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Director of Marketing & Sales

Blue Cypress
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Position: Director of Marketing & Sales

Reporting to: CEO of Blue Cypress

Location: Remote, with preference for Washington, DC, Chicago, New Orleans, Atlanta or Charlotte metro areas

Are you passionate about AI and its potential to transform organizations?
Do you have the experience and drive to lead marketing and sales strategies for a company at the forefront of innovation in the nonprofit space? Are you ready to take on a leadership role in a fast-paced, dynamic environment, helping associations harness emerging technologies to drive meaningful change? If so, Sidecar is the perfect place for you.

About Sidecar
Sidecar is a dynamic digital media and education platform within the Blue Cypress family of companies. We empower association leaders to innovate and thrive in a rapidly changing technological landscape. Sidecar is at the forefront of AI education and digital transformation, offering resources like our AI Learning Hub, industry-leading podcast, Sidecar Sync, and our flagship conference, digitalNow, which brings Silicon Valley-level insights to the association sector.

As part of Blue Cypress, Sidecar is dedicated to maximizing social sector impact through innovation, providing cutting-edge educational resources and driving change within associations. We are committed to helping associations harness the power of AI and other advanced technologies to stay ahead of the curve.

Job Description
We are creating a new position -  Director of Marketing and Sales to take on a strategic leadership role in driving Sidecar's growth and expanding our reach across the association and nonprofit sectors. You will be responsible for leading marketing efforts, optimizing sales strategies, and driving revenue growth through AI Learning Hub sales, sponsorships, and digitalNow partnerships.

You will serve in this role side by side with a peer level position – Sidecar's Director of Content and Learning. Both director positions report to Blue Cypress’ CEO. As a strategic leader, you’ll shape our marketing vision and execute data-driven strategies to create impactful funnels and achieve business growth.

Your primary responsibilities will include:

  • Marketing Strategy & Leadership: Lead and execute Sidecar's comprehensive marketing strategy, including digital advertising, SEO, email marketing, and paid media. Design and optimize sales funnels to drive leads for the AI Learning Hub and sponsorship sales.
  • Sales Growth & Optimization: Manage and lead the entire sales process for Sidecar's products, including sponsorships and partnerships for digitalNow and the AI Learning Hub. Develop and implement strategies to meet or exceed revenue goals.
  • Cross-Functional Collaboration: Work closely with the Director of Content & Learning to ensure that marketing strategies align with Sidecar’s educational initiatives and content offerings.
  • Customer Acquisition: Build and implement go-to-market strategies to attract and convert qualified leads for our AI Learning Hub and sponsorship opportunities.
  • Funnel Performance & Analysis: Use data-driven insights to measure and improve the performance of marketing funnels. Continuously iterate on strategies to optimize conversion rates and maximize sales opportunities.
  • Partnership Development: Develop and nurture relationships with sponsors, vendors, and industry leaders to enhance Sidecar’s brand and expand our reach within the association community.
  • Brand Development: Define and promote Sidecar’s value proposition across the association and nonprofit markets, positioning the brand as a leader in AI, digital transformation, and professional development.

What We’re Looking For
This role is perfect for a strategic and hands-on marketing leader with a passion for driving growth through innovation, technology, and education. Ideally, you are someone who:

  • Unparalleled work ethic. Yeah, we have a lot to get done and you need to be willing to push harder than you’ve ever pushed before to achieve big results. The opportunity is immense and serving as many people as we can is our motivating fuel.
  • Has 3+ years of experience in digital marketing with a proven track record in paid media, SEO, performance marketing, and funnel optimization.
  • Brings strong experience in sales, with a focus on sponsorships, partnerships, and digital media sales.
  • Has a data-driven mindset with the ability to measure marketing performance, iterate strategies, and drive consistent improvements.
  • Is a creative and strategic thinker who can craft compelling marketing campaigns and grow the Sidecar brand.
  • Thrives in a fast-paced environment and can manage multiple projects while delivering high-impact results.
  • Is passionate about AI, digital transformation, and the potential to revolutionize how associations lead and innovate.

Qualifications:

  • A bachelor’s degree or higher.
  • MBA with a strong interest in digital marketing, sales, and strategic leadership preferred.
  • 1-3 years of experience in marketing, sales, or business development
  • Demonstrated ability to think strategically and lead marketing and sales initiatives.
  • Strong analytical skills with the ability to work with data, analyze marketing funnel metrics, and adjust strategies for improvement.
  • A passion for emerging technologies, especially AI, and how they can be applied in the nonprofit and association sectors.
  • Excellent interpersonal and communication skills with the ability to influence and work cross-functionally.
  • Ability to adapt quickly to changing priorities in a fast-paced environment.

Why Sidecar?
This role offers the opportunity to accelerate your career in a leadership role while being mentored by industry experts. You will play a critical part in shaping the marketing and sales strategies of a company at the cutting edge of AI education for associations. You’ll benefit from:

  • A supportive team: We provide mentorship and coaching to help you achieve your full potential.
  • Cutting-edge technology: You’ll be at the forefront of AI adoption, helping to shape the future of the nonprofit sector.
  • Opportunities for growth: As Sidecar grows, so will your opportunities within our company and the broader Blue Cypress ecosystem.
  • A meaningful mission: Your work will directly contribute to helping associations and nonprofits thrive in an era of rapid technological change.

We are committed to fostering an inclusive workplace and welcome individuals from diverse backgrounds to apply. If you're passionate, have an entrepreneurial spirit, a deep sense of curiosity, and a commitment to experimentation and learning, we would love to hear from you!

Location:
While we consider all qualified candidates, those based in the greater DC-area, Chicago-area, Charlotte-area, Atlanta-area or New Orleans-area are preferred.