Keegan Otter

Leading GTM @ Warmly | GTM Advisor | Team Builder | Automation Cowboy | Sales Coach & Mentor | Outreach.io Admin Certified | Salesforce & HubSpot Guru | Sequence Architect

I follow the philosophy that if you can't measure it, you can't manage it. Building top performing teams is what I do, and we generate 75% of our deals leveraging warmly (our own tool).



If you are interviewing with me, mention "Dr. Pepper" during the interview.

Director of Sales & Revenue Operations

Helping lead company revenue growth.

Scaled the sales department from 2-40 in 10 months.

Overseeing Sales, Sales Strategy, Managers, Enablement and RevOps for all revenue facing teams.

Keegan Otter (Software Cowboy 🤠)

📣 Major Product update at Warmly, 📣

Warmly's NEW chat branding & calendar embeds is LIVE 💯 

We heard it from our customer base and prospects, so we listened and applied the feedback into our product. 

Here's what's new and why it matters: 
👉🏻 Calendar link embed: It doesn't matter what calendar tool you use, we can now embed it with our chat
👉🏻 New AI learning model (smarter, better, faster) 
👉🏻 Multiple Chat Agents (Use Warmly for Support chat, PLG chat, Marketing chat etc)
👉🏻 New side bar style and gradient design 
👉🏻 Add banners in chat for an extra layer of promotion 

Reach out to your CSM or an account specialist and we will get you rocking and rolling:

#Warmly #NewRelease #Chatbot #AI #Agents

Keegan  Otter (Software Cowboy 🤠)

Some of the best companies ever were built on bold moves 🫵


→  The founder of FedEx gambled the company’s last cash in Vegas
→  B2C brands go all-in on promotions to create urgency

And a lot of sales advice today sounds safe.
“Don’t be weird.”
“Don’t stand out too much.”
“Just personalize better.”

And honestly?

That’s how you get ignored.
So, why not do what others won’t?

For reps, that looks like⤵️
→ Voice notes instead of text
→ Sending a relevant post instead of a pitch
→ Commenting publicly before DMing
→ Using images or short videos in email

If your outreach feels a little uncomfortable,
it’s probably because it’s different 🙌🏻

One thing that never failed once a prospect agreed to a demo 👇
This is the exact process I’ve taught every team I’ve led.


Step 1️⃣
Share who they’ll be meeting with (the AE)
 → Tag the AE directly in the same thread

Step 2️⃣
Send proposed times

Step 3️⃣ (the part everyone skips)
Before hitting send - add them to a “Times Sent” follow-up sequence

Why?
Because no lead ever slips through the cracks.

And if they still don’t book?
👉 I have the AE ping them on the same thread.

Result?
 📅 Meeting booked, every time.

This follow-up sequence is 3 single emails
And it’s never failed us once.

If you want it, shoot me a note - happy to pass it along.

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You’ll be seeing me on a lot more “hot girl walks” as I work on my goal of 10 miles of movement per week. 

As leaders, we set many team goals but many of us forget to set some personal goals or forget to follow through on them…

Well I’m saying no to that in 2026. 

Selfishly I’m going to do my best to hit my personal goals so I’m a better and sharper leader for my team 🙌🏻

Plus, I have very few distractions when on my walks which allows me to lock in better 🔒

#SoftwareCowboy #Goals #Walks #Remote #Warmly

This one change added ~9% to our win rate ⤵️


Every AE at Warmly follows this post-meeting checklist, no exceptions:

1. Meeting recap sent same day
AI summarizes the call (we use Sybill)
AE edits for clarity and context

2. Recap is attached to an SQO sequence
No “thanks again” emails that go nowhere

3. Follow-up messaging updates quarterly
What worked last quarter won’t work forever

We also tell AEs to:
→ Multi-thread early
→ Use live chat when Warmly alerts fire
→ Re-engage stalled deals with context, not pressure

The result?
From to 21–25% to 30 - 36% win rate. 

If your win rate is stuck, don’t look for a new tool.
Look for the steps your team skips when they’re busy 🙌🏻

Here’s a tip for teams still using generic, static slide decks that don’t reflect the conversation after the call 👇


Stop rebuilding decks from scratch.

I used to spend days on slides.
Now it takes minutes, and they’re tailored to the prospect.

Buyers can open them later, play with the ROI, and revisit exactly what we covered.

I’ve been using Base44 and highly recommend it.

Have you ever paused to look at how you're reaching out on LinkedIn? 📥


A lot of the frustration reps feel often comes down to a few common habits, like:
👉🏻 Relying on generic, automated DMs 
 
 👉🏻 Staying entirely inside the inbox 


What we’ve seen work better is simply trying a few different touches:
👉🏻 Commenting thoughtfully before sending a message
👉🏻 Using voice notes instead of only text
👉🏻 Sharing something genuinely useful to 𝘵𝘩𝘦𝘮
👉🏻 Building familiarity before asking for time


This applies to email and phone, too.
👉🏻 Short videos
👉🏻 Quick screenshots
👉🏻 Visual case studies
👉🏻 Even voicemails

Most phones transcribe voicemails into text, which quietly turns into an extra touch many teams overlook.

Curious how others are coaching their teams to experiment with this.

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Why we expect our AEs to prospect (Especially in Q4)⤵️

Because waiting for pipeline to magically recover in January is a losing strategy.

Here’s what we focus on:
• Closed-lost deals with context
• Multi-threading beyond the original champion
• Framing convos as “quick sync before Jan”

Why it works:
• AEs know the objections
• Credibility is higher
• Pipeline gets revived fast

Wondering if it actually works?
One AE booked two closed-lost deals on the same day

#SelfSource #Prospecting #Sales #Warmly #SoftwareCowboy

Have a great candidate for those looking to bring on a savvy Account Manager, CSM, or AE.

She has 4-5 years of business development and account management, while being remote.

I can vouch for Tatum. 

DM me or her, happy to do any intro's

Due to department reductions at Aya, I was laid off today after nearly four years with the company. While I’m devastated and understandably nervous about what the future holds—especially as a single mother providing for my daughter alone —I believe that when one door closes, another opens. 🤞 
 
I’m hopeful that my experience will be a valuable asset to my next organization. I bring deep experience in account management, client retention, B2B sales, and account growth, and I’m passionate about building strong client partnerships that deliver real results.

I’m currently seeking opportunities in Account Management, Client Success, Business Development, Team Management, Sales, or Event Management. 

I’d truly appreciate any leads, referrals, or conversations. Thank you to everyone in my network for the continued support. ❤️

GTM Engineer | Uber driver turned sales guy

Creative and analytical GTM Engineer with 3 years of experience in tech sales, now focused on building advanced go-to-market, workflows and automation. I am experienced in leveraging tools like Clay, Leadmagic, HubSpot, Make, and Apollo to build scalable outbound systems, streamline prospecting, and drive measurable results. I combines technical expertise with frontline sales knowledge to deliver systems that generate pipeline and revenue.

Particularly interested In AI, great founders, products, and people!

I believe talent exists everywhere and is not bound by location - which is why I champion global hiring and remote work.

Need anything? Let's connect!

Chris Mbanta

POV: when a client makes joke on a call.

Salespeople ⬇️

While I was away for the holidays,
Daniel was in the motherland.

We planned to link up on the evening of Dec 29.

I had returned from Cotonou 🇧🇯 in the morning to make sure it happened
Because he was flying back to Dublin 🇮🇪 the next day 30th Dec.

For some unforeseen reasons we couldn't see on the 29th.

Past 9pm, my phone rang.

“Chris, it’s Dan.”
I screamed, “DANIEEEEL?!”
It was all joy and happiness on both ends of the call.

He said he couldn't leave Nigeria without seeing me
So we made it happen
We saw the next morning, the same day he was to travel.

That was very intentional
And that’s what great friends would do.

Here’s to meeting people on LinkedIn
Who turn into real-life friends…
And friends who become family.

Cheers to more of that in 2026 🤍

Go where you can win the most.

When I was an SDR I was heavily focused on old calling 
Because that was where most of my meetings came from....

Don’t get me wrong,
I was using other channels.

Email sequencing
Social selling (LinkedIn DMs, even tried X for a bit)

What didn’t work was trying to be great everywhere at once.

The phone was the channel that consistently gave me pipeline,
So I anchored on it.

I even had personal KPIs to hit,
Minimum number of calls I must make every day.

Once I mastered the phone
(confident on calls and consistently booking meetings)

I moved to other channels,
Doing multi-channel became easier and more successful.

𝐌𝐲 𝐚𝐝𝐯𝐢𝐜𝐞 𝐢𝐬

Focus on one channel until you’re good at it.
Then layer the rest

That’s how you'll win faster.

Agree or disagree?
Let me know In the CS.

I wouldn’t do a 100% commission-based role.

I've done a few in my career especially in my early days.

I thought it would “build grit” and fast-track my growth.

What it actually did was drain my time
Every day became about survival
I was chasing quick wins
To get paid.

I avoided learning curves I couldn’t afford
There was no room to get better at the craft
No room to slow down and understand what actually worked.

At the end of the day I realized I was wasting my time
I was better off working for free.

WHY?
Because working for free is intentional 
With growth as top focus, I wouldn't expect 
Anything in return and that'll help me learn and grow fast.

100% commission shouldn’t be the norm.

It pushes people to optimize for short-term wins, 
Not long-term skill.

And that’s very different from working for free.

Working for free is a deliberate choice to learn, get reps, and build leverage.

Commission-only roles demand output before you’ve built any.

There’s a big difference between betting on yourself
and being set up to scramble just to stay afloat.

If you think otherwise,
Let me know in the CS.

The fight to “turn off LinkedIn” is real.

Every few weeks, 
Someone posts about why LinkedIn is noisy, or should disappear.

And honestly, I get it
People don’t like what they feel they hate
And make all sorts of opinions on what should be done to it.

I responded to one 
Saying "B2B can't survive without LinkedIn"

And this is absolutely true.

Because for B2B companies, LinkedIn isn’t a distraction
It’s infrastructure.

Where conversations start
It’s where trust compounds
Where companies find leads
Where careers change with/without applications.

So when I see “LinkedIn is useless” takes
I usually assume one thing:

They don’t sell to other companies/agencies.

You don’t have to love LinkedIn
Your personal opinion about it also doesn't matter
Because there are more than a billion people on here.

They love it
And they conduct business here
And in B2B, not being in the room is the real cost.

What do you think?

I wasted time building an outbound campaign the wrong way.

Started with job titles:

CISO
VP of Security
Head of Security

It made sense in my table
But in practice, everything broke.

I kept pulling in companies selling 
What I was trying to sell, rather than those who need it.

That’s when I realized my mistake, 
Was the flawed logic behind the campaign.

I was asking first, “Who should I talk to?”
Instead of asking, “What companies actually need this right now?”

Job titles answer the first question
But they don’t answer the second.

Signals do:

Infra changes
Expansion moves
Specific hiring activities.

This is the reason I started 
Planning out first before building any campaign. 

Once I flipped the order to these two

𝐒𝐢𝐠𝐧𝐚𝐥 𝐟𝐢𝐫𝐬𝐭 → 𝐜𝐨𝐦𝐩𝐚𝐧𝐲 𝐬𝐞𝐜𝐨𝐧𝐝 → 𝐩𝐞𝐫𝐬𝐨𝐧 𝐥𝐚𝐬𝐭
𝐂𝐨𝐦𝐩𝐚𝐧𝐲 𝐟𝐢𝐫𝐬𝐭 → 𝐬𝐢𝐠𝐧𝐚𝐥𝐬 𝐬𝐞𝐜𝐨𝐧𝐝 → 𝐩𝐞𝐫𝐬𝐨𝐧 𝐥𝐚𝐬𝐭

My workflow became better:

Cleaner lists
Fewer false positives.

Learning from my mistakes was my biggest play here
Growth forces you to confront the gaps in your thinking.

Most GTM Engineers come from one of two backgrounds:

Sales
Or engineering.

Sales folks usually understand:
ICPs
Messaging
Objections
What actually gets replies.

Engineers usually understand:
Systems
Data
Automation
How to scale without things breaking.

But to really level up, people coming from sales have to learn the engineering side: data, systems, automation, and scale.

And vice versa for folks coming from engineering.

Because the best GTM Engineers sit somewhere in the middle.

They take commercial instincts
and merge them with engineering execution.

They don’t just know what works.
They know why it works and how to operationalize it at scale.

That’s what turns a background into a GTM Engineer.

Which side did you start from?

If you think otherwise, 
Let me know in the CS.

Give inexperienced candidates a chance.

Every experienced candidate you admire today started somewhere
At some point, someone took a chance on them before they had the proof.

Early in my career, I didn’t have much to point to on paper.

What I did have was hunger, curiosity, and a lot of time to learn
A few people saw that and gave me room to grow.

That changed how I think about experience
It’s useful, but it’s not the whole story.

Progress usually comes from people who are willing to be uncomfortable, make mistakes, and improve fast.

Now when I look at early careers, I remember that growth has a starting point
And that starting point is often inexperience.

If you’re in a position to hire or mentor, consider the upside of potential.

And if you’re early in your career, remember that one “yes” can change everything for you.

Can you remember that one person who gave you a chance?

Giving your employees fair pay isn’t generosity.

It’s the baseline.

A lot of companies talk about “culture” and “loyalty"
That part makes sense.

But if you’re underpaying the people doing the actual work,
That’s not culture.

That’s cost control disguised as values.

Fair pay signals a few simple things:

- You respect the work
- You value your people
- You understand replacement cost
- You’re serious about retention, not just hiring.

People don’t leave teams first,
They leave when effort and compensation stop lining up with output.

You don’t build long-term results by squeezing short-term margins,
You build them by making staying worth it.

Think otherwise?
Let me know in the CS.

P.S. I went to the beach on a monday evening.

taplio

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Keegan Otter (Software Cowboy 🤠)

Chris Mbanta

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The Battle

Keegan Otter (Software Cowboy 🤠)

Chris Mbanta

Followers

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Engagements

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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);}Keegan Otter (Software Cowboy 🤠)'s LinkedIn Performance

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