Director of Marketing

Chicago

We are looking for an experienced Director of Marketing to join our team. This is a unique opportunity for a "full-stack" marketing leader who is both a visionary strategist and a hands-on operator. Reporting directly to the CEO, you will be responsible for defining and executing our marketing strategy to drive lead generation and increase discovery call bookings. A key focus of this role will be implementing and scaling direct response marketing initiatives—campaigns specifically designed to elicit immediate, trackable actions from prospects, such as form fills, demo requests, and call bookings while ensuring they fit within a cohesive long-term brand strategy.

You will lead an established team, overseeing all aspects of marketing, including growth marketing, content, communications, product marketing, and performance-driven direct response campaigns. You’ll collaborate closely with Sales, Client Success, Production, Tech, and Product teams to ensure marketing initiatives are aligned, data-driven, and growth-focused. This role requires someone who understands and connects with an entrepreneurial audience, and who thrives in a fast-moving, founder-led organization where innovation, adaptability, and collaboration are key.

Your success will be measured by your ability to increase pipeline volume, grow our brand awareness, optimize customer acquisition costs, and consistently generate measurable results from targeted marketing efforts.

You’ll be responsible for:

• Strategic Leadership: Develop and execute a comprehensive marketing strategy that aligns with our business objectives, with a primary focus on driving qualified leads and discovery calls.

• Team Management & Development: Lead, mentor, and inspire our marketing team, fostering a culture of high performance, learning, collaboration, and continuous improvement.

• Lead Generation & Funnel Optimization: Architect and manage the entire marketing funnel, from top-of-funnel awareness to bottom-of-funnel conversion as well as client retention. Oversee the implementation of data-driven campaigns to drive pipeline volume and a high volume of discovery call bookings.

• Performance Measurement: Define and be accountable for key performance indicators (KPIs) to measure the effectiveness of all marketing initiatives. This includes pipeline volume, website traffic, customer acquisition cost (CAC), customer lifetime value (CLV), and brand awareness metrics. Use insights to guide strategic decisions, optimize marketing investments, and demonstrate ROI.

• Brand & Content Strategy: Support and promote our brand voice and content strategy to build thought leadership and increase market share. Ensure brand consistency and tone across all marketing and communication channels.

• Digital & SEO/GEO Strategy: Drive our digital marketing efforts, including search engine and generative engine optimization, paid advertising, and social media. Leverage AI to optimize marketing automation, personalization, and data analysis.

• Event & Webinar Management: Oversee the strategy of our key marketing events, including speaking engagements, virtual events, and webinars. Ensure these events are effectively project-managed, promoted, and converted into tangible sales opportunities. Leverage storytelling, partnerships, and media opportunities to build brand awareness and credibility.

• Cross-Functional Collaboration: Partner closely with the Sales, Product, Client Success, and Production teams to ensure a seamless end-to-end client experience and alignment on client journey. Seek input from and work collaboratively with other teams to ensure alignment and to strengthen and reinforce company culture.

An ideal candidate will have:

• 10+ years of experience in a senior marketing role, with at least three years in a leadership position (e.g., Head of Marketing, VP of Marketing, or CMO).

• Proven track record of success in direct response marketing and lead generation with a deep understanding of the full marketing funnel.

• Deep understanding of entrepreneurial audiences and how to market effectively to business owners and founders.

• Demonstrable experience managing and developing a marketing team of at least five to 10 people.

• Experience collaborating with a Production/Art Department, and the tools and workflows to do so.

• Hands-on experience with CRMs, ideally Salesforce.

• Hands-on experience with marketing automation tools like Pardot or Marketing Cloud.

• Strong expertise in digital marketing, SEO, GEO, and leveraging AI for marketing effectiveness.

• Experience with event marketing and webinars as lead-generation tools.

• Strong business acumen—industry knowledge is a plus.

• Ability and willingness to travel cross-border a minimum of 12 times/year.

• A university or college degree.

They will also be:

• Analytical and data-driven, with a mastery of KPIs and ROI analysis.

• Client focused—deep understanding of buyer and client journey.

• Naturally collaborative with the ability to build and maintain strong team and cross-functional relationships.

Preferred Qualifications:

• Passion for and familiarity with entrepreneurs and entrepreneurial mindsets.

• Experience in professional services or education industries.

• Experience with digital asset management systems.

• Experience with project-management tools, e.g., Asana.

Why Strategic Coach? We have:

• Exceptional Clients: As the Director of Marketing, you’ll play a key role in improving people’s lives by leading the creation of compelling content and direct response campaigns that educate and inspire extraordinary, ambitious entrepreneurs to join The Strategic Coach^® Program.We’re a company that thrives on innovation, collaboration, and measurable impact—and your leadership will directly shape how entrepreneurs discover, engage with, and stay connected to our community.

• Extraordinary Culture: As a company that teaches entrepreneurial teamwork and walks our talk, we take a lot of pride in cultivating a collaborative, positive, growth-oriented culture. We’re constantly supporting our team members in their own learning and growth as we evolve and innovate as a company.

You will also receive:

• A hybrid work model. 

• Six weeks of paid time off each year.

• Twenty-one flex hours.

• A flexible and competitive benefits plan.

• Top-tier onboarding and training.

• Insightful assessments to help you identify your unique strengths.

• Access to our first-class workshop programs.

• Fun team challenges, events, and celebrations.

• Three paid days off per year to volunteer with your chosen community.

• Access to a fully equipped gym.

• Unlimited free pop, juice, coffee, and occasional catered lunches.

To support our talent acquisition efforts, Strategic Coach may leverage AI technology as part of the recruitment process. We have also partnered with skills assessment platforms to help streamline and enhance candidate evaluation.

If you think this position is a right-fit for you, please send your résumé to hr@strategiccoach.com today.