Jacob Irizarry
Hey, thanks for stopping by!
I built this site to give you a real sense of who I am, beyond the resume. The short version: I'm an AE with a track record of consistently overachieving quota.
I've spent the last year selling AI agents to technical buyers at Lindy. Before that, I built and led an SDR team at Workday and founded my own business from scratch. That mix of entrepreneurial grit and enterprise sales fundamentals is why I know I’d thrive at Chainguard.
Take a look around. I hope it gives you a feel for how I think, what I’ve done, and why I’d be a great fit for the team.
Career Journey
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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
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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.
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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.
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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 quickly on Chainguard's solutions through enablement, internal resources, and shadowing top-performing AEs.
Meet with product, sales engineering, and customer success teams to understand the value prop, security differentiators, and key use cases.
Map out target accounts in my territory and begin strategic outreach with value-based messaging.
Take intentional action daily to fill pipeline through thoughtful outbound.
Begin building trust with internal and external stakeholders by leveraging my experience selling to technical teams and navigating complex orgs.
30-60-90
60 Days
Build and manage a healthy pipeline of qualified opportunities, while moving early-stage deals through the funnel.
Learn the ins and outs of Chainguard’s space so I can speak confidently with technical stakeholders and build credibility.
Leverage my professional network and former leadership roles to uncover new opportunities and connect with champions across my territory.
Use strong discovery to identify key pain points around software vulnerabilities and compliance, and align Chainguard as the solution.
Continue proactive collaboration with RevOps and product marketing to refine messaging, outbound plays, and positioning against competitors.
90 Days
Exceed ramp quota by closing initial deals and consistently demonstrating pipeline progression and deal velocity.
Establish myself as a top contributor and trusted partner to my customers.
Drive expansion and multi-threading efforts within landed accounts, setting the stage for long-term growth.
Partner closely with sales leadership to win strategic deals and deliver value across the entire sales cycle.
Continue leveling up with a sales coach/mentor while contributing back by sharing successful tactics with the team. Live Chainguard’s value of trusting and learning from each other.
From Manager to Seller
As an SDR Manager at Workday, I inherited a struggling team that hadn't hit quota in over a year. We hunkered down, rebuilt our outbound strategy from scratch, and implemented coaching rhythms that actually stuck. The result: 6 of 7 reps hit quota for the first time in their careers. The one who didn't missed by just 3%.
That experience taught me what it takes to build pipeline from nothing. I learned how to prospect into complex orgs, navigate technical buyers, and create urgency without gimmicks.
At Lindy, I took those fundamentals and applied them as a founding AE selling AI to technical teams. No playbook, no brand recognition. Just product, process, and persistence. I closed over $900K in net-new business in 8 months.
Chainguard is selling a technical product to security and DevOps leaders who don't have time for fluff. That's my wheelhouse: translating complex value into business outcomes, building pipeline through outbound, and earning trust with buyers who know their stuff.
My SDR team sending me off on my final day at Workday
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.
I come from a Hispanic family. My dad is from Puerto Rico and my mom is 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 Chainguard as your next AE.
