Application Head of Demand Generation · an application for Sybill, built as a page

Your best rep already knows who to call.
So does your pipeline.

Sybill learns what wins deals. I do the same thing with demand: find the signal that actually correlates with revenue, then build the engine that acts on it. Fifteen years doing it beside the revenue team, not at them.

15 yrs B2B marketing Built from zero through an exit $2.5M budget owned
Fifteen years across
VeracodeAppSec · acq. CA $614M
Capsule8Runtime · acq. Sophos
ThreatXAPI & app · acq. A10
DeleteMePrivacy · current
The problem

Most demand gen hires fail at Series A for the same three reasons

You are hiring someone to build the thing that does not exist yet. The failure modes are predictable, and they are rarely about effort.

They run the playbook that worked at scale

Programs that need a brand, a category and a content library behind them. At $5M ARR none of that exists yet, so the playbook stalls and the budget burns proving it.

They measure activity because it is easier to count

MQLs, impressions, content velocity. All countable, none of them revenue. The board asks a different question and the answer never reconciles.

They build beside Sales instead of with them

Campaigns land in a territory nobody agreed to, SDRs work a list they do not trust, and the handoff becomes an argument every quarter.

How I'd run it

Signal, system, spend

The same loop your product runs on a deal, applied to a pipeline. Find what actually correlates with won revenue, build the system that acts on it, and put money behind only what returns.

01

Signal

Which behaviours actually precede a closed deal at your ACV. Not every download, not every visit. At ThreatX I owned and deployed 6sense to answer exactly that question, and migrated the team off ZoomInfo onto Apollo to act on it.

02

System

Signal is worthless until it resolves to an account, an owner and a next step. At DeleteMe I architected signal-based lead orchestration for Sales prospecting, then layered AI workflows on it so SDRs worked a prioritised list rather than a lead dump.

03

Spend

Then the money follows the evidence, and the programs that fail to return get cut without ceremony. $2.5M budget today, 186% YoY SQL growth, 20% QoQ pipeline. Unit economics, not vanity.

Your ten asks

Every requirement you listed, in your order

Answered with work that already happened. The one I only partly clear is marked, and it is the fourth row down.

The part I
don't clear

Your second requirement says ideally selling to sales, revenue, or GTM buyers. I have not done that. Every company I have built pipeline for sold to security teams.

What I have done for fifteen years is build the pipeline engine with the revenue team rather than sell to one. Aligning campaigns to territory with Sales leadership. Building the orchestration SDRs actually work from. Carrying pipeline as the number I am judged on rather than lead volume. I have been on the other side of the sale Sybill makes for my entire career.

The transferable part is the harder part. A security practitioner is the most marketing-hostile audience in B2B, and learning to earn attention there is not a skill that expires when the buyer changes. A rep is a warmer room than a CISO.

You should still weigh it. I would rather you weigh it knowing I named it first.

Why Sybill,
and why me

I have spent fifteen years marketing to people who are professionally suspicious of marketing. Application security at Veracode. Runtime detection at Capsule8. API and application protection at ThreatX. All three have since been acquired. I know what it sounds like when a vendor is guessing, because I have watched practitioners walk away from it.

The line that made me apply was "every deal makes the next one easier to win." That is a compounding argument, and compounding is the thing most demand gen never gets to. Programs get judged inside a quarter, so anything that pays back in three never gets funded, and the engine that would have produced next year's pipeline never gets built.

You are at the moment where that is still a choice. $5M ARR, 128% net revenue retention, a product that already proves its value in a rep's first week. The retention number says the product compounds. The job is making the demand side compound with it.

The building-from-zero part is the part I have done best. At Capsule8 I was the first technical marketing hire. No demand gen function, no martech, no process, no playbook to inherit. I built it, and the company went from $300K ARR to over $3.5M before Sophos acquired it. Your posting asks for exactly that, and asks for it twice.

And rather than describe how I work, this is it. I sampled your design system, wrote the copy, built the page and deployed it on my own infrastructure in an afternoon, using the same category of AI tooling this role asks for. Ten fast tests over one perfect plan, as you put it.

Neil DuPaul Manchester, NH · neildupaul@gmail.com · 603‑247‑8382

Happy to be wrong in public

If the buyer gap is disqualifying, tell me and I will stop taking your time. If it isn't, I would like the conversation.

neildupaul@gmail.com