Head of Marketing

👋 About Olly Olly

Ready to roll up your sleeves and help transform local marketing forever? At Olly Olly, we’re blending technology and real-world expertise to empower businesses across the U.S. like never before.

We believe small businesses are the backbone of our economy. That’s why we’re on a mission to provide them with tools, strategies, and insights that help them rank higher, generate high-quality leads, get calls and reviews, and, above all, grow sustainably without the hassle.

The Olly Olly platform complements our hands-on service perfectly: it’s no-nonsense, easy-to-use software that helps local businesses streamline operations and contact management, drive leads, stabilize cash flow, and maximize revenue with minimal effort so they can reclaim their time to focus on what they do best.

🌎 Our Vision

We aim to be the ultimate all-in-one platform for small business growth, allowing owners to manage every part of their business efficiently and effortlessly.

Our journey began as an agency, and we’ve already helped thousands of clients succeed. Now, we’re embracing an exciting new chapter: becoming a SaaS-first company. By combining hard-earned human expertise with AI and automation, we’re creating affordable solutions that give business owners peace of mind while driving measurable success.

🫵 Why We Need You

Olly Olly has scaled to ~$20M ARR with zero marketing — purely through sales execution. We’re profitable, debt-free, and now ready to launch our first-ever marketing engine.

As Head of Marketing, you will roll into the co-founders and owning the 0 → 1 build. From launching our lead generation engine to creating scalable systems and channels, you’ll set the foundation for how marketing fuels Olly Olly’s next stage of growth.

This role is highly hands-on — you’ll execute campaigns, test fast, and prove impact. Think “startup inside a successful company”: all the resources of a $20M ARR business, but the excitement and blank canvas of Day 1 marketing.

🚀 The Impact You’ll Have

Growth & Lead Generation

• Launch our BAR-based (Business Audit Report) lead generation engine
• Build high-converting funnels: email campaigns, landing pages, and lead magnets
• Run rapid experiments across email, content, social, and partnerships
• Analyze performance data and scale what works into repeatable growth channels

Marketing Infrastructure & Team Building

• Stand up marketing ops: HubSpot workflows, reporting, and attribution
• Establish core processes and documentation to support scale
• Hire and mentor your first team member within 6–12 months (content/social)
• Partner closely with Sales to align pipeline and revenue goals

Multi-Channel Expansion

• Launch and manage content marketing, SEO, and social media presence
• Explore referral programs and co-marketing partnerships
• Test paid acquisition once organic channels show traction
• Support event strategy (webinars, conferences, local business networking)

Product Marketing & Strategy

• Shape messaging as we transition from service → SaaS
• Conduct customer research to inform positioning and campaigns
• Build upsell, cross-sell, and win-back campaigns with Customer Success

✅ What We Really Need From You

• 6–10 years in marketing, with 3 years in senior or owner-level roles
• Proven success building marketing 0 → 1 at a startup or early-stage company
• Track record aligning closely with Sales to drive pipeline growth

Skills & Expertise

• Full-stack execution: copywriting, campaign building, funnel optimization
• HubSpot experience (automation, workflows, lead scoring, reporting)
• Email marketing expertise, including high-volume campaign management
• Understanding of SMB/local business markets (contractors, lawyers, home services)
• Data-driven approach with strong analytical and testing skills

Work Style & Culture Fit

• Energized by building from scratch in a scrappy, high-autonomy environment
• Comfortable with lean budgets, ambiguity, and rapid experimentation
• Strong communicator who thrives in a fast-paced, results-focused culture

➕ What Would Be Big Pluses

• Experience scaling SaaS marketing
• Experience leading marketing in partnership with a large (150 reps) outbound sales team focused on high-volume cold calling.
• Background in B2B service-to-SaaS transitions
• High-velocity testing experience with limited budgets
• Proven bootstrap mentality — big outcomes from lean resources

🌟 What You’ll Love About Working at Olly Olly

• Competitive salary based on experience
• Comprehensive health, dental, and vision insurance.
• Remote-friendly, fast-paced, and collaborative team environment.
• A chance to build and innovate inside a scaling, SaaS-first company.
• A supportive, inclusive, and entrepreneurial culture where your ideas are valued.

💡 Why Choose Us?

Join us during this pivotal transition as we transform from an agency to a human-centric SaaS provider.

Your ideas, strategies, and solutions will directly impact the success of small businesses. And our own growth!

Let’s shape the future of small business growth together! Apply now to join a team that’s as committed as they are supportive of each other.

🌈 Diversity and Inclusion at Olly Olly

At Olly Olly, we celebrate differences in background, culture, abilities, and perspectives because diversity drives innovation and creativity. Your voice matters here; it really does! And your unique perspective will help us shape the future of small business growth.