Expert Profile

Executive Advisor | Expert Consultant | Leadership Coach

Mary Winfield

Mary is a seasoned executive with over 30 years of leadership experience across SaaS, fintech, cybersecurity, and transportation, spanning public, private, and PE-backed companies. She now focuses on executive coaching and expert advisory work, helping founders and CXOs scale operations, strengthen GTM strategy, and navigate transformation. Her work includes ad hoc coaching, revenue and CX advisory, and interim executive leadership roles in GTM, operations, and trust and safety. Mary also advises growth-stage companies and investors, and frequently speaks on leadership, operational scale, and customer-centric growth.
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Areas of Expertise

• Founder and Executive Coaching and Mentorship:
Scaling growth through customer-centric strategies, product roadmaps, analytics, and operational transformation. She guides early-stage companies through product-market fit and monetization while coaching leaders to navigate inflection points with clarity, confidence, and impact.

• Leadership:
Fractional/Interim COO/CCO/CRO

• Customer Experience Design & Delivery:
Designs and scales differentiated customer experiences that drive loyalty and growth. Aligns sales and service strategy with product, brand, and go-to-market priorities to deliver seamless, end-to-end customer journeys. Has led teams of 500+ across global sales, marketing, support, onboarding, success, and product management/engineering.

• GTM & Revenue Operations Strategy and Transformation:
Advises go-to-market teams on how to align sales, success, support, and ops for growth. Brings operational rigor to customer-facing functions, builds dashboards and KPIs, and improves handoffs across the funnel.
Drives monetization and retention through process design and insights.

• Operational Scale & Transformation:
Transforms operations during periods of hypergrowth or turnaround. Diagnoses complexity, builds systems for scale, and drives continuous improvement across people, process, and platform.
Known for reducing inefficiencies, increasing productivity, and preparing orgs for their next stage of growth.

• Trust, Safety & Risk Operations:
Builds and scales trust, safety, and risk functions that protect customers and the business. Creates governance frameworks, escalation protocols, and operational controls that support compliance, reduce fraud, and maintain user trust—especially in high-growth or regulated environments.

• Internal Technology Strategy:
Aligns internal tools and infrastructure with operational and product goals. Brings clarity to roadmaps, improves tooling adoption, and drives cross-functional alignment between product, engineering, and ops.
Experienced in leading internal tech transformation and digital enablement initiatives.

• Cross-functional Leadership Development:
Develops leadership capabilities across functions and levels. Supports execs and managers in building trust, driving accountability, and operating effectively in matrixed, fast-changing environments.
Tailors programs to support emerging leaders, new managers, and senior teams.

• Culture Building at Scale:
Partners with leaders to build and scale intentional, values-aligned cultures. Supports culture change during hypergrowth, integration, or turnaround.
Advises on communication strategy, org design, rituals, and leadership behavior that reinforce desired culture outcomes.

 

$450 /HR

BOOK TIME WITH Mary

More About the Expert:

Mary Winfield is a dynamic executive advisor and leadership coach known for helping founders, CEOs, and executive teams navigate inflection points, scale culture, and drive enterprise-wide transformation. With a career spanning leadership roles at GE, IBM, Lyft, Intuit, and multiple startups, Mary brings a proven ability to architect high-performing organizations, unlock executive potential, and steer product, GTM, and operations strategies that deliver measurable business outcomes.

She partners with leaders during hypergrowth, turnaround, and transformation phases—offering an empathetic yet outcomes-focused approach grounded in decades of experience leading customer operations, trust & safety, product operations, revenue delivery, and internal tech strategy. From coaching first-time founders to advising Fortune 500 leaders, Mary accelerates leadership maturity, cross-functional alignment, and operational excellence— helping companies strengthen their go-to-market muscle and drive sustained customer growth.

“You must be the change you wish to see in the world.” – Mahatma Gandhi
Mary Winfield
Executive Advisor | Expert Consultant | Leadership Coach