Delivery & Enablement Architect

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 hiring a Delivery & Enablement Architect to join us at Winning by Design!

This is an opportunity to bring together your real-world enablement experience, your passion for GTM systems, and your talent for translating strategy into execution that actually sticks.

This is a senior delivery role, ideal for someone who has sat inside a GTM organization and now wants to help others build the enablement systems they wish they’d had.

You must love designing programs that actually move the needle.

You must be energized by complexity — by multi-phase engagements with multiple stakeholders across large organizations.

And you must be the kind of person who brings both rigor and empathy to every customer engagement — knowing that lasting change requires both great program design and deep human trust.

What You’ll Do

1. Architect & Orchestrate Complex Training Programs

• Partner closely with customer enablement leaders and internal facilitators to design and orchestrate multi‑phase training and enablement programs that drive measurable productivity and performance outcomes.
• Translate business goals (growth, efficiency, execution rigor) into structured enablement roadmaps aligned to Winning by Design methodologies (Revenue Architecture, SPICED, Bowtie, Manager Coaching, etc.).
• Serve as the delivery lead on complex engagements, ensuring programs are well‑sequenced, role‑appropriate, and tightly connected to operational reality.

2. Lead Delivery on Enablement‑Focused Engagements

• Act as a core delivery partner on Revenue Enablement Accelerator and Impact Assurance engagements, with a particular focus on supporting enablement leaders as they design and operationalize their internal programs.
• Provide hands‑on guidance to customer enablement teams on program design, rollout strategy, certification frameworks, and measurement of impact.
• Ensure high quality, consistency, and repeatability across enablement‑heavy engagements.

3. Strengthen Delivery Operations & Processes

• Be an active contributor to the Delivery Team, helping evolve processes, playbooks, templates, and governance related to enablement‑led engagements.
• Identify patterns, gaps, and opportunities to improve how we scope, design, and execute complex training programs at scale.
• Partner with Product, Enablement, and Delivery leadership to continuously raise the bar on delivery excellence.

4. Support Business Development on Complex Training Opportunities

• Partner with Growth and Sales teams on complex enablement and transformation opportunities.
• Contribute to solution design, scoping, and positioning for high‑impact training and enablement engagements.
• Act as a subject‑matter expert in customer conversations, helping prospects understand what “great” enablement and manager‑led execution looks like in practice.

Skills & Mindset We’re Looking For

• Operator First Mindset – You’ve owned enablement in the real world and know how hard it is to move from theory to execution.
• Program Architect – You can design end‑to‑end enablement journeys, not just individual trainings.
• Trusted Partner – You build credibility quickly with enablement leaders and senior GTM stakeholders.
• Delivery Excellence – You care deeply about quality, sequencing, adoption, and measurable impact.
• Commercial Acumen – You’re comfortable supporting complex deal cycles, shaping scope, and positioning enablement as a value‑creation lever.
• Systems Thinker – You see enablement as part of a broader operating system (process, roles, metrics, coaching, technology), not a standalone function.

Experience We’re Looking For

• Operator experience at a SaaS business in GTM
• Experience with GTM process, enablement and workflows
• Excellent attention to detail and process design
• Navigating stakeholders across multiple departments.

Compensation & Benefits

• $180,000 — $230,000 (depending on experience)
• Full health and retirement benefits (US)
• 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