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. ❤️

Cynthia H.

Sales Leader @ Simera | Building High-Performing Teams

I’m a sales leader who thrives in the trenches with my team. Building and leading high-performing SDR & BDR teams isn’t just my job, it’s my calling.

I love business development, and I’m a true hunter. Many times in my career, I wasn’t always the leader I needed to be. Through mistakes and hard lessons, I learned that real leadership means meeting people where they are and helping them grow. That perspective now shapes how I build, coach, and develop teams. I’ve also learned that growth sometimes means walking away from environments that no longer align with your values.

Originally from Honduras, I broke into tech sales during the pandemic and later moved to Miami. Since May 2022, I’ve been sharing my sales journey and lessons here on LinkedIn, a decision that’s connected me with an incredible community.

Outside of work, I enjoy exploring new cities and great food.

If you want to talk GTM strategy, outbound team building, business development, cold calling, social selling, or content creation, I’m your person.

My DMs are open. Let’s connect.

Brand Ambassador and GTM Community Founding Member

Member at Rev Genius

When I started my career as an SDR back in 2020.
 I’d cold call all day…
 and wonder why I kept getting brushed off.

Turns out ...
 the problem wasn’t the leads.
It was me.
 More specifically, how I was opening calls.

If I got those calls today,
 I’d probably hang up on myself.

They were:
Rambling
Feature-heavy
All about us
Zero reason to stay on the line

Now I know better.
Growth is being able to cringe at old calls.
 That’s how you know you’re improving.

So if your calls are getting shut down right now:
 
Don’t quit cold calling.

Fix your opener.
 
Tighten your message.

And keep dialing. 📞

Revenue & Outbound Sales Leader | SDR / BDR Team Builder | Healthcare

2025 was… a lot.

Built pipeline.
 Led sales teams.
 Planned a wedding 💍(got married and now church wedding is next week)
 Moved to Miami 🌴
 Dealt with immigration lawyers, paperwork, timelines, stress, repeat.
 Worked. Worked some more.
 Pretended I was “fine” (classic).

I did way too much in 2025.

So here’s my 2026 resolution ⬇️
Work Smarter, not Harder. And when I say this, it's quality over quantity
 But do it more consistently.


Sales taught me this the hard way:
Busy ≠ effective.
 More activity ≠ better results.
Discipline beats chaos every time.

Same applies to life.
Fewer priorities.
 Cleaner execution.
 Better boundaries.
 More margin.

Still ambitious.
 Still hungry.
 Just smarter this time.
Here I come.....

Everyone wants more.

More money.
 More title.
 More recognition.

But very few people focus on what really matters to earn more.

That’s why I don’t sell courses or books.

I run a team and stay in the trenches — on purpose.

 I keep my skills sharp.
 I test what works.
 I see what doesn’t.

So when I consult, you’re not getting advice from someone who used to sell or lives off past wins, and I can charge a higher fee because of that.

You’re getting real-time execution.
 Current objections.
 Proven plays.

Longevity doesn’t earn raises.
 Skill does.
 Execution does.
 Growth does.

Money doesn’t follow desire.
 It follows value.

Experience fades.
 Execution keeps you relevant.

It's that time of the year December 35th, my calendar is a mess... my inbox is a mess... and I am just trying to survive 😅

This year didn’t teach me how to work harder.
 It taught me how to lead better.

My focus for 2026:
 Work smarter. Quality over quantity.
Not to do less...
 but to stop putting out fires and start building something that scales.

A few real lessons I’m carrying forward:
• Delegation is leadership, not risk.
 Doing everything myself doesn’t create speed; it creates a bottleneck.

• Trust the team.
 I learned the hard way that holding on too tightly limits growth.
 
• Leadership isn’t control. It’s enablement.
 My role isn’t to be the hero.
 It’s to build systems, coach people, and let them win.

What I want to get better at in 2026:
→ Thinking proactively instead of reactively
 → Coaching instead of fixing
 → Building teams that don’t rely on one person
 → Being intentional about the team and about what I want

The biggest shift?

My success isn’t measured by how much I do.
 It’s measured by how well the team performs without me.

That’s the standard I’m taking into 2026. This is not the Norm...

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Keegan Otter (Software Cowboy 🤠)

Cynthia H.

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The Battle

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Cynthia H.

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