The Arena

We are two complementary businesses under one roof. 

In The Arena Recruiting, we specialize in proactively identifying and attracting game-changing talent for ambitious startups in the defense and federal tech sectors. Traditional recruiting waits for talent to come knocking—we actively engage top performers who aren't even considering a career move yet, compelling them with opportunities they can't ignore. By authentically communicating your company's vision, we transform passive candidates into passionate team members who elevate your mission and drive real impact.

In The Arena University, our mission is personal and powerful, guiding veterans through their transition from military service to rewarding careers in tech sales. We provide a rigorous, hands-on training program designed to leverage the strengths veterans already possess—discipline, resilience, and leadership—and equip them with the specific skills needed to excel in technology sales roles. We don't just train veterans; we unlock their potential and set them on a path to thriving civilian careers.

Bringing these two initiatives together creates a powerful synergy. Graduates from The Arena University become prime candidates to join innovative startups supported by The Arena, effectively establishing a dynamic ecosystem. This integrated approach creates a self-sustaining flywheel, continuously enriching both the talent pipeline for our clients and career opportunities for our graduates.

Whether you're scaling a transformative startup or you're a veteran ready to conquer the next chapter of your life, welcome to The Arena—where talent meets opportunity.

Founder

Pavilion

Member

Salesforce

I'm responsible for supporting the Army as they fight to modernize, use data to make better decisions and leverage technology to advance their mission.

Federal Account Executive - Army

🔬 The Practice Lab

AFCEA Aberdeen Chapter

AFCEA - Emerging Leaders VP of Marketing and Publicity

Top One Percenter

The Top One Percenter is a powerful and private sales network exclusively for T.O.P. members.

Rising sales stars and Top 1% sales professionals come together to prepare, learn, and master the art of sales. It all starts with mastering the mindset to perform at the highest level possible.

Upon acceptance, sales professionals are required to successfully complete the private 90 day Top One Percenter Academy in order to become a Top One Percenter member.

A select few sales professionals are accepted each quarter to attend the Top One Percenter Academy.

Partner

NTT Ltd. is a leading global technology services company. We partner with organizations around the world to shape and achieve outcomes through intelligent technology solutions. 

As a global ICT provider, we employ more than 40,000 people in a diverse and dynamic workplace that spans 57 countries, trading in 73 countries and delivering services in over 200 countries. 

My focus is on information technology consulting and managed services. I help my clients realize their goals by becoming an extension of their team and helping them get business-critical projects over the finish line.

Client Manager

Client Manager with Dimension Data (a subsidiary of NTT Ltd.) focused on generating business outcomes by leveraging the power of technology, people, and processes.

Our approach is consultative and data-driven in nature. We believe that to get you where you want to go we first have to know where you are.  We focus on helping our clients achieve their goals by leveraging our broad and knowledgeable team of experts in areas around digital infrastructure, customer experience, cyber security, hybrid cloud and digital workplace.

Client Manager (Dimension Data)

Softchoice

Outside Sales Representative, responsible for managing and developing a local territory for corporate mid-market. I am responsible for helping businesses in my territory obtain, manage, and deploy technology solutions that help customers meet their business goals while saving them time, money, and resources along the way. 

Teamed with hundreds of internal technical and professional services resources, I have capabilities to help customers with all the major IT vendors, including Microsoft, IBM, Dell, HPE, Cisco, VMware, Citrix, Lenovo, and thousands of others.

Account Executive

US Navy

Manage a 6-person team to train and consult 315 Training Officers and their Commanding Officers Navy-wide.
•	Increased fleet-wide readiness for critical schools and requirements from 72% to 97%
•	Experienced public speaker: created and delivered over 75 presentations to Commanding Officers and crew
•	Spearheaded changes to essential high-profile presentations resulting in a concise product that helped customers improve their overall training programs
•	Supervise prompt corrective action to address training deficiencies, correcting over 100 deficiencies per week

Fleet Training Liaison Officer

Led a unit of 26 sailors as the Officer-in-Charge of the Navy’s only Coastal Command Boat (CCB) – a one of a kind, technologically advanced reconnaissance vessel.
•	Executed highly sensitive surveillance and reconnaissance operations resulting in over 1,500 hours of valuable on-target data of the objective
•	Successfully conducted 3 major overhauls of the CCB and coordinated the logistics of all repair operations 
•	Influenced multiple stakeholders to approve a series of challenging missions 
•	Coordinated with other U.S. ships to accomplish crucial missions 
•	Designed preventative and corrective maintenance systems resulting in a savings to the Navy of over $500,000 
•	Coordinated joint military training exercise between Germany, France, Italy, Bahrain, Australia, and U.S. forces

Platoon Commander, Coastal Riverine Squadron Two

Managed 80 sailors in training, administration, and readiness to maintain and operate critical communication and engineering equipment vital to the ship’s mission
•	Ranked #1 of 13 Junior Officers 
•	Hand selected by Commanding Officer (CO) to lead a challenging division of 26 combat information specialists
•	Led a 45-person team to locate, track, and apprehend Colombian narcotics traffickers; seized over $30M of cocaine en route to U.S.
•	Designated by the CO to train peers on qualifications of a Surface Warfare Officer

Division Officer, USS OAK HILL (LSD-51)

Tech Qualled

I graduated from an intensive training curriculum designed to give transitioning veterans a comprehensive understanding of the high-tech industry and develop key sales skills. The following is a list of core competencies emphasized: 

Product and Industry: 
	• Networking 
	• Collaboration 
	• Data Center Fundamentals 
	• Security 
	• Internet of Things 
	• Cloud Computing 

Sales Techniques: 
	• Sales and Business Acumen 
	• Prospecting, Qualifying, and Investigating 
	• Communication Skills 
	• Extensive Role Playing 
	• Negotiation Skills 
	• Executive Conversations (CxO) 
	• Closing and Objection Handling

Account Executive Candidate

Those who win the battle for talent, win. The explosive growth of federal and defense tech has triggered an intense war for top-tier talent, fundamentally reshaping hiring strategies and industry dynamics. Companies are no longer just competing on product innovation—they're competing on their ability to attract, develop, and retain the right people.

But the solution isn’t as simple as just hiring the “best” talent. The reality is, the best talent has options. They’re not just looking for a job—they're looking for mission alignment, leadership they believe in, and a culture that enables them to thrive. This means companies need to shift their thinking. Instead of simply searching for great talent, they need to ask themselves:

- Are we positioned in a way that makes top talent want to choose us?

- Does our employer brand reflect the mission, challenge, and impact that high-caliber professionals are looking for?

- Are we structuring opportunities in a way that retains top performers once they’re inside the building?

In the fight for defense tech dominance, winning on talent isn’t just about who you hire—it’s about who wants to work for you in the first place. Those who figure this out will outpace the competition. Those who don’t will be left wondering why they can’t attract the people they need to scale.

Most AEs never hit 175% of plan at Salesforce. Jonathan, former Army EOD Officer, did it in year one.

Then got promoted to team lead in year two. 

Jonathan's not special... (sorry Kip)

He just applied the process consistently.  

It worked. 

I'm hosting a last minute little webinar tonight where Jonathan is going to come and join me in a discussion around:

1. How got a job at Salesforce as an AE with ZERO sales experience. He used to blow sh*t up in the army... how did he get that skill to translate to being an AE at the biggest software company in the world?

2. How did he ramp so friggggin fast? It takes most AE's at least a year just to figure out what their job is. He crushed his quota in year 1. 

3. What he learned along the way and how you can apply it to your job hunt or to your AE role. 

4. A bunch of Q&A

Since it's so last minute, if you wanna join 

just DM me  directly 

OR

comment "Kip" 

and i'll shoot you the link to join us. 

It's tonight, September 30th at 8pm EST on Google Meet.

#InTheArena

18th green at bethpage for the ryder cup. Posting an image hoping the linkedin algorithm loves it and stuff.

Andrew Garcia

Vets to Tech Sales | Most common lie veterans believe…. Hiring manager: “Sorry, I love your military background but you don’t have enough experience for a tech sales role.”

Job Opportunity

Senior Account Executive
Working directly for the Head of Sales
7+ years experience selling to Federal Government.
$360K OTE 50/50 split + $200K stock
Must be able to build a business with little guidance

Company is a SaaS platform in the Financial Auditing space

Connect/DM if interested AND you are actually a good fit. 

#InTheArena

Read this before trying to get a higher role in sales.

SDR's and AEs think the next title will save them.

It won't.

You’re not stuck based on performance alone — it's structure, perception, role bias, and mindset too.

If you don’t know which barrier you’re fighting, you’ll keep applying force in the wrong direction.

Here’s how it works: 👇 

1. STRUCTURAL — The Wrong Company, Wrong Vehicle

Your environment determines your ceiling.
If the comp plan, leadership, or business stage is wrong, your skill doesn’t matter.

You can’t out-perform a capped system OR bad leadership OR bad company strategy.

Trying to double your income in a company designed for incremental raises is like pressing the gas with the car in neutral.

What to check:

Is your comp plan uncapped or built with strong multipliers?

Does your company have a track record of promoting people?

Is the company in a growth phase, or has it shifted to efficiency mode?

Does the product/service have expansion potential, or is every deal one-and-done?

If those aren’t true, you’re structurally blocked.
Fix: Don’t work harder — change vehicles. Your output only compounds in a system that scales with you.

2. PERCEPTION — You’re Not Seen as Promotable
If your name doesn’t come up in promotion conversations, you have both a visibility and likability problem.

Performance alone isn’t enough, promotions can be political. They run on perception, sponsorship, and how much people enjoy working with you.

Here’s what works:

Forecast accuracy: Be the AE whose numbers leadership can set their watch to. Predictability builds trust — inconsistency kills it.

Cross-functional allies: Get marketing, CS, and product to vouch for you. Promotions don’t happen in isolation — political capital and peer advocacy matter more than most realize.

Likability: Competence gets you respect, likability gets you sponsorship. Leaders promote people who make their lives easier and represent them well behind closed doors.

Composure: Complain up, not sideways. Emotional control signals leadership potential — volatility signals risk.

3. ROLE — You’re Pigeonholed by Title

You’re filtered by your label before anyone reads your resume.

An “inside sales rep” could outsell an enterprise AE and still be ignored, because recruiters think in categories, not capability.

You don’t escape a label by arguing; you escape by executing differently.

Example:
Year 1 — finished at 72% of quota.
Year 2 — finished at 280% by cutting low-value prospects, doubling time spent with active buyers, and building custom solutions instead of standard demos.

That shift in focus did more for credibility than any LinkedIn headline update.

Fix: Shift your execution pattern first. The title follows the behavior, not the other way around.

4. MINDSET — The “One Promotion Away” Delusion
Believing that the next title will fix everything is what keeps people trapped.
Each level adds pressure, politics, and less freedom not happiness.

If you need permission to multi-thread, you’re already behind.

If you multi-thread without alignment, you’re dead.

From a recent note I got: “I looped in the CEO, and my champion said I betrayed him.” That’s not multi-threading. That’s land-mining.

What works:
Agree on the map with your champion first.
“Who else must say yes?”
“What will they care about?”
“What’s the best order to engage them and why?”

Send the plan back for confirmation.
“Here’s the sequencing I heard: Finance for terms risk, Security for data flow, Ops for rollout, then SVP Eng for budget. I’ll draft intros and role-specific one-pagers so you look like the hero. Anything you’d change?”

Then make your champion look good in every room.
Not by CC’ing execs.
By arming your champion with tight briefs that translate your discovery into each stakeholder’s language.

You didn’t go around them.
You went with them faster.

If you think the close happens at signature, you’ve already lost. Elite sellers close 100 times before the PO hits.


Here are 5 truths about closing and micro-commitments:

1️⃣ Closing = Next Step. The best reps don’t chase the big “yes.” They stack micro “yeses” that build momentum—meeting booked, data shared, stakeholder intro. Each is a close.

 👉 Why it matters: Big closes don’t materialize out of nowhere. Momentum compounds through small agreements, and when you control momentum, you control the deal.

2️⃣ Value-Packed Asks. Don’t beg for time. Anchor every micro-commitment in value. “Can you share last quarter’s audit results so I can map our solution?” Now your close feels essential, not optional.

 👉 Why it matters: Every ask that feels like a waste of time chips away at trust. But when each ask drives their agenda forward, they see you as a partner, not a vendor.

3️⃣ De-Risk in Pieces. Case studies, pilots, reference calls—each one is a mini-close that lowers the barrier. Elite sellers make the big decision feel like the safe, obvious decision.

 👉 Why it matters: Risk kills deals. By removing it layer by layer, you make the “yes” feel inevitable instead of scary.

4️⃣ The Final Close Isn’t a Pitch. It’s a recap. By then, every micro-commitment has already baked in the win. The proposal is just a highlight reel of the journey you walked them through.

 👉 Why it matters: Buyers hate surprises. If your proposal feels brand new, you’ve failed. If it feels familiar, you’ve already won.

5️⃣ Momentum = Cadence. Deals die in drift. Elite AEs close on time: “Can we meet next week so your IT lead can validate integration?” Time-boxed commitments prevent stalls and slippage.

 👉 Why it matters: A deal without deadlines is a deal without direction. Cadence keeps urgency alive and forces progress.


Stop treating closing like a finish line. It’s a discipline of micro-yeses, stacked one after another, until the final signature is just paperwork.


📞 

By the way... none of this happens if you don't learn how to book meetings. 

Go call a stranger today. Amazing things can happen. 

#InTheArena

Your resume isn’t why you’re getting ignored.

It’s your approach.

If you’re a veteran pivoting to tech sales and your plan is “apply to 200 roles and pray,” you’re choosing the slowest, noisiest path in the market.

Here’s the play that keeps beating ATS filters and recruiter bias:

Pick one target company.
Map the team you’d join.
Reach out to 50–100 future peers, not recruiters.

Ask questions you can’t Google:

Who’s the hiring manager?
How long has the role been open?
Why did the last 3 candidates miss?
What territory/accounts are hot vs dead?
What does your boss care about this quarter?

Synthesize that intel into a 45-second pitch and call the manager:

“I’ve spoken with Alex, Priya, and Dan on your team. Sounds like the Northeast patch is dragging because exec access is thin and SFDC hygiene is a mess. That’s fixable. Happy to show you what I’d do in the first 30 days are you free Thursday afternoon?”

You didn’t “submit.”
You solved their hiring problem.

That’s how veterans win transitions in 6–8 weeks without taking a 50% pay cut.

Job seekers are solving the wrong problem.

Stop asking, “How do I get hired?”
Start solving, “How do I help a hiring manager fill the open sales role they have in 30 days?”

This assumes you are a good fit for the open role

Asking, “How do I get hired” as a job seeker is no different from asking “How do I sell my stuff” as an AE.

It’s focused on me and my problems - not the customer’s.

Sales 101 - focus on customer problems first.

Apply that mindset to the job hunt.

“How do I help the hiring manager at XYZ company fill their open sales role in the next 30 days?”

Here’s the process I teach arena members to get offers without formal sales experience:

Run the side-door approach. Slamming the apply button in the careers page is for the masses. You need to differentiate.

Steps to follow:

choose 1 open role

speak with 10 future peers (AE’s on the team or at the company) and ask…

Ask really good questions (discovery mode):
Understand major problems they solve for their customers

When they win why do they win
When they lose why do they lose and who do they typically lose to
Major priorities for the team (typically from the hiring manager)

Details on the open role’s territory
build robust account POV/proposal

Cold call hiring manager and present the plan
Offer yourself as the solution/product they should “buy.”

No “training” required.

Hiring managers aren’t picking resumes.
They’re picking outcomes.
Show them yours ahead of time.

This process is a lot easier to follow when you have a detailed checklist with step-by-step guidance on what to do and when.

Fortunately, I’ve made one.

Comment checklist and i’ll send it over.100’s of folks have gotten jobs just using this checklist.

“Not a priority right now.”
 They’re not lying. You’re just selling the wrong thing.

When a buyer says no, start pushing outcomes no one can refuse 
(“reduce risk,” “close more deals”).

Figure out which of these is true:
They don’t believe your approach gets that outcome.
They’re chasing the outcome via a different approach.

Try this:
“Makes sense. Usually when I hear that, a team either has similar tooling and I
didn’t explain our difference well, or you’re going after the same outcome through a different strategy. Which bucket are you in?”

If they say “different strategy,” ask,
“What would need to be painfully broken in your current approach for you to consider switching this quarter?”

Now you have a real decision timeline.
Or a real disqualify.
Both save you months.

Your account isn’t “tapped out.”
Your view is.

The first instinct is “how do I get the current users to buy more?”
Wrong lens.

Start with: what big problems still exist here that we can actually solve?
Who owns those problems?
How do we use the success we already have to get to them?

Run this inside any account—starting with the end users:
Book 30 minutes with the people actually using your product day to day and ask only these:

“What breaks most often in your week?”

“What did you stop doing because it’s too slow or risky?”

“If you could wave a wand, what metric would move?”

Turn their answers into three intros:
“Could you introduce me to whoever owns release risk? We cut your rollback rate 31%, I think we can help them hit their goal faster.”

You’re not upselling.
You’re expanding impact.
Revenue follows impact.

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