Keegan Otter

SmartScout

Strategic Advisor

Warmly,

Used by J.P. Morgan, Orum, New Relic, Aligned, Arc, Sendoso, Seamless, and Sendspark.

We combine Clearbit, 6Sense & Bombora Intent, AI Chat, Live Chat, and Auto-Sequencing under 1 roof for Sales and Marketing teams.

Head of Revenue & GTM

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

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

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 yoru 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

Referral Partner

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

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

Sendlane

Grew ICP ARR by 205%. Generated $8.6 million in pipeline, $2.74 Million in closed won. 

- Scaled the sales department from 2-40 in 10 months.
- Oversaw Sales Team, Sales Strategy, Managers, Enablement and RevOps for all revenue facing teams
- Expanded and managed a tech stack of 15 revenue facing tools 
- Built out an enablement and Ops team from scratch, growing it from 1-3 people
- Implemented a contract process (Contract Books) that transformed Sendlane's deals from being 70% monthly and only 30% annually to 75% annually committed and only 25% monthly
- Created the rules and process for company attribution and reporting
- Built out the Rules of Engagement between departments and handoff processes
- Rebuilt out our company Notion pages and increased Notion adoption
- Built out the onboarding process and guide leveraging Notion, Spekit and Loom to onboard 24 reps (AEs, BDRs, Managers, and an Enablement Associate)
- Hired on a Enablement specialist

Director of Sales & Revenue Operations

Generated over $3.7 million in pipeline within 6 months, helped sales close over $600k in ARR

BDR efforts lead to 85% of net new ARR

- Built a BDR team from scratch. Went from 0-13 BDRs. 
- Hired on and trained a manager to run the team. 
- Grew our tech stack from 4 to 9 new Sales Tools to increase sales and efficiency 
- Built out the RevOps department and team 
- Built out the enablement program for all of sales, marketing and leadership
- Worked cross-functionally with Marketing 
- Worked with CS to build an up sell process 
- Reduced RAMP down to 65 days leveraging Spekit and training

Sr. Manager, Sales Development & Sales Operations

- Built out the BDR program from scratch.
- Brought on and integrated Outreach with our CRM
- Built out 28 sequences for inbound, outbound and referral motions
- Built automation triggers that lead to 2 minute demo request SLA times 
- Built out the event leads and MQL hand off process 
- Built the BDR to AE hand off process 
- Created dashboards for measurement tracking

Senior Manager of Sales Development

Skaled Consulting

Sales & Sequence Consultant

Postscript

Coached a team of 24 rockstar BDRs 

- Directly Managing 10 MM/ ENT BDRs
- Brought on outbound video as a new channel - Generating 105 opportunities within 4 months 
- Enabling the whole BDR Org through Guru, SFDC reports, SalesLoft training
- Created a virtual BDR bootcamp to onboard new hires utilizing notion and our enablement technology
- Built a Guru Enablement deck (0-52 cards) on Salesloft, Salesforce, Cold Calling, and Outbound video best practices within the first 30 days - Currently has a 95% adoption rate. 
- Appointed as the SalesLoft Admin for the BDR Org
- Rebuilt our cadence library, leading to a 50% increase in opp conversion 
- Increased Call output across the BDR org by 4x within first 30 days (328 dials to 1218 dials per week)
- Increased Week over Week conversion rate by 2x within 30 days
- Co-Filled in for the Director while she was on maternity leave for Q3 and pushed our department to hit 110% of the quarterly goal
- Created and successfully tested 3 new outbound approaches that became adopted org wide - Instagram, ‘Bought From Store’ & ‘Pay to Play’ leading to an increase of 27% in pipeline

Come help sell the leading SMS platform to online brands and celebrity brands you already buy from.

Manager of Business Development & BDR Enablement

GTM Leader & Product Evangelist @ Warmly | 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.

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.

She hit 118% to quota, was the number one AE for the 2nd quarter in a row, but most of you would never have given her a chance… 

Gabrielle Stott (Sales Shark 🦈) had never been an AE prior to joining Warmly. 

She was a top performing SDR and a top performing SDR manager before but never had any “SaaS closing experience” 

What is even wilder is that today most tech leaders would pass on her due to her “lack of experience.” 

But not me. I saw her potential after getting to know Gabi from networking at events and she always kept me up to speed on her progress. Her eagerness to learn and grow was at a different level. 

She already had SDR and even management experience, so I gave her a shot. 

Why? 

Cause I was in a similar situation to Gabi when I started my career and people that show promise need to be given a shot. 

Personally, I could give a rats bum if you have closing experience for certain roles too. In fact sometimes it easier to teach someone with no closing experience how to do it the right way. 

What I look for is tenacity and coachability.

So to those being told that they don’t have enough closing experience…It’s all bull 💩

Keep pushing, keep knocking on doors, don’t settle. 

And remember stories like Gabi. 

Could be you someday 🤠 

So well done Gabi, well done 👏🏻

Excited for another conference season with you to go tear it up and get some great leads!

#Warmly #ShoutOut #Story #AEdevelopment #AE

Keegan  Otter (Software Cowboy 🤠)

No alternative text description for this image

Don’t give up on your health — or you’re giving up on yourself

Life can be hard, and I want to be open as a 28 year old trying to make it in this world of business...

Last month...

End of quarter was looming and I felt like we were slipping behind.

I was knee-deep in a civil suit with a tenant I was evicting.

I was living out of a carry on suitcase for weeks, bouncing between personal and work obligations.

Legal fees and unexpected expenses doubled overnight.

My personal life felt like it was unraveling.

And I was barely sleeping — my mind wouldn’t shut off.

... I’m not going to lie — I thought about numbing it all with a drink which is why I am sharing this (I don't drink much in general but the idea crept into my head at the time)

But instead, I decided to hit the pavement and run.

Not because I wanted to train for something.

Not because it was easy. 

But because I needed to move. I needed those endorphins to lift me out of my own head and burn off the stress before it burned me out completely.

Running didn't solve all my problems, but it kept me SANE and mentally strong while I faced these problems

Well, those 30 days passed since and here’s what happened:
 👉🏻 We finished Q2 at 109% of goal – Shoutout to our amazing team, this was all them rallying to a strong finish!
 
 👉🏻 I won the case against my con-artist tenant and finally got them out of my house (after 6 months of them living there rent-free — in Texas, no less)

 👉🏻 I dropped 7 lbs and started getting cut again

👉🏻 I now run 4–5x a week. I’m even thinking about joining a run club.

👉🏻 My rental property is now up for sale (It's in Dallas if anyone is interested) 

 👉🏻 I’m dating again — and actually have the time and energy for it

👉🏻 I started going out and grabbing dinners and country swing dancing with friends again 🤠 

👉🏻 I actually had the ENERGY to go to local networking events and starting being part of the the Phoenix community again 

All from one small choice: to run instead of numb.

I didn’t change my whole life at once. I just made a single decision to protect my health — and it gave me the strength to face everything else head-on.


For those facing burn out, crashing out, and having a tough time in their career or just life right now, I don't have all the answers, but I can say...

Sometimes the best way to move forward… is to literally move.

Take care of yourself first and you'll be more prepared for the battles ahead

Today I turn 29 🎉 

Birthdays always make me reflect — not just on the wins, but on the failures that taught me more than I could have imagined.

Here’s the professional journey I've had so far:

23 → Broke into sales and made 6 figures as an SDR.

24 → Became a top AE… and made less than when I was an SDR.

24 → Started a B2B agency. Year 1: $15K. Year 3: six figures.

24 → Bought my first property and flipped it into a short-term rental.

24 → Jumped into management at a seed-stage startup. Grew a team of 6… only to lay them off when funding dried up.

25 → Got pushed out of a hyper-growth SaaS company after being the top SDR manager. My “bullish” mindset didn’t fit.

26 → Became Director of Sales at another SaaS company. Helped influence their Series B raise (still in the docs today). But months later… I had to lay off half the team after leadership bet wrong on marketing.

27 → Took a step back to go forward. Joined Warmly. Did founder-led sales with maximus greenwald, selling side by side, committing to build the team as I sold. We grew it by $500k very quickly and hired our first AEs. 


Fast forward to today:
 👉🏻 Warmly grew from <$150K ARR → $5M+ ARR
 👉🏻 On track for $7.5M ARR by EOY
 👉🏻 Launched Warm Legency by Warmly, pacing for $1M–$2M ARR this year 
 👉🏻 Leading ~30 people as Head of GTM & Strategy


Some personal benefits of taking these risks:
24 → Moved from rainy Seattle to sunny Scottsdale, AZ (happiest I could ever be)

24 → Learned to be a home owner at a young age(the good bad and the ugly)

26 → Grew a unique personal brand and started making income on posts

27 → Went to Europe for the first time ever and now go frequently for work

27 → Started public speaking at B2B events and now speak more 

28 → Helped my Dad sell his business for 7 figures through the network I grew

28 → Purchased my dream truck

29 → I will purchase my dream home


If there’s one thing I’ve learned ☝🏻 

Age doesn’t matter. What you do does 🤝🏻 

I’ve failed more times than I’ve succeeded — but those failures are what gave me the wisdom to succeed bigger and faster.

Knowing what not to do is some of the most powerful wisdom you can gain.

Take risks. Expect failures. Keep growing.

#SoftwareCowboy #Reflection

End of month is here and EOQ for some. 

Here’s one tactic I teach AEs to speed up deal velocity (especially when things are “looking good” but still not signed): 👇🏻 

1️⃣  Send a quick video walking through the contract async. And We use Sendspark here for ours (especailly with the Outreach and gmail integration)

Not every buyer wants another live call just to review legal line-by-line. 

A 2–3 min Sendspark video covering key terms, pricing, and next steps gives the buyer everything they need to move it forward.

2️⃣ Set a 15-min placeholder for the next day or that Friday.
 
Position it like this:
“I blocked off 15 mins tomorrow just in case you have questions or need anything before signing — totally optional, but it's there if helpful.”

That light-touch fallback gives your champion a reason to prioritize AND creates a natural deadline without being pushy.

It’s fast. It’s respectful. It works 🤝🏻 

Good luck closing out strong 💪🏻 

#SalesTips #EndOfMonth #AEPlaybook #SalesStrategy #DealVelocity #B2BSales #GTM #Sendspark

⚔️ We just launched Warm Legency by Warmly

If you haven’t been to Skopje, Macedonia… then you probably haven’t met the hardest working SDRs in the world (btw, Aleksander The Great came from Macedonia)

For the last 2 years, Warmly has been quietly building with elite Macedonian talent — and now we’re opening it up to the market.

Warm Legency = SDRs + AI → pipeline at scale.

Because let’s be real:
 ❌ An AI SDR alone? Cool, but limited.
 ✅ An AI-enabled SDR who’s fully trained on GTM tools, AI prompts, and omni-channel outbound? That’s the killer combo.

Our Warm-legionnaires aren’t entry-level contractors. They’re:
👉🏻 Certified in Outreach, Salesloft, LinkedIn Sales Nav, Warmly, Clay, Orum
👉🏻 Warmbound Certified in omni-channel outbound (ready on your GTM stack day one)
👉🏻Trained in AI prompting to maximize ChatGPT output

We recruit, train, onboard, handle payroll, and provide ongoing support. You get pipeline-ready reps — without the operational lift.

The results?
👉🏻 1,000+ SQOs generated from just 11 SDRs in the last 2 years.
👉🏻 A proven playbook blending humanity + AI that’s now scaling to our 400+ customers.

This isn’t theory. It’s what we’ve been running in-house — and it works.
Check out the full details in the comments

PS: If you’re in Macedonia and part of the top 1% talent pool → we’re recruiting for our 3rd placement class. Reach out 🤠

So I own a boat and go out to the lake a lot to surf 🏄 

It’s my hobby, my recharge time, and frankly my motivation sometimes 😂

And when the team comes into town I like to take them out on it and be the “cool” boss. 

Well for a good laugh maximus greenwald knew I was missing a captains hat so he decided to send me one and it’s got that customization to make it even more special. 

Moments like this make me appreciate my friends and coworkers at Warmly.

As the saying goes “ay-aye captain” 

#SoftwareCowboy #BoatCaptain

Useful tip 👉🏻   leverage you LinkedIn headline. It’s prime real estate for Marketing and Sales but highly underutilized. 

1️⃣ It’s the first thing people see when you show up in their feed, comments, or DMs — and it’s your chance to:
 ✅ Show personality
 ✅ Share how you help
 ✅ Stand out from a sea of “Account Executives” and “Founders”

Don't stop at just the headline. Go deeper

2️⃣ If you want your profile to actually work for you, optimize every section like it’s a storefront:
👉🏻 Add skills to every past and current role
👉🏻 Upload images, decks, and links to your experience
👉🏻 Include links that push traffic directly to your site or form (use UTMs too)
👉🏻 Stack your certifications — the more relevant ones you show, the more you look like a subject matter expert. Certifications give instant credibility and build trust at first glance. 

A half-baked profile makes you look like you’re only halfway in the game.

Think of your LinkedIn profile as a 24/7 sales & marketing asset — not a dusty resume.

If you want to drive more leads, your profile needs to be doing heavy lifting before you ever send a message or post.

Your LinkedIn profile is like a mini website for your book of business. Half the effort into it usually leads to half of the results. 

#LinkedInTips #LeadGeneration #MarketingStrategy #PersonalBranding #GTM

Want to scale high-leverage behaviors across your team without another training?

Start embedding instructions directly in your email templates 📧 

It’s a low-lift way to reinforce best practices — especially for those “extra credit” moves that can help nudge a deal across the line.

Here’s one I just added to our contract send template:
 "{{! send a quick video walk-through of the contract }}"

This reminds both new and tenured reps:
 If it’s a tricky deal, take the extra 2 minutes to record a contract walk-through.

It’s often the move that gets it signed this week vs. next.

I also drop in links to video scripts, Spekit cards, or templates right inside the email body to choose from — so enablement lives in the flow of work, not in some folder they’ll forget.

Small tweak. Big impact 📈 
 
Try it. 

#SalesEnablement #SalesOps #RevenueTips #ScaleHack #EmailTips

This is how I know I made it to the big leagues 🙌🏻 

Someone impersonating me 😂

I bet they really want those gift cards…

graphical user interface, text, application, chat or text message

Something new is coming to Warmly, that I've been working on. 

It's going to be a huge impact to modern sales orgs. 

Any guesses? 

#Warmly

A customer ripped into me for a new Go To Market motion I rolled out... 

Didn’t like the approach. Harped on it. Made sure I knew they really didn’t vibe with it. 

So what'd I do?

Honestly, I just laughed it off... as said whelp... "It's not for everyone."

Because that same exact strategy?
➡️  Drove $30K in upsells last month and $65k in pipeline
➡️  Gets praise from other customers who do see the vision and end result
➡️  And has had folks asking to “pick my brain” on how we pulled it off

You’re not going to win them all. Like Ever. 

But that doesn’t mean the playbook is broken.

Sometimes it just means it wasn’t for them — and that’s fine.

You keep iterating. You stay focused on what’s working. And when you catch some flak along the way?

Smile. Laugh. Screenshot the MRR. 

Take some of the feedback (if there is any)

And get back to building 🤝🏻 

#GTM #Startups #Leadership #CustomerExperience #GrowthMindset #KeepGoing

Even the billion dollar companies have bugs or crash... 

Don't worry HubSpot, I am not churning. Big fan of the product and sh*t happens. 

Gave me a good reminder that even the big giants have the same issues as everyone else. 

I am sure it'll be fixed soon 🤠

Hot take this Monday, but AI SDRs & Agents are underdelivering in B2B and suck at their job...

I'm not shocked either.

You hear the buzz—AI agents are replacing SDRs, productivity is soaring, wins are guaranteed... But the reality? It’s bull 💩 

Here’s the real data 👇🏻 
👉🏻 Show rates lag behind: AI-scheduled meeting show rates only deliver 10–20%, while humans were around 30%+ 

👉🏻ROI is not instant or even present for most companies: About two-thirds of revenue teams see real ROI within the first year of AI adoption...

Bottom line: AI SDRs are cool, but they’re not bulletproof—or ready to replace human-centered processes entirely.

Why this matters:
👉🏻 If you’re leaning on AI tools hoping they'll close more deals on autopilot... you're starting from the wrong place. 

Without human oversight, context, or nuanced decision-making, even the most advanced AI can underperform—and your GTM momentum falls apart.

That’s why hybrid models (AI + AI certified human reps working in harmony) are outperforming pure-AI approaches. The chemistry matters.


Yes, we sell agents here at Warmly but we explain that it should be paired with HUMAN oversight and replies.

#Warmly #WarmLegency #AI

What happens when you combine the great buyer signals with the best enrichment and personalization engine?

You get a pipeline cheat code:

Now with Warmly ➡️ Clay, you can push real-time signals directly into your Clay workflows to:
 ✅ Enrich leads
 ✅ Personalize AI copy
 ✅ Trigger 1:1 ad campaigns

Here’s what we’re pushing from Warmly into Clay:
🌐 Website Activity – who visited, what they looked at, and if they chatted
 💬 Social Engagements – who’s liking or commenting on LinkedIn
 🔥 Bombora Intent – accounts and PEOPLE actively researching your category (perfect for 1:1 ad targeting to draw them in)
 📣 Job Changes – when someone new joins your ICP account

This isn’t just data — this is actionable fuel to scale relevance, fast.

With Warmly signals + Clay's automation and enrichment, your GTM motion moves a whole lot quicker.

Want it set up? Takes only minutes which is the best part.

#RevOps #GTM #Outbound #Clay #Warmly #Warmbound #Signals

Who's heading to INBOUND 2025? If you’re a Marketing Leader, join us for an exclusive Dinner where we’ll dive into:

👉🏻 The Agentic Future of GTM
📍 25 Lusk, San Francisco
📅 September 4th, 2025
 🕜 6:00 PM

Hosted by:
maximus greenwald, CEO Warmly,
Lisa Sharapata🌟, VP AI & GTM Strategy Metadata

I'll be there to talk all things GTM 🤠 

RSVP link in the comments 👇🏻

If you’re trying to grow your brand or the company's awareness I'd consider you try leveraging TikTok on top of LinkedIn — it’s a hidden goldmine.

It’s a great channel right now to:
 👉🏻 Drive awareness at scale (and low cost) 
 👉🏻 Educate buyers in a fun, low-barrier way
 👉🏻 Even generate some direct leads to your site

Most B2B leaders dismiss TikTok as “not serious enough.”

Okay John or Susan who's been using Eloqua for email marketing, I'm sure you know the latest trends 🤨 

But the reality? The people buying your software are the same people scrolling TikTok at night (like me).

Why wouldn’t you use the platform where attention is flowing fastest? Why not do an omni-channel approach outside of just LinkedIn?

Awareness fuels trust. Trust fuels leads.

Highly recommend, I know many folks on this platform who've seen success posting on both LinkedIn and Tiktok

#MarketingTips #TikTok #OmniChannel #Brand

They book $50k+ deals that close and are the new wave of SDRs 

The new wave of sales development experts understand
👉🏻 Domain deliverability and best practices
👉🏻 How to prospect by signals 
👉🏻 How to leverage AI like ChatGPT and Perplexity to fast track research and personalization
👉🏻 Account Based prospecting
👉🏻 Omni-channel outreach 
👉🏻 Social selling
👉🏻 Leveraging tools like Clay for massive enrichment


And this video highlights some of those rockstars...

If you want to learn more of what we teach when it comes to Warmbounding comment below. 

If your looking for more SDRs at the fraction of the cost Warm Legency by Warmly, is a good place to start 🤠 

#Warmly #Warmbound #WarmLegency

This is the type of creativity and talent we have ready to go at Warm Legency by Warmly, 

They are locked and loaded to get those meetings across the board 🤝🏻

Well said Voydan Bekarovski

Making GTM Fun 🤩 | Catching Buyers Before They Bounce | Turning Clicks into Conversations & Traffic into Pipeline @ Warmly

9 months ago, I wanted to quit Sales forever.
Burnt out. Done.

I swore I'd never pick up the phone again.

Then I joined Warmly, And everything changed

- Sales became fun again ("Make Sales Fun Again" hat is on the way)
- I met some amazing and vibrant people
- I got to travel, laugh and learn more at company on-sites than I though possible
- AI conferences blew my mind and changed the way I think about my everyday tasks

But the most important one- I got hands on with the best in class AI tools that've helped me succeed like never before.

Looking back... it's one of the best decisions I've ever made

Which is why I am beyond STOKED to share our next chapter: 
Warm Legency by Warmly 

We're building an SDR agency that helps companies tap into top notch, AI powered talent. Reps trained on the latest tools and trends at a fraction of the cost of US-based hires.

So If you're looking to build better pipeline, and work with SDRs that crush quotas... Check out our website!

Find the link in the comments :)

Taplio

Keegan Otter (Software Cowboy 🤠)'s Linkedin Analytics

Who is engaging with Keegan

's Best Posts (last 30 days)

Want to drive more opportunities from LinkedIn?

Taplio

.css-1jgreyo{background-image:linear-gradient(284deg, rgba(39,43,72,1) 0%, rgba(33,47,183,1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Keegan Otter (Software Cowboy 🤠)'s Linkedin Analytics

Who is engaging with Keegan

's Best Posts .css-qqfgvy{font-size:var(--chakra-fontSizes-md);}(last 30 days)

Want to drive more opportunities from LinkedIn?

Keegan Otter (Software Cowboy 🤠)'s Linkedin Analytics

's Best Posts (last 30 days)