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. ❤️

Warmly,

Principal Data Architect

Immagnify (acquired by Warmly)

Immagnify is an AI-powered B2B search engine that allows sales and marketing teams to easily find relevant customers based on publicly available information and create advanced B2B audience research for data-based advertising decisions.

Immagnify's technology aggregates and processes information in real-time to avoid any data discrepancy and provide marketing and sales teams access to any company and decision-makers worldwide by email, landline number, direct mobile, and social media channels.

CTO & Co-Founder

Platterz

Head Of Infrastructure

HERE Technologies

Team Lead

HERE Mobility is a new innovative strategic business unit of HERE Technologies with a mission to make MaaS (Mobility as a Service) easy to use and accessible to everyone worldwide.

HERE Mobility creates intelligent tech and data driven technology-powered solutions for today’s on-demand mobility challenges, connecting businesses with consumers across all modes of transportation. 
Through an open and competitive mobility marketplace we're empowering individuals and businesses to achieve greater freedom of mobility and access across all modes of transportation. 
We’re welcoming the next smart mobility revolution. Connecting the mobility world.

Senior Software Engineer

ironSource

ironSource builds monetization, engagement, analytics and discovery tools for app developers, device manufacturers, mobile carriers and advertisers. Our comprehensive solutions help industry leading companies achieve greater business success, enabling them to find, understand, engage with and monetize their target audiences more effectively.Over 80K app developers are using our developer solutions, and our enterprise technology is shipping on hundreds of millions of devices worldwide, giving ironSource the ability to reach over 800 million unique users every month, globally.

Founded in 2010, ironSource is a truly global company, with offices in Tel Aviv, London, New York, San Francisco, Beijing, Bangalore and Seoul. Read more at http://www.ironsrc.com

Supersonic (Merged with ironSource)

Supersonic is the mobile monetization and marketing platform trusted by the world's top publishers and advertisers. Leading the industry with video meditation, video SDKs and user acquisition technology, Supersonic maximizes revenue and drives effective user acquisition for its developer partners. Supersonic reaches over 800M unique users globally, driving over one million daily installs. In 2015 Supersonic merged with ironSource to create the world’s largest independent platform for mobile monetization, analytics and distribution. Founded in 2009, the company has offices in San Francisco, Tel Aviv, New York, London, Beijing and Bangalore.

Back-End Software Engineer

Dalet Digital Media Systems

• Using C++ as a main development language.

Back-End Developer

Android Game Factory (AGF)

AGF create games using genetic algorithms, from a narrative and rules given by user.

• Responsible for developing a REST Client-Server, which is the core that integrates between the genetic engine and the users (and vice versa).
• Using Java as main development language.
• Using Apache CXF, Spring, MongoDB.

• Using AngularJS, Bootstrap for web application.

Full Stack Developer

Israel - Costa Rica Friendship Assoc. - Nonprofit Organization

Back-End Developer - Nonprofit Organization

CTO at Immagnify

Dror has an extensive area of expertise in developing large scale systems from the ground up, with many years of experience in a variety of technology stacks and industries such as the Food-Tech, Ad-Tech, Smart Mobility, and Sales Intelligence, each comes with its unique challenges and requires for their own unique solutions or ideas.
Dror has strong qualities in leading teams both technologically and personally.

Dror graduated from Ben Gurion University with a B.Sc in Computer Science.
He currently lives in the Tel-Aviv area and enjoys sports, cooking, and playing his guitar in his spare time.

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