one,
are you prioritizing like those follow ups or those subsequent calls first versus
is that something that you’re keeping in mind
or is that not necessarily as relevant as like title, etc.?
So I think first deciding what account am I going to go after
and who are the individuals that I’m going to target doing that activity first.
Second, we can start to think about our contact strategy.
So our sequence cadence, whatever you want to call it,
Orum, Bridge Group, Outreach, Salesloft, all of the sales
engagement vendors, all of their data will generally tell you the same thing.
It takes somewhere between 12 and 15 touches to get in touch
with most prospects.
So the most important thing is that whatever you do, it needs to
be multi-channel.
So it needs to be phone plus email, plus social.
Your contact rate will literally triple by having three channels versus one.
If you guys listening could guess which channel gets neglected the most it’s
definitely the phone.
People don’t pick up the phone.
Multi-day is, I can’t do 12 touches
in one day it needs to be spread out over 2 to 4 weeks.
So multi-channel, multiday,
those are the most kind of key components to it
and the way that you want to think about spreading out the touches
is a weekly touch pattern could look like this.
It’s a Tuesday.
Today I do phone, email, LinkedIn,. I do all of those at once.
I do a triple touch and then I wait two days.
On a Thursday,. I do an email and a follow up phone call.
So that same weekly pattern. I follow three weeks in a row
that’s going to get my 15 touches.
That’s a great starting point.
Now, the FIT piece, what you want to think about
is how you segment and prioritize who you’re spending effort on.
It’s like, David, you’re a VP of sales.
Like in terms of my target market, you’re the person really ultimately
that I want to meet with.
I might be meeting with a sales manager or a director of sales first,
but ultimately I know a VP of sales is a champion.
Like that’s going to be
someone that can mobilize a training engagement to their CRO.
So if I’m reaching out to you, David,. I’m going to do that
full 15 touch sequence because it’s worth it to spend extra time on you
because that meeting is really high value to me.
Now, if I don’t mind meeting with the sales manager, let’s say
one of your managers to get the deal started.
I’m probably not going to exert that much effort,
so I might taper off on some of the phone calls,
like the manual elements of this that require my manual work.
I might taper off on those.
So it’s really important to think about what accounts are most valuable to you,
what types of job titles will typically be most valuable?
And it’s about putting more effort
in the areas where the return is higher and less effort in the areas.
Honestly, where I just
a sales manager
is not getting as much cold outreach as someone like you, right, or a CRO.
So I need to work harder to get that meeting.
And it’s also worth more.
Do that answer your question.
That was kind of a roundabout, really long winded answer, but that’s, that’s how
I think about the sequencing and like the contact strategy.
No, that’s perfect.
And, you know, I was I was thinking about and I can remember the word you used,
but like the combo, right, where historically or even today,
maybe phone calls are the least high contact rate.
But having that multi-channel strategy is super impactful.
So let’s talk about maybe taking a step back.
Talk about activity targets.
Which gets a bad rep from a lot of folks.
But I think we’re I’m curious to understand is, again,
if I’m a sales leader, getting an outbound motion out for the first time.
You talked about looking at historical data
and kind of kind of backing your way into a prescriptive approach.
But let’s say we don’t have a lot of historical data.
So how would you recommend leaders architect
the initial activity targets and adapt from there?
One, I wouldn’t just
pull that number out of thin air, which you’d be very surprised.
The larger the company, the more they just pull numbers out of thin air.
Like are totally arbitrary number that they talk to their peers
and that’s just what they said their activity target was.
You could just use industry benchmarks.
So if we were going to work backwards, like you should know,
you should at least know your win rates
and you should know what percentage of like an intro calls turn into,
you know, a weighted pipeline or a qualified opportunity,
you should at least know those metrics.
So if we work backwards to
how many people would I need to get in touch with in order to get a meeting,
I’ll give you some benchmarks that you could work off of.
So with the total number of contacts that you’re reaching out
to booking meetings with, somewhere between five and 10%
of the everyone that you reach out to, that’s a good starting point to use.
And if you wanted to dial it in per channel,
the average pick up rate for a cold call is 5%.
The average conversion rate of connected
cold call into a meeting is around 10%.
Your best reps should be in that 25 to 30% range.
Email, Your open rates should be around 35% on average.
Your reply rates going to probably be around 1 to 3%.
The average called email reply rate is actually 1% according to Clearbit,
that’s honestly being a little generous from what I see in a lot of companies.
So you could use those benchmarks as a starting point
to kind of work backwards around the math.
And you need to explain the why behind the math if you’re speculating
and don’t have like real numbers to work off of.
I think people sometimes like sales leaders I find
they kind of treat their reps like they’re idiots or something.
You know what I mean?
It’s like, dude explain the why behind it, get them excited about the number,
but also like show them that you’re like using
an objective analysis to come up with the numbers.
I think this era of like, especially with younger
sales reps coming in Gen Z
and this is the case
with all younger generations typically, but I think very much so a Gen Z and I’m
a millennial,
this like I’m going to
blindly follow authority, just doesn’t work anymore.
Like that’s how I was led as a sales rep.
It just doesn’t work.
Like explain the logic behind the number
and what you’re asking your reps to do and you’ll have a lot more buy in.
100% agree.
Maybe just to wrap up, I’d love to hear your thoughts on personalization.
I think that’s a nice young dovetail from what we were just talking about there.
So obviously you talked about quantity and quality both being important, right?
And when doing prospecting, we do need to cast a wide net,
but would love to kind of understand how you think about casting a big net
versus using kind of a sniper rifle.
Right, in some situations.
So, you know,
feels like the one to many approach is a little bit behind in the past.
So is that what you’re seeing with your client base or how do you approach that?
The question really is not like whether you should personalize or not.
It’s it’s really kind of like, how do I do this
and still remain productive and get out emails, right?
So the way that you personalize at scale, as you know, that term has been coined is
how do I find common patterns in the people that I’m reaching out to?
So if I was to give you an example,
I worked with a company that sells into DevOps leaders.
DevOps is essentially the equivalent of sales enablement for reps.
They do it for engineers, they make an engineer’s life easier.
So when they’re reaching out to these DevOps leaders, it’s like,
Hey, the situations you’re looking for, are they hiring engineers right now?
Did they recently release a product?
Did they recently go through M&A?
There’s like all this really common like 5 to 10 triggers,
but you should have an email sequence prepped and ready to go that you can add
slight customization to around all of those situations.
So situation based outreach is how you can really prepare
for the most common scenarios and have a game plan that’s repeatable.
So when you’re going through your account list
and you’re going through the people to reach out to you, you’re
looking for people that fit into the different situations
that are really common so that you don’t really have to customize that much.
That’s that’s the big idea.
That’s how you do that at scale.
That’s perfect.
It’s not about looking at the person’s. LinkedIn profile
to see where they went to school or the content they post.
Make it about the company.
Love it, love it.
All right, folks,
that’s all the time we have for this this episode of Closing Time.
Really appreciate taking the time, Jason.
Really, really relevant content.
Appreciate it.
Yeah, absolutely.
All of our stuff is at
We have a podcast as well, Outbound Squad Podcast
so make sure to check it out if you’re looking for more tips
or how to make a lot of what we talked about today more actionable for you.
Remember to subscribe to the channel, like this video,
and tick the bell for notifications so you don’t miss another episode.
We’ll see you next time.

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