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. I'm an AE who's spent the last year selling AI into the enterprise at Lindy AI. No playbooks, limited brand recognition and buyers who needed real proof that AI would actually move the needle before they'd commit.

That's the same conversation DX is built around. Helping engineering leaders measure what's working and what isn't. I've been on the other side of that conversation every day, building business cases around productivity gains and navigating complex deals with technical and executive stakeholders who don't move unless the data backs it up.

Take a look around. Hopefully it gives you a feel for how I work and why I think I'd be a strong 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 8 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 DX's platform (developer surveys, system metrics, AI measurement framework) and get comfortable running demos

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

  • Study the ICP: VPs of Engineering, CTOs, Heads of Platform/DevEx at mid-market and enterprise companies

  • Learn the competitive landscape (Jellyfish, Pluralsight Flow, LinearB) and where DX wins

  • Understand how the Atlassian integration story strengthens positioning.

30-60-90

60 Days

  • Own end-to-end sales cycles with net-new prospects

  • Lead multi-stakeholder deals (Engineering, Finance, IT). Connect developer productivity gains to business outcomes

  • Use my experience selling AI to enterprise buyers to run discovery that hits. Speak their language on ROI, productivity measurement, and proving AI investments are paying off

  • Run proof of concepts 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 similar point solutions

  • Continue filling top of funnel through outbound, targeting engineering orgs investing heavily in AI without visibility into impact

  • Begin mentoring newer reps on selling into technical, data-driven buyers

  • Continue learning and sharpening my sales skills to exceed annual quota.

Selling AI to Security & IT Leaders

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

At Lindy AI, I spent the last year selling AI to enterprise leaders who had heard every pitch in the book. These aren't buyers who get excited about a flashy demo. They want to know if it actually works, how it fits into what they're already doing, and whether the numbers back it up before they'll move forward.

I got good at selling AI by leading with impact. ROI models built around their workflows, not ours. Business cases ready before they asked for them. That's how I closed Lindy's largest deal, $200K+ with Deltek, Inc., navigating technical and executive stakeholders to get it across the line.

That conversation, "Is AI actually making my team better? Where are we stuck? How do I prove this investment is worth it?,” is the exact conversation DX is built around. I've been having it every day for the last year. I already know how to run that discovery and turn it into a closed deal.

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 DX as your next AE.

About Me