Keegan Otter

Warmly,

Used by Orum, New Relic, Arc, Postal, and Kong.

We combine intent providers like Clearbit, Demandbase, LiveIntent, Bombora Intent and other intent data providers, AI Chat, Live Chat, and Orchestration under 1 roof for Sales and Marketing teams.

Chief Revenue Officer (CRO)

I help shape and envision Warmly's product roadmap for GTM teams. When the team travels to work together... I go with them.

Product Evangelist

Dusted off my old acting skills and stared as Jack in this mini satire movie about sales and the ever going problem they face.

Lead Actor 

I help sales reps get a 15% connection rate with high intent prospects on their site and help automate the prospecting workflow for sales with AI by leveraging Warmly

Overseeing: RevOps, Partnerships, Sales, GTM Strategy 

Joined Warmly, as the founding revenue leader to build a team and scale revenue.

Director of Sales

WarmLegency by Warmly

In charge of recruiting, training and placing SDRs based in Macedonia to be efficient in Outbound, Inbound and Warmbound for Warmly customers.

Sales Development Tool Training Covers the following:
- HubSpot CRM
- Outreach SEP
- Seamless,AI
- Apollo Contact Data & SEP
- SendSpark Video
- Warmly
- Orum Dialer
- Autobound AI personalization
- SimilarWeb
- BuiltWidth
- MailShake (email warm up tool)
- Slack
- ChatGPT

Sales Training Methodology:
- How to Cold Call Outbound Leads
- How to Warm Call Signal Leads
- Leveraging Warmly for prospect targeting
- Following up on Event Leads
- Leveraging LinkedIn Voice messages
- The reason Omni-channel prospecting works
- How to prospect in Sales Navigator
- Creating scalable evergreen videos
- How to use AI in Sales

Co-Founder & President

Sendspark

Sendspark is the #1 video platform for sales teams to connect with customers. Sendspark is easily integrated within Gmail, LinkedIn, Hubspot, Outreach, SalesLoft, Zendesk and other messaging platforms you already use and love, so you can generate up to 400% more email engagement.

See why 10,000+ GTM professionals at companies like Salesforce, Outreach, Zoho, Oracle and LinkedIn use Sendspark: sendspark.com. 

3x your email click rates and 2x response rates with Sendspark video. Leverage dynamic video backgrounds and AI to personalize your videos to everyone. 

Try it out yourself: https://sendspark.com/?via=keegan19

Strategic Advisor

Upvert.io

Upvert tracks all digital ad and marketing campaigns that push people to your site, so you can easily retarget and have easy to use 1:1 messaging that Shows the right message at the right moment to engage visitors, convert leads, and guide them through your product... all without code and powered by AI

Investor & Advisor

Window Screen Guys

We’re a Phoenix-based home services company specializing in window screen installation, repair, retractable screens, and window cleaning. Our mission is simple: deliver fast, reliable, and professional service that makes homes more comfortable, energy-efficient, and bug-free.

👉🏻 Learn more at windowscreenguys.com

President & Cofounder

Enabled Up

I help scale early stage companies and build out GTM teams as a fractional Director/ VP. I specialize in RevOps and Revenue growth. 

Consulting expert on tools such as Outreach.io, Apollo, SalesLoft, Salesforce, HubSpot, Salesforce, Zapier, ZoomInfo, Seamless.ai, LeadIQ, Spekit, Video tools, Loom, Vidyard, Drift, Warmly, Charm.io, and other tools to maximize customer efficiency and increase sales efforts for SMB-Corporate sized businesses.

If you need help with Sales Development, Writing Sequences, our Growth hacking, I am your guy.

CEO & Founder

It's Destiny Recruiting

YOU ARE ENOUGH. It's Destiny Recruiting's job is to help you put your best foot forward.

80% of the candidates we have placed in 2020 and 2021 were women and those of diverse being, thought, and life experiences.


OUR FOCUS
We focus on placing SDRs/MDRs, Account Executives, Customer Success, Account Manager and Executive Level Sales Leadership Professionals.


OUR SPECIALTY
We specialize in SaaS, Cloud, Machine Learning, Data Analytics, Cyber Security and AI Platforms - Mid Market and Enterprise.

Get Away Stayz

I own and rent flipped properties to traveling professionals across the U.S.

Owner

SmartScout

Evabot

With Evabot you can leverage AI to break into new accounts with precision sales triggers. 

Some of the benefits with using Evabot AI
-Crack open twice the conversations.
-With precision sales triggers, not just  job changes.
-Delivered proactively across all accounts.

AI Advisor

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 🤠)

Have to give a shout out to this SDR and the approah that lead to me booking a demo ✅

She saw my post about taking over CS and then sent me an empty LinkedIn connection request 

She then sent a personalized video shortly after me accepting the request. 

I haven’t received a personalized video over LinkedIn in 70 days (I checked) 

2 touch points to get a meeting? Crazy! But it happens when you stand out 🎯

Well done Audrey Murphy keep it up 👏🏻

#SalesDevelopment #Tactics #Tips

Keegan  Otter (Software Cowboy 🤠)

graphical user interface, application, Teams

I just cold called someone and got hung up on... 

Happens to even Execs (no one cares about title when prospecting)😉 

So I did what everyone else should... 

I laughed and hit up the whole rest of the c-suite and kept going until all those other DMs at the account were touched. 

Today I am focusing on booking 2-3 meetings. 

Brushing off the dust and sending it today 

📧 +📞+ LI+ Sendspark Video for full coverage today 

#Warmly #Outbound #CSuite

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Announcing our new launch of Proactive Customer Success by Warmly 

To our customers, this one is for you!

✅ Our Warmly AI Support Agent is live in the platform

✅ Sr Sales Reps & SDRs have been promoted to CSM (we work with demand gen, sales dev and revenue leadership) 

✅ Our Team is now WarmBound Certified 

✅ New Video How To’s and Playbooks are launching 📹

✅ Same Day Support is now available 

✅ 24/7 support is launching in 2026 cause every business operates differently 

✅ Assigned CSMs to customers for the whole term 

All in effort to make our customers more successful.

#Warmly #CustomerSuccess #New

Curious who’s gonna poke holes in this… genuinely. I’m always down for the debate.

But after scaling multiple SDR teams, building AE teams from scratch, and taking 3 companies across the profitability line using this setup and approach…

This is my go-to stack + motion when I’m building a revenue machine.

Agree? Disagree? Let’s hear it.

1️⃣ HubSpot CRM → Assign ICP target accounts
 👉🏻 ~300 per rep + a surplus pool for overflow. Simple. Focused. No chaos.

2️⃣ Outreach
Yeah, it’s expensive.
Yeah, it’s still the best.
 👉🏻 I’ve literally never missed a number when SDRs or AEs use Outreach as their task management command center. Dialer + emailer + scheduler + Gmail extension = money.
... Tried Smartlead, tried AI SDR engines, tried the new AI and "cheaper options"... they all failed

3️⃣ Warmly, (yep, I’m the CRO… So a little biased here) 
 👉🏻  Cold calling ain’t what it used to be. I like to give my reps that low hanging fruit baby
 👉🏻  Person-level + company-level intent + the ability to live call a prospect while they’re on your site is a cheat code 💯 
 👉🏻 We see 28% conversion and 9–12% connect rates doing this.
 👉🏻 Plus it auto-retriggers retargeting leads into sequence. Magic.

4️⃣ Postal by Sendoso (gifting)
 👉🏻 Gifting still works. Especially upmarket and mid-funnel.
 👉🏻  People appreciate real-world touches. Break through the noise.

5️⃣ Orum 🥇 (when reps are trained + ramped)
 👉🏻 Power dialer for the ones who know what they’re doing.
 👉🏻 Output matters and dialing isn’t 2016 anymore. Tried Nooks, didn't work as well for me.

6️⃣ Contact data → Apollo, LeadIQ, or FullEnrich are all solid. 
👉🏻 Use 2 providers, especially if your VC... Don't be a cheapskate. Step up and pay to play. I deer hunt with more than one bullet, it makes sense, trust me.  
👉🏻 Buy one with bulk credits for daily ops, and a second less expensive package tier for additional coverage

7️⃣ Clay (We are integration partners)
👉🏻 We use it for territory and account enrichment. Like who uses a chatbot and which chatbot or intent provider do they use? 
👉🏻 Our integration makes it easy for a cowboy like me to build enrichments too
 
Now connect them, put a bow on it and go make some money.

But, you have to do an omni-channel or bust.. This is where people get lazy IMO, there I said it. 

🎯 Hit that prospect on:
👉🏻 LinkedIn
👉🏻 Email
👉🏻 Calling
👉🏻 AI Chat/ Live Video Chat
👉🏻 Direct Mail / Gifting
👉🏻 Events (great way to meet c-suite) 


This setup will get you there if done right, and yes it's expensive, but I've made companies millions this way, with a fast pay back period or we've broken profitable.

Week 2 leading and managing Customer Success at Warmly… and I’ll be honest — it was a mess.

We have some of the best CSMs on our team, but had little to no process on how to scale it.

To our current customers — I owe you an apology.  We’ve missed on a few things, and I take full responsibility for that.

But here’s the good news: massive strides are already happening.

✅ Customers are getting early access to new beta features — free of charge.
✅ Our New CSMs are not just “success managers,” they’re experienced sellers who’ve used to build chatbot flows and Warmly for a few years now.
✅ We’ve built real process, product automation, and soon — a brand new support chat powered by Warmly’s AI.

The biggest lesson? Without process, you can’t win.

We tried hiring only the best — but we failed, which is on us as leaders.

Because even the most skilled players lose to teams that have both skill and strategy.

Now, we’re rewriting the playbook.

It’s a new chapter — and it’s going to benefit every current and future customer.

Excited to share what we’re learning as I build out CS... While still scaling revenue strategy and passing the sales torch to Lauren Cheshire (we hit 130%+ to goal in Q3 btw 👏🏻 ).

More to come 🤠 

#SoftwareCowboy #Warmly #CustomerSuccess

Anytime I hear a leader or rep say they booked 20+ meetings, my first thought is that those meetings are probably TRASH 🗑️

You booked 20 meetings? 

How many were qualified? 

Only 10? 

So you have a 50% qualified opp rate 

You just wasted 10 hours of your sales teams time with unqualified leads when they could have focused more on those 10 qualified deals and worked more mid funnel projects to move the needle…

Did I mention these AEs usually cost around $150,000+?

It ain’t about quantity Chad, it’s about quality. 

I’d rather have an SDR book 8-10 demos with a 75%+ sales qualified rate than the rep on too many redbulls booking 20+ meetings “for the fun of it.”

You’re wasting company money, which means your putting a target on your back. 

When it comes to the end of quarter review, who do you think is getting fired vs promoted here… 

Quality over quantity always 💯

#SDR #Meeting #SoftwareCowboy #Prospecting

Our CSM and lead chat builder, Slavica Aceva, just broke down the brand-new release of AI Studio — and this one’s a game-changer

For our customers, if you’ve got Chat in your package, it’s live today

For everyone else missing out 👉🏻 interact with the chat on Warmly's site and see for yourself. 

We also have our AI Support agent live in our product for users and on the support pages.

Because with Warmly, you can now spin up multiple AI agents across different use cases, instantly leveling up how your team handles inbound, automation, and customer experience.

One AI chat for all the use cases vs.  2-3 different chat apps to manage.. You do the math 😉 


 #SoftwareCowboy #Warmly #Marketing #AI #AIChat #Chatbots

I’m joining a session on Thursday, Nov 20th at 9AM PST / 6PM CET with Boris Murdjev from Warmly and Milan Savov from SmartClick.

We’ll be talking about something every SaaS team struggles with: turning SEO visibility into actual revenue.

Because revenue happens when the right people show up - and you know how to act on it in real time.Here’s what we’re covering:
How to reveal which accounts are on your site (without anything creepy)

A simple scoring system for ICP + intent

Real-time alerts that route hot accounts to the right rep in minutes

Connecting SEO pages and content to pipeline — not vanity metrics

It’s free - and we’ll be doing a live Q&A.

It's that time of year again... 

Closed lost deals coming back and doing their research, but many of you don't see it coming

Perfect example below 👇🏻 of a closed lost deal engaging with our AE recently and boom - We are back on. 

Most sales rep would sell their kidney for a few more deals this time of year

Just give them Warmly instead. This way, everybody wins.

#Warmly #LiveChat #Sales

Gong says it.

The data proves it.

And honestly… I've seen it at every org I've put this into place.

More emails 📧  (in general just more conversation touch points) on a deal = higher win rates.

Real, intentional multithreading.

So we decided to operationalize it at Warmly.

I built SQO Sequences for our AEs — structured, repeatable touch patterns designed to pull multiple champions, influencers, and decision-makers into the deal at scale.

No more “I’ll multithread later.”

No more “I think I have enough contacts.”

Nope.

If a deal in our house hits the SQO stage, the sequence goes live.

Every time.

And here’s the crazy part… Our AE who uses the SQO Sequence on 80% of her deals is:
👉🏻 No. 1 AE on the team
👉🏻 Sitting at a 35% close-won rate
👉🏻 Turning opportunities into revenue like it’s a habit

It's not a coincidence either, it's process. 

👉🏻 More touches = more conversations.
👉🏻 More conversations = more champions.
👉🏻 More champions = more deals won.

Make process your superpower and make multithreading non-negotiable.
#Warmly #SoftwareCowboy #MidFunnel #WinRates #AE

In the past I've been frustrated when it came to the data enrichment processes...

Usually they require a CSV upload and those are usually janky, or their "CRM Integration" is very limited.

But with FullEnrich my team and I found it way easier. 

We now use it in Clay enrichments and by connecting it to our HubSpot CRM. 

Some of the useful workflows I've found for our team

👉🏻 Warmly intent leads ➡️  HubSpot CRM ➡️ Full Enrich ➡️ Outreach = More emails landing, and more calls being connected ✅ 
 
👉🏻 Conference lead list  ➡️  HubSpot CRM ➡️ Full Enrich ➡️ Outreach  = more phones being added to just those emails we got ✅ 

👉🏻 Target Account list  ➡️  HubSpot CRM ➡️ Full Enrich ➡️ Outreach  = more phones being added to just those emails we got ✅ 

If I am having a human follow up or chase it, I am having it enriched. Period. 

I also appreciate the UI and transparency about credit enrichment usage. If you know, you know... 


Enrichment isn't something you can skip, it's vital to Go-To-Market.

The easiest pick for contact enrichment for me is Full Enrichment. Go check em out 🤠 

#FullEnrich #DataRecommendations #FullEnrichPartner
#SoftwareCowboy

“AI will replace SDRs and salespeople” — Said by someone who’s never carried a quota, handled an objection, or closed a deal in their life.

If you hear this take, just know you’re listening to someone who does not understand how sales actually works.

Here’s a real example:

For the last two weeks, an AI-powered dialer has been calling me 3–4 times a day.

❌ I’ve pressed “9” to be removed.
❌ I’ve told the human it sometimes transfers me to.
❌ I’ve asked—multiple times—to stop calling.

Still getting calls.

I finally had to mention legal action cause it's been so bad and on the weekends… and apparently this “super-intelligent” AI can’t comprehend that either.

So no… AI isn’t even close to replacing this part of the job 😂 

And when I talk to C-suite leaders?

Same story every time:

They’re not hopping on a call with an AI bot.

Not today. Not anytime soon.

AI will augment great reps. It will never replace the ones who can build trust, think critically, and actually sell.


Yes, I called these back to verify it's the same bot just to prove a point here...

#SoftwareCowboy #AI #POV

I tell people all the time not to take one negative piece of feedback as the end all be all. 

One person hated it, while others booked through it and helped my team hit quota. 

So who’s winning? 🤠

ceo of warmly.ai, the #1 intent & signal data platform | sharing behind-the-scenes marketing insights & trends 5x a week | ex-Google & Sequoia scout

Our CRO Keegan Otter got ripped by a customer for a GTM motion he rolled out… Pop-ups! they hated it.

Here’s what happened that same month he implemented it:
- $67K in upsells
- $192K in pipeline

These are Warm Offers (as we call it) - they’re personalized, in-app messages triggered by real user behavior + intent / website de-anonymization.

They're a feature of Warmly,.

They help teams:
- Capture visitors who’ve spent meaningful time on your site - like those digging through pricing or product pages - but haven’t taken action yet.
- Re-engage customers who aren’t getting full value.
- Educate users on new releases or updates.
- Drive upsells and expansion right inside the product or on your website.
- Add CTA

& when the customer said they didn't like them? We just excluded that customer for the future using our filtering.

Hyper-targeted, intent-based pop-ups pair well + increase conversion as part of our Inbound Agent

If pop-ups added an extra $100K in pipeline (for not much work) - would you still hate them?

Learn more about Warm Offer Pop-Ups in Warmly: https://lnkd.in/eiyk8ZRW

I bet my CEO my favorite cowboy hat on this one, so let's settle this debate 👊🏻 

He told me he thinks Apollo, Outreach and other SEPs are all the same. I told him there is a clear difference. 

I am just talking for SDR and AE prospecting flows here. 

Vote and drop a line on why 🤠 

If you mention Smartlead and Instantly I know we are not on the same playing field as those are marketing emails not sales engagement. (We use Smartlead as a marketing nurture tool).

Which Sales Engagement Platform is the best for SDRs and AEs?

For the Sales Reps in the back! 🤚🏻  Let me hear your input. 

There's many Series A - D leaders giving input but I'd love to hear from the reps too. 

Am I trying to prove a point to my CEO? Absolutely

Will it work? Who knows, which is why you should vote 🤠

View Keegan Otter (Software Cowboy 🤠)’s profile

Edward Purmalis

Salescast®

Director of Revenue Operations

Head of Community & Partnerships 

We partner with Visionary Entrepreneurs, and B2B Sales Leaders to produce a podcast that...

- Builds new relationships with your ideal clients
- Serves your community through impactful content &
- Capitalizes on your own platform to drive ethical sales

If you're interested in learning more, shoot me an email at edward@salescast.co and we'll see if you're a good fit for our growing family of salescasters

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