Director 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 small 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.

Our 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.

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 Director of Marketing, you’ll report directly to the Co-Founders and own 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

You’ll be both architect and operator, initially 70% tactical and 30% strategic, evolving to 70% strategic and 30% tactical as you build the team.

In this phase, you’ll balance execution with leadership driving growth campaigns while laying the foundation for a scalable, high-performing marketing organization.

What You'll Own

-Build and scale multi-channel acquisition engines

-Own and optimize paid media strategy across Meta, Google, and LinkedIn to drive efficient, scalable pipeline growth, not just lead volume. Balance CAC across channels, identify high-ROI levers, and continuously improve performance through data-driven experimentation.

-Own the full funnel from click to close

-Drive demand generation and conversion at every stage of the funnel, from paid acquisition to lead nurturing. Develop expertise in SEO/SEM, CRO, and landing page testing that directly impacts pipeline creation and revenue acceleration.

-Create customer growth systems that compound revenue

-Design and launch retention, upsell, and advocacy programs that turn customers into loyal promoters. Build community-driven growth loops through customer newsletters, case studies, and education initiatives that drive engagement and reduce churn.

-Run a marketing team like a laboratory

-Create a testing culture where every campaign is an experiment with clear hypotheses, success metrics, and learnings. Use A/B testing and channel mix optimization to identify what drives sustainable growth and scale it.

Top Priorities in Your First 90 Days

1. Convert Free Trial → Paid: Launch and optimize campaigns turning app trials into paying customers.
2. Marketing Roadmap: Build a 6–12 month plan that defines strategy, channels, and key hires.
3. Team Build: Hire and resource for blog and social media execution.

What We Really Need From You- Experience + Working Style

• 6–10 years in marketing, with 3+ years in senior, owner-level, or leadership roles.
• Proven success building marketing from 0 → 1 in a startup or early-stage environment.
• Track record of partnering closely with Sales to drive qualified pipeline and accelerate revenue growth.
• Startup mentality: thrives in fast-paced, high-ambiguity environments; rolls up sleeves and learns by doing.
• Builder mindset: comfortable operating with limited resources and creating structure where none exists.
• Exceptional communicator: proactive, transparent, and collaborative across teams.
• Values-aligned leader: takes ownership and accountability, acts with integrity, leads with humility and curiosity, and shows up for others.
• Grit and hustle: energized by testing, iterating, and driving measurable business impact.
• Hybrid role: collaborates in person several days a week from our Austin (ATX) or Charlotte (CLT) office to stay connected and move fast as a team.

Must-Have Skills

• Deep expertise in demand generation and growth marketing (paid, organic, CRO, lead gen, funnel optimization).
• Proven success building marketing from 0 → 1 in a startup or high-growth SaaS environment.
• Hands-on proficiency with Meta Ads Manager, HubSpot, Jira, and Google Workspace (G-Suite).
• Strong understanding of SEO, SEM, and multi-channel performance marketing.
• Data-driven mindset: skilled in experimentation, measurement, and ROI optimization.
• Excellent leadership and cross-functional collaboration skills; able to influence at all levels.

Nice to Have

• Experience in home-services, SMB marketing, or digital-agency environments.
• Familiarity with SaaS + services business models.

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. You’ll have the autonomy to build from scratch, the support of seasoned leaders, and the chance to see your work shape the next era of Olly Olly’s story. Let’s shape the future of small-business growth together.

• Full benefits: medical, dental, vision, mental wellness
• 4 weeks PTO + 10 holidays, 401(k) with 3% match
• Future Leader Development Program for career growth

Olly'all Are Welcome

At Olly Olly, we embrace and celebrate our differences. We believe that diverse backgrounds, cultures, abilities, experiences, thoughts and perspectives lead to more creative problem-solving, better outcomes and ultimately a stronger organization. Olly Olly is proud to be an equitable opportunity employer, therefore employment is based solely on an individual’s merit and qualifications directly related to their professional competence. We do not discriminate against any applicant or employee because of race, color, religion, gender, sexual orientation, gender identity, gender expression, national origin, mental or physical disability, age, genetic information, military or veteran status, marital status, pregnancy or related conditions, or any other basis protected by law or local ordinance.