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. ❤️

Josh Norris

Josh Norris is a strategic leader in capital-efficient GTM design and post-raise execution for high-growth SaaS companies. He partners with founders and CFOs to ensure new capital converts into predictable, investor-grade revenue systems rather than uncontrolled burn.

He has advised 60+ Series A-D startups, helping teams eliminate burn drift, professionalize reporting, and build GTM infrastructure that supports follow-on funding. His work has contributed to multiple clients reaching seven-figure ARR within their first year and advancing to subsequent rounds.

Josh previously led GTM, revops, partnerships, and business development at Hyperbound, scaling from zero to $5M ARR in under two years, and at Lavender during the 2022 downturn. He also managed a 36-engineer organization at a publicly traded SaaS company, giving him a rare systems-level perspective on how revenue, product, and capital deployment align.

The moment the wire hits the bank is the most dangerous point in a startup's lifecycle. Josh operates as the architecture partner between board expectations and execution, ensuring every dollar deployed compounds.

GTM Consultant

I consult on sales, marketing, and customer success.

Josh Norris 🐦‍🔥

HubSpot's CEO heralded signals as the hot new thing in outbound. At first, this looks like a validation of our community's thinking, but in reality she's 4 years behind top GTM trends (typical of enterprises her size).

The early stage GTM startup community has been talking about signals since 2021. I know because I was one of the first people to use the word and implement them at Instabug and Lavender. I also remember my friend Saad Khan doing it at Dooly at the same time.

Our community tends to be ahead of the rest of the world on GTM trends because....well, we invent the new tech that eventually catches on and becomes those trends. But we've moved on to bigger things since 2021.

What Yamini refers to here as "signals" only captures half of the picture. Top GTM teams today don't just use signals to send outbound when buyers are ready to book a meeting. That's the most basic part of signals-based GTM.

Top GTM teams today build their whole marketing orgs around 
→ deliberately and methodically introducing buyers to new ideas
→ helping them educate themselves
→ building relationships and trust
→ and asking for the meeting at the perfect time

When people say "moving through the buyer journey", that's what they mean.

And, critically, we do outbound THROUGH THE WHOLE JOURNEY. At the beginning, it's a LinkedIn message with a brief hello. In the middle of the journey, it's an invitation to a dinner or webinar, a link to a new customer story, or a random conversation about something unrelated just to get to know each other.

We collect and use signals to monitor each individual human's progress through that journey, strength of relationships, their company's priorities, etc. And then we ask for the meeting when the time is right.

The GTM of 2021 collected a bunch of signals, stack ranked prospects (hot vs cold, tiered accounts, etc), and then sent outbound starting at the top of the list. It was a passive approach to the market.

That's what Yamini is describing here. Today, we have the tools to do much, much better.

Your competition is taking an active approach. If you don't, you'll fall behind before you know what happened.

GTM Capital Deployment Architect for Post-Raise SaaS | Series A-D Growth & Capital Efficiency

In a call with Zach Wright right now - "We didn't lose a single month-to-month customer in January" 🤯📈

End of year is a rough time for month-to-month contracts. When customers want to cut costs, that's the first place they look.

Really excited to see Syft AI's insane customer loyalty and growth serving outbound sales teams.

Big things coming from them over the next few months, by the way. You've seen me talk about them for the last year or two. They're about to become a breakout name.

My latest toxic opinion is that AI started using the em dash so much because the em dash is a uniquely superior punctuation mark—the best at conveying complex thoughts-within-thoughts—and the only reason the em dash has a stigma now is because most of you aren’t good enough writers to have recognized its value and used it before AI did. So now you see it as new, superfluous, and annoying—just another symbol of AI frivolousness—instead of the useful literary tool that it is. 

Thank you for coming to my Ted talk. Please enjoy this poem from a clothing tag from when I was shopping earlier in Shibuya. 

Words are light.

Ode to penguins.

taplio

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taplio

The Battle

Keegan Otter (Software Cowboy 🤠)

Josh Norris 🐦‍🔥

Followers

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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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