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:

1. What's the largest pipeline target you've personally owned? What was the number, and did you hit it?
2. One demand gen channel or campaign you scaled that drove disproportionate pipeline—what made it work?
3. 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.