Managing Director

About Winning by Design

Winning by Design is the leading growth advisory firm for scaling businesses. From diagnostic insights to system design and deployment, we work with the world’s most prominent brands to architect compounding growth. WbD advisors have mastered the Bowtie Data Model™, the SPICED™ Operating Model, and the GTM Model, having deployed revenue architecture across companies like Canva, Dropbox, Instructure, DocuSign, One Stream, and Five9. These advisors work with your team to help them avoid mistakes, see around corners, and build with confidence while operating at speed.

Forward-thinking investors and executive teams work with Winning by Design to assure scalable, sustainable, and durable growth.

Winning by Design is a 100% remote business and we encourage applicants of all ethnicities, gender identities and expressions, sexual orientation, religions, ages, citizenships, socioeconomic statuses, disabilities, and veteran statuses.

Our core belief: Recurring revenue is the result of recurring impact.

The Opportunity

Winning by Design is looking to hire a Managing Director to join us!

This is an opportunity to bring together your operator experience, your love of GTM systems, and your passion for enabling others to solve complex growth challenges.

This is a senior role, ideal for someone who has sat in the GTM executive seat and is now energized by helping high-growth B2B companies engineer sustainable revenue.

You must love pattern recognition. You must be compelled by systems thinking — by the math behind growth. And you must be the kind of person who can rally internal experts around a customer problem and guide them toward impact.

About the Role

As a Managing Director, you are the commercial lead for recurring-revenue companies across North America.

You’ll work within some of the most vibrant SaaS, AI-native, and PE/VC-backed ecosystems in the world.

You will:

• Conduct thorough SPICED Discovery (Situation, Pain, Impact, Critical Event, Decision Process) to diagnose customer needs and understand the root causes behind their growth challenges.
• Prescribe and sell the right solutions across our Diagnose → Design → Deploy product lines.
• Partner with our global delivery teams to ensure measurable customer impact.
• Evangelize a modern, math-driven approach to growth.

This role is highly consultative, strategic, and senior-level — and suited only for candidates who have successfully operated in or advised B2B recurring revenue GTM teams and organizations. Please note that this role does not require direct people management,  but someone who can truly rally a team of experts to help deliver impact to our customers.

What You’ll Do

Commercial Leadership

• Own and grow a set of named accounts across North America.
• Maintain territory and account plans that engage multiple GTM functions.
• Lead outbound prospecting and opportunity development tailored to growth-stage and PE-backed ecosystems.
• Conduct SPICED Discovery to deeply understand customer needs, map the root causes of GTM breakdowns, and guide customers toward the right WbD Diagnose → Design →
  Deploy solutions.
• Bridge customer problems to the appropriate WbD engagement; delivery teams (not the MD) execute the work.

Market Evangelism

• Represent Winning by Design at conferences, executive dinners, summits, accelerators, and community events.
• Speak publicly and publish thought leadership that advances Revenue Architecture and the science of sustainable growth.

Investor Engagement

• Build relationships with VC and PE partners.
• Support portfolio-level diagnostic, advisory, and enablement initiatives.

Internal Orchestration

• Partner with WbD delivery experts — architects, designers, trainers, PMs — to deliver high-impact outcomes.
• Ensure customers realize measurable improvements in GTM performance.

About You

Experience

• 10+ years in SaaS or GTM consulting, or prior leadership in Sales, Marketing, Customer Success, RevOps, or Sales Strategy.
• Ideally, you’ve been a Winning by Design customer or have deep familiarity with SPICED, Bowtie, and Revenue Architecture.

Skills & Mindset

• You speak GTM fluently and can diagnose complex issues across acquisition, retention, and expansion.
• You create impact through systems thinking — not heroics.
• You separate signals from noise and communicate with crisp executive presence.
• You understand the modern RevTech + AI ecosystem.

Compensation & Benefits

• OTE: $350,000 (50/50 base + commissions)
• Full health and retirement benefits
• Fully remote, with travel flexibility

How to Apply

Before applying, please explore: www.winningbydesign.com and www.youtube.com/winningbydesign

To apply, send your resume and LinkedIn profile to: careers@winningbydesign.com