Head of Demand Generation

Head of Demand Generation
Experience: 12+ years | Time Zone - Eastern Time Zone
About Pepper
Pepper is building a new category of content and SEO growth platform—where strategy, content, technology, automation, and AI come together to drive measurable business outcomes.
Over the last five years, Pepper has built:
A network of 150,000+ content creators, working with the top 5% talent
A customer base of 2,500+ global brands, including large enterprises and fast-scaling B2B companies
A SaaS-enabled content marketing platform that powers content creation, workflow orchestration, and distribution at scale
Now, we're entering our next phase of growth—scaling aggressively into the Mid-Market and Enterprise segments with our AI-powered content and SEO platform. This role is the engine that makes that happen.
The Opportunity
We're looking for a Head of Demand Generation to own one number: pipeline.
Not brand awareness. Not impressions. Not "marketing qualified leads" that sales ignores. Meetings. Pipeline. Revenue.
Your job is to build a demand generation machine that delivers $30–40M in ARR pipeline—the kind of pipeline that actually converts, not the kind that looks good in a board deck.
This is a leadership role for someone who's built demand engines before, knows what it takes to scale B2B pipeline for Mid-Market and Enterprise, and is obsessive about the math behind every campaign, every channel, every dollar spent.
If you've ever founded or scaled a company yourself, even better. You'll know what it means to own a number with no one else to blame.
The Core Goal
Own the meetings target for Mid-Market + Enterprise.
Build and scale multi-channel demand gen programs that drive qualified pipeline. Not leads. Not MQLs. Meetings that turn into revenue.
You'll be measured on:
Meetings booked (this is the number that matters)
Pipeline contribution (SQLs → Opportunities → Revenue)
SDR performance (connect rates, response rates, conversion)
Campaign ROI and CAC efficiency
If you can't tie your work directly to pipeline and revenue, this isn't the role for you.
What You'll Do at Pepper
1. Own Demand Generation Strategy & Execution (End-to-End)
Build and own the overall demand generation strategy across inbound, outbound, and lifecycle campaigns
Design the full-funnel engine: awareness → interest → MQL → SQL → Meeting → Opportunity
Architect campaigns that target Mid-Market and Enterprise buyers—not SMB spray-and-pray
Balance long-term brand building with short-term pipeline pressure (but never lose sight of the number)
2. Build & Lead a High-Performance SDR Engine
Lead, coach, and scale the SDR team to maximize outbound efficiency
Own outbound messaging, sequencing, and cadence optimization
Implement rigorous A/B testing on email, LinkedIn, cold call scripts
Build an SDR culture obsessed with connect rates, response rates, and meeting conversion
Create comp structures and incentives that drive the right behaviors
3. Scale Inbound Demand Channels
Scale inbound pipeline through SEO, SEM, LinkedIn Ads, and paid media
Build a webinar and virtual event engine that drives qualified registrations and conversions
Partner with Content to create assets that actually convert—not just "thought leadership" that goes nowhere
Optimize landing pages, forms, and conversion paths with relentless testing
4. Partner Cross-Functionally to Drive Pipeline
Work closely with the Content team to ensure campaign assets (eBooks, case studies, whitepapers) are built for conversion, not vanity
Collaborate with ABM to run targeted account-based programs for Enterprise logos
Align tightly with Sales leadership on ICP definition, lead quality feedback, and pipeline goals
Partner with Product Marketing to translate product value into demand-driving messaging
5. Build the Analytics & Attribution Infrastructure
Set, track, and report on pipeline contribution goals (MQL → SQL → Meeting → Opp → Revenue)
Build dashboards and reporting systems that give real-time visibility into funnel performance
Obsess over conversion rates at every stage—and know exactly where the leaks are
Run weekly pipeline reviews with Sales to ensure alignment on lead quality and follow-up
6. Constantly Optimize for ROI
Approach every dollar spent as your own money
Kill underperforming channels and campaigns fast—no emotional attachment
Double down on what's working with speed and conviction
Build a culture of experimentation: test, measure, iterate, scale
What We're Looking For
Must-Haves
10+ years in B2B SaaS or Services demand generation, with significant experience in Mid-Market and/or Enterprise segments
Proven track record of owning pipeline targets—not "contributing to" pipeline, but owning the number
Experience building and scaling both inbound and outbound engines from the ground up
Hands-on experience managing SDR teams—you know what good outbound looks like and how to coach it
Deep expertise in multi-channel demand gen: SEO, SEM, LinkedIn, paid media, email, ABM, webinars, events
Analytically rigorous—you live in dashboards, you know your CAC and LTV by channel, you can calculate pipeline coverage in your sleep
Experience with marketing automation and CRM systems (HubSpot, Salesforce, Marketo, or similar)
Comfort operating in high-growth, high-pressure environments where the number is the number
What Will Set You Apart
Ex-founder or early-stage operator experience—you've built something yourself and know what it means to own outcomes with no safety net
Experience scaling demand gen for a company from $10M to $50M+ ARR
Track record of building pipeline for content, marketing tech, or SaaS platforms
Strong POV on where B2B demand gen is heading—and what most companies get wrong
Ability to context-switch between strategy and execution without losing momentum
We value:
Ownership over hierarchy—you own the number, you make the calls
Outcomes over activity—we don't care how many campaigns you ran; we care how much pipeline you built
Speed over perfection—launch, learn, iterate
Data over opinions—bring the numbers, not the narratives
To Apply
Skip the generic cover letter. Tell us:
What's the largest pipeline target you've personally owned? What was the number, and did you hit it?
One demand gen channel or campaign you scaled that drove disproportionate pipeline—what made it work?
What's broken about B2B demand gen today? What would you do differently?
If you've built demand engines before, know what it takes to hit a pipeline number, and want to do it again at a company that's scaling fast into Enterprise—this is your seat at the table.

Work arrangement
Yes