Jacob Irizarry

Hey, thanks for stopping by!

I built this site so you could get a sense of who I am outside of a resume. Quick version: I'm an AE that's been selling AI to IT and security teams for the last year. Not an easy crowd. These are buyers who've heard every pitch and don't move fast unless you earn it.

At Lindy I dealt with SOC2 reviews, procurement, legal redlines, the whole thing. The people I was selling to are the same people buying Adaptive Security. I already know what matters to them and what doesn't.

Look around. Hopefully it gives you a feel for how I work and why I think I'd be a solid fit.

Thanks,

Jacob

Career Journey

  • Joined as the founding AE at an early-stage AI startup. No playbook, no SDR support, no established process. Just a product and a quota.

    I owned the full sales cycle: prospecting, discovery, demos, negotiation, and close. Sold across SMB, Mid-Market, and Enterprise.

    Results:

    • >$900k in closed/won net-new business in 7 months

    • Q2: 275% (ramp) → Q3: 250% → Q4: 140%

    • Sourced and closed the company's first enterprise deal—largest contract since founding

    Building beyond my own number:

    • Developed the GTM playbooks for our first two SDRs

    • Led their cold calling training and outbound ramp




  • Joined Deel to sharpen my full-cycle closing skills at a hyper-growth company.

    Results:

    • $175K closed-won in year one

    • Q1: 87% (ramp) → Q2: 102% → Q3: 120%

    Beyond the numbers:

    • Consistent performance earned me a spot launching Deel's new crypto vertical—a bet the company made on reps they trusted to figure it out.

  • Promoted to SDR manager after 10 months as a top-performing SDR. Inherited a team that hadn't hit 36% quota in over a year—75% of my reps had less than 5 months of experience.

    The turnaround:

    • Q1 FY 25 90% of Quota first quarter in role

    • Q2 FY25 122% of Quota

    • 6 of my 7 reps have hit quota for the first time in their SDR career.

    What I learned: How to coach reps, build repeatable outbound processes, and turn underperformers into closers. I know what good SDR partnership looks like from the management side.

  • Started in SaaS sales with one goal: learn the fundamentals and earn a path to closing. Became a top performer by Q2 and stayed there.

    Results:

    •  Attainment FY24:

      • Q1 191% to quota (Ramp)

      • Q2 165% to quota (Top Performer)

      • Q3 156% to quota (Top Performer)

    Beyond the numbers:

    • Created "Roadmap to Quota". An onboarding session I led for every new-hire cohort

    • Mentored 3 new SDRs through their ramp

    • CORE4 Award Recipient - Mentorship & Collaboration

Feedback

30 Days

  • Ramp on Adaptive's platform (deepfake simulations, phishing, risk scoring) and get comfortable running demos

  • Shadow top AEs on discovery and demos to learn what good looks like here

  • Study the ICP: CISOs, IT security leaders, and security awareness admins at enterprise companies

  • Learn the competitive landscape (KnowBe4, Proofpoint, etc.) and where Adaptive wins

  • Build pipeline through outbound, targeting companies still running legacy security awareness training

30-60-90

60 Days

  • Own end-to-end sales cycles with enterprise prospects

  • Lead multi-stakeholder deals (IT security, compliance, procurement, finance)

  • Use my experience selling AI to security and IT buyers to run discovery that hits. Speak their language on risk reduction, compliance, and behavior change

  • Run pilots and align on success criteria before kicking off

  • Close first deals and maintain accurate weekly forecasts

90 Days

  • Exceed ramp quota

  • Share what's working in competitive deals with the rest of the team, especially against KnowBe4 displacement

  • Continue filling top of funnel through outbound

  • Begin mentoring newer reps on selling into security-conscious buyers

Selling AI to Security & IT Leaders

My SDR team sending me off on my last day at Workday

At Lindy AI, most of my deals ran through IT and security. These aren't buyers who get excited about a flashy demo, they want to know if it integrates with their stack, if it passes their security review, and if it's actually going to work when they roll it out to 500 people.

I got good at selling AI by focusing on risk reduction and operational efficiency, not just hype. SOC2 docs ready before they asked. ROI models built around their workflow, not ours. That's how I closed Lindy's largest deal, $200K+ with Deltek, Inc., through procurement, legal, and a full IT security review.

The people I was selling to are the same people evaluating Adaptive right now. I already know what keeps IT and security leaders up at night, how they vet new vendors, and how long it takes to get security spend approved internally.

I’m originally from Ft. Lauderdale, FL but grew up moving between Texas, Arizona, and Utah. I love to swim laps, hike, and snowboard. In my free time, I enjoy traveling with my wife, playing the guitar, baking and being outdoors.

Languages are a huge passion of mine. Most people don’t know this, but I speak Mandarin, Papiamento, and Spanish.

My roots run deep in a Hispanic family. My dad is from Puerto Rico, my mom from Bolivia. They instilled in me a relentless drive to chase big goals and push through obstacles. That mindset has made me a top performer in every role I've held, and it's exactly what I'm bringing to Adaptive Security as your next AE.

About Me