Flockjay
Director of Marketing (2019–2020)
(YC S19)
01 / Context
Flockjay existed to prove something very simple and very loud: talent is everywhere, access is not.
The company trained people who had been locked out of tech—single parents piecing together three hourly jobs, refugees rebuilding from nothing, people who were smart and capable and hungry but had never once been told “you belong in this room.” We weren’t teaching theory. We were giving people an immediate pathway into SaaS sales roles that paid real salaries, offered stability, and changed what was possible for entire households.
I joined as the first marketing hire. On paper, that means “do growth.” In practice, it meant: build the story, build the trust, build the pipeline, build the systems to handle that pipeline, make sure those systems keep working after people graduate, and make sure the entire company can scale without losing its soul.
My job was to turn a mission into infrastructure.
02 / What I Walked Into
The work was powerful. The operation wasn’t.
Here’s the state of things when I arrived:
Applications lived in spreadsheets and inboxes. If someone didn’t answer the first outreach, they could disappear. There was no reliable tracking, no tagging, no forecasting.
There was no CRM, no owned funnel logic, no automated nurturing. “Admissions” was a Google Form, a calendar link, and a prayer.
The brand voice shifted depending on who you heard from. Founders said one thing. Instructors said another. The website said a third. Graduates said the true thing, but only to each other.
The story we were telling publicly was “learn tech sales.” The story students told privately was “I can finally breathe.”
All those life-changing outcomes—first tech job, first salaried role, first time not living paycheck to paycheck—lived in Slack screenshots and email threads and nowhere scalable.
We had one cohort of ~20 students every few months. We wanted to scale beyond that, but we had no repeatable enrollment motion, no lifecycle structure, no community infrastructure, and no internal way to prove long-term success to hiring partners or investors.
In other words: we had proof that we were changing lives, but no system to carry that change forward.
This is my favorite kind of starting point, because if the impact is real, you can build the rest.
03 / What I Actually Did
My work sat across brand, growth, admissions, curriculum, community, and internal operations. In a company like this, “marketing” is the spine that holds everything together.
What I owned and built:
Repositioned the company and rewrote the full narrative: we stopped talking about “getting into tech sales” and started talking about economic mobility, dignity, and breaking cycles. The message shifted from “get a job” to “change your trajectory.”
Built our entire growth and admissions engine from zero using Airtable, HubSpot, Zapier, and documented process—lead intake, tagging, scoring, interview scheduling, nurturing, and conversions were all automated and trackable.
Personally designed and taught Taking Flight, our internal personal branding and professional identity curriculum. It wasn’t sales training. It was how to show up in the room like you’ve always belonged there.
Created The Flock, our alumni network, and turned it into a self-sustaining referral and mentorship engine that drove almost half of new qualified applicants.
Built and enforced our voice system so the company spoke like one mind. I wrote and/or edited everything outward-facing: website, landing pages, emails, ads, partnership one-pagers, newsletters, student spotlights, founder comms, and investor decks.
Built hiring and onboarding infrastructure as we scaled from 4 to 10 employees. I handled recruiting, interviewing, documentation, and onboarding flows so new teammates could plug in instead of flailing.
Partnered with the CEO to craft the fundraising narrative that supported a $2.3M raise led by Serena Williams’ fund. My job in that room was to make the mission undeniable and the model legible.
In plain terms: I built the demand, formalized the pipeline, helped students become the product proof, and gave investors a story they could not ignore.
04 / How We Did It (The Work)
Step 1 / Listen Like an Archivist
Before I touched copy or spun up a campaign, I sat with students and graduates for hours, one-on-one. I asked about rent. About debt. About what it felt like to tell your mother you finally had benefits.
What came out of those conversations was not “I learned objection handling” or “I love SaaS as a category.” It was: “I get to be home for dinner.” “My kid saw me open my laptop and said, ‘You look like a boss.’” “I don’t wake up scared anymore.”
That was the center.
From there I made a decision: we would never lead with “skills” or “curriculum.” We would lead with transformation—and we would show receipts.
This became the backbone of every story we told:
Not “here’s what we teach.”
“Here’s what your life can look like in six months, and here is someone who is living it.”
That emotional truth set the tone for everything else.
Step 2 / Build the Admissions Engine So It Doesn’t Drop People
At the time, we were losing people who should have been in the program because we didn’t have a real intake flow. I built an actual system.
Tooling:
Airtable as our source of truth. Every applicant became a record with fields like background, current income range, referral source, stage, and notes.
HubSpot as our communication layer and light CRM.
Zapier as the connective tissue so nothing got stuck in someone’s inbox.
Process:
Auto-tagged leads by readiness and urgency so admissions could prioritize humans, not just volume.
Automated nurture sequences that met people where they were. If someone hadn’t booked an interview yet, they got a message calibrated to fear and self-doubt, not fake urgency. If someone was post-interview and nervous about tuition model/commitment, they got a different path.
Calendaring and reminders moved out of someone’s head and into flows. No more “sorry, missed this.”
Result:
Time-to-response dropped by ~60%.
Completed applications doubled in under a quarter.
We were finally able to forecast cohort size accurately instead of guessing.
This sounds operational. It was also deeply human. When you’re talking to someone who’s never been told “you should be in tech,” every minute of silence from us reads like rejection. Automating touchpoints wasn’t about scale. It was about care.
Step 3 / Give Students A Voice Before Anyone Else Gave Them Permission
Most of our students had never built a LinkedIn presence, never cold-emailed a VP, never said “I help companies grow revenue” out loud without apologizing in their tone.
I built Taking Flight for that.
Taking Flight was a 10-module live curriculum I wrote and taught. It focused on:
Personal narrative: telling your story without shrinking it.
Language and presence: how to talk like you’re in the industry you’re about to enter.
LinkedIn mechanics: how to build a profile that signals “professional” in under a week, and how to post in a way that draws inbound attention from recruiters.
Emotional readiness: how to survive being “the only one” in a new environment without folding.
This wasn’t fluff. This was career armor.
Outcomes we started seeing:
Graduates began presenting themselves like professionals, not applicants.
Recruiters commented on how “polished” and “senior” our grads felt.
Alumni used those same skills to advocate for raises and promotions within months.
And here’s the multiplier: once they learned to claim their story publicly, they also became the single best marketing channel we had. Nothing converts like someone saying “this changed my life and I’ll prove it.”
Step 4 / Turn Alumni Into A Flywheel Instead Of A Footnote
Before I built The Flock, graduates would leave the program with gratitude and momentum and then… just disappear unless someone remembered to check in.
That’s a waste—emotionally and strategically.
I formalized The Flock as a living network:
Alumni Slack channels where grads could share wins (“I just closed my first deal”) and ask for help (“I think I’m underpaid for this role, can someone gut check my comp?”).
Structured mentorship loops pairing new cohorts with recent grads.
A tracked referral pipeline: every time an alum sent someone our way, that got logged, nurtured, and attributed.
Two things happened fast:
Belonging became self-reinforcing. New students walked in already knowing someone “like them” had made it.
Referrals exploded. Within months, ~40% of new students were coming in through alumni. That channel converted at ~2x the rate of cold inbound. Zero paid spend required.
We weren’t just placing people into jobs. We were creating upward mobility networks that outlived us.
Step 5 / Scale The Team Without Letting Culture Get Diluted
Growth exposes seams. We started at 4 people doing everything. Then we needed admissions support, partnerships, student success, career placement, operations.
I stepped in and ran hiring.
I built our internal job descriptions, screened, interviewed, and created our onboarding structure. I wrote internal documentation for how we talk to applicants, how we talk to grads, how we talk to hiring partners, how we report outcomes.
We scaled from 4 to 10 in under six months. That’s not just headcount. That’s institutional memory getting written down so the mission doesn’t live in one person’s head.
I also ran weekly “impact syncs,” where every department shared one student story. Not vanity metrics—real stories. “She moved her family out of a shared room.” “He sent his mom money for the first time instead of the other way around.” It kept the company aligned on why we existed when the days got heavy.
Step 6 / Build An Investor Narrative That Could Not Be Ignored
I worked directly with the CEO on packaging our impact for investors. The pitch wasn’t “bootcamp for tech sales.” The pitch was “this is an engine for economic mobility. Here’s how it works, here’s why it scales, and here’s why no one else can fake this.”
We told the truth and backed it with data.
That story helped drive a $2.3M round led by Serena Williams’ fund. The capital wasn’t raised on hype. It was raised on evidence of generational shift.
05 / What Moved (Impact)
We didn’t just get more leads or close a round. We changed the slope of people’s lives.
Operationally:
Cohorts scaled from ~20 to ~80 students. That’s 4x in under a year.
Qualified applications grew 200% after we rebuilt admissions and messaging.
Placement success went up ~22%. Not just “got a job,” but “got a job and stayed.”
Alumni referrals drove ~40% of new student enrollment, converting at ~2x the rate of cold.
We expanded the internal team from 4 to 10 with hiring structure, onboarding, and documentation so the mission could scale without burning out the people doing the work.
Financially and structurally:
Helped support a $2.3M fundraise grounded in impact, not just TAM.
Created a predictable, trackable admissions pipeline so we could forecast cohort size instead of guessing and hoping.
Humanly:
We watched parents go from piecing together night shifts to earning stable six-figure on-target earnings.
We saw families move out of multigenerational, shared single bedrooms into their own apartments.
We saw first-generation professionals negotiate salaries and equity for the first time in their lives using language they practiced in Taking Flight.
We saw students send money home out of choice, not desperation.
We saw people who were told “you’re not professional enough for tech” become top performers on SaaS sales teams in under 90 days.
Those aren’t marketing outcomes. Those are generational outcomes. That’s the work.
06 / Notes + What I’d Do Next
In 2022, Flockjay evolved into a B2B sales enablement platform as the founders pursued a new direction. That pivot changed the model, but it didn’t erase what we built.
If I ran this play again, I’d add one more layer early: longitudinal impact tracking. Not just “did you get hired,” but “where are you 12 months later, 24 months later, what did that do to household income, what did that do for your family.” Because that’s the real ROI. That’s the data that rewrites policy, not just landing pages.
Flockjay is the work I’m proudest of because it proved what I believe: good marketing is not decoration. It is architecture for economic change.
I didn’t just launch campaigns. I built an on-ramp to a different life—and I built the systems that let it scale.
