Co-Founder & Chief Revenue Officer – SaaS Platform (Equity Partnership)
Company: Drip Pilot
Location: Remote (USA-based)
Compensation: 2-5% Founding Equity + Revenue-Based Performance Bonuses
About Drip Pilot
Drip Pilot is an early-stage SaaS platform that helps businesses automate their text and email follow-up with leads. Our solution integrates seamlessly with any CRM (Salesforce, HubSpot, etc.), lead source, or funnel, enabling powerful email and SMS drip campaigns in minutes — no technical expertise required.
We serve a diverse range of industries including Real Estate, Auto Sales, Insurance, and virtually any sales vertical where leads are generated. From SaaS companies and coaching businesses to healthcare, financial services, and professional services, our AI-powered platform delivers measurable ROI through automated email and SMS lead nurturing and conversion optimization across all lead-driven industries.
Current Stage: Pre-revenue with validated product-market fit and strong early customer interest
Funding Status: Bootstrapped opportunity with plan to scale organically through revenue generation
Our Mission: Empower sales professionals to follow up faster, convert more leads, and scale their revenue predictably through integrated email and SMS automation.
Our Vision: Build the leading email and SMS marketing automation platform for underserved verticals and position for strategic acquisition by major CRM/MarTech players.
Why Join as Co-Founder?
✅ Ground Floor Opportunity – Join at pre-revenue stage with maximum equity upside potential
✅ Bootstrapped Growth Model – Scale sustainably through revenue generation without dilutive funding
✅ Proven Market Opportunity – $85/month ARPU target ($1,020 annually) with strong unit economics
✅ Broad Addressable Market – Works across virtually any sales vertical with lead generation
✅ Strategic Positioning – Built for acquisition by Salesforce, HubSpot, Twilio, or MarTech giants
✅ Advanced Technology Stack – AI-powered email and SMS platform with 50+ CRM integrations
✅ Founding Equity Upside – 2-5% ownership with significant long-term exit potential
✅ Revenue Participation – Performance bonuses tied to company growth milestones
✅ Strategic Decision Authority – Board participation and company direction influence
The Bootstrapping Opportunity
Revenue-Driven Growth Strategy
• Self-Funding Model: Scale the business through customer revenue rather than external investment
• Capital Efficiency: Focus on high-margin, recurring revenue with minimal upfront capital requirements
• Organic Scaling: Reinvest revenue into team building, product development, and market expansion
• Founder Control: Maintain maximum ownership and decision-making authority without investor dilution
Early-Stage Advantages
• Maximum Equity Opportunity: Join before significant value creation and revenue scaling
• Shape the Foundation: Influence core business model, go-to-market strategy, and company culture
• Customer Development: Direct involvement in early customer acquisition and product-market fit validation
• Strategic Positioning: Build the company from day one for optimal acquisition or exit positioning
What You’ll Own & Build
Revenue Strategy & Execution
• Own complete go-to-market strategy and revenue operations from pre-revenue to $50M+ ARR
• Build and scale sales organization from individual contributor to multi-team enterprise
• Develop strategic partnerships with CRM vendors, email/SMS platforms, and industry partners
• Drive revenue diversification across target verticals (Real Estate, Auto, Insurance, B2B SaaS) with integrated email and SMS solutions
Market Expansion & Strategic Positioning
• Lead market penetration strategy across target industries and geographies
• Position company for strategic acquisition through revenue scaling and market dominance
• Develop API monetization and white-label partnership opportunities for email and SMS automation
• Build strategic relationships with potential acquirers (Salesforce, HubSpot, Twilio, Microsoft, etc.)
Organizational Building & Leadership
• Recruit, hire, and develop world-class sales, marketing, and customer success teams
• Establish sales processes, methodologies, and performance metrics for scalable growth
• Build company culture and values around customer success and revenue excellence
• Participate in board meetings, strategic planning, and long-term value creation initiatives
Product & Market Strategy
• Collaborate on product roadmap and feature prioritization based on market feedback for email and SMS capabilities
• Lead pricing strategy, packaging, and monetization optimization for multi-channel communication solutions
• Drive customer research, competitive analysis, and market positioning in email/SMS automation space
• Influence technical architecture decisions for revenue optimization and communications platform partnerships
Ideal Co-Founder Profile
Leadership & Scaling Experience
• 10+ years of revenue leadership experience with proven track record of scaling companies
• VP/C-Suite Experience – Previous CRO, VP Sales, or CEO roles with P&L responsibility
• Scaling Expertise – Experience growing companies from early stage to $25M+ ARR
• Team Building – Built and managed sales organizations of 20+ people
• Strategic Partnerships – Developed major channel partnerships and strategic alliances
Early-Stage & Bootstrapping Experience
• Startup DNA – Previous experience at pre-revenue or early-stage companies
• Bootstrapping Mindset – Comfortable building sustainable, capital-efficient growth models
• Resource Optimization – Experience scaling with limited resources and creative problem-solving
• Revenue Focus – Track record of driving early revenue generation and sustainable unit economics
Industry & Technical Expertise
• SaaS/MarTech Experience – Deep understanding of subscription business models and customer success
• Email/SMS Marketing – Experience with Salesforce, HubSpot, Mailchimp, Twilio, or adjacent email and SMS technologies
• Target Vertical Knowledge – Real Estate, Insurance, Auto, or other lead-driven industries highly valued
• API/Integration Experience – Understanding of technical partnerships and communications platform strategies
Entrepreneurial & Exit Experience
• Founder Experience – Previous experience as entrepreneur/founder or early employee at startups
• Exit Experience – Participated in successful acquisitions, IPOs, or strategic exits
• Equity Mindset – Comfortable with equity-heavy compensation and long-term value creation
• Risk Tolerance – Thrives in uncertain, high-growth environments with significant upside potential
Equity Structure & Compensation
Founding Equity Package
• 2-5% founding equity based on experience, network, and strategic value
• Vesting Schedule: 4-year vest with 1-year cliff
• Board Participation: Observer or voting board seat based on equity percentage
• Strategic Decision Authority: Co-founder level input on company direction and major decisions
Performance-Based Bonuses
• Revenue Milestone Bonuses: Cash bonuses tied to ARR growth targets (funded from company revenue)
• First $1M ARR: $25,000 bonus
• $5M ARR: $50,000 bonus
• $10M ARR: $100,000 bonus
• $25M ARR: $200,000 bonus
• Exit Success Fees: Additional equity or cash bonuses upon successful acquisition/IPO
• Customer Milestone Rewards: Bonuses for customer acquisition and retention goals
Exit Value Projections
Based on comparable SaaS acquisitions and market multiples:
• $50M Exit (5x ARR): 2% = $1M, 3% = $1.5M, 5% = $2.5M
• $100M Exit (10x ARR): 2% = $2M, 3% = $3M, 5% = $5M
• $200M Exit (Strategic Premium): 2% = $4M, 3% = $6M, 5% = $10M
Ideal Candidate Backgrounds
Serial Entrepreneurs & Founders
• Previous co-founders or CEOs with successful exits, especially from bootstrapped companies
• Experience building companies from pre-revenue concept to acquisition
• Strong network of advisors and strategic partners for business development
• Proven ability to scale revenue organizations with limited initial capital
Early-Stage SaaS Revenue Leaders
• CRO or VP Sales at early-stage SaaS companies with 100%+ revenue growth
• Experience building revenue operations from scratch in pre-revenue or seed-stage companies
• Deep understanding of SaaS metrics, customer success, and bootstrapped growth strategies
• Track record of capital-efficient scaling and sustainable unit economics
Email/SMS Marketing Industry Veterans
• Senior executives from email marketing, SMS platforms, or communications technology companies
• Former leaders at MarTech companies (Mailchimp, Constant Contact, Twilio, SendGrid, etc.) seeking entrepreneurial opportunity
• Experience with TCPA compliance, deliverability optimization, and multi-channel messaging strategies
• Understanding of email/SMS automation workflows and customer journey optimization
Industry Veterans & Specialists
• Senior executives from Real Estate, Insurance, or Auto industries with technology background
• Former leaders at CRM/MarTech companies (Salesforce, HubSpot, etc.) seeking entrepreneurial opportunity
• Consultants or advisors with deep expertise in target verticals and early-stage companies
• Channel partnership leaders with strategic relationship building experience in communications or marketing technology
Partnership Philosophy & Culture
True Partnership Approach
• Co-Founder Treatment: Equal voice in strategic decisions and company direction
• Mutual Respect: Collaborative leadership style with shared accountability for success
• Long-Term Alignment: Equity structure designed for sustainable value creation and strategic exit
• Transparent Communication: Open dialogue on challenges, opportunities, and strategic pivots
Bootstrapping Mindset
• Resource Efficiency: Creative problem-solving and capital-efficient growth strategies
• Customer-Funded Growth: Scaling through revenue generation rather than external funding
• Sustainable Development: Building for long-term value creation rather than rapid burn
• Founder Control: Maintaining ownership and decision-making authority throughout growth
Growth & Exit Strategy
Revenue Scaling Roadmap
• Phase 1: Achieve first $1M ARR with foundation team and processes
• Phase 2: Scale to $10-15M ARR with multi-channel go-to-market strategy
• Phase 3: Reach $25-50M ARR with strategic partnerships and market expansion
• Exit Readiness: Position for strategic acquisition when market conditions and company scale align optimally
Strategic Exit Opportunities
• CRM Giants: Salesforce, HubSpot, Microsoft acquisition for email and SMS integration capabilities
• MarTech Leaders: Mailchimp, Constant Contact, Campaign Monitor for email and SMS vertical expansion
• Communications Platforms: Twilio, SendGrid acquisition for enhanced multi-channel messaging capabilities
• Private Equity: Roll-up opportunities with other email and SMS marketing automation platforms
• Strategic Timeline: Flexible approach based on market conditions, company scale, and optimal valuation opportunities
How to Apply
We’re seeking exceptional leaders who:
• Thrive in pre-revenue, bootstrapped environments with high equity upside
• Have scaled revenue organizations from early stage through significant growth
• Bring strategic networks and industry relationships for immediate impact
• Want to build and own significant company value creation over the long term
• Understand the email and SMS marketing automation landscape and compliance requirements
Send us your information including:
• Executive Resume highlighting early-stage experience, scaling achievements, and equity participation
• Strategic Vision – 1-page outline of your approach to scaling Drip Pilot from pre-revenue to $50M+ ARR
• References from previous co-founders, early-stage CEOs, or board members who can verify leadership performance
• Network Overview – Description of your strategic relationships and partnership potential in email/SMS or target verticals
Subject Line: “Co-Founder Application – [Your Background] – Email/SMS Automation Equity Partnership”
Include in your message:
• Previous early-stage or pre-revenue scaling achievements and exit experiences
• Your approach to capital-efficient, revenue-driven growth strategies
• Strategic networks and partnership opportunities you would bring
• Experience with email/SMS marketing, communications platforms, or target verticals
• Comfort level with bootstrapped, equity-heavy compensation structure
• Long-term commitment and vision for strategic value creation
We’ll respond to qualified candidates within 24 hours with next steps and detailed equity term discussions.
Drip Pilot represents a unique opportunity to build significant value from the ground up in the email and SMS marketing automation space. Join us as a co-founder and help create a bootstrapped success story positioned for strategic acquisition when the time is right.
Job Type: Full-time
Pay: $200,000.00 – $10,000,000.00 per year
Work Location: Remote
