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Head of Revenue - Enterprise Sales

Paragraph, Bloomington, Indiana, United States, 47401

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Head of Revenue – Enterprise Sales for Agency Market Company:

[Stealth Mode Startup]

Location:

Bloomington, IN or Remote

Employment Type:

Full-time

Compensation:

Base salary + Commission + Equity package

About the Role We are seeking an exceptional Head of Revenue to spearhead our go‑to‑market strategy and drive rapid growth in our stealth‑mode startup. This foundational leadership role will be responsible for building our revenue engine from the ground up, establishing processes, and scaling our sales organization as we emerge from stealth and enter aggressive growth mode.

Key Responsibilities Strategic Revenue Leadership

Develop and execute comprehensive revenue strategy aligned with company objectives

Build scalable sales processes, methodologies, and infrastructure from inception

Create and refine our ideal customer profile and go‑to‑market positioning

Establish pricing strategy and deal structuring frameworks

Partner closely with product team to ensure market‑product fit

Enterprise Sales Execution

Drive complex, high‑value enterprise sales cycles with agency marketing leaders

Build and maintain relationships with C‑level executives at top‑tier marketing agencies

Navigate multi‑stakeholder decision processes typical in agency environments

Develop deep understanding of agency pain points, workflows, and procurement processes

Create compelling value propositions that resonate with agency business models

Revenue Operations & Analytics

Implement CRM systems, sales tools, and reporting infrastructure

Establish key metrics, forecasting models, and pipeline management processes

Analyze sales performance data to identify optimization opportunities

Create board‑level revenue reporting and insights

Required Qualifications

Enterprise sales experience, especially selling to or in collaboration with marketing agencies

Proven track record of exceeding revenue targets in high‑growth environments

Experience building sales organizations from early stage through scale (Series A or B preferred)

Deep understanding of agency marketing landscape, including holding companies, independent agencies, and specialist firms

History of closing deals $100K+ ARR with 6+ month sales cycles

Strong relationships within the agency marketing ecosystem

Experience with SaaS, MarTech, or AdTech solutions preferred

Demonstrated ability to sell transformational technology to conservative buyers

Excellent communication and presentation skills for C‑level audiences

Preferred Qualifications

Previous startup leadership experience, ideally in stealth or pre‑launch phase

Experience with venture‑backed companies and board reporting

Background in marketing operations, campaign management, or media planning

Track record of building strategic partnerships and channel relationships

International sales experience

How We Will Know This Person is Doing a Good Job Year 1 Success Metrics

Achieves or exceeds $2M ARR target with enterprise agency clients

Builds qualified pipeline worth 4x quarterly targets consistently

Maintains average deal size of $100K+ ARR

Achieves sales cycle length of 6 months or less for qualified opportunities

Establishes relationships with 10+ top‑tier agencies (holding company level)

Implements scalable sales process with documented playbooks and methodologies

Ongoing Performance Indicators

Quarterly revenue targets met or exceeded with 90%+ accuracy in forecasting

Pipeline coverage maintains healthy 3‑4x multiple of quarterly goals

Win rate against qualified opportunities exceeds 25%

Customer acquisition cost (CAC) remains within target thresholds

Net revenue retention from existing accounts exceeds 110%

Sales team productivity metrics show consistent improvement quarter‑over‑quarter

Board and investor feedback reflects confidence in revenue trajectory and execution

Cultural & Leadership Excellence

Demonstrates company values in all interactions and decision‑making

Maintains high employee net promoter score (eNPS) within organization

Successfully collaborates cross‑functionally without creating organizational friction

Provides strategic insights that influence product development and company direction

Acts as effective company spokesperson in market‑facing activities

Builds sustainable processes that support long‑term scalability beyond individual contribution

What We Offer

Base salary commensurate with experience

Significant equity package with high growth potential

Aggressive incentive compensation

Comprehensive health, dental, and vision insurance

Flexible PTO and remote work options

Opportunity to build something transformational from the ground up

Direct access to executive team and board members

Potential for rapid career advancement as company scales

Next Steps This role requires someone who thrives in ambiguous, fast‑paced environments and has the vision to see around corners in an evolving market. You'll be joining at a pivotal moment where your contributions will directly shape our trajectory and market position.

If you're energized by the prospect of building revenue operations from scratch while selling cutting‑edge solutions to sophisticated agency buyers, we want to hear from you.

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