About Winning by Design

Winning by Design is a global B2B revenue consulting and training company specializing in scientific frameworks and proven models to architect sustainable growth for our clients. Our expertise empowers Sales, Marketing, and Customer Success teams within B2B enterprises to drive predictable, scalable revenue. Recognized as one of the fastest-growing companies in Silicon Valley, Winning by Design’s success is intrinsically linked to our exceptional team. We foster a dynamic, remote-first environment where innovative thinking and transformative impact flourish.

The Opportunity

Do you possess the strategic acumen, consulting experience, and entrepreneurial drive to accelerate business growth on a global scale? As a Winning by Design Managing Director, you’ll be an instrumental force in our continued expansion. This role empowers you to diagnose client pain points, design and deliver game-changing solutions informed by your revenue enablement expertise, and cultivate executive-level relationships – all while building your own path within our growing company. We’ll provide the structure, resources, and qualified leads, enabling you to focus on delivering value and expanding your sphere of influence.

What You'll Do

  • Strategic Territory Ownership: Establish yourself as a trusted advisor, guiding executive teams within key accounts toward long-term growth and measurable results.
  • Brand Champion: Become an influential voice for Winning by Design through public speaking, expert content creation, and active networking within your local business community.
  • Lead with Purpose: Collaborate with our world-class internal team to craft client solutions that excel in both strategy and execution. Oversee all project phases to ensure a seamless client experience.
  • Forge Strategic Alliances: Nurture valuable relationships with VCs, PE firms, and key industry organizations to open up a pipeline of high-potential opportunities.
  • Mentor and Inspire: Share your in-depth SaaS knowledge and revenue enablement insights, guiding team members on their journey to become top performers.

Why You'll Thrive in This Role

  • Performance-Driven Growth: Your success is our success. Unleash your growth mindset and directly influence the trajectory of Winning by Design while unlocking significant earning potential.
  • The Power of Flexibility: Enjoy the autonomy and work-life integration of a remote environment, without sacrificing access to a supportive, global team.
  • Measurable Impact: Witness the transformative results of your strategic and enablement guidance on high-growth companies as they scale and optimize their revenue operations.
  • Continuous Development: Stay at the forefront of the evolving SaaS landscape with access to Winning by Design’s renowned methodologies and continuous learning opportunities.

Are You the Right Fit?

  • Seasoned SaaS Leader: You have 10+ years of demonstrated success in leadership roles within marketing, sales, customer success, sales strategy, or revenue operations, including 2-3 years of direct consulting experience.
  • Analytical Powerhouse: Your track record and case studies reveal an unwavering data-driven approach to analysis and decision-making.
  • Relationship Builder: You confidently establish rapport with C-suite executives, tailoring your recommendations to their specific business needs.
  • Tech-Forward Strategist: Your proficiency in modern revenue tech platforms and revenue enablement best practices empowers you to optimize sales processes and enhance team performance.

Compensation and Benefits

  • Competitive Base Salary + Uncapped Commission: Enjoy significant earning potential through a model that rewards exceptional performance. Target earnings for an MD1 are $350,000.
  • Comprehensive Benefits Package: US candidates have access to health and retirement benefits.
  • Global, Remote-First Team: Work alongside a talented team of innovators within a culture that embraces a distributed workforce.


East coast of the US, preferably new New York or Boston

Join a Winning Culture

We celebrate diversity and foster an inclusive environment for all, offering equal opportunities regardless of background or identity. If you’re eager to make a lasting impact, accelerate your career, and collaborate with passionate professionals, then Winning by Design is where you belong.

How to Apply

Visit our website and YouTube channel. Send your resume and LinkedIn profile to careers@winningbydesign.com