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. ❤️

Account Executive @ Warmly,

I’ve spent the last 5 years in SaaS helping early stage teams build pipeline, close deals, and drive revenue growth from the ground up. 

I’m currently a Mid-Market AE at Social Snowball, helping DTC brands grow through word of mouth channels (affiliate, influencer, referral). It combines my passion for SaaS sales, eCom, community growth, and new tech that actually drives results.

I love engaging in conversations around
• tactical tips to build & close more pipeline 
• eCommerce trends & growth hacks 
• modern tools for revenue teams 
• customer psychology + emotional resonance 

Outside of work, I love listening to live music in Austin, going to pilates, traveling, and practicing my French.

Let’s connect: https://tinyurl.com/bdetzvh6

Katherine Barnes (Sales Khaleesi) 🐉

hellloooo 2026, I’m ready for you. 
(now that I’ve had four shots of espresso and finally caught up on sleep)

one of my new years resolutions: create instead of consume.

because creating = an energy giver.
doom-scrolling = an energy thief. 

and since I love a good challenge...

I'm committing to my version of 75 hard:
posting every business day for the next 75 days.

but I never want to post just to post. I want to share things that actually earn a spot on your feed.

creative campaigns, real learnings, insights, and memes (because who doesn't love a good meme?)

sooo I need your help...
what do you actually enjoy seeing on LinkedIn? 💭

Katherine Barnes 

Mid-Market AE @ Social Snowball | I post about brand marketing & sales execution | eCommerce obsessed 🛍️

the best brands don’t need to sell you anything.

I drove an hour out of my way this weekend to go to the Disney World of gas stations.

Buc-ee's, Ltd. has a special place in my heart.

because I used to drive 14 hours straight from Virginia to Mississippi...and I hated every second of stopping for gas.

if you’ve ever road-tripped, you know how awful it is:

the bathrooms...
food options few and far between.
waiting forever for a pump.

vs buc-ee’s:

spotless bathrooms.
more pumps than you can possibly imagine.
food that doesn’t suck. (brisket sandwich, beaver nuggets, pecans are my personal fav)

and somehow, you're also shopping for a cowhide rug, camping gear, and household products you didn't even know you needed.

they solved a real problem, obsessed over the details, and branded the heck out of it.

now it’s not just a gas station. it’s a destination.

because once you’ve been to buc-ee’s, every other gas station feels.. unacceptable.

which brands do you think actually get this right? 🛍️

me: does my LinkedIn post sound cringe?
my brother:


“you’re like that carrie bradshaw meme”

... when carrie showed up unannounced at bigs door.

I started posting on LinkedIn after learning so much from other sales reps' tips and wanting to pay it forward. 

it felt vulnerable and definitely outside my comfort zone at first, but it turned into something I actually enjoy. 

here's why you should post too:

the worst that can happen is your post doesn't perform as expected and your ego takes a hit.

the best that can happen? 

+1 person who learned from you
+1 lead that turns into a sale
+1 brand partnership
+1 new connection that leads to a future business partner, mentor, or friend
+1 person who was scrolling through a bunch of AI brain rot and your post actually brightened their day in some way.

I joined Melissa Gaglione ⭐️'s Citrine creator program, which has been absolutely incredible. 

melissa has taught me so much about how to create valuable content, that feels authentically me!

and now I officially do not feel cringe, like carrie with the riding crop.

thank you, Melissa <3

so many brands are sleeping on something so simple…

a successful customer referral play.

83% of consumers are more likely to make a purchase if a friend or family member recommends it.

but the problem with most referral programs is they’re an afterthought.

they get tossed into post-purchase email flows
(I have thousands of unread promotional emails from brands)

there’s no real customer activation. 
ok so if I have to manually sign up or dig for my referral link… what’s in it for me?

...and then the incentives aren’t sexy.

a good referral program makes it stupid simple.

ClassPass does this really well:

in-app push notifications, right when booking a workout is top of mind 
bring a friend, get more credits.
one click. text your referral link.

easy. I’ve done this countless times without thinking about it.

Social Snowball ☃️ does the same thing for ecommerce brands.

it’s automated. no hoops for the customer to jump through.

the referral link is ready to go at checkout, when excitement is high and they’re thinking about their order on the way. 

met with a prospect yesterday and asked what made him book a call.

“my boss bought something online, they were using you, and he loved the referral flow.”

something the brand didn’t really think about…until someone else did it better 🤷🏼‍♀️

no one wants to be hard sold to.

learned that the hard way and it completely changed the way that I sell 👇🏼

I got into sales because I needed a job.
it was during covid, so I took the first offer I got.

minimum wage + commission.
selling tanning salon memberships and products.

I remember thinking, “the commission is probably just there to make the job sound better.”

and also…
no one is actually going to spend $200 on tanning lotion.

I had zero sales experience, so I memorized every product benefit.

when I pitched I sounded like a bad actress reading lines.

until I stopped trying to sound smart and perfectly polished.

I tried the products myself and ditched the science-backed jargon for “it’s like botox in a bottle.”

it felt way more natural and authentic.

once I stopped hard selling and started telling a real story, sales actually became kind of fun...

and the commission was very real.

my numbers didn’t go up because I was pushing harder,
they went up because what I was saying actually resonated.

what's the first sales lesson you learned the hard way? 😅

idk who needs to hear this…


but get off your damn phone this weekend 🙂

my screen time was at an all time high this week.

first week back after the holidays, had a lot on my plate, and my brain was in overdrive.

I have a lot that I want to accomplish this year….
but I absolutely do not wanna burn myself out to do it.

so yesterday, I finally put my phone and laptop away and pulled out my scrapbook.

it’s full of photos, matches, plane tickets, stickers
all to tell a story around some of my favorite memories:

spontaneously going to work with Gabrielle Stott in sayulita, mexico for a week
having a blast taking on saastr with Marissa Massaro
taking Nicole Baylis to all of my favorite spots in ATX

a few hours offline and I went from feeling exhausted to inspired about what’s coming in 2026.

what are your some of your favorite ways to unwind on the weekend? 🤸‍♂️ ✨ 🎨

taplio

The Battle

Keegan Otter (Software Cowboy 🤠)

Katherine Barnes (Sales Khaleesi) 🐉

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taplio

The Battle

Keegan Otter (Software Cowboy 🤠)

Katherine Barnes (Sales Khaleesi) 🐉

Followers

Posts

Engagements

Likes

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

Performance ScoreKatherine Barnes (Sales Khaleesi) 🐉's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreKeegan Otter (Software Cowboy 🤠)'s LinkedIn Performance