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.

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.

No alternative text description for this image

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. ❤️

Taking my dad’s promotional product business stuck in the 90s and bringing it into the new age! 

PLEASE don’t judge me on our current website…it’s being worked on as you read this🫠

Need some merch or swag for your company but are tired of the same old water bottle, cotton t-shirt, or pen? Is your kid having a sweet sixteen and has to have the coolest giveaway at the party? Let’s connect and get your team, customers, friends, and families set up with promo products they’ll WANT TO KEEP!

For promotional product needs reach out at Maclaine@creativealternatives.com

For partnership opportunities reach out at Maclainescherpartnerships@gmail.com

When I'm not working I’m definitely:
🌭Cuddling my Mini Australian Shepherd Swizzy and Mini Dachshunds Suge Knight & Nipsey Hussle
🏋🏻‍♀️ Letting my personal trainer push me way too hard at the gym 
🏈 Watching the Browns lose, but hey at least they occasionally win!
🎧 Listening to music ranging from hip-hop to show-tunes

I'm also an avid world traveler, sparked by a year spent abroad in Switzerland and a degree in tourism.

🌎30 Countries Traveled: Mexico, Canada, Switzerland, Albania, Croatia, Greece, Liechtenstein, Italy, Spain, Netherlands, Germany, Morocco, Finland, Sweden, Estonia, Austria, England, Denmark, Hungary, Czech Republic, Belgium, Ireland, Israel, Philippines, Vietnam, Indonesia, Thailand, Cambodia, Jamaica, Portugal

Maclaine Scher

How to go from entry-level employee to Vice President 👇

Step 1: Quit your entry-level job
Step 2: Start working for your dad
Step 3: Ask him if you can be Vice President
Step 4: Change your title on LinkedIn

HR and Finance were consulted.
(Okay, HR and Finance is also my dad.)

Stick around for more foolproof tips on how to climb the corporate ladder 🪜 

(Results may vary. Dad not included)

Vice President @ Creative Alternatives l Obsessed with talking about my wiener dogs 🌭 l Making promotional products worth keeping ✨

LinkedIn, I’m back! 👋🏼👋🏼 (but don’t call it a comeback)

Six months ago, I left my tech job to step into my lifelong goal / fear / prophecy: joining my dad’s company.

After years of non-stop LinkedIn scrolling and prospecting, I went on a full LinkedIn hiatus—
except for logging in daily to play the games (iykyk).

From July to December, I went through a crash-course “internship,” learning everything there is to know about selling promotional products—from sourcing to designing to pricing to closing to stalking UPS trucks to make sure merch arrives to events on time. 

Most importantly, I began learning how to manage a personal / professional relationship with my dad / now boss. 

Now the goal is simple: growth. 📈

I’m taking a successful business model that’s been living comfortably in the 90s and dragging it into 2026 — with modern sales tactics, cold outreach, and tech platforms that have been blowing my dad’s mind. 

Posting consistently here will keep me accountable, help me learn from people way smarter than me, and, ideally, connect me with new customers along the way.

So follow along as I try to generate $1M in sales this year. (Shoot high, right? 😅)

When I started working for my dad he had OVER $700k IN UNPAID INVOICES 😱😱😱

Why? Like a typical boomer he was only accepting payments by check. He was also way too busy writing up current orders to worry about silly things like getting paid in a timely manner.  (Weird flex Kenny…Bold strategy)

What did I do? A very simple former tech employee answer - I bought a software!

• Purchased the online version of Intuit QuickBooks
• Transferred over everything from the pre-historic desktop version of quickbooks
• Set up online payments.

Within MINUTES I was able to send out every unpaid invoice at once with the option to pay by debit, credit, Apple Pay, or ACH. 

What happened next? An absolute torrential downpour of money nonstop for a few weeks. 

🤑🤑🤑🤑 <— my dad every time he got a quickbooks notification that another invoice was paid 

Quickly the $700k dwindled down to a very normal ~$100k (mostly consisting of open orders).

Flash forward 6 months:

• Invoices go out consistently on the 1st and 15th
• Money comes in
• No more check chasing 

Follow for more stories on how I’m dragging a boomer business into the new age

It’s Weenie Wednesday and Suge Knight’s 5th birthday!!

Happy birthday to the weenie that started it all 🎂

Never would’ve uncovered my ~obsession~ with dachshunds, joined the best cult on earth, or probably ever started dating Ryan if he hadn’t posted a photo of Suge on slack his first day as an sdr on my team. 

I’m sure I’ll have dozens more weenies throughout my life (all named after gangsters obviously) but none will be quite like the original 🩵🩵

Everyone wish the sweetest weenie the happiest birthday!!! 🎈🥳🎈

At the happiest place on earth today…
No, not Disney World - a trade show 😄

I’m walking the floor at Advertising Specialty Institute Orlando, hunting for the coolest, newest, actually-useful promo products 🚶‍♀️✨

Hundreds of vendors, thousands of ideas, and zero interest in the stuff that ends up in a junk drawer.

This is the fun part - spotting trends, finding fresh products, and bringing better ideas back to our customers so their brand actually stands out.

The day has only just started, but I’m giving an early award for best product to these custom squishmallows from BamBams. What camp or elementary school wouldn’t want these?!

If you’re tired of the same old promo and want ideas people will keep, I’m your girl 👀

More to come 🚀

Before you click the website on my profile… just know I’m painfully aware 😅

Yes, it is really that bad. Like built in 1999 and immediately abandoned bad (which is exactly what happened)

And somehow… this business still grew to $3M annual revenue with:
❌ no SEO
❌ no marketing
❌ no ads
❌ no online presence in the slightest (no, I’m not counting this website… we truly like to pretend it doesn’t exist)

Why?

Because my dad built something most companies never do: unwavering trust!

His personality, creativity, and obsession with solving customer problems turns EVERY client into a loyal for life customer and the easiest referral. 

That’s how this has stayed a 100% word-of-mouth business for decades. 

Now I’m here to add…the internet.

If you click the site today, please view it as a historical artifact.

The glow-up is coming 😅✨

“Hope this email finds you well.”

This is exactly how your email is finding me.

Happy Weenie Wednesday 🌭🌭

Please drop a photo of your wiener dog so I can find my people (cult members) on here!!


Will accept photos of other breeds 🐶

Results of posting on LinkedIn every day for one week:

97K post impressions
2,100 profile views
156 new followers
3 promo product inquiries
1 actual sale!! 💰

Who knew all I had to do to get some sales was (lovingly) roast my dad on LinkedIn?! Should’ve started this way sooner 😂

Lately I’ve been thinking about who all this work is really for.

The big life changes.
The pressure to get it right.

It’s for them.

This is hands down the toughest job I’ve ever had - not because the work is hard, but because of what it means.

Stepping into something my dad built with his whole heart.

Caring in a way that doesn’t shut off.

Wanting to do right by someone who’s given me such a huge opportunity.

It’s stressful. It’s personal.
And somehow, it’s also the most rewarding thing I’ve ever done.

Not every job gets to mean this much 🩵



PS: Hi, I’m Maclaine and I moved across the country to forcibly drag my dad’s boomer business into the new age. Stick around while I introduce Creative Alternatives to insane things like “systems” and “the internet.”

When it’s the last selling day of the tech fiscal year but you quit tech so for the first time in 5 years your only quota is ✨vibes✨





Anyway hope everyone’s nervous system is okay today 🫶

I need you all to understand how truly unhinged this decision looked on paper 😅

I moved from a downtown San Diego penthouse overlooking Petco Park - where I could literally watch baseball games and concerts FROM MY BED - to the absolute middle of nowhere in Chapin, South Carolina (population: under 2,000).

Yes….Voluntarily.

For almost a decade, I had a million reasons why joining my dad’s business wouldn’t work.
Wrong time. Wrong place.
Worst-case-scenario thoughts that I’d somehow kill the business. 

And then one day, the excuses just… stopped.

Maybe it was finally being with the right, supportive partner.  
Maybe it was doing all the inner work needed to take on something this big.
Maybe I wanted a slower pace of life and a big yard for my dogs. 
Maybe after living across the country from my dad for so long, I finally wanted the chance to have a real, in-person relationship with him as an adult.
Maybe it was just for the bit (I LOVE a good bit). 

Honestly? I don’t know which reason it was.

I just know I followed the urge, and I’m really glad I did.

Sometimes the move that makes the least sense on paper ends up being the right one 🩵

Has anyone else made crazy life-altering decisions but trusted the vibes and hoped for the best?

I asked my friends to describe me and immediately got emotionally body-slammed.

While trying to find my own style and voice here on LinkedIn, Melissa Gaglione ⭐️  gave me a task: ask three friends to be brutally honest and describe me.

If Melissa says jump, I’m LEAPING - so off I went to what I assumed would become the Comedy Central Roast of Maclaine. 

What I thought my friends would say:
* sensitive
* annoying
* an absolute idiot
* talks way too much
* memory of a peanut

Why would I think those things?
What can I say, I’m my own worst bully.

What they actually said:
🩵 a mix of radical honesty and creativity
🩵 carefree without being careless
🩵 passionate and spontaneous
🩵 credibly funny (compliment of a lifetime)
🩵 live by the seat of your pants
🩵 you never let outside noise phase you or change how you operate

And then one friend sent me this, and I haven’t stopped thinking about it:

“You’re like one of those paint pens we’d play with as kids. You have the natural ability to turn any bland or boring situation into something colorful, magical, more full of life. We’d use those pens to color in outlines, and while yeah the outline was great before, it’s even better when it’s brought to life with color. I think you bring color to people’s lives where maybe life was good before — but better with you in it.”

INSTANT TEARS I FEAR 😭

What this little project taught me:
the voice in my head needs to SHUT UP AND SIT BACK - because apparently, to other people, I’m actually a whole vibe ✨

Just a reminder to be kind to yourself.
How you see yourself is most likely completely different than how others truly see you. 

Don’t believe me, go ask 3 friends to truthfully describe you🩷

Get ready LinkedIn because unhinged, funny, authenticly myself Mick is here to stay 🥳🥳🥳

You all may have done 2016, but NO ONE did 2016 like me. 

A full year studying abroad in Switzerland. 
Traveled to 20 different countries on 2 continents. 
Majored in tourism to justify a new adventure every weekend. 

Shoutout dad for not questioning the credit card statements and more importantly that BEAUTIFUL welcome home sign!

Who needs merch and wants to help me make some sales from LinkedIn to restore balance to the universe (and Kenny’s books)? 😅

When someone calls my dad for promotional product ideas, this is how it usually goes:

“Go to this website”
“Type in XYZ”
Or even worse…“I’ll send you options” <— aka an email containing A TON of links 🫣🥴

Which to most people is honestly insane.
Sorry dad, love you but no one is wanting to do all that.
𝐕𝐄𝐑𝐘 𝐛𝐨𝐨𝐦𝐞𝐫 𝐛𝐞𝐡𝐚𝐯𝐢𝐨𝐫.

In comes the millennial daughter to solve the problem.

Instead of sending people off to do their own research, I wanted something visual, easy to skim, and actually enjoyable to look at - not homework.

Over the holiday weekend I went fully feral (in the most fun way) playing around with Gamma and I’m honestly obsessed.

With Gamma, I can pull together product ideas, pricing, and context and turn it into a clean, curated, CUTE presentation in minutes. No links. No chaos. Just immaculate vibes.

Now when a customer asks for ideas, they get something that feels more like a brochure rather than a scavenger hunt - who would’ve guessed that’s what people prefer?! (Me, I’m people)

I attached an example of one I made this weekend for clients looking for fun high-end products under $100 per unit! Not too shabby for my first go at it if I do say so myself. 

If you’re tired of the same old swag and want some creative alternatives for the perfect branded gift to send your employees or customers, flip through and slide into my DMs 😜

*Not sponsored (yet 👀), just truly in love with tools that make my job easier and more fun!



PS: Hi, I’m Maclaine and I’m forcibly dragging my dad’s boomer business into the new age. Stay tuned to see what I decide to revolutionize next!

A Creative Alternative to Branded Gifts

🌨️How you’ll catch me and my weenies all weekend during my first winter storm living back on the East Coast. 

Fingers crossed power doesn’t go out so I don’t lose my LinkedIn games streaks!! 

Stay safe everyone!! 🩵

My first Creative Alternatives sale happened when I was 17.

I was a high school senior and the class merch was…boring.

I asked my dad if hypothetically I designed cooler merch, would he make it?
He said yes — clearly assuming I’d sell maybe 12 shirts and forget about it.

Instead, I:
• drew designs on a teacher’s chalkboard
• taught myself how to make mockups and an order form
• posted in our grade’s Facebook group
• gave everyone one week to order

It was 2013 so no Venmo back then. Just cash and checks… collected during school hours. 

Every day that week I came home with bigger stacks of money, and my dad was FLOORED.
What we thought might be a few orders turned into 1000+ items sold!

I’d call it a smashing success — except for the small detail where the Vice Principal threatened to ban me from prom and graduation for “selling on school grounds.”
(They later admitted to my dad that they loved the designs and just needed to scare me so no one else tried it)

Fast forward 10+ years: We still make merch every year for each grade at my high school! 

Turns out selling promo products was always my destiny.

Tasks I accomplished over the weekend to avoid Sunday Scaries / Manic Monday as a VP.

• Caught up on accounts payable
• Everything shower (the hardest task of all, IYKYK)
• Created + sent proposals to potential customers
• Baked gluten-free dairy-free chocolate chip cookies (the essential bad weather activity) 🍪🍪🍪
• Used Gamma + Canva to design flyers for a camp trade show this week
• Worked on my paint-by-numbers of Nipsey
• Watched Traitors and Heated Rivalry (highest priority) 

Now heading into the week without a massive to-do list and with a fully recharged battery 🔋

Reminder: big titles don’t mean you can’t also big-time vibe on the weekends. 

What do you do on the weekends to start the week refreshed and ready to go?

This might be a hot take but…


the merch was always my favorite part of any sweet 16 / bat mitzvah.

If you didn’t wear the hoodie to school on the following Monday, were you even there?!

Creative Alternatives recently turned a simple Sweet 16 sweat set into a full merch drop designed like an actual storefront

Truly, what’s cooler than that?? Couldn’t tell you - my sweet 16 hoodies were just handed out in a matching tote bag.

People forget that a huge part of the promo product industry lives in personal events — and it’ll always be my favorite part.

What was your theme of your Bat Mitzvah/Sweet 16 and do you still have the merch?

taplio

The Battle

Keegan Otter (Software Cowboy 🤠)

Maclaine Scher

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taplio

The Battle

Keegan Otter (Software Cowboy 🤠)

Maclaine Scher

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

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