Jesse Ouellette

Founder

Growth & AI Automation Expert | Helping Sales & Marketing Teams Land in the Primary Inbox with the Right People | Modern Outbound Strategy

LeadMagic has two core SaaS Products for B2B Sales/Marketing Teams.

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Sales leader with a strong foundation in mathematics and a passion for driving results through strategic outbound sales initiatives. With a proven track record in pipeline generation, coaching, and multichannel outreach, I've successfully built and mentored high-performing sales teams across various SaaS companies. My experience includes implementing AI-based automation, developing effective sales processes, and delivering training that has generated significant pipeline growth. 

Before entering sales, I was a mathematics teacher, where I honed my skills in problem-solving and critical thinking. Notably, my team tied with Harvard in a prestigious math contest sponsored by the NSA. 

Visit my website www.thejoyce.net to schedule some time and discuss sales coaching and subscribe to my newsletter at thejoyce.substack.com

Patrick William Joyce

I don’t talk about this much, but getting clean and sober changed my life.

Not to be cheesy - I am sharing this here because every time I do, someone reaches out struggling with the same things I did. 

Seems like addiction is common among sales pros. Correlation is not causation, but I mean… I feel like there’s a connection…

I had what I’d call a spiritual awakening. A lightning bolt moment. I was living on hard mode by choice. I thought I was managing stress. I was really just numbing it and creating more of it.

Life didn’t suddenly get easier when I got sober. The stresses are mostly the same. Work. Money. Kids. Marriage. Expectations. Pressure. That part didn’t disappear.

What did disappear was a huge chunk of self inflicted chaos.

How I handle stress is different now. I pause. I don’t spiral as fast. I don’t make it worse trying to escape it. I can sit with discomfort without needing to run from it.

The biggest impact has been on my family.

I’m present. Actually present. Not physically there and mentally gone. My kids get the best version of me more often. My wife gets consistency instead of unpredictability. Trust rebuilt slowly (still rebuilding)

Mentally, things are clearer. Not perfect. Clearer.

Anxiety still shows up. Fear still shows up. Doubt still shows up. The difference is I don’t let those things drive the bus anymore. I can see them for what they are. Temporary, manageable, non emergencies.

If you’re in it right now and wondering if it’s worth it, I won’t sell you a miracle story. I’ll just say this - getting through the door is very difficult, but once you’re on the other side, you’ll wonder how you made it so long without removing the handicap.

Life is still hard. There’s no need to make it harder.

Outsourced Cold Calling for B2B That Actually Works | CEO @ Outboundless

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Couple thoughts going into the new year-

1) most people on LinkedIn sales influencers space are full of shit

2) cold calling will always be basically the same

3) fastest channels for getting new customers as an agency are inbounds and referrals. 

3) Content informed leads (ie people who read your stuff) are extremely slow but pay off huge in the long tail

4) there are literally no short cuts


PS me and this guy James Bawden are working on something cool. Did a little business trip to Raleigh and met up with him 

And my 19 month old son just pooped in the bathtub so I guess I’m done with this post. PEACE!

Couple things I’m fired up about at Outboundless -

1) building a client acquisition funnel that isn’t me grinding and doing “guerilla marketing”. 

This has gotten me pretty far, but I only scale to a certain point. 

This also means tightening up my offer and niche (already pretty tight)

2) removing myself from as many core business functions as possible. 

This is extremely difficult. It means building systems around what I do instead of just looking at it and figuring it out - anyone should be able to pick it up and follow a process.

3) expanding - January is looking pretty hot for a small team like us. 

Ultimately I’m passionate about helping early stage founders derisk outbound. It sounds cheesy but I have been the guy they over invested in, I’ve been on the teams that weren’t ready to exist yet - both of these are bad experiences for everyone.

If I can save just one team from doing this by offering fractional help and giving them a blueprint to naile their niche, talk tracks, segment the ICP (the actual one, not the imagined one pitched to investors) then I am feeling successful.

All good on this front! Let me know if you need a push with anything. See you in the DMs

Steal this hook:

"I noticed you used to work at [company], they're a client of ours -- we help them with xyz, was hoping to go over some similar ideas with you"

Have heard of people systematizing this via clay tables, Jed Mahrle, Kellen Casebeer maybe?

A client asked me a deceptively simple question last week.
“Can you build two lookalike lists based on our best customers from the last six months?”

Here’s what I actually did:

I took their customer list and dropped the domains into DiscoLike.

 No Frankenstein workflow -- just pattern matching against real sites.

Within minutes, I had two clean lookalike cohorts, one for each 

From there, the rest was boring in the best way.

I exported the account lists.
Uploaded them into LinkedIn Sales Navigator.
Pulled the exact titles their team already closes.
Ran a clean export via PhantomBuster.

End result:
Two outbound-ready lists.
Accounts they actually resemble.
Contacts our SDR can call today.

Total time: <60 min

Here’s the point I keep coming back to.

Most sales teams don’t have a data problem. They have a workflow problem.
They treat list building like a data science project.
 
When it should feel closer to search.
“Show me companies like this.”
“Now narrow it.”
"Now give me the people.”

When you remove the automation puzzle, you get speed.

When you get speed, you get reps actually using the list.

When reps use the list, pipeline happens.

If you’re an SDR, agency or solo operator, ask yourself this.

How often do you lose a good targeting idea because it feels too annoying to execute?

That gap is where most outbound momentum dies.

Curious how others are handling lookalike builds today, especially outside the usual Clay-first stack.

Do Not Launch Outbound Until This Is True (A Checklist)

Most outbound fails for one simple reason. People hire an SDR before the system exists.

They think activity creates clarity. It does not.

Outbound only works when a few things are already true. If they are not, you are just paying to learn lessons the hard way.

Here is the checklist.

1. You can name a specific wedge you are attacking

If your target is “any company that could use this,” stop.

You should be able to say:

One industry
One role
One broken workflow
One reason it matters now

If you cannot explain this in one sentence, your SDR(s) will not be able to either.

2. Your ICP is defined by pain and stakes, not job titles

Job titles do not buy things. Problems do.

You should know:

What they are actively trying to do
What keeps breaking
What happens if it does not get fixed this quarter

If the consequence of inaction is unclear, cold outbound will feel interruptive instead of relevant.

3. You have real language from real buyers

Not positioning statements.

You need:

Words customers use to describe the pain
The moment they lean in on calls
The sentence that makes them say “yeah, that is exactly it”

If you cannot point to this language, your messaging will sound generic no matter how polished it is.

4. Your list is built intentionally, not in bulk

Every account on your list should have a reason it belongs:

Tech stack
Business model
Recent change
Known friction

If you cannot explain why a company is on the list, it should not be there.

6. Your message passes the “cold test”

Read your opener and ask one question.

If I received this with no context, would I immediately know:

Why you are reaching out
Why now
Why I should care

If the message needs explanation, outbound will struggle.

7. You have an execution cadence, not a campaign

Outbound is a weekly operating system.

You should already have:

A plan to test messaging weekly
A way to review calls and replies
A simple feedback loop between results and changes

If you are just “letting it run,” you are not ready.

Copy this checklist before you launch

  ☑️ One clear wedge defined (industry, role, workflow, urgency)
  ☑️ICP written as pain plus stakes, not persona fluff
  ☑️Real buyer language documented and reused
  ☑️Early success and failure signals defined
  ☑️Lists built with intent, not volume
  ☑️Cold message that passes the clarity test
  ☑️Weekly execution and review cadence locked

If you are missing two or more of these, pause. Fix the system first.

Save this post.

It is easier to check a box now than unwind a broken outbound motion later. This pairs with the outbound engine post for a reason.

One is how to build it.

This is how to know you are ready.

I’ve been playing Magic: The Gathering since 1998.

I started as a kid -  long before content creators, deck trackers, or tier lists were a thing. You found a local shop or a friend’s kitchen table and figured it out as you went. Mostly by losing.

Lately I’ve been back at my local game store playing regularly. Draft nights, Commander games, the whole thing. Same game I grew up with, but it hits differently now that I’ve spent years in sales.

I hit mythic rank # 281 in December. Thats out of about 10 million people. 

What stands out though is the business model.

Magic is pure B2C. It’s an entertainment product with actual demand. No one needs to be educated on why it exists. The product already has pull. Marketing, positioning, and timing matter more because people are already looking for more product to spend money on.

We like to imagine B2B is fundamentally different but most B2B purchases are still anchored in want. It’s just framed differently.

"Want" shows up as something they’re already trying to do- Move faster, reduce friction, prove a decision etc.

Your product doesn’t create that desire. It either aligns with it or it doesn’t.

Magic makes this obvious because no one pretends it’s rational. Sales often forgets the same rule applies.

People buy what they want, especially when it helps them do what they’re already trying to do.

How would you answer "sell me this pen" in an interview?

Here’s the uncomfortable truth about “nurturing” in B2B.

Most of it is theater.

Sending articles. Forwarding podcasts. Adding someone to a drip and calling it relationship building.

It feels productive. It is also easy to ignore.

Enterprise buyers do not build conviction through links. They build it through proximity.

Face to face does a few things nothing else can.

It creates friction.
Friction creates attention.
Attention creates memory.

When you sit across from someone, you get real signals. Hesitation. Interest. Resistance. Politics. None of that shows up on Zoom. None of it shows up in email replies written by committee.

Flying out changes the dynamic. Hosting a dinner changes the power balance. Putting people in the same room creates shared context.

That is what “nurture” actually means at the enterprise level. Shared context over time.

If you want to nurture ANY account, stop hiding behind content.
Use the marketing budget to bring people together.

Host a small dinner. Create an event with a reason to exist. Show up in person.

It is expensive.
It does not scale cleanly.
It works.

Everything else is just hoping someone reads what you sent and feels something later.

Here is a step by step process to set up an outbound sales engine. It is built to be repeatable and for strangers who owe you nothing. 

Step 1: Pick ONE market wedge

You do not start with “anyone who could use this.” You start with a wedge you can win.

A wedge is:
One industry
One role
One painful workflow
One reason to care now

If you cannot name the workflow, you cannot write messaging that lands. 

Step 2: Make 3 to 6 segments based on external facts, not vibes:
Tech stack
Business model
Headcount band
Geography
Compliance environment
Trigger events (hiring, funding, new region, new system)
Each segment gets its own “this is why you should care” story.

Step 3: Define the ICP inside each segment

For each segment, answer these:

Who feels the pain daily?
Who owns the budget?
Who gets blamed when this breaks?
What metric do they get judged on this quarter?

Write what they are trying to do, what blocks it, and what happens if they fail. 

Step 4: Extract founder knowledge, then distill it

This is the part most teams skip. 

Do a 60-minute extraction session and capture:
10 deals you won and why
10 deals you lost and why
The moment prospects “lean in”
The exact words customers use to describe the pain
The “before” state they want out of

You are hunting for one sentence that hits the nerve.

Step 5: Write messaging that taps into existing urgency

You cannot manufacture urgency. You can only tap into it. 

For each segment, write:
2 pain hooks (workflow friction)
2 stake hooks (risk, cost, missed goal)
2 proof hooks (who this works for, what changed)

Then build:
A two sentence cold email
A 30 second cold call opener
If your message needs explanation, it will not convert cold. 

Step 6: Data that matches the segmentation

Do not buy from a single expensive data source. Instead, use your segmentation and ICP definition as filters in LinkedIn Sales Navigator, export those lists via PhantomBuster or similar, and enrich via Clay. 

You don't need a computer science degree to figure this out. 

Tradeoff is a little bit of time list building, but you get hyper-specific targeting in exchange.

Step 7: Minimum tool stack (keep it boring)

You do not need a “modern stack.” You need a working engine.
Minimum:

Email sequencer (Smartlead, Instantly.ai, et al.)
Dialer (we use Trellus (YC W22), there are many options)
Data (mentioned above)
Google sheets

That is it. Tools do not fix unclear targeting or weak messaging. 

Step 8: Execution cadence (this is the engine)

Weekly
Build 1 new segment list (or refresh an old one)
Run 2 message tests per segment
QA 20 accounts manually (sanity check)
Review calls and replies, then adjust

Daily
Minimum 30 new accounts in
Calls first, emails second (if your market is noisy) 
Track the real bottleneck (connect rate, interest rate, meeting rate)

Save this if you are building outbound right now.

It is the stuff you forget when you are stressed and chasing meetings.

I have been really picky about picking up clients. It needs to be the right fit. 

Things that have worked well for me to avoid:

-outsized expectations

I work with early stage startups, most of which have never done outbound before. The founders who have "seen this movie before" (classic) are generally much easier to work with and kind of just get it. 

-looking for a pay per meeting model

I don't do this. My costs are too high. The shops that offer this are most likely doing something that doesn't require a bunch of capital to execute, like email blasts -- catchall email addresses are basically free in 2026 and you can run 20 clients with one person and outsource an inbox manager -- this is not what I'm doing. 

Experienced reps work with me who I pay pretty well for the work they do, set them up with the dialer + mobile numbers they need to execute. 

We position Outboundless against internal hiring. There's opportunity cost associated with doing this. I de-risk the process of getting started with outbound. 

-calling outside US

Have tried this, we don't do it well. Know where you're strong. Don't try to sell to everyone. My customers perspective is really important to understand. 

The way they view me has a huge impact on how well the engagement goes, whether or not they will leave a review or send a referral in the future. In order to grow this thing, I need to be able to Xerox the good clients and fade the bad ones. 

Does this apply to you? Idk. Probably not unless you're building a cold calling agency.

Most outbound problems don’t start with copy.

They start with bad data.

If you run outbound across multiple clients, you’ve felt this:
Deliverability is fine.
Then it swings.
A domain burns.
Replies drop.
Now you’re explaining variance instead of booking meetings.

That’s not a messaging problem.
That’s stale data showing up late.

This is why Prospeo.io V2 matters.

Most data providers refresh contacts monthly.
Some even less than that.
By the time you use the data, people have moved, inboxes are dead, and titles are wrong.

Prospeo refreshes its data every 7 days.
That’s a big difference when you’re running live campaigns.

On top of that, the data is triple verified.
SMTP checks.
Crowd outcomes.
Catch-all handling and spam trap removal.

That combo matters.
Fresh plus verified is how you avoid torching domains across clients.

What V2 really changes is how you work with data.

It’s not just enrichment anymore.
It’s a searchable lead gen engine where data quality is the foundation.

What I care about most:

-Contact data refreshed every 7 days, not monthly

-Triple verified emails that actually deliver

-Mobiles you can reach on live dials

-Segmentation that goes deeper than job title and headcount

Cleaner inputs create calmer systems.
Better deliverability.
Less list cleanup.
More predictable outcomes.
Healthier margins.

Prospeo V2 is live now.
I’ve been using it in real outbound workflows and feeding feedback directly into the product as I go.

If you run outbound or lead gen, the fastest way to judge a data tool is simple.
Put it into a live campaign.
Watch what breaks.
Or what doesn’t.

Prospeo V2 is built to not break.

Here’s an idea for your demos-

Write down every feature. Next to each one, write the problem it solves, the payoff in plain English, and the exact phrase to explain it.

Disclaimer - I got this from an ad for someone selling their questions for $4.95 on Facebook. 

You could just do it yourself though. I’ve been on a lot of demos and most AEs don’t do this. 

I, for one, would appreciate this approach.

Top 5 tips for enterprise multithreading

Most deals do not die because the product is bad. They die because you bet everything on one person.

1. Start wide, not deep
 Do not “earn the right” to talk to others later.
 Map the buying group early.
 Exec sponsor, economic buyer, daily user, blocker, influencer.
 If you only know one name, you are already behind.

2. Give each persona a different reason to care
 Same pitch, different titles, different outcome.
 Finance cares about risk and cost.
 Ops cares about workflow and time.
 IT cares about control and fallout.
 If everyone gets the same message, no one owns the deal.

3. Use meetings to unlock more meetings
 Every call should end with a name, not just a next step.
 Who else will want to pressure test this?
 Who usually kills deals like this?
 If your champion cannot introduce you, that is a signal.

4. Do not hide multithreading from your champion
 Going around them quietly creates distrust.
 Be explicit.
 I do not want this to die late because we missed someone.
 Strong champions respect this. Weak ones get exposed.

5. Track power, not activity
 Ten conversations mean nothing if none of them have pull.
 Write down who can say yes, who can say no, and who can stall.
 If you do not know that by mid-cycle, the deal is fragile.

Enterprise deals reward paranoia. Assume people will leave, get promoted, go on vacation, or get vetoed. Multithreading is how you stay alive when that happens.


If you have lost a deal because your contact went dark, this is why.

taplio

The Battle

Jesse Ouellette

Patrick William Joyce

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taplio

The Battle

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Patrick William Joyce

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Patrick William Joyce's LinkedIn Performance

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